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Sample records for tryptophan octyl ester

  1. Morphological studies of DHSA/ DHSA-Octyl ester/ RBD palm kernel olein/ medium chain triglycerides system

    International Nuclear Information System (INIS)

    Anuar Kassim; Nadarajan, Rathidevi; Mohd Zaizi Desa; Atan Mohd Sharif; Dzulkefly Kuang; Mohd Jelas Haron

    2007-01-01

    Dihydroxystearic acid (DHSA) and octyl dihydroxystearate (DHSA-octyl ester) have been previously prepared from palm oleic acid and preliminary results showed that these compounds are suitable in personal care and cosmetics products. The objective of this research is to study the phase behavior in ternary system of DHSA/DHSA-octyl ester/RBD Palm Kernel Olein (RBDPKOo) and MCT at 85 degree Celsius. From the ternary phase diagram, results showed that all ratios of were completely in two-phase region with various concentrations of RBDPKOo and MCT. The phase changes were observed through polarizing light while the formation of texture was confirmed using polarizing microscope combination with heating. Needles and spherulite textures were found in this system. (author)

  2. The Octyl Ester of Ginsenoside Rh2 Induces Lysosomal Membrane Permeabilization via Bax Translocation

    Directory of Open Access Journals (Sweden)

    Fang Chen

    2016-04-01

    Full Text Available Ginsenoside Rh2 is a potential pharmacologically active metabolite of ginseng. Previously, we have reported that an octyl ester derivative of ginsenoside Rh2 (Rh2-O, has been confirmed to possess higher bioavailability and anticancer effect than Rh2 in vitro. In order to better assess the possibility that Rh2-O could be used as an anticancer compound, the underlying mechanism was investigated in this study. The present results revealed that lysosomal destabilization was involved in the early stage of cell apoptosis in HepG2 cells induced by Rh2-O. Rh2-O could induce an early lysosomal membrane permeabilization with the release of lysosomal protease cathepsins to the cytosol in HepG2 cells. The Cat B inhibitor (leu and Cat D inhibitor (pepA inhibited Rh2-O-induced HepG2 apoptosis as well as tBid production and Δφm depolarization, indicating that lysosomal permeabilization occurred upstream of mitochondrial dysfunction. In addition, Rh2-O induced a significant increase in the protein levels of DRAM1 and Bax (p < 0.05 in lysosomes of HepG2 cells. Knockdown of Bax partially inhibited Rh2-O-induced Cat D release from lysosomes. Thus it was concluded that Rh2-O induced apoptosis of HepG2 cells through activation of the lysosomal-mitochondrial apoptotic pathway involving the translocation of Bax to the lysosome.

  3. Photolysis of carotenoids in chloroform: enhanced yields of carotenoid radical cations in the presence of a tryptophan ester

    International Nuclear Information System (INIS)

    El-Agamey, Ali; Burke, Marc; Edge, Ruth; Land, Edward J.; McGarvey, David J.; Truscott, T. George

    2005-01-01

    The presence of an acetyl tryptophan ester gives rise to enhanced yields of carotenoid radical cations in chloroform following 355 nm laser excitation of the carotenoid, even though the tryptophan does not absorb at this wavelength. The increase is attributed to positive charge transfer from semi-oxidized tryptophan itself generated by light absorbed by the carotenoid. The mechanism of these radical processes has been elucidated by pulse radiolysis studies

  4. Tryptophan

    Science.gov (United States)

    Tryptophan is an amino acid needed for normal growth in infants and for nitrogen balance in adults. ... The body uses tryptophan to help make niacin and serotonin. Serotonin is thought to produce healthy sleep and a stable mood. In order ...

  5. Synthesis of novel octyl sinapate to enhance antioxidant capacity of rapeseed-linseed oil mixture.

    Science.gov (United States)

    Szydłowska-Czerniak, Aleksandra; Rabiej, Dobrochna; Krzemiński, Marek

    2018-03-01

    Lipophilisation allows the formation of new functionalised antioxidants having beneficial properties compared to natural hydrophilic phenolic acids. Therefore, this work focused on the synthesis of lipophilic antioxidants, such as a new octyl sinapate, octyl caffeate and octyl ferulate using the modified Fischer esterification of selected hydroxycinnamic acids with 1-octanol. The lipophilic octyl sinapate was obtained for the first time with satisfactory yield (83%) after purification by column chromatography. The identity of the synthesised phenolipids was confirmed by chromatographic and spectroscopic analyses. Antioxidant capacity of phenolipids was determined by DPPH (IC 50  = 35.87-52.24 μg mL -1 ) and ABTS (IC 50  = 39.45-48.72 μg mL -1 ) methods and compared with IC 50 values (7.37-35.30 μg mL -1 and 7.55-41.67 μg mL -1 , respectively) for well known antioxidants. The antioxidant capacity of rapeseed-linseed oil enriched with the purified esters was about two to 30 times higher in comparison with a non-supplemented oil. The novel octyl sinapate as well as octyl caffeate and octyl ferulate have antioxidant properties and lipophilic character, therefore they may be added to vegetable oils as potential antioxidants for tackling oxidative processes. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

  6. Tryptophan analogues. 1. Synthesis and antihypertensive activity of positional isomers.

    Science.gov (United States)

    Safdy, M E; Kurchacova, E; Schut, R N; Vidrio, H; Hong, E

    1982-06-01

    A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  7. Octyl Phenol Synthesis Using Natural Clays

    Directory of Open Access Journals (Sweden)

    S. Casuscelli

    2000-03-01

    Full Text Available A series of clay minerals, HB, NB and Al-PILC have been studied in the alkylation reactions of 2-octanol with phenol at 180°C, under conditions of alcohol/phenol = 1 (mole ratio and W/FAo °= 64,27 ghmol-1. The selectivity of Al-PILC was 77,12% for octyl phenol and 16,5% for dioctyl phenol.

  8. Mutagenic activity of phthalate esters in bacterial liquid suspension assays.

    OpenAIRE

    Seed, J L

    1982-01-01

    The mutagenic activities of several phthalate esters have been evaluated in an 8-azaguanine resistance assay in Salmonella typhimurium. Three phthalate esters were found to be mutagenic: dimethyl phthalate, diethyl phthalate and di-n-butyl phthalate. A number of other phthalate esters were not found to be mutagenic, including di(2-ethylhexyl) phthalate, di-n-octyl phthalate, diallyl phthalate, diisobutyl phthalate and diisodecyl phthalate. A metabolite of di(2-ethylhexyl) phthalate, 2-ethylhe...

  9. n-Octyl gallate as inhibitor of pyruvate carboxylation and lactate gluconeogenesis.

    Science.gov (United States)

    Eler, Gabrielle Jacklin; Santos, Israel Souza; de Moraes, Amarilis Giaretta; Comar, Jurandir Fernando; Peralta, Rosane Marina; Bracht, Adelar

    2015-04-01

    The alkyl gallates are found in several natural and industrial products. In the latter products, these compounds are added mainly for preventing oxidation. In the present work, the potencies of methyl gallate, n-propyl gallate, n-pentyl gallate, and n-octyl gallate as inhibitors of pyruvate carboxylation and lactate gluconeogenesis were evaluated. Experiments were done with isolated mitochondria and the isolated perfused rat liver. The potency of the gallic acid esters as inhibitors of pyruvate carboxylation in isolated mitochondria obeyed the following decreasing sequence: n-octyl gallate > n-pentyl gallate > n-propyl gallate > methyl gallate. A similar sequence of decreasing potency for lactate gluconeogenesis inhibition in the perfused liver was found in terms of the portal venous concentration. Both actions correlate with the lipophilicity of the compounds. The effects are harmful at high concentrations. At appropriate concentrations, however, octyl gallate should act therapeutically because its inhibitory action on gluconeogenesis will contribute further to its proposed antihyperglycemic effects. © 2014 Wiley Periodicals, Inc.

  10. Kinetics and mechanism of the condensation of pyridoxal hydrochloride with L-tryptophan and D-tryptophan, and the chemical transformation of their products

    Science.gov (United States)

    Pishchugin, F. V.; Tuleberdiev, I. T.

    2017-10-01

    The kinetics and mechanism of interaction between pyridoxal and L-tryptophan, D-tryptophan, and their derivatives are studied. It is found that condensation reactions proceed via three kinetically distinguishable stages: (1) the rapid intraplanar addition of the NH2 groups of the amino acids to pyridoxal with the formation of amino alcohols; (2) the rotational isomerism of amino alcohol fragments with their subsequent dehydration and the formation of a Schiff base with a specific configuration; (3) the abstraction of α-hydrogen in the product of condensation of pyridoxal with L-tryptophan, or the abstraction of CO2 in the product of condensation of pyridoxal with D-tryptophan with the formation of quinoid structures, hydrolysis of which results in the preparation of pyridoxamine and keto acid or pyridoxal and tryptamine, respectively. Schiff bases resistant to further chemical transformations are formed in the reaction with tryptophan methyl ester.

  11. Chirální separace tryptofanu a jeho derivátů metodou HPLC

    OpenAIRE

    Voborná, Markéta

    2015-01-01

    This bachelor thesis is focused on study of retention and enantioseparation of tryptophan and its derivatives by high performance liquid chromatography. The set of chiral analytes contained D,L-tryptophan, 5-hydroxy-D,L-tryptophan, 5-fluoro- D,L-tryptophan, D,L-tryptophanol, D,L-tryptophan methyl ester, D,L-tryptophan butyl ester, D,L-tryptophan octyl ester, D,L-tryptophan benzyl ester and N-BOC-D,L-tryptophan. Four different chiral stationary phases were used, i.e. cyclofructan-based (Larihc...

  12. L-Tryptophan

    Science.gov (United States)

    ... tryptophan for 3 days before exercising can improve power during exercise. This improvement in power helps increase the distance an athlete can go ... to 5-HTP (5-hyrdoxytryptophan), and then to serotonin, melatonin, and vitamin B6 (nicotinamide). Serotonin is a ...

  13. Rotational spectrum of tryptophan

    Energy Technology Data Exchange (ETDEWEB)

    Sanz, M. Eugenia, E-mail: maria.sanz@kcl.ac.uk; Cabezas, Carlos, E-mail: ccabezas@qf.uva.es; Mata, Santiago, E-mail: santiago.mata@uva.es; Alonso, Josè L., E-mail: jlalonso@qf.uva.es [Grupo de Espectroscopia Molecular (GEM), Edificio Quifima, Laboratorios de Espectroscopia y Bioespectroscopia, Unidad Asociada CSIC, Parque Científico Uva, Universidad de Valladolid, 47011 Valladolid (Spain)

    2014-05-28

    The rotational spectrum of the natural amino acid tryptophan has been observed for the first time using a combination of laser ablation, molecular beams, and Fourier transform microwave spectroscopy. Independent analysis of the rotational spectra of individual conformers has conducted to a definitive identification of two different conformers of tryptophan, with one of the observed conformers never reported before. The analysis of the {sup 14}N nuclear quadrupole coupling constants is of particular significance since it allows discrimination between structures, thus providing structural information on the orientation of the amino group. Both observed conformers are stabilized by an O–H···N hydrogen bond in the side chain and a N–H···π interaction forming a chain that reinforce the strength of hydrogen bonds through cooperative effects.

  14. Tryptophan Metabolism in Allergic Disorders

    Science.gov (United States)

    Gostner, Johanna M.; Becker, Katrin; Kofler, Heinz; Strasser, Barbara; Fuchs, Dietmar

    2017-01-01

    Allergic diseases such as asthma and rhinitis, as well the early phase of atopic dermatitis, are characterized by a Th2-skewed immune environment. Th2-type cytokines are upregulated in allergic inflammation, whereas there is downregulation of the Th1-type immune response and related cytokines, such as interferon-γ (IFN-γ). The latter is a strong inducer of indoleamine 2,3-dioxygenase-1 (IDO-1), which degrades the essential amino acid tryptophan, as part of an antiproliferative strategy of immunocompetent cells to halt the growth of infected and malignant cells, and also of T cells – an immunoregulatory intervention to avoid overactivation of the immune system. Raised serum tryptophan concentrations have been reported in patients with pollen allergy compared to healthy blood donors. Moreover, higher baseline tryptophan concentrations have been associated with a poor response to specific immunotherapy. It has been shown that the increase in tryptophan concentrations in patients with pollen allergy only exists outside the pollen season, and not during the season. Interestingly, there is only a minor alteration of the kynurenine to tryptophan ratio (Kyn/Trp, an index of tryptophan breakdown). The reason for the higher tryptophan concentrations in patients with pollen allergy outside the season remains a matter of discussion. To this regard, the specific interaction of nitric oxide (NO˙) with the tryptophan-degrading enzyme IDO-1 could be important, because an enhanced formation of NO˙ has been reported in patients with asthma and allergic rhinitis. Importantly, NO˙ suppresses the activity of the heme enzyme IDO-1, which could explain the higher tryptophan levels. Thus, inhibitors of inducible NO˙ synthase should be reconsidered as candidates for antiallergic therapy out of season that may abrogate the arrest of IDO-1 by decreasing the production of NO˙. Considering its association with the pathophysiology of atopic disease, tryptophan metabolism may play a

  15. Tryptophan Oxidative Metabolism Catalyzed by : A Thermophile Isolated from Kuwait Soil Contaminated with Petroleum Hydrocarbons

    Directory of Open Access Journals (Sweden)

    Jassim M. Al-Hassan

    2011-01-01

    Full Text Available Tryptophan metabolism has been extensively studied in humans as well as in soil. Its metabolism takes place mainly through kynurenine pathway yielding hydroxylated, deaminated and many other products of physiological significance. However, tryptophan metabolism has not been studied in an isolated thermophilic bacterium. Geobacillus stearothermophilus is a local thermophile isolated from Kuwait desert soil contaminated with petroleum hydrocarbons. The bacterium grows well at 65 °C in 0.05 M phosphate buffer (pH 7, when supplied with organic compounds as a carbon source and has a good potential for transformation of steroids and related molecules. In the present study, we used tryptophan ethyl ester as a carbon source for the bacterium to study the catabolism of the amino acid at pH 5 and pH 7. In this endeavor, we have resolved twenty one transformation products of tryptophan by GC/LC and have identified them through their mass spectral fragmentation.

  16. Chromatographic analysis of tryptophan metabolites.

    Science.gov (United States)

    Sadok, Ilona; Gamian, Andrzej; Staniszewska, Magdalena Maria

    2017-08-01

    The kynurenine pathway generates multiple tryptophan metabolites called collectively kynurenines and leads to formation of the enzyme cofactor nicotinamide adenine dinucleotide. The first step in this pathway is tryptophan degradation, initiated by the rate-limiting enzymes indoleamine 2,3-dioxygenase, or tryptophan 2,3-dioxygenase, depending on the tissue. The balanced kynurenine metabolism, which has been a subject of multiple studies in last decades, plays an important role in several physiological and pathological conditions such as infections, autoimmunity, neurological disorders, cancer, cataracts, as well as pregnancy. Understanding the regulation of tryptophan depletion provide novel diagnostic and treatment opportunities, however it requires reliable methods for quantification of kynurenines in biological samples with complex composition (body fluids, tissues, or cells). Trace concentrations, interference of sample components, and instability of some tryptophan metabolites need to be addressed using analytical methods. The novel separation approaches and optimized extraction protocols help to overcome difficulties in analyzing kynurenines within the complex tissue material. Recent developments in chromatography coupled with mass spectrometry provide new opportunity for quantification of tryptophan and its degradation products in various biological samples. In this review, we present current accomplishments in the chromatographic methodologies proposed for detection of tryptophan metabolites and provide a guide for choosing the optimal approach. © 2017 The Authors. Journal of Separation Science published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  17. TRYPTOPHAN PROMOTES CHARITABLE DONATING

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    Laura eSteenbergen

    2014-12-01

    Full Text Available The link between serotonin (5-HT and one of the most important elements of prosocial behavior, charity, has remained largely uninvestigated. In the present study, we tested whether charitable donating can be promoted by administering the food supplement L-Tryptophan (TRP, the biochemical precursor of 5-HT. Participants were compared with respect to the amount of money they donated when given the opportunity to make a charitable donation. As expected, compared to a neutral placebo, TRP appears to increase the participants’ willingness to donate money to a charity. This result supports the idea that the food we eat may act as a cognitive enhancer modulating the way we think and perceive the world and others.

  18. Glass transition behavior of octyl β-D-glucoside and octyl β-D-thioglucoside/water binary mixtures.

    Science.gov (United States)

    Ogawa, Shigesaburo; Asakura, Kouichi; Osanai, Shuichi

    2010-11-22

    The lyotropic behavior and glass-forming properties of octyl β-D-glucoside (C8Glu) and octyl β-D-thioglucoside (C8SGlu)/water binary mixtures were evaluated using differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). The results clearly indicate that the mixture forms a glass in the supercooling state of liquid crystalline phases such as cubic, lamellar, and smectic. The glass transition temperature (T(g)) of the mixture was strongly dependent on solute concentration, with a higher concentration correlating with a higher T(g). The experimental T(g) was consistent with the predicted value calculated using the Couchman-Karasz equation in both the C8Glu and C8SGlu/water mixtures. The change of heat capacity at T(g) showed the two bending points under variation of concentrations. And the highest temperature of phase transition from lamellar to isotropic solution was observed at around 50% molar concentration. It was expected that non-percolated state of water existed in extremely higher concentration ranges. Copyright © 2010 Elsevier Ltd. All rights reserved.

  19. Metabolism of an oral tryptophan load. I: Effects of dose and pretreatment with tryptophan.

    OpenAIRE

    Green, A R; Aronson, J K; Curzon, G; Woods, H F

    1980-01-01

    1 The metabolism of three oral doses of L-tryptophan (50, 25 and 10 mg/kg) in healthy young males has been investigated. 2 There was a linear relationship between both peak and area under curve of the total plasma tryptophan concentrations whilst the relationship between these parameters and plasma free tryptophan was hyperbolic. 3 Before the tryptophan load about 85% of plasma tryptophan was bound to albumin. As plasma tryptophan concentrations increased there was a hyperbolic increase in fr...

  20. Tryptophan Research in Panic Disorder

    Directory of Open Access Journals (Sweden)

    Eduard Maron

    2008-01-01

    Full Text Available A considerable body of evidence suggests the involvement of serotonin neurotransmission in the pathogenesis of panic disorder. Research on pathways and functions of tryptophan, an essential amino acid converted into serotonin, may advance our understanding of serotonergic actions in panic disorder and related phenomena. The investigative approaches in this field include manipulations of tryptophan availability as well as genetic association and functional brain imaging studies. In this review we examine the principle findings of these studies and propose further research directions.

  1. Pysico-chemical properties of hydrophobic ionic liquids containing1-octylpyridinium, 1-octyl-2-methylpyridinium or1-octyl-4-methylpyridinium cations

    Energy Technology Data Exchange (ETDEWEB)

    Papaiconomou, Nicolas; Salminen, Justin; Lee, Jong-Min; Prausnitz, John M.

    2006-09-15

    This paper reports synthesis of some ionic liquids based on cations 1-octylpyridinium, 1-octyl-2-methylpyridinium or 1-octyl-4-methylpyridinium and anions dicyanamide [N(CN)2]-, bis(trifluoromethylsulfonyl)imide [Tf2N]-, bis(pentafluoroethylsulfonyl)imide [BETI]-, trifluoromethyl sulfonate [TfO]-, nonafluorobutyl sulfonate [NfO]-, tetrafluoroborate [BF4]-, trifluorophenylborate [BF3Ph]- or hexafluoroarsenate [AsF6]-. Melting points, decomposition temperatures, densities, mutual solubilities with water, and viscosities have been measured. Unlike similar ionic liquids containing imidazolium cations, pyridinium ionic liquids studied here are nearly immiscible in water. Viscosities are similar and water content is slightly lower than those for ionic liquids containing imidazolium cations.

  2. The stability of tryptophan, 5-methyl-tryptophan and α-methyl-tryptophan during NaOH hydrolysis of selected foods.

    Science.gov (United States)

    Rutherfurd, Shane M; Richardson, Russell K; Moughan, Paul J

    2015-12-01

    This study evaluated the use of 5-methyl-tryptophan, α-methyl-tryptophan or synthetic tryptophan to correct for the losses of protein-bound tryptophan in foods during NaOH hydrolysis. Synthetic tryptophan and each protein source was incubated in 4.5M NaOH containing 5-methyl-tryptophan and α-methyl-tryptophan in nitrogen gas-sparged Teflon vials for 0-144 h at 110 °C. The hydrolysis and loss rates of protein-bound tryptophan, 5-methyl-tryptophan, α-methyl-tryptophan and synthetic tryptophan were predicted using least-squares nonlinear regression. Using 5-methyl-tryptophan or synthetic tryptophan to correct for hydrolytic losses of tryptophan overestimated the tryptophan content by 8.2-19% and -0.3-8.8% respectively, while correction using α-methyl-tryptophan underestimated tryptophan by between 0.2% and 8.1% across the protein sources. Correction using α-methyl-tryptophan or synthetic tryptophan was more accurate than using 5-methyl-tryptophan, but when highly accurate tryptophan composition data are required, least-squares nonlinear regression is the best approach as it removes the need for a hydrolysis correction factor. Copyright © 2015 Elsevier Ltd. All rights reserved.

  3. Tryptophan-induced pathogenesis of breast cancer

    African Journals Online (AJOL)

    determine the influence of tryptophan towards interleukin-10 (IL-10) secretion by CD4+ T cell. Results: Targeted metabolomics of amino acids showed that the level of tryptophan significantly (p<0.05) increased in patients with breast cancer. Furthermore, the biological function of tryptophan was determined through ...

  4. Novel applications of Dermabond (2-octyl -cyanoacrylate) in cardiothoracic surgery.

    Science.gov (United States)

    Aziz, Omer; Rahman, M S; Hadjianastassiou, V G; Kokotsakis, John; Vitali, Malinovski; Cherian, Ashok; Darzi, Ara; Athanasiou, Thanos

    2007-01-01

    Dermabond (Ethicon Inc., Somerville, NJ, USA) is a cyanoacrylate adhesive normally indicated for skin wound closure. This study describes the emergency use of this adhesive to control bleeding close to coronary anastomoses in exceptional cases. Dermabond was used in 17 patients who underwent cardiac surgery during an eight-month period, where other haemostatic interventions were unsuitable. It was applied for haemorrhage in 15 patients and control air leaks in two of the patients. Haemostasis was successful with Dermabond alone in 11 patients; the remaining four required additional interventions. It effectively controlled haemorrhage from ventricular pacing wires, vascular sling holes, peri-anastomotic bleeding, and epicardial tears. The adhesive was not placed directly on any graft because of embolic risk. In the two patients with visible air leaks, it was successfully used. No patient events were recorded as a result of haemorrhage and no reported toxicity. Dermabond may be indicated in circumstances in which haemostasis with traditional methods has failed or is inappropriate. A need for further high-quality objective research exists on the effectiveness and long-term safety of 2-octyl cyanoacrylate in cardiac surgery.

  5. In vivo and in vitro evaluation of octyl methoxycinnamate liposomes.

    Science.gov (United States)

    Mota, Aline de Carvalho Varjão; de Freitas, Zaida Maria Faria; Ricci Júnior, Eduardo; Dellamora-Ortiz, Gisela Maria; Santos-Oliveira, Ralph; Ozzetti, Rafael Antonio; Vergnanini, André Luiz; Ribeiro, Vanessa Lira; Silva, Ronald Santos; dos Santos, Elisabete Pereira

    2013-01-01

    Solar radiation causes damage to human skin, and photoprotection is the main way to prevent these harmful effects. The development of sunscreen formulations containing nanosystems is of great interest in the pharmaceutical and cosmetic industries because of the many potential benefits. This study aimed to develop and evaluate an octyl methoxycinnamate (OMC) liposomal nanosystem (liposome/OMC) to obtain a sunscreen formulation with improved safety and efficacy by retaining OMC for longer on the stratum corneum. The liposome/OMC nanostructure obtained was tested for enzymatic hydrolysis with lipase from Rhizomucor miehei and biodistribution with liposomes labeled with technetium-99m. The liposome/OMC formulation was then incorporated in a gel formulation and tested for ocular irritation using the hen's egg test-chorio-allantoic membrane (HET-CAM) assay, in vitro and in vivo sun protection factor, in vitro release profile, skin biometrics, and in vivo tape stripping. The liposome/OMC nanosystem was not hydrolyzed from R. miehei by lipase. In the biodistribution assay, the liposome/OMC formulation labeled with technetium-99m had mainly deposited in the skin, while for OMC the main organ was the liver, showing that the liposome had higher affinity for the skin than OMC. The liposome/OMC formulation was classified as nonirritating in the HET-CAM test, indicating good histocompatibility. The formulation containing liposome/OMC had a higher in vivo solar photoprotection factor, but did not show increased water resistance. Inclusion in liposomes was able to slow down the release of OMC from the formulation, with a lower steady-state flux (3.9 ± 0.33 μg/cm(2)/hour) compared with the conventional formulation (6.3 ± 1.21 μg/cm(2)/hour). The stripping method showed increased uptake of OMC in the stratum corneum, giving an amount of 22.64 ± 7.55 μg/cm(2) of OMC, which was higher than the amount found for the conventional formulation (14.57 ± 2.30 μg/cm(2)). These results

  6. 76 FR 6342 - n-Octyl Alcohol and n-Decyl Alcohol; Exemption From the Requirement of a Tolerance

    Science.gov (United States)

    2011-02-04

    ... ENVIRONMENTAL PROTECTION AGENCY 40 CFR Part 180 [EPA-HQ-OPP-2010-0181; FRL-8860-7] n-Octyl Alcohol and n-Decyl Alcohol; Exemption From the Requirement of a Tolerance AGENCY: Environmental Protection... of a tolerance for residues of n-octyl alcohol (CAS Reg. No. 111-87-5); and n-decyl alcohol (CAS Reg...

  7. In vivo and in vitro evaluation of octyl methoxycinnamate liposomes

    Directory of Open Access Journals (Sweden)

    de Carvalho Varjão Mota A

    2013-12-01

    Full Text Available Aline de Carvalho Varjão Mota,1 Zaida Maria Faria de Freitas,1 Eduardo Ricci Júnior,1 Gisela Maria Dellamora-Ortiz,1 Ralph Santos-Oliveira,2 Rafael Antonio Ozzetti,3 André Luiz Vergnanini,3 Vanessa Lira Ribeiro,4 Ronald Santos Silva,4 Elisabete Pereira dos Santos11Faculty of Pharmacy, Federal University of Rio de Janeiro, 2Nuclear Engineering Institute, National Nuclear Energy Commission, 3Allergisa Dermatocosmetic Research, University of Campinas, São Paulo, 4Pharmacology and Toxicology Department, National Insitute of Quality Control in Health, Oswaldo Cruz Foundation, Rio de Janeiro, BrazilAbstract: Solar radiation causes damage to human skin, and photoprotection is the main way to prevent these harmful effects. The development of sunscreen formulations containing nanosystems is of great interest in the pharmaceutical and cosmetic industries because of the many potential benefits. This study aimed to develop and evaluate an octyl methoxycinnamate (OMC liposomal nanosystem (liposome/OMC to obtain a sunscreen formulation with improved safety and efficacy by retaining OMC for longer on the stratum corneum.Methods: The liposome/OMC nanostructure obtained was tested for enzymatic hydrolysis with lipase from Rhizomucor miehei and biodistribution with liposomes labeled with technetium-99m. The liposome/OMC formulation was then incorporated in a gel formulation and tested for ocular irritation using the hen’s egg test-chorio-allantoic membrane (HET-CAM assay, in vitro and in vivo sun protection factor, in vitro release profile, skin biometrics, and in vivo tape stripping.Results: The liposome/OMC nanosystem was not hydrolyzed from R. miehei by lipase. In the biodistribution assay, the liposome/OMC formulation labeled with technetium-99m had mainly deposited in the skin, while for OMC the main organ was the liver, showing that the liposome had higher affinity for the skin than OMC. The liposome/OMC formulation was classified as nonirritating in

  8. 40 CFR 180.1130 - N-(n-octyl)-2-pyrrolidone and N-(n-dodecyl)-2-pyrrolidone; exemptions from the requirement of a...

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 23 2010-07-01 2010-07-01 false N-(n-octyl)-2-pyrrolidone and N-(n... EXEMPTIONS FOR PESTICIDE CHEMICAL RESIDUES IN FOOD Exemptions From Tolerances § 180.1130 N-(n-octyl)-2-pyrrolidone and N-(n-dodecyl)-2-pyrrolidone; exemptions from the requirement of a tolerance. N-(n-octyl)-2...

  9. Allergic contact dermatitis from 2-n-octyl-4-isothiazolin-3-one, a paint mildewcide

    DEFF Research Database (Denmark)

    Mathias, C G; Andersen, Klaus Ejner; Hamann, K

    1983-01-01

    Severe allergic contact dermatitis from a paint mildewcide, 2-n-octyl-4-isothiazolin-3-one, developed in a worker formulating latex paints within a paint manufacturing company, Guinea pig maximization testing demonstrated this to be a moderate sensitizer. Further cases of allergic contact...

  10. Tryptophan: a key nutrient in pig diets

    NARCIS (Netherlands)

    Jansman, A.J.M.; Floc'h Le, N.; Melchior, N.; Melchior, D.

    2007-01-01

    During the past decades, the interest in the essential amino acid tryptophan has steadily increased, especially in piglets because they are particularly sensitive to tryptophan. However, how much does the animal actually require in terms of diet, age, health and sanitary housing conditions? This

  11. Acceleration effect of ionic liquids on polycyclotrimerization of dicyanate esters

    Directory of Open Access Journals (Sweden)

    A. Fainleib

    2016-09-01

    Full Text Available The polycyclotrimerization reaction of dicyanate ester of bisphenol E (DCBE in the presence of varying amounts (from 0.5 to 5 wt% of 1-octyl-3-methylimidazolium tetrafluoroborate ([OMIm][BF4] ionic liquid has been investigated using differential scanning calorimetry (DSC and Fourier transform infrared spectroscopy (FTIR techniques, after a curing stage at 150 °C for 6 h. It is noteworthy that an amount of [OMIm][BF4] as low as 0.5 wt% accelerates dramatically the thermal curing process leading to the formation of a polycyanurate network. The conversion of DCBE increased with increasing [OMIm][BF4] content in the temperature range studied. A reaction mechanism associated with the ionic liquid-catalyzed DCBE polycyclotrimerization is newly proposed via the involvement of a [CN]δ+–[OMIm]δ– complex as a key intermediate.

  12. Structural Characterization of New Microcystins Containing Tryptophan and Oxidized Tryptophan Residues

    Science.gov (United States)

    Puddick, Jonathan; Prinsep, Michèle R.; Wood, Susanna A.; Miles, Christopher O.; Rise, Frode; Cary, Stephen Craig; Hamilton, David P.; Wilkins, Alistair L.

    2013-01-01

    Microcystins are cyclic peptides produced by cyanobacteria, which can be harmful to humans and animals when ingested. Eight of the (more than) 90 microcystin variants presently characterized, contain the amino acid tryptophan. The well-researched oxidation products of tryptophan; kynurenine, oxindolylalanine, and N-formylkynurenine, have been previously identified in intact polypeptides but microcystin congeners containing oxidized tryptophan moieties have not been reported. Liquid chromatography-tandem mass spectrometric analysis of an extract of Microcystis CAWBG11 led to the tentative identification of two new tryptophan-containing microcystins (MC‑WAba and MC-WL), as well as eight other microcystin analogs containing kynurenine, oxindolylalanine and N‑formylkynurenine (Nfk). Investigation of one of these congeners (MC‑NfkA) by nuclear magnetic resonance spectroscopy was used to verify the presence of Nfk in the microcystin. Liquid chromatography-mass spectrometry analysis of a tryptophan oxidation experiment demonstrated that tryptophan-containing microcystins could be converted into oxidized tryptophan analogs and that low levels of oxidized tryptophan congeners were present intracellularly in CAWBG11. MC-NfkR and MC-LNfk were detected in standards of MC-WR and MC-LW, indicating that care during storage of tryptophan-containing microcystins is required. PMID:23966035

  13. [Acute tryptophan depletion in eating disorders].

    Science.gov (United States)

    Díaz-Marsa, M; Lozano, C; Herranz, A S; Asensio-Vegas, M J; Martín, O; Revert, L; Saiz-Ruiz, J; Carrasco, J L

    2006-01-01

    This work describes the rational bases justifying the use of acute tryptophan depletion technique in eating disorders (ED) and the methods and design used in our studies. Tryptophan depletion technique has been described and used in previous studies safely and makes it possible to evaluate the brain serotonin activity. Therefore it is used in the investigation of hypotheses on serotonergic deficiency in eating disorders. Furthermore, and given the relationship of the dysfunctions of serotonin activity with impulsive symptoms, the technique may be useful in biological differentiation of different subtypes, that is restrictive and bulimic, of ED. 57 female patients with DSM-IV eating disorders and 20 female controls were investigated with the tryptophan depletion test. A tryptophan-free amino acid solution was administered orally after a two-day low tryptophan diet to patients and controls. Free plasma tryptophan was measured at two and five hours following administration of the drink. Eating and emotional responses were measured with specific scales for five hours following the depletion. A study of the basic characteristics of the personality and impulsivity traits was also done. Relationship of the response to the test with the different clinical subtypes and with the temperamental and impulsive characteristics of the patients was studied. The test was effective in considerably reducing plasma tryptophan in five hours from baseline levels (76%) in the global sample. The test was well tolerated and no severe adverse effects were reported. Two patients withdrew from the test due to gastric intolerance. The tryptophan depletion test could be of value to study involvement of serotonin deficits in the symptomatology and pathophysiology of eating disorders.

  14. Selective oxidation of cyclohexanol to cyclohexanone in the ionic liquid 1-octyl-3-methylimidazolium chloride.

    Science.gov (United States)

    Chen, Long; Zhou, Teng; Chen, Lifang; Ye, Yinmei; Qi, Zhiwen; Freund, Hannsjörg; Sundmacher, Kai

    2011-09-07

    Ionic liquid (IL) 1-octyl-3-methylimidazolium chloride was found to effectively intensify cyclohexanol oxidation and resulted in 100% conversion of cyclohexanol with 100% selectivity to cyclohexanone using hydrogen peroxide as an oxidant and WO(3) as a catalyst. The effect of the IL as a solvent is discussed with the support of COSMO-RS theory. This journal is © The Royal Society of Chemistry 2011

  15. Ester Tuiksoo / Ester Tuiksoo ; interv. Piret Tali

    Index Scriptorium Estoniae

    Tuiksoo, Ester, 1965-

    2007-01-01

    Juhan Partsi valitsuse (05.04.2004-13.04.2005) ja Andrus Ansipi valitsuse (13.04.2005-) põllumajandusminister Ester Tuiksoo oma lapsepõlvest ja elukutsevalikust, poliitilise karjääri algusest ja erakonna valikust, ministritöö kogemustest, naistest poliitikas

  16. Ultrafast polarized fluorescence measurements on tryptophan and a tryptophan-containing peptide

    NARCIS (Netherlands)

    Larsen, O.F.A.; van Stokkum, I.H.M.; Pandit, A.; van Grondelle, R.; van Amerongen, H.

    2003-01-01

    In this work polarized picosecond fluorescence measurements were performed on isolated tryptophan and tryptophan in a small 22-mer peptide using a streak camera coupled to a spectrograph as a detection system. In both cases the fluorescence decay was multiexponential with decay times of ∼500 ps and

  17. Ultrafast polarized fluorescence measurements on Tryptophan and a Tryptophan-containing peptide

    NARCIS (Netherlands)

    Larsen, O.F.A.; Stokkum, van I.H.M.; Pandit, A.; Grondelle, van R.; Amerongen, van H.

    2003-01-01

    In this work polarized picosecond fluorescence measurements were performed on isolated tryptophan and tryptophan in a small 22-mer peptide using a streak camera coupled to a spectrograph as a detection system. In both cases the fluorescence decay was multiexponential with decay times of similar

  18. Tryptophan auxotrophs were obtained by random transposon insertions in the Methanococcus maripaludis tryptophan operon.

    Science.gov (United States)

    Porat, Iris; Whitman, William B

    2009-08-01

    Methanococcus maripaludis is an anaerobic, methane-producing archaeon that utilizes H(2) or formate for the reduction of CO(2) to methane. Tryptophan auxotrophs were constructed by in vitro insertions of the Tn5 transposon into the tryptophan operon, followed by transformation into M. maripaludis. This method could serve for rapid insertions into large cloned DNA regions.

  19. Amide and Ester-Functionalized Humic Acid for Fuel Combustion Enhancement

    Science.gov (United States)

    Riggs, Mark

    Humic acid is a class of naturally occurring molecules composed of large sheet-like regions of cyclic aromatic hydrocarbon networks with surface and edge functional groups including phenols, carboxylic acids, and epoxides. These naturally occurring molecules are found in brown coal deposits near lignite formations. Humic acid has gained attention from the scientific community as a precursor for graphene. Graphene is a 2-dimensional honeycomb structure of fully unsaturated carbon atoms that has exceptional material properties and inherent aromaticity. Graphene's incredible properties are matched by the difficulty associated with reproducibly manufacturing it on a large scale. This issue has limited the use of graphene for commercial applications. The polar functional groups of humic acid contribute to the hydrophilic nature of the molecule, limiting its miscibility in any alkyl-based solvent. Surfactants containing long alkyl chains can affect the miscibility of the molecule in an organic solvent. Surfactants are often difficult to remove from the system. It is theorized that alkylation of the functional sites of humic acid can affect the hydrophilic nature of the molecule, and effectively enable its dispersion into organic solvents without simultaneous incorporation of surfactants. This dissertation investigated the amidation and esterification of humic acid molecules extracted from leonardite. The resulting change in the modified humic acid dispersibility in organic solvents and its potential usage as a fuel additive were evaluated. Butyl, hexyl, octyl, and decyl amide-modified and ester-modified humic acids were synthesized. These products were characterized to confirm successful chemical reaction through thermogravimetric analysis, Fourier-transform infrared spectroscopy, and scanning electron microscopy. The decyl-modified humic acids remained suspended in kerosene mixtures for longer than 1 week. Other organo-humic acids showed varying degrees of flocculation

  20. Tryptophan catabolizing enzymes – party of three

    Directory of Open Access Journals (Sweden)

    Helen J Ball

    2014-10-01

    Full Text Available Indoleamine 2,3-dioxygenase (IDO and tryptophan 2,3-dioxygenase (TDO are tryptophan-degrading enzymes that have independently evolved to catalyze the first step in tryptophan catabolism via the kynurenine pathway. The depletion of tryptophan and formation of kynurenine pathway metabolites modulates the activity of the mammalian immune, reproductive and central nervous systems. IDO and TDO enzymes can have overlapping or distinct functions depending on their expression patterns. The expression of TDO and IDO enzymes in mammals differs not only by tissue/cellular localization but also by their induction by distinct stimuli. To add to the complexity, these genes also have undergone duplications in some organisms leading to multiple isoforms of IDO or TDO. For example, many vertebrates, including all mammals, have acquired two IDO genes via gene duplication, although the IDO1-like gene has been lost in some lower vertebrate lineages. Gene duplications can allow the homologs to diverge and acquire different properties to the original gene. There is evidence for IDO enzymes having differing enzymatic characteristics, signaling properties and biological functions. This review analyses the evolutionary convergence of IDO and TDO enzymes as tryptophan-catabolizing enzymes and the divergent evolution of IDO homologs to generate an enzyme family with diverse characteristics not possessed by TDO enzymes, with an emphasis on the immune system.

  1. Purification and Characterization of Tryptophan Hydroxylase

    DEFF Research Database (Denmark)

    Haahr, Lærke Tvedebrink

    catalyzes the hydroxylation of tryptophan to 5-hydroxytryptophan, which is the rate-limiting step in the biosynthesis ofserotonin. Serotonin is an important neurotransmitter, which is involved in a range of psychiatric disorders including depression and obsessive-compulsive disorder. The goal...... compared to the Fe(III) form. Furthermore, the addition of substrates and cofactor only stabilizes chTPH2 when Fe(II) is present. Isothermal titration calorimetry measurements on chTPH2 determined the dissociation constant of BH2 to 5 μM, while the dissociation constant for tryptophan is somewhat higher...

  2. Mechanism of decline in rat brain 5-hydroxytryptamine after induction of liver tryptophan pyrrolase by hydrocortisone: roles of tryptophan catabolism and kynurenine synthesis

    OpenAIRE

    Young, Simon N.

    1981-01-01

    1 Two mechanisms have been proposed to explain the decline in brain tryptophan and 5-hydroxytryptamine (5-HT) after administration of hydrocortisone and the subsequent induction of liver pyrrolase. These are depletion of tryptophan by high rates of tryptophan catabolism and inhibition of tryptophan uptake by elevated levels of the tryptophan catabolite, kynurenine.

  3. Preparation of novel cross-linked and octylated caseinates using a biphasic enzymatic procedure and their functional properties.

    Science.gov (United States)

    Zhang, Yaqiong; Niu, Yuge; Yao, Fangyi; Dai, Bona; Wang, Qin; Yu, Liangli Lucy

    2014-08-27

    A novel microbial transglutaminase-catalyzed aqueous-organic biphasic reaction system was successfully developed to prepare caseinate derivatives by cross-linking and incorporating nonpolar octyl tails for the first time. SDS-PAGE and (1)H NMR analysis confirmed that cross-linking and octyl conjugation occurred simultaneously. The octyl substitution degree (SD) was measured by (1)H NMR and used as an index to determine a suitable reaction condition. It was found that at the condition of 0.125% (w/v) protein concentration and 6 h of reaction time, the modified caseinate had the highest SD of 28.96%. The modified caseinate also had an increased surface hydrophobicity, better emulsifying activity, and improved thermal and salt stabilities. However, its emulsion stability or in vitro enzymatic digestibility was slightly lower than that of the native caseinate.

  4. Synthesis of Octyl Dihydrocaffeate and Its Transesterification with Tricaprylin Catalyzed by Candida antarctica Lipase

    DEFF Research Database (Denmark)

    Feddern, Vivian; Yang, Zhiyong; Xu, Xuebing

    2011-01-01

    This work aimed at producing a phenolic ester from dihydrocaffeic acid (DHCA), besides carrying out transesterification reactions of this ester with tricaprylin. The esterification reaction was performed in two ratios (1:1 and 1:3 DHCA:octanol), and the transesterification was done in four ratios...

  5. Improving therapeutics in anorexia nervosa with tryptophan.

    Science.gov (United States)

    Haleem, Darakhshan Jabeen

    2017-06-01

    A growing body of evidence suggests that our diet is an important contributing factor in the development, management and prevention of a number of psychiatric illnesses. Tryptophan, an essential amino acid, is the sole precursor of neurotransmitter 5-hydroxytryptamine (5-HT; serotonin). Administration of tryptophan can boost serotonin neurotransmission to produce therapeutically important effects in serotonin deficiency disorders. Anorexia nervosa (AN) an eating disorder associated with high levels of psychiatric comorbidity including psychosis, hyperactivity, depression and anxiety has highest lethality of all psychiatric illnesses. Evidence suggests that excessive dieting and food restriction can decrease brain tryptophan and serotonin in AN patients to precipitate depression, psychosis and hyperactivity. There are currently no FDA approved pharmacological treatments available for AN patients; antidepressants and antipsychotics, largely used to treat associated psychiatric comorbidities are also not very effective. The aim of this non-systematic review article is to evaluate and document a potential importance of tryptophan supplementation in improving therapeutics in AN patients. Copyright © 2017 Elsevier Inc. All rights reserved.

  6. Tryptophan and kynurenines: continuing to court controversy.

    Science.gov (United States)

    Stone, Trevor W

    2016-08-01

    The role of the amino acid tryptophan in the generation of 5-hydroxy-tryptamine (5-HT) has been expanded over the past 30 years with recognition that its oxidation by indoleamine-2,3-dioxygenase (IDO) results in the formation of kynurenine and metabolites which regulate neuronal excitability, psychiatric status, immune cell activity and balance, and probably implantation and the development of embryos. While the amount of work on this kynurenine pathway continues to accelerate, it is important that disagreements about results, differences of interpretation or problems with technical issues are presented openly and discussed thoroughly so that new research is not mis-led in ways that could have been foreseen. In this issue of Clinical Science, Badawy et al. discuss in depth two opposing views of how changes in tryptophan availability or utilisation bring about their effects on cell function. The original concept that local depletion of tryptophan is responsible seems to be less attractive than the view that kynurenine and its metabolites have direct, potent actions on cells. This conclusion not only clarifies our understanding of the importance of tryptophan metabolism to kynurenine but also raises the possibility that the actions of those metabolites could be novel targets for the development of agonists and antagonists with a range of medical implications. © 2016 The Author(s). published by Portland Press Limited on behalf of the Biochemical Society.

  7. A comparison of 2-octyl cyanoacrylate with nylon for wound closure of knee arthroscopy portals.

    Science.gov (United States)

    Imbuldeniya, A M; Rashid, A; Murphy, J P

    2014-09-01

    To compare the cosmetic results, complications and patient satisfaction of 2-octyl cyanoacrylate (Dermabond, Ethicon Inc. Somerville, NJ, USA), a liquid bonding agent, with 3-0 nylon sutures (Ethilon, Ethicon Inc) skin closure in two groups of patients undergoing elective knee arthroscopy at 6 weeks. The retrospective clinical audit recruited patients undergoing knee surgery for the first time between October 2010 and August 2011. The patients were either treated with the liquid bonding agent or nylon sutures. The patients in the bonding agent group were allowed to shower as normal on postoperative day one, while patients in the suture group kept their wounds dry for 2 weeks. Between the two groups (40 patients per group) there was no difference in the cosmetic outcome (p=0.285), patient satisfaction (p=0.29), pain scores (p=0.44) or wound complication rate (pnylon sutures if undergoing the same procedure in the future as they could shower the next day and avoid suture removal. 2-octyl cyanoacrylate is safe to use in the short term in knee arthroscopy providing comparable results to nylon suture closure. Allowing patients to shower the next day appears to cause no adverse effects. The authors would like to state that they do not have any economic or social interest in any of the products used or mentioned. No grant or finance was received for this study, nor any input from other sources.

  8. The Effects of Dietary Tryptophan on Affective Disorders

    Science.gov (United States)

    Lindseth, Glenda; Helland, Brian; Caspers, Julie

    2014-01-01

    Using a randomized crossover study design, 25 healthy young adults were examined for differences in anxiety, depression, and mood after consuming a high tryptophan and a low tryptophan diet for four days each. There was a two week washout between the diets. A within-subjects analysis of the participants’ mood indicated significantly (p tryptophan diet as compared to a low tryptophan diet. Negative affect differences between the diets were not statistically significant (p > .05). Also, consuming more dietary tryptophan resulted in (p < .05) less depressive symptoms and decreased anxiety. PMID:25858202

  9. Adsorption and self-assembly of octyl hydroxamic acid at a fluorite surface as revealed by sum-frequency vibrational spectroscopy.

    Science.gov (United States)

    Wang, Xuming; Liu, Jin; Miller, Jan D

    2008-09-15

    In the study described here, the surface structure of a self-assembly octyl hydroxamic acid at a calcium fluoride (CaF(2)) surface is evaluated using sum-frequency vibrational spectroscopy (SFVS). Of particular significance are the results that show octyl hydroxamic acid adsorbs at the fluorite surface from octanol solution and has more ordering and molecular conformation than the octyl hydroxamic acid adsorbed from solution. At the fluorite/0.1 M octyl hydroxamic acid octanol solution interface a bilayer-like structure consisting of an octyl hydroxamic acid layer in contact with fluorite and a tilted alcohol layer was observed by SFVS. The alcohol molecules are oriented with respect to the hydroxamic acid monolayer with the OH groups directed towards the bulk alcohol phase and the terminal CH(3) group oriented to face the alkyl chains of the hydroxamic acid monolayer.

  10. Tryptophan Transport in Human Fibroblast Cells—A Functional Characterization

    Directory of Open Access Journals (Sweden)

    Ravi Vumma

    2011-01-01

    Full Text Available There are indications that serotonergic neurotransmission is disturbed in several psychiatric disorders. One explanation may be disturbed transport of tryptophan (precursor for serotonin synthesis across cell membranes. Human fibroblast cells offer an advantageous model to study the transport of amino acids across cell membranes, since they are easy to propagate and the environmental factors can be controlled. The aim of this study was to functionally characterize tryptophan transport and to identify the main transporters of tryptophan in fibroblast cell lines from healthy controls. Tryptophan kinetic parameters ( V max and K m at low and high concentrations were measured in fibroblasts using the cluster tray method. Uptake of 3 H (5-L-tryptophan at different concentrations in the presence and absence of excess concentrations of inhibitors or combinations of inhibitors of amino acid transporters were also measured. Tryptophan transport at high concentration (0.5 mM had low affinity and high V max and the LAT1 isoform of system-L was responsible for approximately 40% of the total uptake of tryptophan. In comparison, tryptophan transport at low concentration (50 nM had higher affinity, lower V max and approximately 80% of tryptophan uptake was transported by system-L with LAT1 as the major isoform. The uptake of tryptophan at the low concentration was mainly sodium (Na + dependent, while uptake at high substrate concentration was mainly Na + independent. A series of different transporter inhibitors had varying inhibitory effects on tryptophan uptake. This study indicates that tryptophan is transported by multiple transporters that are active at different substrate concentrations in human fibroblast cells. The tryptophan transport trough system-L was mainly facilitated by the LAT1 isoform, at both low and high substrate concentrations of tryptophan.

  11. A novel method of defective vascular reconstruction using 2-octyl-cyanoacrylate and homemade prosthetic component.

    Science.gov (United States)

    Liang, Xiangdang; Cai, Hongfei; Sun, Geng; Liu, Zihao; Chen, Wen; Tang, Peifu

    2014-01-01

    Currently, adhesive technique is popular in vascular repair but not widely used for defective vessels. This study aimed to determine the feasibility and effectiveness of repairing defective vessels with 2-octyl-cyanoacrylate and a homemade prosthetic component. Homemade prosthetic component consisting of expanded polytetrofluoroethylene (ePTFE), terylene film, and homemade soluble hollow stent mixed with adhesive can replace autologous graft and suture in repairing defective vessels, can fix vessels better using the stent without occlusive bleeding. Forty male mongrel dogs were used, 20 for biomechanical tests and 20 for animal experiments. In the biomechanical test, dogs were randomly divided into two groups (n = 10 each), one group repaired on the two sides of the carotid arteries with 2-octyl-cyanoacrylate and homemade component and another group repaired with suture and ePTFE. Of the 40 specimens, 10 were used for adhesive and 10 for suture specimens for tension strength test, whereas the remaining specimens were used for bursting pressure test. In animal experiments, dogs were also divided into adhesive and suture groups (n = 10), only of the left carotid artery. Recording the operational time, bleeding or not. Vessels were tested using color Doppler ultrasound, the inner diameter was measured, and the degree of stenosis at 8 weeks was evaluated digital subtraction angiography (DSA) were also performed. Specimens were then analyzed histologically. In the adhesive and suture groups, the specimens could afford atension strength of (23.80 ± 1.51) N versus (24.60 ± 1.08) N (P > 0.05), the bursting pressure was (52.03 ± 2.43) kPa versus (50.04 ± 3.51) kPa (P > 0.05), and the mean time of anastomosis was (15.20 ± 0.55) minutes versus (25.97 ± 0.58) minutes (P < 0.05). One dog in the adhesive group was bleeding from the suture. One dog from each group presented with thrombosis at 1 week. After measuring using ultrasound, the stenosis degree of all dogs were no

  12. Expression, Purification and Characterisation of Tryptophan Hydroxylases

    DEFF Research Database (Denmark)

    Windahl, Michael Skovbo

    2007-01-01

    og co-substratet tetrahydrobiopterin spalter dioxygen (O2) så det ene oxygen-atom indsættes i aminosyren tryptophan. Der findes to forskellige former af TPH: TPH-1 findes flere forskellige steder i kroppen, mens TPH-2 findes i hjernen hvor det har afgørende betydning for mængden af serotonin i...... tetrahydro-biopterin og O2. Denne opdagelse er meget vigtig for udvikling af lægemidler, som individuelt kan regulere TPH-1s eller TPH-2s enzymaktivitet. Desuden er det vist, at tryptophan binder til TPH før tetrahydrobiopterin og O2. Den 3-dimensionelle struktur af TPH-1 er bestemt ved brug af...

  13. Friction Blisters on the Hands Treated Successfully Using 2-Octyl Cyanoacrylate: A Case Report.

    Science.gov (United States)

    Gearhart, Peter A; Gaspar, Michael P; Jacoby, Sidney M

    Friction blisters on the hand are challenging to treat as conventional dressings are prone to saturation, contamination, and loosening with active hand use and other mechanical stresses. Alternative methods and materials for dressing hand blisters warrant exploration. A 48-year-old male surgeon presented with friction blisters over his bilateral thumbs. The patient complained of significant difficulty in keeping his dressings clean and dry, significant pain with hand hygiene, and functional limitations at work. The patient's blisters were dressed with 2-octyl cyanoacrylate (Dermabond; Ethicon US LLC, Somerville, New Jersey), applied directly onto the wound bed. The patient was able to perform his normal duties immediately, without the need for additional intervention. Six days postapplication, the Dermabond sloughed off, revealing an epithelialized surface. Dermabond is a promising agent for dressing unroofed blisters of the hand, as it provides a barrier to moisture and contamination, while allowing the wound to epithelialize, without functional cost.

  14. Pulsed laser thin film growth of di-octyl substituted polyfluorene and its co-polymers

    Energy Technology Data Exchange (ETDEWEB)

    Gupta, R.K.; Ghosh, K.; Kahol, P.K. [Department of Physics, Astronomy and Materials Science, Missouri State University, Springfield, MO 65897 (United States); Yoon, J. [Department of Physics and Astronomy, University of Missouri, Columbia, MO 65211 (United States); Guha, S. [Department of Physics and Astronomy, University of Missouri, Columbia, MO 65211 (United States)], E-mail: guhas@missouri.edu

    2008-08-30

    Matrix-assisted pulsed laser deposition (PLD) allows a controlled layer-by-layer growth of polymer films. Di-octyl substituted polyfluorene (PF8) and its copolymers were deposited as thin films using matrix-assisted PLD by employing a KrF excimer laser with a fluence of 125 mJ/pulses. The optical and structural properties of these films are compared with spincoated films via Raman spectroscopy, absorption and photoluminescence. The Raman spectra of both PLD and spincoated films are similar indicating that the polymer films deposited via PLD maintain their molecular structure. Both the spincoated and the PLD grown PF8 films that were cast from toluene show the presence of the {beta} phase. Benzothiadiazole substituted PF8 (F8BT) and butyl phenyl-substituted PF8 (PFB) PLD grown films show a slightly broader emission compared to the spincoated films, which is attributed to an enhanced intermolecular interaction in the PLD grown thin films.

  15. Pulsed laser thin film growth of di-octyl substituted polyfluorene and its co-polymers

    International Nuclear Information System (INIS)

    Gupta, R.K.; Ghosh, K.; Kahol, P.K.; Yoon, J.; Guha, S.

    2008-01-01

    Matrix-assisted pulsed laser deposition (PLD) allows a controlled layer-by-layer growth of polymer films. Di-octyl substituted polyfluorene (PF8) and its copolymers were deposited as thin films using matrix-assisted PLD by employing a KrF excimer laser with a fluence of 125 mJ/pulses. The optical and structural properties of these films are compared with spincoated films via Raman spectroscopy, absorption and photoluminescence. The Raman spectra of both PLD and spincoated films are similar indicating that the polymer films deposited via PLD maintain their molecular structure. Both the spincoated and the PLD grown PF8 films that were cast from toluene show the presence of the β phase. Benzothiadiazole substituted PF8 (F8BT) and butyl phenyl-substituted PF8 (PFB) PLD grown films show a slightly broader emission compared to the spincoated films, which is attributed to an enhanced intermolecular interaction in the PLD grown thin films

  16. Pulsed laser thin film growth of di-octyl substituted polyfluorene and its co-polymers

    Science.gov (United States)

    Gupta, R. K.; Ghosh, K.; Kahol, P. K.; Yoon, J.; Guha, S.

    2008-08-01

    Matrix-assisted pulsed laser deposition (PLD) allows a controlled layer-by-layer growth of polymer films. Di-octyl substituted polyfluorene (PF8) and its copolymers were deposited as thin films using matrix-assisted PLD by employing a KrF excimer laser with a fluence of 125 mJ/pulses. The optical and structural properties of these films are compared with spincoated films via Raman spectroscopy, absorption and photoluminescence. The Raman spectra of both PLD and spincoated films are similar indicating that the polymer films deposited via PLD maintain their molecular structure. Both the spincoated and the PLD grown PF8 films that were cast from toluene show the presence of the β phase. Benzothiadiazole substituted PF8 (F8BT) and butyl phenyl-substituted PF8 (PFB) PLD grown films show a slightly broader emission compared to the spincoated films, which is attributed to an enhanced intermolecular interaction in the PLD grown thin films.

  17. [Removal of oral Prevotella intermedia Endotoxin by octyl phenyl polyoxyethylene ether extraction method].

    Science.gov (United States)

    Wang, Ai-wu; Liu, Yan; Hu, Kong-xin; Cheng, Qian

    2012-12-01

    To investigate an effective purification method for removing endotoxin from Prevotella intermedia. The main protein ingredients of bacteria prepared from ammonium sulfate precipitation were further treated with octyl phenyl polyoxyethylene ether (Triton X-114), and then processed at 4°C, 37°C and 25°C. The obtained aqueous phase after at least two more cycle repeated operations was assayed for endotoxin by Western blotting, LAL-clotting method, in vitro cell stimulation and in vivo animal experiments. Western blotting and LAL-clotting method demonstrated that the reduction in endotoxin level was greater than 99.99% and recovery of the proteins after endotoxin removal was greater than 90% with Triton X-114 treatment for 3 cycles. The cytokines expression level was lower in both in vitro cell stimulation and in vivo animal experiments than in untreated group (P Prevotella intermedia.

  18. Itaconic Acid Based Surfactants: I. Synthesis and Characterization of Sodiumn-Octyl Sulfoitaconate Diester Anionic Surfactant.

    Science.gov (United States)

    Xu, Jun; Cao, Fengzhi; Li, Tong; Zhang, Shuai; Gao, Chuanhui; Wu, Yumin

    A novel itaconate-based surfactant, namely sodium n -octyl sulfoitaconate diester (SOSID), has been synthesized from itaconic acid (IA) and n -octanol by sulfonation and esterification reaction processes. The effects of reaction temperature, reaction time, molar ratios of n -octanol to IA and the catalyst dosage on the esterification were investigated. The chemical structure of the surfactants SOSID was characterized by means of LC-MS and confirmed by FT-IR and 1 H NMR spectroscopy. The surface tension γ and the critical micelle concentration (CMC) were determined as 25.02 mN/m and 4.0 × 10 -4 mol/L by using surface tensiometer at 20 °C. Further investigations showed that SOSID possess excellent wetting, emulsifying and lime soap dispersing properties.

  19. Enzymes of the tryptophan pathway in Acinetobacter calco-aceticus.

    Science.gov (United States)

    Twarog, R; Liggins, G L

    1970-10-01

    All enzymes of the tryptophan synthetic pathway were detectable in extracts from wild-type Acinetobacter calco-aceticus. The levels of these enzymes were determined in extracts from a number of auxotrophs grown under limiting tryptophan. In each case only anthranilate synthetase was found to be present in increased amounts, whereas the specific activities of the remaining enzymes remained unchanged and unaffected by the tryptophan concentration. Derepression of anthranilate synthetase was found to occur as the concentration of tryptophan became limiting. Anthranilate synthetase and phosphoribosyl transferase activities are both feedback-inhibited by tryptophan. Molecular weight determination carried out by gel filtration and zonal centrifugation in sucrose revealed that all the enzymes are less than 100,000, and no molecular aggregates of these enzymes were detected. The data indicate that tryptophan synthesis in Acinetobacter is regulated both by feedback inhibition of the first two enzymes of the pathway and by repression control of anthranilate synthetase.

  20. Dietary tryptophan intake and suicide rate in industrialized nations.

    Science.gov (United States)

    Voracek, Martin; Tran, Ulrich S

    2007-03-01

    The objective of this study was to assess the ecological association of dietary tryptophan intake and suicide rates across industrialized nations. Tryptophan, an essential amino acid, is the rate-limiting precursor of serotonin biosynthesis. The serotonergic system has been strongly implicated in the neurobiology of suicide. Contemporary male and female suicide rates for the general population (42 countries) and the elderly (38 countries) were correlated with national estimates of dietary tryptophan intake. Measures of tryptophan intake were significantly negatively associated to national suicide rates. Controlling for national affluence, total alcohol consumption and happiness levels slightly attenuated these associations, but left all of them negative. The effect is an ecological (group-level) finding. Estimated per capita tryptophan supply is only a proxy for actual consumption. Developed nations ranking high in dietary tryptophan intake rank low in suicide rates, independent of national wealth, alcohol intake and happiness.

  1. Valyl benzyl ester chloride

    Directory of Open Access Journals (Sweden)

    Grzegorz Dutkiewicz

    2010-02-01

    Full Text Available In the title compound (systematic name: 1-benzyloxy-3-methyl-1-oxobutan-2-aminium chloride, C12H18NO2+·Cl−, the ester group is approximately planar, with a maximum deviation of 0.040 (2 Å from the least-squares plane, and makes a dihedral angle of 28.92 (16° with the phenyl ring. The crystal structure is organized by N—H...Cl hydrogen bonds which join the two components into a chain along the b axis. Pairs of chains arranged antiparallel are interconnected by further N—H...Cl hydrogen bonds, forming eight-membered rings. Similar packing modes have been observed in a number of amino acid ester halides with a short unit-cell parameter of ca 5.5 Å along the direction in which the chains run.

  2. Requirement of young pigs for apparent ileal digestible tryptophan

    NARCIS (Netherlands)

    Schutte, J.B.; Verstraten, A.J.M.A.; Lenis, N.P.; Jong, de J.; Diepen, van J.Th.M.

    1995-01-01

    In 5 growth trials with a total of 420 pigs, tryptophan requirements from 20 to 40 kg liveweight were estimated. L-Tryptophan 0, 0.15, 0.30, 0.45 and 0.60 g/kg was added to a basal diet containing tapioca, barley and maize, with CP 162 g/kg and tryptophan 1.65 g/kg. The control diet was supplemented

  3. Tryptophan availability modulates serotonin release from rat hypothalamic slices

    Science.gov (United States)

    Schaechter, Judith D.; Wurtman, Richard J.

    1989-01-01

    The relationship between the tryptophan availability and serononin release from rat hypothalamus was investigated using a new in vitro technique for estimating rates at which endogenous serotonin is released spontaneously or upon electrical depolarization from hypothalamic slices superfused with a solution containing various amounts of tryptophan. It was found that the spontaneous, as well as electrically induced, release of serotonin from the brain slices exhibited a dose-dependent relationship with the tryptophan concentration of the superfusion medium.

  4. Tryptophan hydroxylase-1 regulates immune tolerance and inflammation

    OpenAIRE

    Nowak, Elizabeth C.; de Vries, Victor C.; Wasiuk, Anna; Ahonen, Cory; Bennett, Kathryn A.; Le Mercier, Isabelle; Ha, Dae-Gon; Noelle, Randolph J.

    2012-01-01

    Nutrient deprivation based on the loss of essential amino acids by catabolic enzymes in the microenvironment is a critical means to control inflammatory responses and immune tolerance. Here we report the novel finding that Tph-1 (tryptophan hydroxylase-1), a synthase which catalyses the conversion of tryptophan to serotonin and exhausts tryptophan, is a potent regulator of immunity. In models of skin allograft tolerance, tumor growth, and experimental autoimmune encephalomyelitis, Tph-1 defic...

  5. Tryptophan and kynurenine determination in human hair by liquid chromatography.

    Science.gov (United States)

    Dario, Michelli F; Freire, Thamires Batello; Pinto, Claudinéia Aparecida Sales de Oliveira; Prado, María Segunda Aurora; Baby, André R; Velasco, Maria Valéria R

    2017-10-15

    Tryptophan, an amino acid found in hair proteinaceous structure is used as a marker of hair photodegradation. Also, protein loss caused by several chemical/physical treatments can be inferred by tryptophan quantification. Kynurenine is a photo-oxidation product of tryptophan, expected to be detected when hair is exposed mainly to UVB (290-320nm) radiation range. Tryptophan from hair is usually quantified directly as a solid or after alkaline hydrolysis, spectrofluorimetrically. However, these types of measure are not sufficiently specific and present several interfering substances. Thus, this work aimed to propose a quantification method for both tryptophan and kynurenine in hair samples, after alkali hydrolysis process, by using high-performance liquid chromatography (HPLC) with fluorimetric and UV detection. The tryptophan and kynurenine quantification method was developed and validated. Black, white, bleached and dyed (blond and auburn) hair tresses were used in this study. Tryptophan and kynurenine were separated within ∼9min by HPLC. Both black and white virgin hair samples presented similar concentrations of tryptophan, while bleaching caused a reduction in the tryptophan content as well as dyeing process. Unexpectedly, UV/vis radiation did not promote significantly the conversion of tryptophan into its photo-oxidation product and consequently, kynurenine was not detected. Thus, this works presented an acceptable method for quantification of tryptophan and its photooxidation metabolite kynurenine in hair samples. Also, the results indicated that bleaching and dyeing processes promoted protein/amino acids loss but tryptophan is not extensively degraded in human hair by solar radiation. Copyright © 2017 Elsevier B.V. All rights reserved.

  6. Synthesis, characterization, antimicrobial and antitumor reactivity of new palladium(II) complexes with methionine and tryptophane coumarine derivatives

    Science.gov (United States)

    Stojković, Danijela Lj; Jevtić, Verica V.; Vuković, Nenad; Vukić, Milena; Čanović, Petar; Zarić, Milan M.; Mišić, Milena M.; Radovanović, Dragče M.; Baskić, Dejan; Trifunović, Srećko R.

    2018-04-01

    In reaction of 3-acetyl-4-hydroxy coumarine with methionine methyl ester hydrochloride and tryptophane methyl ester hydrochloride the corresponding enamine ligands were obtained. Palladium (II) complexes were prepared in reaction of potassium-tetrachloridopalladate (II) and corresponding enamine. All compounds were characterized by microanalysis, infrared, 1H and 13C NMR spectroscopy. In vitro antitumor activity of the mentioned ligands and corresponding palladium (II) complexes, as well as me-Gly and me-Val ligands and [Pd (me-Gly)]Cl and [Pd (me-Val)2] complexes was determined by MTT assay against two leukemia cell lines (JVM-13 and MOLT-4) and against primary leukemic cells isolated from chronic lymphocytic leukemia (CLL) patients. Antimicrobial activity of the tested compound was evaluated by determining the minimum inhibitory concentration (MIC) and minimum microbicidal concentration (MMC) against three reference bacterial strains: E. faecalis, P. aeruginosa, S. aureus and one clinical isolate of yeast: Candida spp.

  7. Method of making alkyl esters

    Science.gov (United States)

    Elliott, Brian

    2010-09-14

    Methods of making alkyl esters are described herein. The methods are capable of using raw, unprocessed, low-cost feedstocks and waste grease. Generally, the method involves converting a glyceride source to a fatty acid composition and esterifying the fatty acid composition to make alkyl esters. In an embodiment, a method of making alkyl esters comprises providing a glyceride source. The method further comprises converting the glyceride source to a fatty acid composition comprising free fatty acids and less than about 1% glyceride by mass. Moreover, the method comprises esterifying the fatty acid composition in the presence of a solid acid catalyst at a temperature ranging firm about 70.degree. C. to about 120.degree. C. to produce alkyl esters, such that at least 85% of the free fatty acids are converted to alkyl esters. The method also incorporates the use of packed bed reactors for glyceride conversion and/or fatty acid esterification to make alkyl esters.

  8. Tryptophan promotes morphological and physiological differentiation in Streptomyces coelicolor.

    Science.gov (United States)

    Palazzotto, Emilia; Renzone, Giovanni; Fontana, Pietro; Botta, Luigi; Scaloni, Andrea; Puglia, Anna Maria; Gallo, Giuseppe

    2015-12-01

    The molecular mechanisms regulating tryptophan biosynthesis in actinomycetes are poorly understood; similarly, the possible roles of tryptophan in the differentiation program of microorganism life-cycle are still underexplored. To unveil the possible regulatory effect of this amino acid on gene expression, an integrated study based on quantitative teverse transcription-PCR (qRT-PCR) and proteomic approaches was performed on the actinomycete model Streptomyces coelicolor. Comparative analyses on the microorganism growth in a minimal medium with or without tryptophan supplementation showed that biosynthetic trp gene expression in S. coelicolor is not subjected to a negative regulation by the presence of the end product. Conversely, tryptophan specifically induces the transcription of trp genes present in the biosynthetic gene cluster of the calcium-dependent antibiotic (CDA), a lipopeptide containing D- and L-tryptophan residues. In addition, tryptophan stimulates the transcription of the CDA gene cluster regulator cdaR and, coherently, CDA production. Surprisingly, tryptophan also promotes the production of actinorhodin, another antibiotic that does not contain this amino acid in its structure. Combined 2D-DIGE and nano liquid chromatography electrospray linear ion trap tandem mass spectrometry (LC-ESI-LIT-MS/MS) analyses revealed that tryptophan exerts a growth-stage-dependent global effect on S. coelicolor proteome, stimulating anabolic pathways and promoting the accumulation of key factors associated with morphological and physiological differentiation at the late growth stages. Phenotypic observations by scanning electron microscopy and spore production assays demonstrated an increased sporulation in the presence of tryptophan. Transcriptional analysis of catabolic genes kynA and kynB suggested that the actinomycete also uses tryptophan as a carbon and nitrogen source. In conclusion, this study originally provides the molecular basis underlying the stimulatory

  9. Apomorphine and its esters

    DEFF Research Database (Denmark)

    Borkar, Nrupa; Chen, Zhizhong; Saaby, Lasse

    2016-01-01

    Oral delivery of apomorphine via prodrug principle may be a potential treatment for Parkinson's disease. The purpose of this study was to investigate the transport and stability of apomorphine and its esters across Caco-2 cell monolayer and their affinity towards chylomicrons. Apomorphine......, monolauroyl apomorphine (MLA) and dilauroyl apomorphine (DLA) were subjected to apical to basolateral (A-B) and basolateral to apical (B-A) transport across Caco-2 cell monolayer. The stability of these compounds was also assessed by incubation at intestinal pH and physiological pH with and without Caco-2...

  10. Development of Bacillus subtilis mutants to produce tryptophan in pigs

    DEFF Research Database (Denmark)

    Bjerre, Karin; Cantor, Mette D.; Nørgaard, Jan Værum

    2017-01-01

    Objectives To generate tryptophan-overproducing Bacillus subtilis strains for in situ use in pigs, to reduce the feed cost for farmers and nitrogen pollution. Results A novel concept has been investigated—to generate B. subtilis strains able to produce tryptophan (Trp) in situ in pigs. Mutagenesis...

  11. Tryptophan Predicts the Risk for Future Type 2 Diabetes.

    Science.gov (United States)

    Chen, Tianlu; Zheng, Xiaojiao; Ma, Xiaojing; Bao, Yuqian; Ni, Yan; Hu, Cheng; Rajani, Cynthia; Huang, Fengjie; Zhao, Aihua; Jia, Weiping; Jia, Wei

    2016-01-01

    Recently, 5 amino acids were identified and verified as important metabolites highly associated with type 2 diabetes (T2D) development. This report aims to assess the association of tryptophan with the development of T2D and to evaluate its performance with existing amino acid markers. A total of 213 participants selected from a ten-year longitudinal Shanghai Diabetes Study (SHDS) were examined in two ways: 1) 51 subjects who developed diabetes and 162 individuals who remained metabolically healthy in 10 years; 2) the same 51 future diabetes and 23 strictly matched ones selected from the 162 healthy individuals. Baseline fasting serum tryptophan concentrations were quantitatively measured using ultra-performance liquid chromatography triple quadruple mass spectrometry. First, serum tryptophan level was found significantly higher in future T2D and was positively and independently associated with diabetes onset risk. Patients with higher tryptophan level tended to present higher degree of insulin resistance and secretion, triglyceride and blood pressure. Second, the prediction potential of tryptophan is non-inferior to the 5 existing amino acids. The predictive performance of the combined score improved after taking tryptophan into account. Our findings unveiled the potential of tryptophan as a new marker associated with diabetes risk in Chinese populations. The addition of tryptophan provided complementary value to the existing amino acid predictors.

  12. Tryptophan Metabolism and White Matter Integrity in Schizophrenia.

    Science.gov (United States)

    Chiappelli, Joshua; Postolache, Teodor T; Kochunov, Peter; Rowland, Laura M; Wijtenburg, S Andrea; Shukla, Dinesh K; Tagamets, Malle; Du, Xiaoming; Savransky, Anya; Lowry, Christopher A; Can, Adem; Fuchs, Dietmar; Hong, L Elliot

    2016-09-01

    Schizophrenia is associated with abnormalities in the structure and functioning of white matter, but the underlying neuropathology is unclear. We hypothesized that increased tryptophan degradation in the kynurenine pathway could be associated with white matter microstructure and biochemistry, potentially contributing to white matter abnormalities in schizophrenia. To test this, fasting plasma samples were obtained from 37 schizophrenia patients and 38 healthy controls and levels of total tryptophan and its metabolite kynurenine were assessed. The ratio of kynurenine to tryptophan was used as an index of tryptophan catabolic activity in this pathway. White matter structure and function were assessed by diffusion tensor imaging (DTI) and (1)H magnetic resonance spectroscopy (MRS). Tryptophan levels were significantly lower (ptryptophan ratios were correspondingly higher (p=0.018) in patients compared with controls. In patients, lower plasma tryptophan levels corresponded to lower structural integrity (DTI fractional anisotropy) (r=0.347, p=0.038). In both patients and controls, the kynurenine/tryptophan ratio was inversely correlated with frontal white matter glutamate level (r=-0.391 and -0.350 respectively, p=0.024 and 0.036). These results provide initial evidence implicating abnormal tryptophan/kynurenine pathway activity in changes to white matter integrity and white matter glutamate in schizophrenia.

  13. Effects of rumen-protected tryptophan on performance, nutrient ...

    African Journals Online (AJOL)

    Jane

    2011-06-27

    Jun 27, 2011 ... Thirty-six Liaoning cashmere goat wethers (28.72 ± 0.59 kg) were used to determine the effects of rumen-protected tryptophan (RPT) on performance, nutrient utilization and plasma tryptophan (Trp) during the cashmere fast-growing period. The goats were randomly assigned to the following treatments: ...

  14. Human myeloid dendritic cells are refractory to tryptophan metabolites.

    Science.gov (United States)

    von Bubnoff, Dagmar; Wilms, Helene; Scheler, Marina; Brenk, Manuela; Koch, Susanne; Bieber, Thomas

    2011-10-01

    The enzyme indoleamine 2,3-dioxygenase (IDO) degrades the essential amino acid tryptophan and is expressed, among other cell types, in immune cells such as dendritic cells (DCs), monocytes, and macrophages. It has been shown that the activity of IDO has a broad regulatory function in the immune system by inhibiting effector T-cell responses, inducing regulatory T cells and facilitating the development of regulatory DCs. The degradation of tryptophan has 2 consequences, both of which have been postulated to be physiologically relevant, namely the reduction of tryptophan levels and the accumulation of tryptophan catabolites. Recently, we have shown that DCs that had differentiated under low-tryptophan conditions acquire a tolerogenic phenotype with increased expression of the inhibitory receptors immunoglobulin-like transcript 2 (ILT2), ILT3, and ILT4. In the present study, we investigated the effect of distinct tryptophan catabolites on the function of human DCs and the expression of ILT2, ILT3, and ILT4 on these cells. We show that, in contrast to low tryptophan levels alone, the combination of several metabolites along the tryptophan-kynurenine degradation pathway during DC differentiation does not induce ILT2, ILT3, or ILT4 on these DCs and does not reduce the T-cell stimulatory capacity of these DCs. Copyright © 2011 American Society for Histocompatibility and Immunogenetics. Published by Elsevier Inc. All rights reserved.

  15. The tryptophan requirements of pullets in the early production stage

    African Journals Online (AJOL)

    per day (1,519 per kg diet at a consumption rate of 1109 per bird per day). This estimate is valid for an economic situation when the marginal cost of 1 kg tryptophan is 20 times the marginal value of 1 kg egg. Under the same price structure and potential egg output the estimated daily tryptophan requirement for a flock was ...

  16. Confirmation of antibodies against L-tryptophan-like epitope in ...

    African Journals Online (AJOL)

    Confirmation of antibodies against L-tryptophan-like epitope in human African trypanosomosis serological diagnostic. ... number of patients in Congo. A diagnostic test based on this synthetic epitope, especially in combination with other tests, might improve the HAT diagnostic test in field conditions. Key words: Tryptophan ...

  17. protein, tryptophan and lysine contents in quality protien maize

    African Journals Online (AJOL)

    owner

    study of protein, tryptophan and lysine composition of quality protein maize varieties (9). The tryptophan content of eleven superior QPM genotypes was much higher than those of wheat,. * Jimma University, College of Agriculture and Veterinary Medicine, Department of Crop Sciences, P.O. Box 307,. Jimma , Ethiopia.

  18. Extended fatigue life of a catalyst-free self-healing acrylic bone cement using microencapsulated 2-octyl cyanoacrylate

    Science.gov (United States)

    Brochu, Alice B.W.; Matthys, Oriane B.; Craig, Stephen L.; Reichert, William M.

    2014-01-01

    The tissue adhesive 2-octyl cyanoacrylate (OCA) was encapsulated in polyurethane microshells and incorporated into bone cement to form a catalyst free, self-healing bone cement comprised of all clinically approved components. The bending strength, modulus, and fatigue lifetime were investigated in accordance with ASTM and ISO standards for the testing of PMMA bone cement. The bending strength of bone cement specimens decreased with increasing wt% capsules content for capsules without or with OCA, with specimens of formulation. PMID:24825796

  19. Esters with water esters 2-c to 6-c

    CERN Document Server

    Getzen, F W; Hefter, G T; Maczynski, Andrzej

    1992-01-01

    This volume is the first of two devoted to esters and water. It includes solubility data for binary systems containing an ester and water up to the end of 1988. The critical evaluations were all prepared by one author and an introductory section has been included to elaborate the philosophy and methodology followed in the evaluations.

  20. Radiosynthesis of 1-[{sup 18}F]fluoroethyl-L-tryptophan as a novel potential amino acid PET tracer

    Energy Technology Data Exchange (ETDEWEB)

    Sun Ting, E-mail: beibeisun2008@163.com [Department of Cardiac Function, Shanghai Ninth People' s Hospital Affiliated to Shanghai Jiao Tong University School of Medicine, Shanghai 200011 (China); Tang Ganghua, E-mail: gtang0224@yahoo.com.cn [Department of Nuclear Medicine, the first affiliated hospital, SunYat-Sen University, Guangzhou 510080 (China); Tian Hua [State Key Laboratory of Oncogenes and Related Genes, Shanghai Cancer Institute, Renji Hospital, Shanghai Jiao Tong University School of Medicine, Shanghai 200032 (China); Wang Xiaoyan [Department of Nuclear Medicine, the first affiliated hospital, SunYat-Sen University, Guangzhou 510080 (China); Chen Xianghua [Department of Cardiac Function, Shanghai Ninth People' s Hospital Affiliated to Shanghai Jiao Tong University School of Medicine, Shanghai 200011 (China); Chen Zhifeng [Department of Nuclear Medicine, the first affiliated hospital, SunYat-Sen University, Guangzhou 510080 (China); Wang Shihchen [Department of Nuclear Medicine, Peking Union Medical College and Chinese Academy of Medical Sciences, Peking Union Medical College Hospital, 1 Shuaifuyuan Wangfujing Beijing 100730 (China)

    2012-04-15

    {sup 18}F labeled natural amino acids have been introduced as promising tumor imaging agents. A novel [{sup 18}F]fluoro amino acid analog 1-[{sup 18}F]fluoroethyl-L-tryptophan (1-[{sup 18}F]FETrp) was designed and synthesized by a two-pot three-step procedure, including the synthesis of 1-[{sup 18}F]fluoro-2- (tosyloxy)ethane, the [{sup 18}F]fluoroethylation of the precursor N-Boc-L-tryptophan ethyl ester and following the deprotection of the tert-butoxycarbonyl and ethyl ester protecting groups. 1-[{sup 18}F]FETrp was resulted in 0.9{+-}0.2% (n=5) radiochemical yields (no decay corrected) by HPLC purification, within a total synthesis time of 65 min. The radiochemical purity of 1-[{sup 18}F]FETrp was 95-97%. The radiosynthetic method needs to be further optimized to get a satisfying radiochemical yield. - Highlights: Black-Right-Pointing-Pointer We designed and synthesized the novel amino acid analog 1-[{sup 19}F]FETrp. Black-Right-Pointing-Pointer We radiosynthesized 1-[{sup 18}F]FETrp using the two-pot three-step procedure. Black-Right-Pointing-Pointer The total synthesis time was 65 min and the yield was very low. Black-Right-Pointing-Pointer The synthetic strategy via [{sup 18}F]FCH{sub 2}CH{sub 2}OTs needs to be optimized or changed.

  1. 2-octyl-cyanoacrylate glue for fixation of STSG in genitourinary tissue defects due to Fournier gangrene: a preliminary trial.

    Science.gov (United States)

    Sivrioğlu, Nazan; Irkören, Saime; Ceylan, Ender; Sonel, Ali Murat; Copçu, Eray

    2013-05-01

    In these reported cases, we observed the outcomes of skin take and wound healing using 2-octyl-cyanoacrylate glue, which was used as tissue glue in the reconstruction of complex genital skin loss due to fournier gangrene. Fifteen patients with Fournier's gangrene were treated in this study. After initial surgical debridement, all defects were repaired using STSG. In this method a thin layer of 2-octyl-cyanoacrylate was dripped on the recipient site immediately before graft application. All wounds were followed up postoperatively and observed for evidence of graft take, seroma or hematoma formation, drainage, and infection. Patient and physician satisfaction were also determined. Grafts were completely accepted in all fifteen patients. None of the patients had wound infection, seroma, hematoma, or other complications. Use of 2-octyl-cyanoacrylate glue (Glueseal) for STSG fixation in complex genital skin defects after Fournier gangrene may be an acceptable alternative to conventional surgical closure with a good cosmetic outcome. Further studies are needed to confirm our initial success with this approach.

  2. Alleviation of hysteria in laying hens with dietary tryptophan.

    Science.gov (United States)

    Laycock, S R; Ball, R O

    1990-01-01

    A commercial layer breeder flock that was suffering from hysteria was fed a diet containing 5 grams tryptophan/kg for six days. The incidence of episodes of hysteria declined from five times/hour on day 0 to once/hour on day 6 and none on day 8. Feed consumption increased from 107 g to 145 g/hen/day and egg production increased 23% during the six day feeding period. The tryptophan concentration in plasma doubled (from 95.6 to 188.2 mumol/mL). Plasma phenylalanine and tyrosine also increased. Birds that were not in lay, by postmortem examination, had significantly higher plasma valine concentrations (476.4 vs 372.7 mumol/mL). Tryptophan, serotonin and related metabolites increased in both the hypothalamic region and the remainder of the brain following tryptophan feeding, and subsequently declined. High levels of dietary tryptophan may be useful in alleviating hysteria in poultry. PMID:2357668

  3. The Effect of Quartz on the Flotation of Fine Wolframite with Octyl Hydroxamic Acid

    Directory of Open Access Journals (Sweden)

    Qingyou Meng

    2017-09-01

    Full Text Available The influence of quartz on the flotation of fine wolframite using octyl hydroxamic acid (OHA as the collector was investigated by micro-flotation tests, inductively coupled plasma (ICP measurements, adsorption experiments, zeta potential, and Fourier transform infrared spectroscopy (FT-IR analysis. Micro-flotation tests showed that a large difference in floatability existed between fine wolframite and quartz in the pH range of 7.0 to 10.0. However, in a synthetic mixture, the flotation separation of fine wolframite from quartz became more difficult as the particle size of the latter decreased. When a dissolved solution of wolframite was used as the flotation medium, quartz floatability improved significantly. Zeta potentials of quartz particles shifted positively in the dissolved solution of wolframite compared to distilled water, especially at a pH level of 7.0–10.0, which was attributed to the metal ions dissolved from the wolframite being adsorbed onto the quartz surface. The surface activation of quartz led to an increase in the OHA adsorption and made the surface hydrophobic. FT-IR analysis further demonstrated that OHA could adsorb onto the activated quartz surface through a dominantly chemical process.

  4. Stabilization of Candida antarctica Lipase B (CALB Immobilized on Octyl Agarose by Treatment with Polyethyleneimine (PEI

    Directory of Open Access Journals (Sweden)

    Sara Peirce

    2016-06-01

    Full Text Available Lipase B from Candida antarctica (CALB was immobilized on octyl agarose (OC and physically modified with polyethyleneimine (PEI in order to confer a strong ion exchange character to the enzyme and thus enable the immobilization of other enzymes on its surface. The enzyme activity was fully maintained during the coating and the thermal stability was marginally improved. The enzyme release from the support by incubation in the non-ionic detergent Triton X-100 was more difficult after the PEI-coating, suggesting that some intermolecular physical crosslinking had occurred, making this desorption more difficult. Thermal stability was marginally improved, but the stability of the OCCALB-PEI was significantly better than that of OCCALB during inactivation in mixtures of aqueous buffer and organic cosolvents. SDS-PAGE analysis of the inactivated biocatalyst showed the OCCALB released some enzyme to the medium during inactivation, and this was partially prevented by coating with PEI. This effect was obtained without preventing the possibility of reuse of the support by incubation in 2% ionic detergents. That way, this modified CALB not only has a strong anion exchange nature, while maintaining the activity, but it also shows improved stability under diverse reaction conditions without affecting the reversibility of the immobilization.

  5. Photolysis and cellular toxicities of the organic ultraviolet filter chemical octyl methoxycinnamate and its photoproducts.

    Science.gov (United States)

    Stein, Hannah V; Berg, Courtney J; Maung, Jessica N; O'Connor, Lauren E; Pagano, Alexandra E; MacManus-Spencer, Laura A; Paulick, Margot G

    2017-06-21

    Organic ultraviolet filter chemicals (UVFCs) are the active ingredients used in many sunscreens to protect the skin from UV light; these chemicals have been detected in numerous aquatic environments leading to concerns about how they might affect aquatic organisms and humans. One commonly used organic UVFC is octyl methoxycinnamate (OMC), better known by its commercial name, octinoxate. Upon exposure to UV light, OMC degrades rapidly, forming numerous photoproducts, some of which have been previously identified. In this study, we isolated and completely characterized the major products of OMC photolysis, including the two major stable OMC cyclodimers. One of these cyclodimers is a δ-truxinate, resulting from a head-to-head dimerization of two OMC molecules, and the other cyclodimer is an α-truxillate, resulting from a head-to-tail dimerization of two OMC molecules. Additionally, the cellular toxicities of the individual photoproducts were determined; it was found that the parent UVFC, OMC, 4-methoxybenzaldehyde, and two cyclodimers are significantly toxic to cells. The photoproduct 2-ethylhexanol is not cytotoxic, demonstrating that different components of OMC photolysate contribute differently to its cellular toxicity. This study thus provides an enhanced understanding of OMC photolysis and gives toxicity data that can be used to better evaluate OMC as a sunscreen agent.

  6. Lipid nanoparticles as carrier for octyl-methoxycinnamate: in vitro percutaneous absorption and photostability studies.

    Science.gov (United States)

    Puglia, Carmelo; Bonina, Francesco; Rizza, Luisa; Blasi, Paolo; Schoubben, Aurelie; Perrotta, Rosario; Tarico, Maria Stella; Damiani, Elisabetta

    2012-01-01

    The aim of the present study was the evaluation of lipid nanoparticles (solid lipid nanoparticles, SLN, and nanostructured lipid carriers, NLC) as potential carriers for octyl-methoxycinnamate (OMC). The release pattern of OMC from SLN and NLC was evaluated in vitro, determining its percutaneous absorption through excised human skin. Additional in vitro studies were performed in order to evaluate, after UVA radiation treatment, the spectral stability of OMC-loaded lipid nanoparticles. From the obtained results, ultrasonication method yielded both SLN and NLC in the nanometer range with a high active loading and a particle shape close to spherical. Differential scanning calorimetry data pointed out the key role of the inner oil phase of NLC in stabilizing the particle architecture and in increasing the solubility of OMC as compared with SLN. In vitro results showed that OMC, when incorporated in viscosized NLC dispersions (OMC-NLC), exhibited a lower flux with respect to viscosized SLN dispersions (OMC-SLN) and two reference formulations: a microemulsion (OMC-ME) and a hydroalcoholic gel (OMC-GEL). Photostability studies revealed that viscosized NLC dispersions were the most efficient at preserving OMC from ultraviolet-mediated photodegradation. Copyright © 2011 Wiley-Liss, Inc.

  7. Self-organization of the ternary didecyldimethylammonium bromide/octyl-beta-D-glucopyranoside/water system.

    Science.gov (United States)

    Junquera, Elena; Del Burgo, Patricia; Boskovic, Jasminka; Aicart, Emilio

    2005-08-02

    The spontaneous and thermodynamically stable mixed vesicles constituted by a double-chain cationic surfactant with 10 carbon atoms hydrophobic tail, didecyldimethylammonium bromide (di-C(10)DMAB), and a nonionic single-chain surfactant, octyl-beta-d-glucopyranoside (OBG), have been characterized in aqueous media by means of a series of experimental techniques, as well as a theoretical approach. Conductivity data allow for the determination of the concentrations at which the monomer-to-vesicle (CVC) and/or vesicle-to-micelle (CMC) transitions occur. Electrophoretic mobilities, obtained from laser-doppler-electrophoresis experiments, permit the determination of zeta-potentials and, from them, the surface charge density of the vesicle aggregates. Cryogenic transmission electron microscopy (cryo-TEM) provides pictures of the vesicles, their size and shape being, thus, determined. Finally, the sensitivity of the emission spectra of some fluorescent probes, such as the cationic TNS and the nonionic PRODAN, to the polarity of the environment, allow for a complete study of different pre- and post-vesicle microdomains, of variable rigidity and micropolarity. This, in turn, yield interesting information about the vesicle surface and bilayer, as well as, about the existence of clusters and/or nanoaggregates prior to the formation of vesicles, as was proposed by us in a previous paper.

  8. L-Tryptophan depletion bioreactor, a possible cancer therapy

    Directory of Open Access Journals (Sweden)

    Rolf Bambauer

    2015-04-01

    Full Text Available The cancer therapeutic strategies knownto date are not adequate for all cancer patients. Most of them are followed by a high rate of side effects and complications. The L-tryptophan depletion bioreactor is described as a possible new method of cancer therapy. L-tryptophan is an essential amino acid which has been recognized as an important cancer nutrient and its removal can lead to destruction of the tumour. Normal human cells or tumor cells cannot synthesize L-tryptophan and therefore tumor resistance is unlikely to develop. L-tryptophan is also a constituent for different bio-molecules such as Serotonin, Melatonin, and is needed for other synthesis processes in the cell growth. L-tryptophan degrading enzymes with 3 iso-enzymes called tryptophan side chain oxydase (TSO I, II, III were isolated. The 3 iso-enzymes can be differentiated by tryptic digestion. They have different molecular weights with different effectivenesses. All the TSO enzymes have heme that can catalyze essentially similar reactions involving L-tryptophan as a substrate. The most effective TSO is the type TSO III. A column which contained TSO as a bioreactor was integrated in a plasmapheresis unit and tested it in different animals. In sheep and rabbits L-tryptophan depletion in plasma was shown at 95% and 100% rates respectively by a single pass through the bioreactor. The results in immune supprimized rats with tumors were impressive, too. In 20 different tumor cell lines there were different efficacies. Brest cancer and medulloblastoma showed the greatest efficacy of L-tryptophan degrading. The gene technology of TSO production from Pseudomonas is associated with formation of endotoxins. This disadvantage can be prevented by different washing procedures or by using fungal sources for the TSO production. TSO III is developed to treat cancer diseases successfully, and has low side effects. A combination of L-tryptophan depletion with all available cancer therapies is

  9. Regulation of the tryptophan synthetic enzymes in Clostridium butyricum.

    Science.gov (United States)

    Baskerville, E N; Twarog, R

    1972-10-01

    Experiments concerned with the regulation of the tryptophan synthetic enzymes in anaerobes were carried out with a strain of Clostridium butyricum. Enzyme activities for four of the five synthetic reactions were readily detected in wild-type cells grown in minimal medium. The enzymes mediating reactions 3, 4, and 5 were derepressed 4- to 20-fold, and the data suggest that these enzymes are coordinately controlled in this anaerobe. The first enzyme of the pathway, anthranilate synthetase, could be derepressed approximately 90-fold under these conditions, suggesting that this enzyme is semicoordinately controlled. Mutants resistant to 5-methyl tryptophan were isolated, and two of these were selected for further analysis. Both mutants retained high constitutive levels of the tryptophan synthetic enzymes even in the presence of repressing concentrations of tryptophan. The anthranilate synthetase from one mutant was more sensitive to feedback inhibition by tryptophan than the enzyme from wild-type cells. The enzyme from the second mutant was comparatively resistant to feedback inhibition by tryptophan. Neither strain excreted tryptophan into the culture fluid. Tryptophan inhibits anthranilate synthetase from wild-type cells noncompetitively with respect to chorismate and uncompetitively with respect to glutamine. The Michaelis constants calculated for chorismate and glutamine are 7.6 x 10(-5)m and 6.7 x 10(-5)m, respectively. The molecular weights of the enzymes estimated by zonal centrifugation in sucrose and by gel filtration ranged from 24,000 to 89,000. With the possible exception of a tryptophan synthetase complex, there was no evidence for the existence of other enzyme aggregates. The data indicate that tryptophan synthesis is regulated by repression control of the relevant enzymes and by feedback inhibition of anthranilate synthetase. That this enzyme system more closely resembles that found in Bacillus than that found in enteric bacteria is discussed.

  10. Regulation of the Tryptophan Synthetic Enzymes in Clostridium butyricum1

    Science.gov (United States)

    Baskerville, E. N.; Twarog, Robert

    1972-01-01

    Experiments concerned with the regulation of the tryptophan synthetic enzymes in anaerobes were carried out with a strain of Clostridium butyricum. Enzyme activities for four of the five synthetic reactions were readily detected in wild-type cells grown in minimal medium. The enzymes mediating reactions 3, 4, and 5 were derepressed 4- to 20-fold, and the data suggest that these enzymes are coordinately controlled in this anaerobe. The first enzyme of the pathway, anthranilate synthetase, could be derepressed approximately 90-fold under these conditions, suggesting that this enzyme is semicoordinately controlled. Mutants resistant to 5-methyl tryptophan were isolated, and two of these were selected for further analysis. Both mutants retained high constitutive levels of the tryptophan synthetic enzymes even in the presence of repressing concentrations of tryptophan. The anthranilate synthetase from one mutant was more sensitive to feedback inhibition by tryptophan than the enzyme from wild-type cells. The enzyme from the second mutant was comparatively resistant to feedback inhibition by tryptophan. Neither strain excreted tryptophan into the culture fluid. Tryptophan inhibits anthranilate synthetase from wild-type cells noncompetitively with respect to chorismate and uncompetitively with respect to glutamine. The Michaelis constants calculated for chorismate and glutamine are 7.6 × 10−5m and 6.7 × 10−5m, respectively. The molecular weights of the enzymes estimated by zonal centrifugation in sucrose and by gel filtration ranged from 24,000 to 89,000. With the possible exception of a tryptophan synthetase complex, there was no evidence for the existence of other enzyme aggregates. The data indicate that tryptophan synthesis is regulated by repression control of the relevant enzymes and by feedback inhibition of anthranilate synthetase. That this enzyme system more closely resembles that found in Bacillus than that found in enteric bacteria is discussed. PMID

  11. Destabilization of artificial biomembrane induced by the penetration of tryptophan

    Energy Technology Data Exchange (ETDEWEB)

    Chen Liuhua [Department of Chemistry, Tongji University, Shanghai 200092 (China); Gan Lihua, E-mail: ganlh@tongji.edu.cn [Department of Chemistry, Tongji University, Shanghai 200092 (China); Liu Mingxian; Fan Rong; Xu Zijie; Hao Zhixian; Chen Longwu [Department of Chemistry, Tongji University, Shanghai 200092 (China)

    2011-03-15

    The effect of tryptophan on the membrane stability was studied by using three artificial biological membranes including liposome, Langmuir monolayer and solid supported bilayer lipid membrane (s-BLM) as models. All the results indicate that the penetration of tryptophan can destabilize different artificial biological membranes. The diameter of liposome and the leakage of calcein from liposome increased with the increase of tryptophan concentration because the penetration of tryptophan was beneficial for dehydrating the polar head groups of lipids and the formation of fusion intermediates. {pi}-A isotherms of lecithin on the subphase of tryptophan solution further confirm that tryptophan can penetrate into lipid monolayer and reduce the stability of lipid monolayer. When the concentration of tryptophan increased from 0 to 2 x 10{sup -3} mol L{sup -1}, the limiting molecular area of lecithin increased from 110.5 to 138.5 A{sup 2}, but the collapse pressure of the monolayer decreased from 47.6 to 42.3 mN m{sup -1}, indicating the destabilization of lipid monolayer caused by the penetration of tryptophan. The resistance spectra of s-BLM demonstrate that the existence of tryptophan leads to the formation of some defects in s-BLM and the destabilization of s-BLM. The values of electron-transfer resistance and double layer capacitance respectively decreased from 5.765 x 10{sup 6} {Omega} and 3.573 x 10{sup -8} F to 1.391 x 10{sup 6} {Omega} and 3.340 x 10{sup -8} F when the concentration of tryptophan increased from 0 to 2 x 10{sup -3} mol L{sup -1}. Correspondingly, the breakdown voltage of s-BLM decreased from 2.51 to 1.72 V.

  12. The metabolism of L-tryptophan by isolated rat liver cells. Effect of albumin binding and amino acid competition on oxidatin of tryptophan by tryptophan 2,3-dioxygenase.

    OpenAIRE

    Smith, S A; Pogson, C I

    1980-01-01

    1. Novel methods, using L-[ring-2-14C]tryptophan, are described for the measurement of tryptophan 2,3-dioxygenase activity and tryptophan accumulation in isolated rat liver cells. 2. The effects of bovine serum albumin, non-esterified fatty acids and neutral amino acids on tryptophan oxidation by hepatocytes and on the partition of tryptophan between free and albumin-bound forms were investigated. 3. Oxidation of physiological concentrations (0.1 mM) of tryptophan was inhibited by approx. 50%...

  13. Carboxylic ester hydrolases from hyperthermophiles

    NARCIS (Netherlands)

    Levisson, M.; Oost, van der J.; Kengen, S.W.M.

    2009-01-01

    Carboxylic ester hydrolyzing enzymes constitute a large group of enzymes that are able to catalyze the hydrolysis, synthesis or transesterification of an ester bond. They can be found in all three domains of life, including the group of hyperthermophilic bacteria and archaea. Esterases from the

  14. Lipoate ester multifunctional lubricant additives

    Science.gov (United States)

    Seven lipoate esters were synthesized by esterification of lipoic acid with different structures of alcohols in the presence of a solid acid catalyst and without solvent. The esters were obtained in good yield, characterized using 1H NMR and GPC; and their physical properties investigated. Four of t...

  15. Influence of Tryptophan Contained in 1-Methyl-Tryptophan on Antimicrobial and Immunoregulatory Functions of Indoleamine 2,3-Dioxygenase

    Science.gov (United States)

    Schmidt, Silvia K.; Siepmann, Stephan; Kuhlmann, Katja; Meyer, Helmut E.; Metzger, Sabine; Pudelko, Sabine; Leineweber, Margret; Däubener, Walter

    2012-01-01

    Indoleamine 2,3-dioxygenase (IDO) has been identified as an important antimicrobial and immunoregulatory effector molecule essential for the establishment of tolerance by regulating local tryptophan (Trp) concentrations. On the other hand, the immunosuppressive capacity of IDO can have detrimental effects for the host as it can lead to deleterious alterations of the immune response by promoting tolerance to some types of tumors. To suppress this disadvantageous IDO effect, the competitive inhibitor 1-Methyl-Tryptophan (1-MT) is being tested in clinical trials. However, it remains inconclusive which stereoisomer of 1-MT is the more effective inhibitor of IDO-mediated immunosuppression. While IDO enzyme activity is more efficiently inhibited by 1-L-MT in cell-free or in vitro settings, 1-D-MT is superior to 1-L-MT in the enhancement of anti-tumor responses in vivo. Here, we present new data showing that commercially available 1-L-MT lots contain tryptophan in amounts sufficient to compensate for the IDO-mediated tryptophan depletion in vitro. The addition of 1-L-MT abrogated IDO-mediated antimicrobial effects and permitted the growth of the tryptophan-auxotroph microorganisms Staphylococcus aureus and Toxoplasma gondii. Consistent with this, the tryptophan within 1-L-MT lots was sufficient to antagonize IDO-mediated inhibition of T cell responses. Mass spectrometry (MS) analysis revealed not only tryptophan within 1-L-MT, but also the incorporation of this tryptophan in bacterial and human proteins that were generated in the presence of 1-L-MT in otherwise tryptophan-free conditions. In summary, these data reveal that tryptophan within 1-L-MT can affect the results of in vitro studies in an L-stereospecific and IDO-independent way. PMID:23028625

  16. Soil contamination by phthalate esters in Chinese intensive vegetable production systems with different modes of use of plastic film

    International Nuclear Information System (INIS)

    Wang, Jun; Luo, Yongming; Teng, Ying; Ma, Wenting; Christie, Peter; Li, Zhengao

    2013-01-01

    The concentrations of six priority phthalic acid esters (PAEs) in intensively managed suburban vegetable soils in Nanjing, east China, were analyzed using gas chromatography–mass spectrometry (GC–MS). The total PAE concentrations in the soils ranged widely from 0.15 to 9.68 mg kg −1 with a median value of 1.70 mg kg −1 , and di-n-butyl phthalate (DnBP), bis-(2-ethylhexyl) phthalate (DEHP) and di-n-octyl phthalate (DnOP) were the most abundant phthalate esters. Soil PAE concentrations depended on the mode of use of plastic film in which PAEs were incorporated as plasticizing agents and both the plastic film and poultry manure appeared to be important sources of soil PAEs. Vegetables in rotation with flooded rice led to lower concentrations of PAEs in soil. The results indicate that agricultural plastic film can be an important source of soil PAE contamination and further research is required to fully elucidate the mechanisms of PAE contamination of intensive agricultural soils with different use modes of use of plastic film. -- Highlights: •Phthalate esters in soils from suburban intensive vegetable production systems were investigated. •Phthalate levels and risks of the vegetable soils with different plastic film use modes were examined. •Sources of phthalate esters in vegetable production soils were analyzed. -- PAE contamination of intensively managed vegetable soils varied widely depending on the mode of use of plastic film in different production systems

  17. Photochemical hydrogen-deuterium exchange reaction of tryptophan: the role in nonradiative decay of singlet tryptophan

    International Nuclear Information System (INIS)

    Saito, I.; Sugiyama, H.; Yamamoto, A.; Muramatsu, S.; Matsuura, T.

    1984-01-01

    The mechanism of nonradiative decay of singlet excited tryptophan (Trp) in aqueous solution was investigated by a highly selective photosubstitution of the C-4 hydrogen of Trp with deuterium of solvent D 2 O. It was concluded that intramolecular proton transfer from the α-ammonia group giving rise to formation of a protonated species plays an important role in the nonradiative decay of singlet Trp at neutral pH. 11 references, 1 figure

  18. Mood, food, and cognition: role of tryptophan and serotonin.

    Science.gov (United States)

    Strasser, Barbara; Gostner, Johanna M; Fuchs, Dietmar

    2016-01-01

    Food is not only necessary as a metabolic fuel for the body, it becomes more and more evident that there exists an association between food and brain functions like mood and cognition. Tryptophan represents a key element for brain functioning, because of its role as a precursor for production of neurotransmitter serotonin (5-hydroxytryptamine). In clinical conditions, which involve chronic immune system activation or under cytokine therapy, lower tryptophan levels because of high catabolism of tryptophan as indicated by the kynurenine to tryptophan ratio are common and often associate with depressive mood. Studies in the in vitro model of mitogen-stimulated peripheral blood mononuclear cells revealed that several phytocompounds, mainly antioxidants like polyphenols and vitamins, can interfere with inflammatory signaling cascades including tryptophan breakdown. If extrapolated to the in vivo situation, such compounds could increase blood and brain tryptophan availability for serotonin production. Although there is some in vivo evidence for the effect of such compounds, outcomes are hardly predictable and most likely depend on the individual's immunological state. Not only a diet rich in tryptophan but also a diet rich in antioxidants can have a positive impact on mood and cognition. This could be of special relevance for individuals who present with low grade inflammation conditions.

  19. A Mathematical Model of Tryptophan Metabolism via the Kynurenine Pathway Provides Insights into the Effects of Vitamin B-6 Deficiency, Tryptophan Loading, and Induction of Tryptophan 2,3-Dioxygenase on Tryptophan Metabolites123

    Science.gov (United States)

    Rios-Avila, Luisa; Nijhout, H. Frederik; Reed, Michael C.; Sitren, Harry S.; Gregory, Jesse F.

    2013-01-01

    Vitamin B-6 deficiency is associated with impaired tryptophan metabolism because of the coenzyme role of pyridoxal 5′-phosphate (PLP) for kynureninase and kynurenine aminotransferase. To investigate the underlying mechanism, we developed a mathematical model of tryptophan metabolism via the kynurenine pathway. The model includes mammalian data on enzyme kinetics and tryptophan transport from the intestinal lumen to liver, muscle, and brain. Regulatory mechanisms and inhibition of relevant enzymes were included. We simulated the effects of graded reduction in cellular PLP concentration, tryptophan loads and induction of tryptophan 2,3-dioxygenase (TDO) on metabolite profiles and urinary excretion. The model predictions matched experimental data and provided clarification of the response of metabolites in various extents of vitamin B-6 deficiency. We found that moderate deficiency yielded increased 3-hydroxykynurenine and a decrease in kynurenic acid and anthranilic acid. More severe deficiency also yielded an increase in kynurenine and xanthurenic acid and more pronounced effects on the other metabolites. Tryptophan load simulations with and without vitamin B-6 deficiency showed altered metabolite concentrations consistent with published data. Induction of TDO caused an increase in all metabolites, and TDO induction together with a simulated vitamin B-6 deficiency, as has been reported in oral contraceptive users, yielded increases in kynurenine, 3-hydroxykynurenine, and xanthurenic acid and decreases in kynurenic acid and anthranilic acid. These results show that the model successfully simulated tryptophan metabolism via the kynurenine pathway and can be used to complement experimental investigations. PMID:23902960

  20. Metabolism and serum levels of tryptophan in senile cataract patients.

    Science.gov (United States)

    Costa, C; Angi, M R; De Carli, M; Vanzan, S; Allegri, G

    1982-03-30

    In order to clarify the role of tryptophan in the patogenesis of senile cataract, we have studied the serum total and free levels of tryptophan in cataract patients as compared with age and sex-matched controls, and the urinary excretion of 10 metabolites after oral load of the amino acid. This excretion increases in the cataract group both as total per cent and as kynurenine. No difference has been found in the free and total serum tryptophan between normal subjects and cataract patients. A possible role of the kynurenines in the pathogenesis of senile cataract is suggested.

  1. Exploring the mechanism of tryptophan 2,3-dioxygenase

    Science.gov (United States)

    Thackray, Sarah J.; Mowat, Christopher G.; Chapman, Stephen K.

    2008-01-01

    The haem proteins TDO (tryptophan 2,3-dioxygenase) and IDO (indoleamine 2,3-dioxygenase) are specific and powerful oxidation catalysts that insert one molecule of dioxygen into L-tryptophan in the first and rate-limiting step in the kynurenine pathway. Recent crystallographic and biochemical analyses of TDO and IDO have greatly aided our understanding of the mechanisms employed by these enzymes in the binding and activation of dioxygen and tryptophan. In the present paper, we briefly discuss the function, structure and possible catalytic mechanism of these enzymes. PMID:19021508

  2. Photolysis study of octyl p-methoxycinnamate loaded microemulsion by molecular fluorescence and chemometric approach

    Science.gov (United States)

    Nascimento, Danielle Silva; Insausti, Matías; Band, Beatriz Susana Fernández; Grünhut, Marcos

    2018-02-01

    Octyl p-methoxycinnamate (OMC) is one of the most widely used sunscreen agents. However, the efficiency of OMC as UV filter over time is affected due to the formation of the cis-isomer which presents a markedly lower extinction coefficient (εcis = 12,600 L mol- 1 cm- 1 at 291 nm) than the original trans-isomer (εtrans = 24,000 L mol- 1 cm- 1 at 310 nm). In this work, a novel carrier for OMC based on an oil-in-water microemulsion is proposed in order to improve the photostability of this sunscreen. The formulation was composed of 29.2% (w/w) of a 3:1 mixture of ethanol (co-surfactant) and decaethylene glycol mono-dodecyl ether (surfactant), 1.5% (w/w) of oleic acid (oil phase) and 69.2% (w/w) of water. This microemulsion was prepared in a simple way, under moderate stirring at 25 °C and using acceptable, biocompatible and accessible materials for topical use. OMC was incorporated in the vehicle at a final concentration of 5.0% (w/w), taking into account the maximum permitted levels established by international norms. Then, a photolysis study of the loaded formulation was performed using a continuous flow system. The direct photolysis was monitored over time by molecular fluorescence. The recorded spectra data between 370 y 490 nm were analyzed by multivariate curve resolution-alternating least squares algorithm. The kinetic rate constants corresponding to the photolysis of the trans-OMC were calculated from the concentration profiles, resulting in 0.0049 s- 1 for the trans-OMC loaded microemulsion and 0.0131 s- 1 for the trans-OMC in aqueous media. These results demonstrate a higher photostability of the trans-OMC when loaded in the proposed vehicle with respect to the free trans-OMC in aqueous media.

  3. Molecular analysis of intragenic recombination at the tryptophan ...

    Indian Academy of Sciences (India)

    /fulltext/jgen/092/03/0523-0528. Keywords. mutation; recombination; DNA sequence; primary metabolism; trp-3. Abstract. Fifteen different classically generated and mapped mutations at the tryptophan synthetase locus in Neurospora crassa ...

  4. Kernel modifications and tryptophan content in QPM segregating generations

    Directory of Open Access Journals (Sweden)

    -Ignjatović-Micić Dragana

    2010-01-01

    Full Text Available Maize has poor nutritional value due to deficiency of two essential amino acids - tryptophan and lysine. Although recessive opaque2 (o2 mutation significantly increases their content in the endosperm, incorporation of opaque2 into high yielding cultivars was not commercially successful, because of its numerous agronomic and processing problems due to soft endosperm. Quality protein maize - QPM has lately been introduced as opaque2 maize with improved endosperm hardness and improved agronomic traits, but mostly within tropical and subtropical germplasm. The ongoing breeding project at MRI includes improvement of MRI opaque2 lines and conversion of standard lines to QPM germplasm. The main selection steps in QPM breeding involve assessing kernel modifications and tryptophan level in each generation. Herein, we present the results of the analysis for these traits on F3 and BC1F1 generations of QPM x opaque2, opaque2 x QPM and standard lines x QPM crosses. The results showed that the majority the genotypes had kernel types 2 and 3 (good modifications. The whole grain tryptophan content in F3 and BC1F1 genotypes of crosses between QPM and opaque2 germplasm was at the quality protein level, with a few exceptions. All BC1F1 genotypes of standard lines x QPM had tryptophan content in the range of normal maize, while majority of F3 genotypes had tryptophan content at level of QPM. The progeny (with increased tryptophan levels of QPM and opaque2 crosses had significantly higher tryptophan content compared to the progeny of crosses between standard and QPM lines - 0.098 to 0.114 and 0.080, respectively. All genotypes that had poorly modified kernels and/or low tryptophan content will be discarded from further breeding.

  5. Utilization of DL- and L-tryptophan in young pigs

    NARCIS (Netherlands)

    Schutte, J.B.; Van Weerden, E.J.; Koch, F.

    1988-01-01

    Two trials involving young pigs (total numbers 288 and 400, respectively) were performed to compare the biological activity of Dl- and L-tryptophan under restricted (trial 1) and ad libitum (trial 2) feeding conditions. In trial 1, three additions of Dl-tryptophan (0·3, 0·6 and 0·9 g/kg) and two

  6. Preparation of nuclear pure uranium trioxide from El Atshan crude yellow cake using Tri-octyl-phosphine oxide

    International Nuclear Information System (INIS)

    Hammad, A.K.; Serag, H.M.; Abdallah, A.M.

    1995-01-01

    Tri n-octyl phosphine oxide (TOPO) has been investigated as a refinery extractant for crude yellow cake prepared from El Atshan ore, Eastern Desert, Egypt. Relevant factors namely: type and concentration of acid, TOPO concentration, effect of temperature, residence time and organic/ aqueous ratio have been studied and optimized. The required number of extraction and stages was determined. Further purification could be achieved for the final product by selective precipitation of uranium peroxide from the stripped solution using hydrogen peroxide followed by its calcination. Complete chemical analysis of the final product has proved its nuclear purity. 8 figs., 3 tabs

  7. Electrochemical studies of UO22+ in 1-octyl 3- methylimidazolium hexafluorophosphate (omimPF6) room temperature ionic liquid

    International Nuclear Information System (INIS)

    Kamat, J.V.; Gopinath, N.; Lohithakshan, K.V.; Aggarwal, S.K.

    2007-01-01

    The effect of the degraded products on the Electrochemical Window (EW) of l-octyl 3- methylimidazolium hexafluorophosphate (OmimPF 6 ) were studied. Studies were also carried to optimize conditions for extraction of UO 2 2+ to investigate its redox behavior in OmimPF6 and determine the number of electrons involved in the redox chemistry. The Chronoamperometric technique of evaluating n without knowing diffusion coefficient, D, was devised by Kakihana et al. and has been applied in the present work. The number of electrons involved was determined from the values of slope and intercept of the Cottrell plot. The results of these studies are presented in this paper

  8. Extended fatigue life of a catalyst free self-healing acrylic bone cement using microencapsulated 2-octyl cyanoacrylate.

    Science.gov (United States)

    Brochu, Alice B W; Matthys, Oriane B; Craig, Stephen L; Reichert, William M

    2015-02-01

    The tissue adhesive 2-octyl cyanoacrylate (OCA) was encapsulated in polyurethane microshells and incorporated into bone cement to form a catalyst free, self-healing bone cement comprised of all clinically approved components. The bending strength, modulus, and fatigue lifetime were investigated in accordance with ASTM and ISO standards for the testing of PMMA bone cement. The bending strength of bone cement specimens decreased with increasing wt % capsules content for capsules without or with OCA, with specimens of formulation. © 2014 Wiley Periodicals, Inc.

  9. Photosensitized oxidation of tryptophan and hepatic dysfunction in neonatal gerbils.

    Science.gov (United States)

    Bhatia, J; Rassin, D K

    1985-01-01

    Hepatic dysfunction is a common metabolic complication of parenteral nutrition. Studies in animals have suggested that several amino acids, especially tryptophan, may play a role in the development of hepatic dysfunction. Further, photoirradiation of amino acids in the presence of photosensitizers, such as riboflavin, causes photooxidative changes in several amino acids. The present study was undertaken to determine the effect of tryptophan, after photoirradiation in the presence of riboflavin, on hepatic function in neonatal gerbils. Two-week-old suckling gerbils received approximately 4 mmol/kg/day of light-exposed or nonlight-exposed tryptophan or received saline intraperitoneally for 4 days. An increase in the activity of serum gamma-glutamyl transpeptidase was found in gerbils receiving both light-exposed and nonlight-exposed tryptophan compared to control. Concentrations of tryptophan were significantly higher in animals receiving saline than in the other two groups. There were no significant differences in the major tissue amino acids among the three groups of animals. Our data suggest the role of photosensitized oxidation of tryptophan in the pathogenesis of hepatic dysfunction in neonatal gerbils. It is possible that similar photooxidation occurring during infusion of parenteral amino acid solutions containing vitamins exposed to constant illumination in the newborn nursery is responsible for the observed hepatic dysfunction in parenterally fed neonates.

  10. Suppression of Th1 differentiation by tryptophan supplementation in vivo.

    Science.gov (United States)

    Lanz, Tobias V; Becker, Simon; Mohapatra, Soumya R; Opitz, Christiane A; Wick, Wolfgang; Platten, Michael

    2017-07-01

    Metabolism of the essential amino acid tryptophan (trp) is a key endogenous immunosuppressive pathway restricting inflammatory responses. Tryptophan metabolites promote regulatory T cell (Treg) differentiation and suppress proinflammatory T helper cell (Th)1 and Th17 phenotypes. It has been shown that treatment with natural and synthetic tryptophan metabolites can suppress autoimmune neuroinflammation in preclinical animal models. Here, we tested if oral intake of tryptophan would increase immunosuppressive tryptophan metabolites and ameliorate autoimmune neuroinflammation as a safe approach to treat autoimmune disorders like multiple sclerosis (MS). Without oral supplementation, systemic kynurenine levels decrease during the initiation phase of experimental autoimmune encephalomyelitis (EAE), a mouse model of MS, indicating systemic activation of tryptophan metabolism. Daily oral gavage of up to 10 mg/mouse/day was safe and increased serum kynurenine levels by more than 20-fold for more than 3 h after the gavage. While this treatment resulted in suppression of myelin-specific Th1 responses, there was no relevant impact on clinical disease activity. These data show that oral trp supplementation at subtoxic concentrations suppresses antigen-specific Th1 responses, but suggest that the increase in trp metabolites is not sustained enough to impact neuroinflammation.

  11. Tryptophan depletion and aggressive responding in healthy males.

    Science.gov (United States)

    Moeller, F G; Dougherty, D M; Swann, A C; Collins, D; Davis, C M; Cherek, D R

    1996-07-01

    In order to study the effect of decreasing plasma tryptophan levels on aggressive responding in a controlled laboratory setting, we administered two doses (25 g and 100 g) of a tryptophan-free amino acid mixture to ten healthy male subjects after 24 h of a low tryptophan diet. Subjects were screened for current or past psychiatric, or non-psychiatric medical illness. Aggressive responding on a free-operant laboratory measure of aggression (the Point Subtraction Aggression Paradigm) and plasma tryptophan levels were measured before and after drinking the amino acid mixture. There was a significant increase in aggressive responding 5 h after the 100 g mixture and a significant increase in aggressive responding 6 h after the 25 g mixture compared to a baseline day when no drink was administered. There was also a significant decrease in plasma tryptophan at 5 hours after ingestion compared to baseline for both doses of amino acid mixture. This study supports the hypothesis that tryptophan depletion increases aggressive responding in healthy males in a laboratory setting, probably by decreasing brain serotonin.

  12. Carbon dots from tryptophan doped glucose for peroxynitrite sensing

    Energy Technology Data Exchange (ETDEWEB)

    Simões, Eliana F.C. [CIQ-UP, Grupo de Ciências Biológicas e Bioanalíticas, Faculdade de Farmácia da Universidade de Coimbra, Pólo das Ciências da Saúde, 3000-548 Coimbra (Portugal); CIQ-UP, Departamento de Química, Faculdade de Ciências da Universidade do Porto, R. Campo Alegre 687, 4169-007 Porto (Portugal); Esteves da Silva, Joaquim C.G. [CIQ-UP, Departamento de Química, Faculdade de Ciências da Universidade do Porto, R. Campo Alegre 687, 4169-007 Porto (Portugal); Leitão, João M.M., E-mail: jleitao@ff.uc.pt [CIQ-UP, Grupo de Ciências Biológicas e Bioanalíticas, Faculdade de Farmácia da Universidade de Coimbra, Pólo das Ciências da Saúde, 3000-548 Coimbra (Portugal)

    2014-12-10

    Highlights: • Synthesis of tryptophan doped carbon dots. • Experimental design optimization of the tryptophan doped carbon dots synthesis. • Fluorescence sensing of peroxynitrite by tryptophan doped carbon dots. • Peroxynitrite quantification in serum samples by tryptophan doped carbon dots. - Abstract: Tryptophan doped carbon dots (Trp-CD) were microwave synthesized. The optimum conditions of synthesizing of the Trp-CD were established by response surface multivariate optimization methodologies and were the following: 2.5 g of glucose and 300 mg of tryptophan diluted in 15 mL of water exposed for 5 min to a microwave radiation of 700 W. Trp-CD have an average size of 20 nm, were fluorescent with a quantum yield of 12.4% and the presence of peroxynitrite anion (ONOO{sup −}) provokes quenching of the fluorescence. The evaluated analytical methodology for ONOO{sup −} detection shows a linear response range from 5 to 25 μM with a limit of detection of 1.5 μM and quantification of 4.9 μM. The capability of the ONOO{sup −} quantification was evaluated in standard solutions and in fortified serum samples.

  13. OPTIMASI PRODUKSI METIL ESTER SULFONAT DARI METIL ESTER MINYAK JELANTAH

    Directory of Open Access Journals (Sweden)

    Sri Hidayati

    2012-11-01

    Full Text Available OPTIMATION OF METHYL ESTER SULFONATES PRODUCTION FROM WASTE COOKING METHYL ESTER. An experiment of sulfonation process of methyl ester to produce methyl ester sulfonates (MES was caried out using waste palm methyl ester and sulfuric acid as sulfonating agent with variation of H2SO4 concentration (60% (K1, 70% (K2, dan 80% (K3 and sulfonation time (60 minute (L1, 75 minute (L2 and 90 minute (L3 using factorial on Randomized Complete Design Block. The experiment result showed the best sulfonation condition present in 80% H2SO4 concentration and sulfonation time of 90 minutes.  The best characteristic of MES is produced showed surface tension of 27.35 dyne/cm, emulsion stability of 89.44%, acid value of 17.72 mg KOH/g and interfacial tension of 0.0361 dyne/cm at MES concentration of 2% in 10,000 ppm salinity water. Sebuah penelitian tentang proses produksi metil ester sulfonat menggunakan minyak bekas kelapa sawit dilakukan dengan menggunakan H2SO4 sebagai agen pensulfonasi dengan variasi konsentrasi H2SO4 (60% (K1, 70% (K2, dan 80% (K3 dan lama sulfonasi (60 menit (L1, 75 menit (L2 and 90 menit (L3 dengan menggunakan faktorial dalam Rancangan Kelompok Teracak Lengkap. Hasil penelitian menunjukkan bahwa kondisi proses sulfonasi terbaik terdapat pada konsentrasi H2SO4 80% dan lama reaksi 90 menit. Karakteristik Metil Ester Sulfonat (MES terbaik yang dihasilkan memperlihatkan nilai tegangan permukaan 27,35 dyne/cm, stabilitas emulsi 89,44%, nilai bilangan asam antara 17,72 mg KOH/g dan nilai tegangan antar muka pada konsentrasi MES 2% di dalam air dengan salinitas 10.000 ppm yaitu 0,0361 dyne/cm.

  14. Photolysis study of octyl p-methoxycinnamate loaded microemulsion by molecular fluorescence and chemometric approach.

    Science.gov (United States)

    Nascimento, Danielle Silva; Insausti, Matías; Band, Beatriz Susana Fernández; Grünhut, Marcos

    2018-02-15

    Octyl p-methoxycinnamate (OMC) is one of the most widely used sunscreen agents. However, the efficiency of OMC as UV filter over time is affected due to the formation of the cis-isomer which presents a markedly lower extinction coefficient (ε cis =12,600L mol -1 cm -1 at 291nm) than the original trans-isomer (ε trans =24,000L mol -1 cm -1 at 310nm). In this work, a novel carrier for OMC based on an oil-in-water microemulsion is proposed in order to improve the photostability of this sunscreen. The formulation was composed of 29.2% (w/w) of a 3:1 mixture of ethanol (co-surfactant) and decaethylene glycol mono-dodecyl ether (surfactant), 1.5% (w/w) of oleic acid (oil phase) and 69.2% (w/w) of water. This microemulsion was prepared in a simple way, under moderate stirring at 25°C and using acceptable, biocompatible and accessible materials for topical use. OMC was incorporated in the vehicle at a final concentration of 5.0% (w/w), taking into account the maximum permitted levels established by international norms. Then, a photolysis study of the loaded formulation was performed using a continuous flow system. The direct photolysis was monitored over time by molecular fluorescence. The recorded spectra data between 370 y 490nm were analyzed by multivariate curve resolution-alternating least squares algorithm. The kinetic rate constants corresponding to the photolysis of the trans-OMC were calculated from the concentration profiles, resulting in 0.0049s -1 for the trans-OMC loaded microemulsion and 0.0131s -1 for the trans-OMC in aqueous media. These results demonstrate a higher photostability of the trans-OMC when loaded in the proposed vehicle with respect to the free trans-OMC in aqueous media. Copyright © 2017 Elsevier B.V. All rights reserved.

  15. Bromocontryphan: post-translational bromination of tryptophan.

    Science.gov (United States)

    Jimenez, E C; Craig, A G; Watkins, M; Hillyard, D R; Gray, W R; Gulyas, J; Rivier, J E; Cruz, L J; Olivera, B M

    1997-02-04

    We demonstrate that post-translational bromination of a tryptophan residue occurs in the biologically active octapeptide bromocontryphan, purified and characterized from Conus radiatus venom. Clones encoding bromocontryphan were identified from a cDNA library made from C. radiatus venom ducts. The mRNA sequence obtained predicts a prepropeptide which has the mature peptide sequence at the C-terminal end, with the L-6-bromotryptophan residue encoded by UGG, the Trp codon. These data provide the first direct evidence for post-translational bromination of a polypeptide which is translated through the normal cellular machinery. In addition to bromination, the peptide, which induces a "stiff tail" syndrome in mice, has several other modifications as shown by the sequence [Formula: See Text] in which Hyp = hydroxyproline. Asterisks indicate post-translational modifications (left to right): proteolytic cleavage at the N-terminus; hydroxylation of Pro3; epimerization of Trp4; bromination of Trp7, and C-terminal amidation. Bromocontryphan appears to have the highest density of post-translational modifications known among gene-encoded polypeptides. The overall result is a molecule which closely resembles marine natural products produced through specialized biosynthetic pathways comprising many enzyme-catalyzed steps.

  16. N-mercapto acetyl-N'-octyl-O, N″-glycol chitosan as an efficiency oral delivery system of paclitaxel.

    Science.gov (United States)

    Huo, Meirong; Fu, Ying; Liu, Yanhong; Chen, Qinyu; Mu, Yan; Zhou, Jianping; Li, Lingchao; Xu, Wei; Yin, Tingjie

    2018-02-01

    Herein, thioglycolic acid modified N-octyl-O, N'-glycol chitosan (N-mercapto acetyl-N'-octyl-O, N″-glycol chitosan, abbreviated as SH-OGC) was synthesized to improve the oral bioavailability of paclitaxel (PTX). PTX was readily solubilized into the hydrophobic inner core of SH-OGC. Pharmacokinetic studies demonstrated that the bioavailability of PTX was greatly enhanced when delivered by SH-OGC compared to Taxol ® or non-sulfhydrylated OGC micelles. Caco-2 cell experiments confirmed PTX or rhodamine-123-loaded SH-OGC demonstrated effective cellular accumulation via caveola-mediated endocytosis along with the inhibition of P-gp efflux. Furthermore, Caco-2 transport studies demonstrated that the mechanistic basis of SH-OGC efficacy was attributed to P-gp inhibition, enhanced permeability of tight junctions and clathrin-mediated transcytosis across the endothelium. In addition, SH-OGC exhibited increased intestinal retention through thiol-mediated mucoadhesion compared with OGC according to results of mucoadhesion evaluation on freshly excised rat intestine. In summary, SH-OGC micelles may present as a promising delivery vehicle for enhancing the oral bioavailability of P-gp substrates. Copyright © 2017 Elsevier Ltd. All rights reserved.

  17. The Antimalarial Drug Quinine Disrupts Tat2p-mediated Tryptophan Transport and Causes Tryptophan Starvation*

    Science.gov (United States)

    Khozoie, Combiz; Pleass, Richard J.; Avery, Simon V.

    2009-01-01

    Quinine is a major drug of choice for the treatment of malaria. However, the primary mode of quinine action is unclear, and its efficacy is marred by adverse reactions among patients. To help address these issues, a genome-wide screen for quinine sensitivity was carried out using the yeast deletion strain collection. Quinine-sensitive mutants identified in the screen included several that were defective for tryptophan biosynthesis (trp strains). This sensitivity was confirmed in independent assays and was suppressible with exogenous Trp, suggesting that quinine caused Trp starvation. Accordingly, quinine was found to inhibit [3H]Trp uptake by cells, and the quinine sensitivity of a trp1Δ mutant could be rescued by overexpression of Trp permeases, encoded by TAT1 and TAT2. The site of quinine action was identified specifically as the high affinity Trp/Tyr permease, Tat2p, with which quinine associated in a Trp-suppressible manner. A resultant action also on Tyr levels was reflected by the Tyr-suppressible quinine hypersensitivity of an aro7Δ deletion strain, which is auxotrophic for Tyr (and Phe). The present genome-wide dataset provides an important resource for discovering modes of quinine toxicity. That potential was validated with our demonstration that Trp and Tyr uptake via Tat2p is a major target of cellular quinine toxicity. The results also suggest that dietary tryptophan supplements could help to avert the toxic effects of quinine. PMID:19416971

  18. Fructose malabsorption is associated with decreased plasma tryptophan.

    Science.gov (United States)

    Ledochowski, M; Widner, B; Murr, C; Sperner-Unterweger, B; Fuchs, D

    2001-04-01

    Fructose malabsorption is characterized by the inability to absorb fructose efficiently. As a consequence fructose reaches the colon where it is broken down by bacteria to short fatty acids, CO2, H2, CH4 and lactic acid. Bloating, cramps, osmotic diarrhea and other symptoms of irritable bowel syndrome are the consequence and can be seen in about 50% of fructose malabsorbers. Recently it was found that fructose malabsorption was associated with early signs of depressive disorders. Therefore, it was investigated whether fructose malabsorption is associated with abnormal tryptophan metabolism. Fifty adults (16 men, 34 women) with gastrointestinal discomfort were analyzed by measuring breath hydrogen concentrations after an oral dose of 50 g fructose after an overnight fast. They were classified as normals or fructose malabsorbers according to their breath H2 concentrations. All patients filled out a Beck depression inventory questionnaire. Blood samples were taken for plasma tryptophan and kynurenine measurements. Fructose malabsorption (breath deltaH2 production >20 ppm) was detected in 35 of 50 individuals (70%). Subjects with fructose malabsorption showed significantly lower plasma tryptophan concentrations and significantly higher scores in the Beck depression inventory compared to those with normal fructose absorption. Fructose malabsorption is associated with lower tryptophan levels that may play a role in the development of depressive disorders. High intestinal fructose concentration seems to interfere with L-tryptophan metabolism, and it may reduce availability of tryptophan for the biosynthesis of serotonin (5-hydroxytryptamine). Fructose malabsorption should be considered in patients with symptoms of depression and disturbances of tryptophan metabolism.

  19. Kynurenine pathway in psychosis: evidence of increased tryptophan degradation.

    LENUS (Irish Health Repository)

    Barry, Sandra

    2009-05-01

    The kynurenine pathway of tryptophan degradation may serve to integrate disparate abnormalities heretofore identified in research aiming to elucidate the complex aetiopathogenesis of psychotic disorders. Post-mortem brain tissue studies have reported elevated kynurenine and kynurenic acid in the frontal cortex and upregulation of the first step of the pathway in the anterior cingulate cortex of individuals with schizophrenia. In this study, we examined kynurenine pathway activity by measuring tryptophan breakdown, a number of pathway metabolites and interferon gamma (IFN-gamma), which is the preferential activator of the first-step enzyme, indoleamine dioxygenase (IDO), in the plasma of patients with major psychotic disorder. Plasma tryptophan, kynurenine pathway metabolites were measured using high-performance liquid chromatography (HPLC) in 34 patients with a diagnosis on the psychotic spectrum (schizophrenia or schizoaffective disorder) and in 36 healthy control subjects. IFN-gamma was measured using enzyme-linked immunosorbent assay (ELISA). The mean tryptophan breakdown index (kynurenine\\/tryptophan) was significantly higher in the patient group compared with controls (P < 0.05). IFN-gamma measures did not differ between groups (P = 0.23). No relationship was found between measures of psychopathology, symptom severity and activity in the first step in the pathway. A modest correlation was established between the tryptophan breakdown index and illness duration. These results provide evidence for kynurenine pathway upregulation, specifically involving the first enzymatic step, in patients with major psychotic disorder. Increased tryptophan degradation in psychoses may have potential consequences for the treatment of these disorders by informing the development of novel therapeutic compounds.

  20. Tryptophan metabolism in breast cancers: molecular imaging and immunohistochemistry studies

    International Nuclear Information System (INIS)

    Juhász, Csaba; Nahleh, Zeina; Zitron, Ian; Chugani, Diane C.; Janabi, Majid Z.; Bandyopadhyay, Sudeshna; Ali-Fehmi, Rouba; Mangner, Thomas J.; Chakraborty, Pulak K.; Mittal, Sandeep; Muzik, Otto

    2012-01-01

    Introduction: Tryptophan oxidation via the kynurenine pathway is an important mechanism of tumoral immunoresistance. Increased tryptophan metabolism via the serotonin pathway has been linked to malignant progression in breast cancer. In this study, we combined quantitative positron emission tomography (PET) with tumor immunohistochemistry to analyze tryptophan transport and metabolism in breast cancer. Methods: Dynamic α-[ 11 C]methyl-L-tryptophan (AMT) PET was performed in nine women with stage II–IV breast cancer. PET tracer kinetic modeling was performed in all tumors. Expression of L-type amino acid transporter 1 (LAT1), indoleamine 2,3-dioxygenase (IDO; the initial and rate-limiting enzyme of the kynurenine pathway) and tryptophan hydroxylase 1 (TPH1; the initial enzyme of the serotonin pathway) was assessed by immunostaining of resected tumor specimens. Results: Tumor AMT uptake peaked at 5–20 min postinjection in seven tumors; the other two cases showed protracted tracer accumulation. Tumor standardized uptake values (SUVs) varied widely (2.6–9.8) and showed a strong positive correlation with volume of distribution values derived from kinetic analysis (P < .01). Invasive ductal carcinomas (n = 6) showed particularly high AMT SUVs (range, 4.7–9.8). Moderate to strong immunostaining for LAT1, IDO and TPH1 was detected in most tumor cells. Conclusions: Breast cancers show differential tryptophan kinetics on dynamic PET. SUVs measured 5–20 min postinjection reflect reasonably the tracer's volume of distribution. Further studies are warranted to determine if in vivo AMT accumulation in these tumors is related to tryptophan metabolism via the kynurenine and serotonin pathways.

  1. Extraction of tryptophan with ionic liquids studied with molecular dynamics simulations.

    Science.gov (United States)

    Seduraman, Abirami; Wu, Ping; Klähn, Marco

    2012-01-12

    Extraction of amino acids from aqueous solutions with ionic liquids (ILs) in biphasic systems is analyzed with molecular dynamics (MD) simulations. Extraction of tryptophan (TRP) with the imidazolium-based ILs [C(4)mim][PF(6)], [C(8)mim][PF(6)], and [C(8)mim][BF(4)] are considered as model cases. Solvation free energies of TRP are calculated with MD simulations and thermodynamic integration in combination with an empirical force field, whose parametrization is based on the liquid-phase charge distribution of the ILs. Calculated solvation free energies reproduce successfully all observed experimental trends according to the previously reported partition of TRP between water and IL phases. Water is present in ILs as a cosolvent, due to direct contact with the aqueous phase during extraction, and is found to play a major role in the extraction of TRP. Water improves solvation of cationic TRP by 7.8 and 5.1 kcal/mol in [C(4)mim][PF(6)] and [C(8)mim][PF(6)], respectively, which is in the case of [C(4)mim][PF(6)] sufficient to extract TRP. Extraction in [C(8)mim][PF(6)] is not feasible, since the hydrophobic octyl groups of the cations limit the water concentration in the IL. The solvation of cationic TRP is 2.4 kcal/mol less favorable in [C(8)mim][PF(6)] than in [C(4)mim][PF(6)]. Water improves the solvation of TRP in ILs mostly through dipole-dipole interactions with the polar backbone of TRP. Extraction is most efficient with [C(8)mim][BF(4)], where hydrophilic BF(4)(-) anions substantially increase the water concentration in the IL. Additionally, stronger direct electrostatic interactions of TRP with BF(4)(-) anions improve its solvation in the IL further. The solvation of cationic TRP in [C(8)mim][BF(4)] is 3.4 kcal/mol more favorable than in [C(8)mim][PF(6)]. Overall, the extractive power of the ILs correlates with the water saturation concentration of the IL phase, which in turn is determined by the hydrophilicity of the constituting ions. The results of this work

  2. Disturbed tryptophan metabolism in cardiovascular disease.

    Science.gov (United States)

    Mangge, H; Stelzer, I; Reininghaus, E Z; Weghuber, D; Postolache, T T; Fuchs, D

    2014-06-01

    Atherosclerosis (AS), a major pathologic consequence of obesity, is the main etiological factor of cardiovascular disease (CVD), which is the most common cause of death in the western world. A systemic chronic low grade immune- mediated inflammation (scLGI) is substantially implicated in AS and its consequences. In particular, proinflammatory cytokines play a major role, with Th1-type cytokine interferon-γ (IFN-γ) being a key mediator. Among various other molecular and cellular effects, IFN-γ activates the enzyme indoleamine 2,3-dioxygenase (IDO) in monocyte-derived macrophages, dendritic, and other cells, which, in turn, decreases serum levels of the essential amino acid tryptophan (TRP). Thus, people with CVD often have increased serum kynurenine to tryptophan ratios (KYN/TRP), a result of an increased TRP breakdown. Importantly, increased KYN/TRP is associated with a higher likelihood of fatal cardiovascular events. A scLGI with increased production of the proinflammatory adipokine leptin, in combination with IFN-γ and interleukin-6 (IL-6), represents another central link between obesity, AS, and CVD. Leptin has also been shown to contribute to Th1-type immunity shifting, with abdominal fat being thus a direct contributor to KYN/TRP ratio. However, TRP is not only an important source for protein production but also for the generation of one of the most important neurotransmitters, 5-hydroxytryptamine (serotonin), by the tetrahydrobiopterin-dependent TRP 5-hydroxylase. In prolonged states of scLGI, availability of free serum TRP is strongly diminished, affecting serotonin synthesis, particularly in the brain. Additionally, accumulation of neurotoxic KYN metabolites such as quinolinic acid produced by microglia, can contribute to the development of depression via NMDA glutamatergic stimulation. Depression had been reported to be associated with CVD endpoints, but it most likely represents only a secondary loop connecting excess adipose tissue, scLGI and

  3. One-step of tryptophan attenuator inactivation and promoter swapping to improve the production of L-tryptophan in Escherichia coli

    Science.gov (United States)

    2012-01-01

    Background L-tryptophan is an aromatic amino acid widely used in the food, chemical and pharmaceutical industries. In Escherichia coli, L-tryptophan is synthesized from phosphoenolpyruvate and erythrose 4-phosphate by enzymes in the shikimate pathway and L-tryptophan branch pathway, while L-serine and phosphoribosylpyrophosphate are also involved in L-tryptophan synthesis. In order to construct a microbial strain for efficient L-tryptophan production from glucose, we developed a one step tryptophan attenuator inactivation and promoter swapping strategy for metabolic flux optimization after a base strain was obtained by overexpressing the tktA, mutated trpE and aroG genes and inactivating a series of competitive steps. Results The engineered E. coli GPT1002 with tryptophan attenuator inactivation and tryptophan operon promoter substitution exhibited 1.67 ~ 9.29 times higher transcription of tryptophan operon genes than the control GPT1001. In addition, this strain accumulated 1.70 g l-1 L-tryptophan after 36 h batch cultivation in 300-mL shake flask. Bioreactor fermentation experiments showed that GPT1002 could produce 10.15 g l-1 L-tryptophan in 48 h. Conclusions The one step inactivating and promoter swapping is an efficient method for metabolic engineering. This method can also be applied in other bacteria. PMID:22380540

  4. Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters.

    Science.gov (United States)

    Ahmad, Anis; Ahmad, Aiman; Sudhakar, Raja; Varshney, Himani; Subbarao, Naidu; Ansari, Saba; Rauf, Abdul; Khan, Asad U

    2017-11-01

    In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1 H NMR, 13 C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8'R)-8' hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2'R)(2'-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8'R)-8'-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation

  5. Tryptophan metabolism, disposition and utilization in pregnancy

    Science.gov (United States)

    Badawy, Abdulla A.-B.

    2015-01-01

    Tryptophan (Trp) requirements in pregnancy are several-fold: (1) the need for increased protein synthesis by mother and for fetal growth and development; (2) serotonin (5-HT) for signalling pathways; (3) kynurenic acid (KA) for neuronal protection; (4) quinolinic acid (QA) for NAD+ synthesis (5) other kynurenines (Ks) for suppressing fetal rejection. These goals could not be achieved if maternal plasma [Trp] is depleted. Although plasma total (free + albumin-bound) Trp is decreased in pregnancy, free Trp is elevated. The above requirements are best expressed in terms of a Trp utilization concept. Briefly, Trp is utilized as follows: (1) In early and mid-pregnancy, emphasis is on increased maternal Trp availability to meet the demand for protein synthesis and fetal development, most probably mediated by maternal liver Trp 2,3-dioxygenase (TDO) inhibition by progesterone and oestrogens. (2) In mid- and late pregnancy, Trp availability is maintained and enhanced by the release of albumin-bound Trp by albumin depletion and non-esterified fatty acid (NEFA) elevation, leading to increased flux of Trp down the K pathway to elevate immunosuppressive Ks. An excessive release of free Trp could undermine pregnancy by abolishing T-cell suppression by Ks. Detailed assessment of parameters of Trp metabolism and disposition and related measures (free and total Trp, albumin, NEFA, K and its metabolites and pro- and anti-inflammatory cytokines in maternal blood and, where appropriate, placental and fetal material) in normal and abnormal pregnancies may establish missing gaps in our knowledge of the Trp status in pregnancy and help identify appropriate intervention strategies. PMID:26381576

  6. Development of Bacillus subtilis mutants to produce tryptophan in pigs.

    Science.gov (United States)

    Bjerre, Karin; Cantor, Mette D; Nørgaard, Jan V; Poulsen, Hanne D; Blaabjerg, Karoline; Canibe, Nuria; Jensen, Bent B; Stuer-Lauridsen, Birgitte; Nielsen, Bea; Derkx, Patrick M F

    2017-02-01

    To generate tryptophan-overproducing Bacillus subtilis strains for in situ use in pigs, to reduce the feed cost for farmers and nitrogen pollution. A novel concept has been investigated-to generate B. subtilis strains able to produce tryptophan (Trp) in situ in pigs. Mutagenesis by UV was combined with selection on Trp and purine analogues in an iterative process. Two mutants from different wild types were obtained, mutant 1 (M1) produced 1 mg Trp/l and mutant 2 (M2) 14 mg Trp/l. Genome sequence analysis revealed that M1 had three single nuclear polymorphisms (SNPs) and M2 had two SNPs compared to the wild type strains. In both mutants SNPs were found in genes regulating tryptophan synthesis. Reverse transcription PCR confirmed up-regulation of the tryptophan synthesis genes in both mutants, the expression was up to 3 times higher in M2 than in M1. Tryptophan-excreting B. subtilis strains were obtained with UV-mutagenesis and analogue selection and can be used in animal feed applications.

  7. Chemically defined media modifications to lower tryptophan oxidation of biopharmaceuticals.

    Science.gov (United States)

    Hazeltine, Laurie B; Knueven, Kristine M; Zhang, Yan; Lian, Zhirui; Olson, Donald J; Ouyang, Anli

    2016-01-01

    Oxidation of biopharmaceuticals is a major product quality issue with potential impacts on activity and immunogenicity. At Eli Lilly and Company, high tryptophan oxidation was observed for two biopharmaceuticals in development produced in Chinese hamster ovary cells. A switch from historical hydrolysate-containing media to chemically defined media with a reformulated basal powder was thought to be responsible, so mitigation efforts focused on media modification. Shake flask studies identified that increasing tryptophan, copper, and manganese and decreasing cysteine concentrations were individual approaches to lower tryptophan oxidation. When amino acid and metal changes were combined, the modified formulation had a synergistic impact that led to substantially less tryptophan oxidation for both biopharmaceuticals. Similar results were achieved in shake flasks and benchtop bioreactors, demonstrating the potential to implement these modifications at manufacturing scale. The modified formulation did not negatively impact cell growth and viability, product titer, purity, charge variants, or glycan profile. A potential mechanism of action is presented for each amino acid or metal factor based on its role in oxidation chemistry. This work served not only to mitigate the tryptophan oxidation issue in two Lilly biopharmaceuticals in development, but also to increase our knowledge and appreciation for the impact of media components on product quality. © 2015 American Institute of Chemical Engineers.

  8. Environmental effect of rapeseed oil ethyl ester

    International Nuclear Information System (INIS)

    Makareviciene, V.; Janulis, P.

    2003-01-01

    Exhaust emission tests were conducted on rapeseed oil methyl ester (RME), rapeseed oil ethyl ester (REE) and fossil diesel fuel as well as on their mixtures. Results showed that when considering emissions of nitrogen oxides (NO x ), carbon monoxide (CO) and smoke density, rapeseed oil ethyl ester had less negative effect on the environment in comparison with that of rapeseed oil methyl ester. When fuelled with rapeseed oil ethyl ester, the emissions of NO x showed an increase of 8.3% over those of fossil diesel fuel. When operated on 25-50% bio-ester mixed with fossil diesel fuel, NO x emissions marginally decreased. When fuelled with pure rapeseed oil ethyl ester, HC emissions decreased by 53%, CO emissions by 7.2% and smoke density 72.6% when compared with emissions when fossil diesel fuel was used. Carbon dioxide (CO 2 ) emissions, which cause greenhouse effect, decreased by 782.87 g/kWh when rapeseed oil ethyl ester was used and by 782.26 g/kWh when rapeseed oil methyl ester was used instead of fossil diesel fuel. Rapeseed oil ethyl ester was more rapidly biodegradable in aqua environment when compared with rapeseed oil methyl ester and especially with fossil diesel fuel. During a standard 21 day period, 97.7% of rapeseed oil methyl ester, 98% of rapeseed oil ethyl ester and only 61.3% of fossil diesel fuel were biologically decomposed. (author)

  9. Synthesis of substituted 2-cyanoarylboronic esters

    DEFF Research Database (Denmark)

    Lysén, Morten; Hansen, Henriette M; Begtrup, Mikael

    2006-01-01

    The synthesis of substituted 2-cyanoarylboronic esters is described via lithiation/in situ trapping of the corresponding methoxy-, trifluoromethyl-, fluoro-, chloro-, and bromobenzonitriles. The crude arylboronic esters were obtained in high yields and purities and with good regioselectivities....

  10. Isoform-Specific Substrate Inhibition Mechanism of Human Tryptophan Hydroxylase

    DEFF Research Database (Denmark)

    Tidemand, Kasper Damgaard; Peters, Günther H.J.; Harris, Pernille

    2017-01-01

    Tryptophan hydroxylase (TPH) catalyzes the initial and rate-limiting step in the biosynthesis of serotonin, which is associated with a variety of disorders such as depression and irritable bowel syndrome. TPH exists in two isoforms: TPH1 and TPH2. TPH1 catalyzes the initial step in the synthesis...... of serotonin in the peripheral tissues, while TPH2 catalyzes this step in the brain. In this study, the steady-state kinetic mechanism for the catalytic domain of human TPH1 has been determined. Varying substrate tryptophan (Trp) and tetrahydrobiopterin (BH4) results in a hybrid Ping Pong-ordered mechanism...... in which the reaction can either occur through a Ping Pong or a sequential mechanism depending on the concentration of tryptophan. The catalytic domain of TPH1 shares a sequence identity of 81% with TPH2. Despite the high sequence identity, differences in the kinetic parameters of the isoforms have been...

  11. Determination of phthalate esters in physiological saline solution by monolithic silica spin column extraction method

    Directory of Open Access Journals (Sweden)

    Lu Lu

    2011-05-01

    Full Text Available Monolithic silica spin column extraction (MonoSpin-SPE was developed as a simple, sensitive, and eco-friendly pretreatment method which combined with ultra-fast liquid chromatography-mass spectrometry (UFLC-MS to determine the levels of six phthalate esters, dimethyl-(DMP, diethyl-(DEP, dipropyl- [DPrP], butyl-benzyl-(BBP, dicyclohexyl(DcHP, and di- n-octyl-(DOP phthalate in physiological saline samples. Under optimized experimental conditions, the method was linear in the following ranges: 0.2- 50 μ/L for DMP, DEP, DPrP, DcHP and DOP; 5 – 100 μ/L for BBP. The correlation coefficients (R2 were in the range of O. 9951 – O. 9995 for all the analytes and the limits of detection (LODs and limits of quantification (LOQs were in the ranges of 0.02 – 0.9 μ/L and 0.08 – 2.7 μ/L, respectively. The pretreatment process showed good reproducibility with inter-day and intra-day relative standard deviations (RSDs below 8.5% and 11.2%, respectively. This method was used to determine the levels of six phthalate esters in physiological saline samples and the recoveries ranged from 71.2% to 107. 3%. DMP and DEP were found in actual physical saline samples (brand A and brand B. Keywords: Monolithic silica spin column, Phthalate esters, Physiological saline samples, Ultra fast liquid chromatographymass spectrometry (UFLC-MS

  12. Structural elucidation of biologically active neomycin N-octyl derivatives in a regioisomeric mixture by means of liquid chromatography/ion trap time-of-flight mass spectrometry

    NARCIS (Netherlands)

    Giera, M.; de Vlieger, J.S.B.; Lingeman, H.; Irth, H.; Niessen, W.M.A.

    2010-01-01

    Structural elucidation of six regioisomers of mono-N-octyl derivatized neomycin is achieved using MSn (up to n1/4 4) on an ion trap time-of-flight (IT-TOF) instrument equipped with electrospray ionization. The mixture of six derivatized neomycin analogues was generated by reductive amination in a

  13. Phasor approaches simplify the analysis of tryptophan fluorescence data in protein denaturation studies

    NARCIS (Netherlands)

    Bader, A.N.; Visser, N.V.; Amerongen, van H.; Visser, A.J.W.G.

    2014-01-01

    The intrinsic fluorescence of tryptophan is frequently used to investigate the structure of proteins. The analysis of tryptophan fluorescence data is challenging: fluorescence (anisotropy) decays typically have multiple lifetime (correlation time) components and fluorescence spectra are broad and

  14. Incorporation of tryptophan analogues into the lantibiotic nisin.

    Science.gov (United States)

    Zhou, Liang; Shao, Jinfeng; Li, Qian; van Heel, Auke J; de Vries, Marcel P; Broos, Jaap; Kuipers, Oscar P

    2016-05-01

    Lantibiotics are posttranslationally modified peptides with efficient inhibitory activity against various Gram-positive bacteria. In addition to the original modifications, incorporation of non-canonical amino acids can render new properties and functions to lantibiotics. Nisin is the most studied lantibiotic and contains no tryptophan residues. In this study, a system was constructed to incorporate tryptophan analogues into nisin, which included the modification machinery (NisBTC) and the overexpression of tryptophanyl-tRNA synthetase (TrpRS). Tryptophan and three different tryptophan analogues (5-fluoroTrp (5FW), 5-hydroxyTrp (5HW) and 5-methylTrp (5MeW)) were successfully incorporated at four different positions of nisin (I1W, I4W, M17W and V32W). The incorporation efficiency of tryptophan analogues into mutants I1W, M17W and V32W was over 97 %, while the mutant I4W showed relatively low incorporation efficiency (69-93 %). The variants with 5FW showed relatively higher production yield, while 5MeW-containing variants showed the lowest yield. The dehydration efficiency of serines or threonines was affected by the tryptophan mutants of I4W and V32W. The affinity of the peptides for the cation-ion exchange and reverse phase chromatography columns was significantly reduced when 5HW was incorporated. The antimicrobial activity of IIW and its 5FW analogue both decreased two times compared to that of nisin, while that of its 5HW analogue decreased four times. The 5FW analogue of I4W also showed two times decreased activity than nisin. However, the mutant M17W and its 5HW analogue both showed 32 times reduced activity relative to that of nisin.

  15. Mechanical properties and chemical stability of pivalolactone-based poly(ether ester)s

    NARCIS (Netherlands)

    Tijsma, E.J.; Tijsma, E.J.; van der Does, L.; Bantjes, A.; Bantjes, A.; Vulic, I.

    1994-01-01

    The processing, mechanical and chemical properties of poly(ether ester)s, prepared from pivalolactone (PVL), 1,4-butanediol (4G) and dimethyl terephthalate (DMT), were studied. The poly(ether ester)s could easily be processed by injection moulding, owing to their favourable rheological and thermal

  16. Regioselective Synthesis of Cellulose Ester Homopolymers

    Science.gov (United States)

    Daiqiang Xu; Kristen Voiges; Thomas Elder; Petra Mischnick; Kevin J. Edgar

    2012-01-01

    Regioselective synthesis of cellulose esters is extremely difficult due to the small reactivity differences between cellulose hydroxyl groups, small differences in steric demand between acyl moieties of interest, and the difficulty of attaching and detaching many protecting groups in the presence of cellulose ester moieties without removing the ester groups. Yet the...

  17. Octyl-methoxycinnamate (OMC), an ultraviolet (UV) filter, alters LHRH and amino acid neurotransmitters release from hypothalamus of immature rats.

    Science.gov (United States)

    Szwarcfarb, B; Carbone, S; Reynoso, R; Bollero, G; Ponzo, O; Moguilevsky, J; Scacchi, P

    2008-02-01

    OMC (octyl-methoxycinnamate), is an endocrine disruptor with estrogenic activity, which is used in sunscreen creams as a UV filter. We studied its " IN VITRO" effects on the hypothalamic release of LHRH as well as on the amino acid neurotransmitter system in immature rats of 15 (prepubertal) and 30 (peripubertal) days of age. OMC decreased the LH-RH release significantly in male and female rats of both age. In male rats OMC increased the release of GABA while in the female ones It diminished the excitatory amino acid aspartate (ASP) and Glutamate (GLU) without modifications in the hypothalamic GABA release. These results suggest that during sexual maturation the inhibitory effect of OMC on LH-RH release appears to be related to its action on the inhibitory and excitatory amino acid neurotransmitters in male and female rats.

  18. Tryptophan-kynurenine and lipid related metabolites as blood biomarkers for first-episode drug-naïve patients with major depressive disorder: An exploratory pilot case-control study.

    Science.gov (United States)

    Kuwano, Nobuki; Kato, Takahiro A; Setoyama, Daiki; Sato-Kasai, Mina; Shimokawa, Norihiro; Hayakawa, Kohei; Ohgidani, Masahiro; Sagata, Noriaki; Kubo, Hiroaki; Kishimoto, Junji; Kang, Dongchon; Kanba, Shigenob

    2018-04-15

    Early intervention in depression has been critical to prevent its negative impact including suicide. Recent blood biomarker studies for major depressive disorder (MDD) have suggested that tryptophan-kynurenine and lipid related metabolites are involved in the pathophysiology of MDD. However, there have been limited studies investigating these blood biomarkers in first-episode drug-naïve MDD, which are particularly important for early intervention in depression. As an exploratory pilot case-control study, we examined the above blood biomarkers, and analyzed how these biomarkers are associated with clinical variables in first-episode drug-naïve MDD patients, based on metabolome/lipidome analysis. Plasma tryptophan and kynurenine levels were significantly lower in MDD group (N = 15) compared to healthy controls (HC) group (N = 19), and plasma tryptophan was the significant biomarker to identify MDD group (area under the curve = 0.740). Lower serum high density lipoprotein-cholesterol (HDL-C) was the predictive biomarker for severity of depression in MDD group (R 2 = 0.444). Interestingly, depressive symptoms were variously correlated with plasma tryptophan-kynurenine and lipid related metabolites. Moreover, plasma tryptophan-kynurenine metabolites and cholesteryl esters (CEs) were significantly correlated in MDD group, but not in HC group. This study had small sample size, and we did not use the multiple test correction. This is the first study to suggest that not only tryptophan-kynurenine metabolites but also HDL-C and CEs are important blood biomarkers for first-episode drug-naïve MDD patients. The present study sheds new light on early intervention in clinical practice in depression, and further clinical studies especially large-scale prospective studies are warranted. Copyright © 2018 Elsevier B.V. All rights reserved.

  19. The Tryptophan Depletion Theory in Delirium: Not Confirmed in Elderly Hip Fracture Patients

    NARCIS (Netherlands)

    de Jonghe, Annemarieke; van Munster, Barbara C.; Fekkes, Durk; van Oosten, Hannah E.; de Rooij, Sophia E.

    2012-01-01

    Background: The tryptophan depletion theory assumes that low tryptophan levels are present in delirium. These lower levels may be regarded as a biochemical marker for cellular immune activation, which may lead to increased catabolism of tryptophan into kynurenine via stimulation of the enzyme

  20. Tryptophan requirement of the enterally fed term infant in the first month of life

    NARCIS (Netherlands)

    Huang, Lisha; Hogewind-Schoonenboom, Jacomine E.; Zhu, Li; Kraaijenga, Juliette V. S.; van Haren, Nicky P. C.; Voortman, Gardi J.; Schierbeek, Henk; Twisk, Jos W. R.; Huang, Ying; Chen, Chao; van Goudoever, Johannes B.

    2014-01-01

    Tryptophan not only is an amino acid essential to protein synthesis but also serves as a precursor in 2 important metabolic pathways: the serotonin and the kynurenine pathways. Tryptophan is related to sleeping patterns. The objective of the present study was to determine the tryptophan requirement

  1. Catalytic Ester to Stannane Functional Group Interconversion via Decarbonylative Cross-Coupling of Methyl Esters

    KAUST Repository

    Yue, Huifeng

    2018-01-03

    An unprecedented conversion of methyl esters to stannanes was realized, providing access to a series of arylstannanes via nickel catalysis. Various common esters including ethyl, cyclohexyl, benzyl, and phenyl esters can undergo the newly developed decarbonylative stannylation reaction. The reaction shows broad substrate scope, can differentiate between different types of esters, and if applied in consecutive fashion, allows the transformation of methyl esters into aryl fluorides or biaryls via fluororination or arylation.

  2. Modeling operon dynamics: the tryptophan and lactose operons as paradigms.

    Science.gov (United States)

    Mackey, Michael C; Santillán, Moisés; Yildirim, Necmettin

    2004-03-01

    Understanding the regulation of gene control networks and their ensuing dynamics will be a critical component in the understanding of the mountain of genomic data being currently collected. This paper reviews recent mathematical modeling work on the tryptophan and lactose operons which are, respectively, the classical paradigms for repressible and inducible operons.

  3. Dimeric Complexes of Tryptophan with M2+ Metal Ions

    NARCIS (Netherlands)

    Dunbar, R. C.; Steill, J. D.; Polfer, N. C.; Oomens, J.

    2009-01-01

    IRMPD spectroscopy using the FELIX free electron laser and a Fourier transform ICR mass spectrometer was used to characterize the structures of electrosprayed dimer complexes M(2+)Trp(2) of tryptophan with a series of eight doubly charged metal ions, including alkaline earths Ca, Sr, and Ba, and

  4. Tryptophan as a link between psychopathology and somatic states

    NARCIS (Netherlands)

    Russo, Sascha; Kema, Ido P; Fokkema, M Rebecca; Boon, Jim C; Willemse, Pax H B; de Vries, Elisabeth G E; den Boer, Johannes A; Korf, Jakob

    2003-01-01

    OBJECTIVE: Several somatic illnesses are associated with psychiatric comorbidity. Evidence is provided that availability of the essential amino acid tryptophan, which is the precursor of serotonin, may cause this phenomenon. METHODS: We performed a database search to find relevant articles published

  5. Association between Tryptophan Hydroxylase 2 Gene Polymorphism and Completed Suicide

    Science.gov (United States)

    Fudalej, Sylwia; Ilgen, Mark; Fudalej, Marcin; Kostrzewa, Grazyna; Barry, Kristen; Wojnar, Marcin; Krajewski, Pawel; Blow, Frederic; Ploski, Rafal

    2010-01-01

    The association between suicide and a single nucleotide polymorphism (rs1386483) was examined in the recently identified tryptophan hydroxylase 2 (TPH2) gene. Blood samples of 143 suicide victims and 162 age- and sex-matched controls were examined. The frequency of the TT genotype in the TPH2 polymorphism was higher in suicide victims than in…

  6. Preliminary study: voluntary food intake in dogs during tryptophan supplementation.

    Science.gov (United States)

    Fragua, Víctor; González-Ortiz, Gemma; Villaverde, Cecilia; Hervera, Marta; Mariotti, Valentina Maria; Manteca, Xavier; Baucells, María Dolores

    2011-10-01

    Tryptophan, a precursor of important molecules such as serotonin, melatonin and niacin, is an essential amino acid for dogs. In pigs, tryptophan supplementation has been shown to induce a significant increase in food intake. The aim of the present study was to assess whether long-term tryptophan supplementation increases voluntary food intake in dogs and to observe whether this was accompanied by a change in serum ghrelin. In the present study, sixteen adult Beagle dogs were used, with four male and four female dogs fed diets supplemented with tryptophan (1 g/dog per d) during 81 d (Trp) and four male and four female dogs that were not supplemented (control). A voluntary food intake test was performed during 5 d following the supplementation period. The Trp group tended to show a higher food intake during the voluntary food intake test (58.0 (SE 5.37) v. 77.5 (SE 3.65) g/kg metabolic weight per d; P = 0.074). No significant differences were found for serum ghrelin concentrations.

  7. Palladium(II)-catalyzed oxidation of L-tryptophan by ...

    Indian Academy of Sciences (India)

    The rate law associated with the reaction mechanism is derived. Keywords. Kinetics; oxidation; L-tryptophan; hexacyanoferrate(III); palladium(II). 1. Introduction. A large number of kinetic investigations on the oxida- tion of amino acids are being carried out using various oxidants under different experimental conditions1–16.

  8. Fluorescence resonance energy transfer from tryptophan in human ...

    Indian Academy of Sciences (India)

    TECS

    and free energy change for the process have been reported. The AODIQ–HSA complex results in fluores- cence resonance energy transfer (FRET) from the tryptophan moiety of HSA to the probe. The critical energy-transfer distance (R0) for FRET and the Stern–Volmer constant (Ksv) for the fluorescence quench- ing of the ...

  9. Analysis of Grain Protein, Tryptophan and Lysine Contents of Quality ...

    African Journals Online (AJOL)

    Maize proteins, however, have poor nutritional value for humans, because of reduced content of essential amino acids such as lysine, tryptophan and threonine. Maize proteins contain on an average about 2% lysine, which is less than one-half of the concentration recommended for human nutrition. Therefore, healthy diets ...

  10. Palladium (II)-catalyzed oxidation of L-tryptophan by ...

    Indian Academy of Sciences (India)

    A first order dependence in [hexacyanoferrate(III)] and fractional-first order dependences in both [L-tryptophan] and [palladium(II)] were obtained. The reaction exhibits fractional-second order kinetics with respect to [H+]. Reaction rate increased with increase in ionic strength and dielectric constant of the medium. The effect ...

  11. Confirmation of antibodies against L-tryptophan-like epitope in ...

    African Journals Online (AJOL)

    Rachel Oneya

    2016-09-07

    Sep 7, 2016 ... test based on this synthetic epitope, especially in combination with other tests, might improve the HAT diagnostic test in field conditions. Key words: Tryptophan, enzyme-linked immunosorbent assay (ELISA), human African trypanosomosis, serological diagnostic. INTRODUCTION. Trypanosoma brucei ...

  12. Isolation and characterization of arginine ester hydrolase from Heloderma horridum (beaded lizard) venom.

    Science.gov (United States)

    Nikai, T; Imai, K; Komori, Y; Sugihara, H

    1992-03-01

    1. An arginine ester hydrolase was isolated from Heloderma horridum (beaded lizard) venom by Sephadex G-75, DEAE-Sephacel and Q-Sepharose column chromatography, resulting in 5.4 mg of purified enzyme from 320.0 mg of crude venom. 2. The enzyme was shown to be homogeneous by both SDS and non-SDS disc electrophoresis on polyacrylamide gel at pH 8.3. 3. The enzyme possesses arginine ester hydrolase and transglutaminase-like activities, but did not exhibit clotting activity. 4. Molecular weight was determined to be ca 29 kDa, with an isoelectric point of 4.4. 5. The enzyme was stable to heat treatment (95 degrees C, 10 min) and to pH changes over the range 2-11. 6. The arginine ester hydrolase was inactivated by diisopropylfluorophosphate (DFP), beta-mercaptoethanol and N-bromosuccinimide, suggesting that serine, disulfide bonds and tryptophan are involved in enzymatic activity. 7. Amino terminal sequences were determined and appear to be similar to porcine pancreatic kallikrein.

  13. INDOLEAMINE 2,3-DIOXYGENASE INDUCES EXPRESSION OF A NOVEL TRYPTOPHAN TRANSPORTER IN MOUSE AND HUMAN TUMOR CELLS1

    Science.gov (United States)

    Silk, Jonathan D.; Lakhal, Samira; Laynes, Robert; Vallius, Laura; Karydis, Ioannis; Marcea, Cornelius; Boyd, C. A. Richard; Cerundolo, Vincenzo

    2011-01-01

    Indoleamine 2,3 dioxygenase (IDO) is the rate-limiting enzyme in the kynurenine pathway, catabolizing tryptophan to kynurenine. Tryptophan depletion by IDO expressing tumors is a common mechanism of immune evasion inducing regulatory T cells and inhibiting effector T cells. As mammalian cells cannot synthesize tryptophan, it remains unclear how IDO positive tumor cells overcome the detrimental effects of local tryptophan depletion. We demonstrate that IDO positive tumor cells express a novel amino acid transporter, which accounts for approximately 50% of the tryptophan uptake. The induced transporter is biochemically distinguished from the constitutively expressed tryptophan transporter System L by increased resistance to inhibitors of System L, resistance to inhibition by high concentrations of most amino acids tested, and high substrate specificity for tryptophan. Under conditions of low extracellular tryptophan, expression of this novel transporter significantly increases tryptophan entry into IDO positive tumors relative to tryptophan uptake through the low affinity System L alone, and further decreases tryptophan levels in the microenvironment. Targeting this additional tryptophan transporter could be a way of pharmacological inhibition of IDO mediated tumor escape. These findings highlight the ability of IDO-expressing tumor cells to thrive in a tryptophan depleted microenvironment by expressing a novel, highly tryptophan-specific transporter, which is resistant to inhibition by most other amino acids. The additional transporter allows tumor cells to strike the ideal balance between supply of tryptophan essential for their own proliferation and survival, and depleting the extracellular milieu of tryptophan to inhibit T cell proliferation. PMID:21742973

  14. Laser Desorption of Tryptophan from Tryptophan-HCl Salt on a Graphite Substrate

    Energy Technology Data Exchange (ETDEWEB)

    Jeong, Hae Jun; Kim, Jeong Jin; Kang, Hyuk [Ajou University, Suwon (Korea, Republic of)

    2016-03-15

    Laser spectroscopy of biological molecules in the gas phase has been pioneered by Levy and coworkers when they first produced a supersonic molecular beam of tryptophan (Trp) and obtained its electronic spectrum. They were able to obtain enough vapor pressure needed for spectroscopy by heating a powder sample of Trp, although a special thermal spray was used to minimize fragmentation during heating. Many amine compounds, including biomolecules like amino acids and peptides, are usually available only as HCl salt form in order to prevent oxidation in air. Chemical processing is required to recover a neutral amine compound from its salt, thus limiting the applicability of laser-desorption spectroscopy of biomolecules. The experimental setup is a standard molecular beam machine composed of a pulsed valve with a laser-desorption module in a vacuum chamber, a second buffer chamber, a skimmer that separates the first and the second chambers, and a third vacuum chamber that is a time-of-flight mass spectrometer (TOF MS)

  15. Consumption of peptide-included and free tryptophan induced by peroxyl radicals: A kinetic study.

    Science.gov (United States)

    Fuentes, E; López-Alarcón, C

    2014-10-01

    It is well-known that tryptophan residues are efficiently oxidized by peroxyl radicals, generating kynurenine, and N-formyl kynurenine as well as hydroperoxide derivatives as products. In the present work we studied the kinetic of such reaction employing free and peptide-included tryptophan. Two azocompounds were used to produce peroxyl radicals: AAPH (2,2'-Azobis(2-methylpropionamidine) dihydrochloride) and ABCVA (4,4'-Azobis(4-cyanovaleric acid)), which generate cationic and anionic peroxyl radicals, respectively. Tryptophan consumption was assessed by fluorescence spectroscopy and the reactions were carried out in phosphate buffer (75mM, pH 7.4) at 45°C. Only a slight effect of the peroxyl radical charge was evidenced on the consumption of free tryptophan and the dipeptide Gly-Trp. Employing AAPH as peroxyl radical source, at low free tryptophan concentrations (1-10µM) near 0.3 mol of tryptophan were consumed per each mol of peroxyl radicals introduced into the system. However, at high free tryptophan concentrations (100µM-1mM) such stoichiometry increased in a tryptophan concentration-way. At 1mM three moles of tryptophan were consumed per mol of AAPH-derived peroxyl radicals, evidencing the presence of chain reactions. A similar behavior was observed when di and tri-peptides (Gly-Trp, Trp-Gly, Gly-Trp-Gly, Trp-Ala, Ala-Trp-Ala) were studied. Nonetheless, at low initial concentration (5µM), the initial consumption rate of tryptophan included in the peptides was two times higher than free tryptophan. In contrast, at high concentration (1mM) free and peptide-included tryptophan showed similar initial consumption rates. These results could be explained considering a disproportionation process of tryptophanyl radicals at low free tryptophan concentrations, a process that would be inhibited when tryptophan is included in peptides. Copyright © 2014. Published by Elsevier Inc.

  16. Increased serum free tryptophan in patients with diarrhea-predominant irritable bowel syndrome.

    Science.gov (United States)

    Christmas, David M; Badawy, Abdulla A-B; Hince, Dana; Davies, Simon J C; Probert, Christopher; Creed, Tom; Smithson, John; Afzal, Muhammad; Nutt, David J; Potokar, John P

    2010-10-01

    Irregularities of serotonin function in irritable bowel syndrome (IBS) may be due to changes in the metabolism of the serotonin precursor l-tryptophan. Dietary alteration of tryptophan intake may impact upon the mood and bowel symptoms of IBS. We hypothesized that diarrhea-predominant irritable bowel syndrome (d-IBS) patients would exhibit an increase in plasma tryptophan due to alterations in tryptophan metabolism. We also hypothesized that a diet low in tryptophan would reverse this change and reduce symptoms. Thirteen patients with d-IBS had fasting serum free and total tryptophan, large neutral amino acids, and 6 kynurenine metabolites measured before and after 2 weeks of a strict dairy-free diet. Baseline tryptophan parameters were compared with an age- and sex-matched control group. Changes in the specific tryptophan parameters before and after dairy-free diet were correlated with symptoms of IBS and mood. Compared with the control group, d-IBS patients at baseline exhibited significantly higher free serum tryptophan (10.5 ± 4.35 vs 4.75 ± 2.43 μmol/L [means ± standard deviation], P = .006) and significantly lower tryptophan dioxygenase and total tryptophan oxidation as measured by the kynurenine to free tryptophan and total kynurenines to free tryptophan ratios (23.37 ± 10.12 vs 55.33 ± 16.02, P < .001 and 49.34 ± 17.84 vs 258.46 ± 98.67, P < .001, respectively). Dairy-free diet did not modulate metabolites of the kynurenine pathway or symptoms. Tryptophan metabolism along the kynurenine pathway is inhibited in d-IBS, and a dairy-free diet does not alter this. Our findings are consistent with possible enhanced serotonin activity in d-IBS. Copyright © 2010 Elsevier Inc. All rights reserved.

  17. Studies on tryptophan residues of Abrus agglutinin. Stopped-flow kinetics of modification and fluorescence-quenching studies.

    OpenAIRE

    Patanjali, S R; Swamy, M J; Surolia, A

    1987-01-01

    The presence of two essential tryptophan residues/molecule was implicated in the binding site of Abrus agglutinin [Patanjali, Swamy, Anantharam, Khan & Surolia (1984) Biochem. J. 217, 773-781]. A detailed study of the stopped-flow kinetics of the oxidation of tryptophan residues revealed three classes of tryptophan residues in the native protein. A discrete reorganization of tryptophan residues revealed three classes of tryptophan residues in the native protein. A discrete reorganization of t...

  18. Ester Tuiksoo. Proua Suhkru kibedad päevad / Ester Tuiksoo ; interv. Piret Tali

    Index Scriptorium Estoniae

    Tuiksoo, Ester, 1965-

    2005-01-01

    Põllumajandusminister Ester Tuiksoo, kellel peagi täitub ministri ametis aasta Euroopa Liidu suhkrutrahvist, maaettevõtlusest, põllumajandusest, Euroopa Liidu toetustest, ministri elu- ja teenistuskäigust. Lisa: Ester Tuiksoo

  19. Method of making a cyanate ester foam

    Science.gov (United States)

    Celina, Mathias C.; Giron, Nicholas Henry

    2014-08-05

    A cyanate ester resin mixture with at least one cyanate ester resin, an isocyanate foaming resin, other co-curatives such as polyol or epoxy compounds, a surfactant, and a catalyst/water can react to form a foaming resin that can be cured at a temperature greater than 50.degree. C. to form a cyanate ester foam. The cyanate ester foam can be heated to a temperature greater than 400.degree. C. in a non-oxidative atmosphere to provide a carbonaceous char foam.

  20. Steroidal esters from Ferula sinkiangensis.

    Science.gov (United States)

    Li, Guangzhi; Li, Xiaojin; Cao, Li; Shen, Liangang; Zhu, Jun; Zhang, Jing; Wang, Junchi; Zhang, Lijing; Si, Jianyong

    2014-09-01

    Two new steroidal esters with an unusual framework, Sinkiangenorin A and B, a new organic acid glycoside, Sinkiangenorin C, and four known lignin compounds were isolated from the seeds of Ferula sinkiangensis. The structures of these compounds were established by spectroscopic analysis and single-crystal X-ray diffraction. All of the isolated compounds were tested against Hela, K562 and AGS human cancer cell lines. Sinkiangenorin C showed cytotoxic activity against AGS cells with an IC50 of 36.9 μM. Copyright © 2014 Elsevier B.V. All rights reserved.

  1. Tryptophan Synthase Uses an Atypical Mechanism To Achieve Substrate Specificity.

    Science.gov (United States)

    Buller, Andrew R; van Roye, Paul; Murciano-Calles, Javier; Arnold, Frances H

    2016-12-27

    Tryptophan synthase (TrpS) catalyzes the final steps in the biosynthesis of l-tryptophan from l-serine (Ser) and indole-3-glycerol phosphate (IGP). We report that native TrpS can also catalyze a productive reaction with l-threonine (Thr), leading to (2S,3S)-β-methyltryptophan. Surprisingly, β-substitution occurs in vitro with a 3.4-fold higher catalytic efficiency for Ser over Thr using saturating indole, despite a >82000-fold preference for Ser in direct competition using IGP. Structural data identify a novel product binding site, and kinetic experiments clarify the atypical mechanism of specificity: Thr binds efficiently but decreases the affinity for indole and disrupts the allosteric signaling that regulates the catalytic cycle.

  2. Archetypal tryptophan-rich antimicrobial peptides: properties and applications.

    Science.gov (United States)

    Shagaghi, Nadin; Palombo, Enzo A; Clayton, Andrew H A; Bhave, Mrinal

    2016-02-01

    Drug-resistant microorganisms ('superbugs') present a serious challenge to the success of antimicrobial treatments. Subsequently, there is a crucial need for novel bio-control agents. Many antimicrobial peptides (AMPs) show a broad-spectrum activity against bacteria, fungi or viruses and are strong candidates to complement or substitute current antimicrobial agents. Some AMPs are also effective against protozoa or cancer cells. The tryptophan (Trp)-rich peptides (TRPs) are a subset of AMPs that display potent antimicrobial activity, credited to the unique biochemical properties of tryptophan that allow it to insert into biological membranes. Further, many Trp-rich AMPs cross bacterial membranes without compromising their integrity and act intracellularly, suggesting interactions with nucleic acids and enzymes. In this work, we overview some archetypal TRPs derived from natural sources, i.e., indolicidin, tritrpticin and lactoferricin, summarising their biochemical properties, structures, antimicrobial activities, mechanistic studies and potential applications.

  3. Kynurenines: Tryptophan's metabolites in exercise, inflammation, and mental health.

    Science.gov (United States)

    Cervenka, Igor; Agudelo, Leandro Z; Ruas, Jorge L

    2017-07-28

    Kynurenine metabolites are generated by tryptophan catabolism and regulate biological processes that include host-microbiome signaling, immune cell response, and neuronal excitability. Enzymes of the kynurenine pathway are expressed in different tissues and cell types throughout the body and are regulated by cues, including nutritional and inflammatory signals. As a consequence of this systemic metabolic integration, peripheral inflammation can contribute to accumulation of kynurenine in the brain, which has been associated with depression and schizophrenia. Conversely, kynurenine accumulation can be suppressed by activating kynurenine clearance in exercised skeletal muscle. The effect of exercise training on depression through modulation of the kynurenine pathway highlights an important mechanism of interorgan cross-talk mediated by these metabolites. Here, we discuss peripheral mechanisms of tryptophan-kynurenine metabolism and their effects on inflammatory, metabolic, oncologic, and psychiatric disorders. Copyright © 2017 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. No claim to original U.S. Government Works.

  4. Evidence for an altered tryptophan metabolism in fibromyalgia.

    Science.gov (United States)

    Schwarz, M J; Offenbaecher, M; Neumeister, A; Ewert, T; Willeit, M; Praschak-Rieder, N; Zach, J; Zacherl, M; Lossau, K; Weisser, R; Stucki, G; Ackenheil, M

    2002-12-01

    Fibromyalgia (FM) is a prevalent syndrome with chronic pain and a hypothesized underlying disturbance of the tryptophan (TRP) metabolism. We performed a tryptophan depletion (TD) test in 17 FM patients and 17 controls. TRP, 5-hydroxyindoleacetic acid (5-HIAA), kynurenine (KYN), and interleukin-6 (IL-6) were measured. Additionally pain perception was monitored in the FM patients. FM patients and controls exhibited a decrease of TRP and KYN during TD. 5-HIAA levels also decreased in all controls and in 11 FM patients, but showed a marked increase in 6 FM patients. IL-6 significantly increased during TD in the patients, but not in the controls. Pain perception was not affected in the FM patients. These data demonstrate an altered TRP metabolism in a subgroup of FM patients, where the TD seems to activate 5-HT metabolism. Our findings may have diagnostic as well as therapeutic implications in the field of fibromyalgia.

  5. Experimental evaluation of an altered tryptophan metabolism in fibromyalgia.

    Science.gov (United States)

    Schwarz, Markus J; Offenbaecher, Martin; Neumeister, Alexander; Ackenheil, Manfred

    2003-01-01

    Fibromyalgia (FM) is a prevalent syndrome with chronic pain and a hypothesised underlying disturbance of the tryptophan (TRP) metabolism. We performed a tryptophan depletion (TD) test in 17 FM patients and 17 controls. TRP, 5-hydroxyindoleacetic acid (5-HIAA), kynurenine (KYN), and Interleukin-6 (IL-6) were measured. Additionally pain perception was monitored in the FM patients. FM patients and controls exhibited a decrease of TRP and KYN during TD. 5-HIAA levels also decreased in all controls and in 11 FM patients, but showed a marked increase in 6 FM patients. IL-6 significantly increased during TD in the patients, but not in the controls. Pain perception was not affected in the FM patients. These data demonstrate an altered TRP metabolism in a subgroup of FM patients, where the TD seems to activate 5-HT metabolism and IL-6 production. Our findings may have diagnostic as well as therapeutic implications in the field of fibromyalgia.

  6. Digestible tryptophan requirements of meat quails in the growth phase

    Directory of Open Access Journals (Sweden)

    Ana Paula Silva Ton

    2012-05-01

    Full Text Available The objective of this experiment was to estimate the digestible tryptophan (DTrp requirements for growing meat quails. In the first experiment (1-14 days of age, 1,950 quails were distributed in a completely randomized design, with six levels of DTrp (0.27; 0.30; 0.33; 0.36; 0.39 and 0.42% of diet, five replications and 65 quails per experimental unit. There was a linear increase of feed intake, tryptophan intake, weight gain and body weight with the DTrp levels increase. In the second experiment (15-35 days of age, 1,350 quails were distributed in a completely randomized design, with six levels of DTrp (0.22; 0.25; 0.28; 0.31; 0.34 and 0.37% of diet, five replications and 45 quails per experimental unit. There was a linear increase for tryptophan intake, carcass yield, ash levels and protein deposition rate with the DTrp levels increase. In the third experiment (28-35 days of age, conducted to determine the nitrogen balance, 150 males were housed in galvanized wire cages featuring drinker, feeder and individual metal tray lined with plastic to collect the excreta. The design was completely randomized, with six levels of DTrp (0.22; 0.25; 0.28; 0.31; 0.34 and 0.37% of diet, five replicates and five quails per experimental unit. Linear decrease was observed on the nitrogen balance and metabolization coefficient with the DTrp levels increase. The nutritional requirement of digestible tryptophan for maximum growing of meat quail, in the period from 1 to 14 days of age, is higher or equal to 0.42%; in the period from 15 to 35 days, it is 0.22%.

  7. Gramicidin tryptophans mediate formamidinium-induced channel stabilization

    OpenAIRE

    Seoh, S.A.; Busath, D.

    1995-01-01

    Compared with alkali metal cations, formamidinium ions stabilize the gramicidin A channel molecule in monoolein bilayers (Seoh and Busath, 1993a). A similar effect is observed with N-acetyl gramicidin channel molecules in spite of the modified forces at the dimeric junction (Seoh and Busath, 1993b). Here we use electrophysiological measurements with tryptophan-to-phenylalanine-substituted gramicidin analogs to show that the formamidinium-induced channel molecule stabilization is eliminated wh...

  8. Isoform-Specific Substrate Inhibition Mechanism of Human Tryptophan Hydroxylase.

    Science.gov (United States)

    Tidemand, Kasper D; Peters, Günther H; Harris, Pernille; Stensgaard, Eva; Christensen, Hans E M

    2017-11-21

    Tryptophan hydroxylase (TPH) catalyzes the initial and rate-limiting step in the biosynthesis of serotonin, which is associated with a variety of disorders such as depression and irritable bowel syndrome. TPH exists in two isoforms: TPH1 and TPH2. TPH1 catalyzes the initial step in the synthesis of serotonin in the peripheral tissues, while TPH2 catalyzes this step in the brain. In this study, the steady-state kinetic mechanism for the catalytic domain of human TPH1 has been determined. Varying substrate tryptophan (Trp) and tetrahydrobiopterin (BH 4 ) results in a hybrid Ping Pong-ordered mechanism in which the reaction can either occur through a Ping Pong or a sequential mechanism depending on the concentration of tryptophan. The catalytic domain of TPH1 shares a sequence identity of 81% with TPH2. Despite the high sequence identity, differences in the kinetic parameters of the isoforms have been identified; i.e., only TPH1 displays substrate tryptophan inhibition. This study demonstrates that the difference can be traced to an active site loop which displays different properties in the TPH isoforms. Steady-state kinetic results of the isoforms, and variants with point mutations in a loop lining the active site, show that the kinetic parameters of only TPH1 are significantly changed upon mutations. Mutations in the active site loop of TPH1 result in an increase in the substrate inhibition constant, K i , and therefore turnover rate. Molecular dynamics simulations reveal that this substrate inhibition mechanism occurs through a closure of the cosubstrate, BH 4 , binding pocket, which is induced by Trp binding.

  9. Self-Assembly, Surface Activity and Structure of n-Octyl-β-D-thioglucopyranoside in Ethylene Glycol-Water Mixtures

    Directory of Open Access Journals (Sweden)

    Cristóbal Carnero Ruiz

    2013-02-01

    Full Text Available The effect of the addition of ethylene glycol (EG on the interfacial adsorption and micellar properties of the alkylglucoside surfactant n-octyl-β-D-thioglucopyranoside (OTG has been investigated. Critical micelle concentrations (cmc upon EG addition were obtained by both surface tension measurements and the pyrene 1:3 ratio method. A systematic increase in the cmc induced by the presence of the co-solvent was observed. This behavior was attributed to a reduction in the cohesive energy of the mixed solvent with respect to pure water, which favors an increase in the solubility of the surfactant with EG content. Static light scattering measurements revealed a decrease in the mean aggregation number of the OTG micelles with EG addition. Moreover, dynamic light scattering data showed that the effect of the surfactant concentration on micellar size is also controlled by the content of the co-solvent in the system. Finally, the effect of EG addition on the microstructure of OTG micelles was investigated using the hydrophobic probe Coumarin 153 (C153. Time-resolved fluorescence anisotropy decay curves of the probe solubilized in micelles were analyzed using the two-step model. The results indicate a slight reduction of the average reorientation time of the probe molecule with increasing EG in the mixed solvent system, thereby suggesting a lesser compactness induced by the presence of the co-solvent.

  10. Study of interactions between octyl-β-D-glucopyranoside and the hydroxyethyl-cellulose biopolymer in aqueous solution

    International Nuclear Information System (INIS)

    Villegas-Pañeda, Ximena; Pérez-Casas, Silvia; Hernández-Baltazar, Efrén; Chávez-Castellanos, Angel E.

    2014-01-01

    Graphical abstract: - Highlights: • Interactions in mixed micelles to be used as drug carriers were studied. • We tested this system to nanoencapsulate the metronidazole as a drug model. • Characteristic concentrations for the micelle formation process were obtained. • The micelles formation in all cases is spontaneous, and entropy driven. • Thermodynamic properties of demicellization for the mixed micelles were determined. - Abstract: (Surfactant + polymer) systems play an important role in drug delivery. They control the drug release rate by improving solubility, minimizing degradation, contributing to the reduction of toxicity and facilitating drug administration. Physicochemical properties of surfactant/polymer systems used in controlled drug release are affected by the composition of the mixture. The study of the physicochemical behavior of these mixtures allows the design of more suitable drug pharmaceutical formulation according to its chemical structure. In this paper, critical micelle concentration (CMC), saturation concentration (C 2 ), critical aggregation concentration (CAC) and thermodynamic parameters, such as enthalpy (ΔH), Gibbs free energy (ΔG) and the temperature multiplied by entropy (TΔS) for the demicellization process were determined by isothermal titration calorimetry (ITC), for octyl-β-D-glucopyranoside (OGP) and hydroxyethyl-cellulose (HEC) aqueous solutions in order to construct a phase diagram suitable for the study of the interactions in each region and to choose the appropriate system for drug delivery. The interpretation of the results is supported by the analysis of particle size measurements by dynamic light scattering (DLS)

  11. Development of Octyl Methoxy Cinnamates (OMC/Silicon Dioxide (SiO2 Nanoparticles by Sol-Gel Emulsion Method

    Directory of Open Access Journals (Sweden)

    Pey-Shiuan Wu

    2017-12-01

    Full Text Available Although octyl methoxy cinnamates (OMC is the most used Ultraviolet B (UVB filter in sunscreen, it has poor light stability in emulsion system. In this study, OMC/SiO2 nanoparticles were prepared via sol-gel emulsion method. Tetraethoxy silane (TEOS was used as the silica source to encapsulate OMC. Modification of experimental parameters such as stirring speed of condensation reaction and emulsion condition, pH value of acid-catalyzed, surfactant and different percentage of TEOS and OMC, adding of OMC and surfactant to different phase may affect the particle size, and yield and entrapment efficiency in preparation process of OMC/SiO2 nanoparticles. Concluding all the parameter, we found that when condensation reaction and emulsion conditions are at 1000 rpm, pH 1.5, Span 80/Tween 20, TEOS/OMC ratios 1:1, OMC and surfactants added in oil phase, resulting in smaller particle sizes 476.5 nm, higher yield 95.8%, and higher entrapment efficiency 61.09%. Fourier transform infrared (FTIR analysis demonstrated that OMC/SiO2 nanoparticles were successfully prepared. In vitro release profile supposed that OMC/SiO2 nanoparticles can delay OMC releasing and had 60.83% decreasing of cumulative amount. Therefore, the OMC/SiO2 nanoparticles have the potential to develop as new sunscreen materials in the use for cosmetics field in the future.

  12. All-Polymer Photovoltaic Devices of Poly(3-(4- n -octyl)-phenylthiophene) from Grignard Metathesis (GRIM) Polymerization

    KAUST Repository

    Holcombe, Thomas W.

    2009-10-14

    (Graph Presented) The synthesis of poly[3-(4-n-octyl)-phenylthiophene] (POPT) from Grignard Metathesis (GRIM) is reported. GRIM POPT is found to have favorable electronic, optical, and processing properties for organic photovoltaics (OPVs). Space-charge limited current and field effect transistor measurements for POPT yielded hole mobilities of 1 × 10-4 cm2/(V s) and 0.05 cm2/(V s), respectively. Spincasting GRIM POPT from chlorobenzene yields a thin film with a 1.8 eV band gap, and PC61BM:POPT bulk heterojection devices provide a peak performance of 3.1%. Additionally, an efficiency of 2.0% is achieved in an all-polymer, bilayer OPV using poly[2-methoxy-5-(2′-ethylhexyloxy)-1,4-(1-cyanovinylene) phenylene] (CNPPV) as an acceptor. This state-of-the-art all-polymer device is analyzed in comparison to the analogous poly(3-hexylthiophene) (P3HT)/CNPPV device. Counter to expectations based on more favorable energy level alignment, greater active layer light absorption, and similar hole mobility, P3HT/CNPPV devices perform less well than POPT/CNPPV devices with a peak efficiency of 0.93%. © 2009 American Chemical Society.

  13. Development of Octyl Methoxy Cinnamates (OMC)/Silicon Dioxide (SiO2) Nanoparticles by Sol-Gel Emulsion Method

    Science.gov (United States)

    Wu, Pey-Shiuan; Lee, Yi-Ching; Kuo, Yi-Ching

    2017-01-01

    Although octyl methoxy cinnamates (OMC) is the most used Ultraviolet B (UVB) filter in sunscreen, it has poor light stability in emulsion system. In this study, OMC/SiO2 nanoparticles were prepared via sol-gel emulsion method. Tetraethoxy silane (TEOS) was used as the silica source to encapsulate OMC. Modification of experimental parameters such as stirring speed of condensation reaction and emulsion condition, pH value of acid-catalyzed, surfactant and different percentage of TEOS and OMC, adding of OMC and surfactant to different phase may affect the particle size, and yield and entrapment efficiency in preparation process of OMC/SiO2 nanoparticles. Concluding all the parameter, we found that when condensation reaction and emulsion conditions are at 1000 rpm, pH 1.5, Span 80/Tween 20, TEOS/OMC ratios 1:1, OMC and surfactants added in oil phase, resulting in smaller particle sizes 476.5 nm, higher yield 95.8%, and higher entrapment efficiency 61.09%. Fourier transform infrared (FTIR) analysis demonstrated that OMC/SiO2 nanoparticles were successfully prepared. In vitro release profile supposed that OMC/SiO2 nanoparticles can delay OMC releasing and had 60.83% decreasing of cumulative amount. Therefore, the OMC/SiO2 nanoparticles have the potential to develop as new sunscreen materials in the use for cosmetics field in the future. PMID:29215572

  14. Development of Octyl Methoxy Cinnamates (OMC)/Silicon Dioxide (SiO₂) Nanoparticles by Sol-Gel Emulsion Method.

    Science.gov (United States)

    Wu, Pey-Shiuan; Lee, Yi-Ching; Kuo, Yi-Ching; Lin, Chih-Chien

    2017-12-07

    Although octyl methoxy cinnamates (OMC) is the most used Ultraviolet B (UVB) filter in sunscreen, it has poor light stability in emulsion system. In this study, OMC/SiO₂ nanoparticles were prepared via sol-gel emulsion method. Tetraethoxy silane (TEOS) was used as the silica source to encapsulate OMC. Modification of experimental parameters such as stirring speed of condensation reaction and emulsion condition, pH value of acid-catalyzed, surfactant and different percentage of TEOS and OMC, adding of OMC and surfactant to different phase may affect the particle size, and yield and entrapment efficiency in preparation process of OMC/SiO₂ nanoparticles. Concluding all the parameter, we found that when condensation reaction and emulsion conditions are at 1000 rpm, pH 1.5, Span 80/Tween 20, TEOS/OMC ratios 1:1, OMC and surfactants added in oil phase, resulting in smaller particle sizes 476.5 nm, higher yield 95.8%, and higher entrapment efficiency 61.09%. Fourier transform infrared (FTIR) analysis demonstrated that OMC/SiO₂ nanoparticles were successfully prepared. In vitro release profile supposed that OMC/SiO₂ nanoparticles can delay OMC releasing and had 60.83% decreasing of cumulative amount. Therefore, the OMC/SiO₂ nanoparticles have the potential to develop as new sunscreen materials in the use for cosmetics field in the future.

  15. Dispersive liquid-liquid microextraction of silver nanoparticles in water using ionic liquid 1-octyl-3-methylimidazolium hexafluorophosphate.

    Science.gov (United States)

    Chen, Sha; Sun, Yuanjing; Chao, Jingbo; Cheng, Liping; Chen, Yun; Liu, Jingfu

    2016-03-01

    Using the ionic liquid (IL) 1-octyl-3-methylimidazolium hexafluorophosphate as the extractant and methanol as the dispersion solvent, a dispersive liquid-liquid microextraction method was developed to extract silver nanoparticles (AgNPs) from environmental water samples. Parameters that influenced the extraction efficiency such as IL concentration, pH and extraction time were optimized. Under the optimized conditions, the highest extraction efficiency for AgNPs was above 90% with an enrichment factor of >90. The extracted AgNPs in the IL phase were identified by transmission electron microscopy and ultraviolet-visible spectroscopy, and quantified by inductively coupled plasma mass spectrometry after microwave digestion, with a detection limit of 0.01μg/L. The spiked recovery of AgNPs was 84.4% with a relative standard deviation (RSD) of 3.8% (n=6) at a spiked level of 5μg/L, and 89.7% with a RSD of 2.2% (n=6) at a spiked level of 300μg/L, respectively. Commonly existed environmental ions had a very limited influence on the extraction efficiency. The developed method was successfully applied to the analysis of AgNPs in river water, lake water, and the influent and effluent of a wastewater treatment plant, with recoveries in the range of 71.0%-90.9% at spiking levels of 0.11-4.7μg/L. Copyright © 2015. Published by Elsevier B.V.

  16. Altered placental tryptophan metabolic pathway in human fetal growth restriction.

    Science.gov (United States)

    Murthi, Padma; Wallace, Euan M; Walker, David W

    2017-04-01

    Tryptophan is a substrate for kynurenine pathway metabolism in the placenta. We investigated if kynurenine metabolites change over gestation, if they are different between pregnancies with normal and fetal growth restriction (FGR), and if the oxygen environment modulated kynurenine pathway activity in the human placenta. Tryptophan, kynurenine, and downstream kynurenine metabolites were determined in maternal venous blood, umbilical cord blood, and placental samples obtained in 1st and 3rd trimester pregnancies including FGR, and in the media of placental explants incubated with 20% or 5-8% O 2 for 24, 48 or 72 h. All the major kynurenine metabolites were present in cord blood, and in general were higher than in maternal blood. IDO and TDO mRNA and protein expression, responsible for kynurenine production from tryptophan, were significantly lower in placentas from FGR pregnancies compared with control. Explants prepared from 1st and 3rd trimester placentas actively produced all the major kynurenine pathway metabolites which, together with expression of IDO, TDO, KYN-OHase and 3HAO mRNAs, were significantly lower after 24 h exposure to 5-8% O 2 compared to 20% O 2 CONCLUSIONS: Expression and activity of the kynurenine pathway is present in the placenta from early gestation, and is down-regulated by hypoxia and in FGR pregnancies. Copyright © 2017 Elsevier Ltd. All rights reserved.

  17. Tryptophan-Rich and Proline-Rich Antimicrobial Peptides

    Directory of Open Access Journals (Sweden)

    Awdhesh Kumar Mishra

    2018-04-01

    Full Text Available Due to the increasing emergence of drug-resistant pathogenic microorganisms, there is a world-wide quest to develop new-generation antibiotics. Antimicrobial peptides (AMPs are small peptides with a broad spectrum of antibiotic activities against bacteria, fungi, protozoa, viruses and sometimes exhibit cytotoxic activity toward cancer cells. As a part of the native host defense system, most AMPs target the membrane integrity of the microorganism, leading to cell death by lysis. These membrane lytic effects are often toxic to mammalian cells and restrict their systemic application. However, AMPs containing predominantly either tryptophan or proline can kill microorganisms by targeting intracellular pathways and are therefore a promising source of next-generation antibiotics. A minimum length of six amino acids is required for high antimicrobial activity in tryptophan-rich AMPs and the position of these residues also affects their antimicrobial activity. The aromatic side chain of tryptophan is able to rapidly form hydrogen bonds with membrane bilayer components. Proline-rich AMPs interact with the 70S ribosome and disrupt protein synthesis. In addition, they can also target the heat shock protein in target pathogens, and consequently lead to protein misfolding. In this review, we will focus on describing the structures, sources, and mechanisms of action of the aforementioned AMPs.

  18. Tryptophan biosynthesis protects mycobacteria from CD4 T cell-mediated killing

    Science.gov (United States)

    Zhang, Yanjia J.; Reddy, Manchi C.; Ioerger, Thomas R.; Rothchild, Alissa C.; Dartois, Veronique; Schuster, Brian M.; Trauner, Andrej; Wallis, Deeann; Galaviz, Stacy; Huttenhower, Curtis; Sacchettini, James C.; Behar, Samuel M.; Rubin, Eric J.

    2014-01-01

    Summary Bacteria that cause disease rely on their ability to counteract and overcome host defenses. Here we present a genome-scale study of Mycobacterium tuberculosis (Mtb) that uncovers the bacterial determinants of surviving host immunity, sets of genes we term “counteractomes.” Through this, we find that CD4 T cells attempt to starve Mtb of tryptophan through a mechanism that limits Chlamydia and Leishmania infections. In those cases, tryptophan starvation works well, since those pathogens are natural tryptophan auxotrophs. Mtb, however, can synthesize tryptophan, and thus starvation fails as an Mtb-killing mechanism. We then describe a small molecule inhibitor of Mtb tryptophan synthesis, which turns Mtb into a tryptophan auxotroph and restores the efficacy of a failed host defense. Together, our findings demonstrate that the Mtb determinants for surviving host immunity—Mtb’s immune counteractomes—serve as probes of host immunity, uncovering immune-mediated stresses that can be leveraged for therapeutic discovery. PMID:24315099

  19. Preparation of Spirocyclic β-Proline Esters

    DEFF Research Database (Denmark)

    Fjelbye, Kasper; Marigo, Mauro; Clausen, Rasmus Prætorius

    2017-01-01

    A series of novel N-Bn-protected spirocyclic β-proline esters were prepared using [3+2] cycloaddition and subsequently converted into their corresponding aldehydes. In addition, two novel N-Cbz-protected spirocyclic β-proline esters were prepared using intramolecular cyclization starting from sim...

  20. Proton transfer in histidine-tryptophan heterodimers embedded in helium droplets

    Energy Technology Data Exchange (ETDEWEB)

    Bellina, Bruno; Merthe, Daniel J.; Kresin, Vitaly V. [Department of Physics and Astronomy, University of Southern California, Los Angeles, California 90089-0484 (United States)

    2015-03-21

    We used cold helium droplets as nano-scale reactors to form and ionize, by electron bombardment and charge transfer, aromatic amino acid heterodimers of histidine with tryptophan, methyl-tryptophan, and indole. The molecular interaction occurring through an N–H ⋅ ⋅ ⋅ N hydrogen bond leads to a proton transfer from the indole group of tryptophan to the imidazole group of histidine in a radical cationic environment.

  1. Digestible tryptophan levels for male broilers in pre-starter and starter diets

    Directory of Open Access Journals (Sweden)

    Bruno Samuel Borges

    2016-09-01

    Full Text Available The objective was to determine the digestible tryptophan requirements for male broilers in pre-starter and starter phases. Two experiments using 400 Cobb broilers were performed 200 males in the first experiment for the pre-starter phase (one to seven days old, and 200 males in the second experiment for the starter phase (eight to 21 days old. Chicks were housed in batter boxes made of galvanized steel as an experimental shed. The experiments were performed in a completely randomized design, with four treatments and five replicates, with ten birds each. In both experiments, the tryptophan requirement was determined using diets with different levels of digestible tryptophan. A tryptophan-deficient diet was formulated, as a basal diet, which was supplemented with increased levels of L-tryptophan in order to achieve the desirable digestible tryptophan levels. Treatments consisted of 0.209% (basal diet; 0.223%; 0.235% and 0.248% digestible tryptophan for the pre-starter phase (experiment 1 and 0.187% (basal diet; 0.200%, 0.211% and 0.223% digestible tryptophan for the starter phase (experiment 2. We evaluated feed intake, weight gain and feed conversion, as well as the metabolizability of feed nutrients. The performance and metabolic data were subjected to analysis of variance, and estimates of digestible tryptophan levels were made through polynomial regression models at 5% probability. There was no significant difference between the digestible tryptophan levels in the diet over performance and digestibility in both treatments. It is possible to conclude that the basal diet with 0.209% digestible tryptophan for the pre-starter phase and 0.187% for the starter phase, at a tryptophan: lysine ratio of 16%, as sufficient to meet the broilers requirements.

  2. Suppression of aggression in rainbow trout (Oncorhynchus mykiss) by dietary L-tryptophan.

    Science.gov (United States)

    Winberg, S; Øverli, Ø; Lepage, O

    2001-11-01

    Juvenile rainbow trout Oncorhynchus mykiss were isolated in individual compartments in observation aquaria and allowed to acclimate for 1 week, during which they were fed commercial trout feed. Thereafter, the fish were tested for aggressive behaviour using a resident/intruder test. Following this first resident/intruder test, the feed was exchanged for an experimental wet feed supplemented with 0.15 % or 1.5 % L-tryptophan (by wet mass). Controls received the same feed but without L-tryptophan supplementation. The fish were fed to satiety daily, and their individual feed intake was recorded. Aggressive behaviour was quantified again after 3 and 7 days of L-tryptophan feeding using the resident/intruder test. Feeding the fish L-tryptophan-supplemented feed for 3 days had no effect on aggressive behaviour, whereas feeding the fish L-tryptophan-supplemented feed for 7 days significantly suppressed aggressive behaviour in the fish, an effect seen at both levels of L-tryptophan supplementation. Fish fed L-tryptophan-supplemented feed showed elevated plasma and brain levels of L-tryptophan. The amino acid L-tryptophan is the precursor of serotonin, and supplementary dietary L-tryptophan was found to elevate levels of 5-hydroxyindoleacetic acid (5-HIAA) and the 5-HIAA/serotonin concentration ratio in the brain. Neither feed intake nor plasma cortisol level was significantly affected by dietary L-tryptophan. Central serotonin is believed to have an inhibitory effect on aggressive behaviour, and it is suggested that the suppressive effect of dietary L-tryptophan on aggressive behaviour is mediated by an elevation of brain serotonergic activity.

  3. Anticholinesterase activity of fluorochloronitroacetic acid esters

    Energy Technology Data Exchange (ETDEWEB)

    Ivanov, Yu.Ya.; Brel, V.K. Martynov, I.V.

    1984-11-01

    Results are presented from pharmacologic and biochemical experiments leading to the conclusion that fluorochloronitroacetic acid esters have anticholinesterase activity. Since the esters caused muscular weakness in mice, experiments were performed on isolated tissue preparation. The biochemical experiments consisted of finding the biomolecular constants of irreversible inhibition of acetylcholinesterase by the esters, using acetylcholinesterase from human erythrocytes, as well as horse serum cholinesterase. The ethyl and n-propyl esters of halogen nitroacetic acid were used in all experiments. It was found that the propyl ester caused an increase in the force of individual contractions in the isolated muscle specimens, plus an inability of the muscle to retain tetanus. The substances were determined to have an anticholinesterase effect. The mechanism of cholinesterase inhibition is not yet known. It is probable that the substances acylate the serine hydroxyl of the esterase center of the cholinestersase. 7 references, 1 figure.

  4. Enhanced enzymatic degradation of tryptophan by indoleamine 2,3-dioxygenase contributes to the tryptophan-deficient state seen after major trauma.

    Science.gov (United States)

    Pellegrin, Katharina; Neurauter, Gabriele; Wirleitner, Barbara; Fleming, Arthur W; Peterson, Verlyn M; Fuchs, Dietmar

    2005-03-01

    Decreased lymphocyte proliferation, lymphopenia, immunodepression, and opportunistic infections are common after major trauma. Early alimentation in these patients corrects lymphopenia, enhances immunity, and reduces the incidence of infections, but the underlying mechanisms are poorly understood. Tryptophan is essential for the production and function of rapidly proliferating cells such as lymphocytes. Tryptophan is enzymatically degraded by indoleamine 2,3-dioxygenase (IDO), whose activity is solely dependent on expression of interferon-gamma (IFN-gamma). Because increased expression of IFN-gamma has been reported in trauma patients, we investigated whether enhanced IDO-mediated tryptophan degradation is associated with lymphopenia and poor outcomes after major trauma. The incidence of bacteremic sepsis (BS), adult respiratory distress syndrome (ARDS), multiple organ dysfunction/failure syndromes (MODS/MOF), and death was prospectively documented in 22 trauma patients with a mean ISS of 24.9 +/- 2.2. Sequential blood samples were obtained from admission through postinjury day 10. Five patients developed BS, three of whom developed ARDS; two of the three ARDS patients developed MOF and died on day 10. Trauma patients had significantly lower tryptophan levels (days 1-10), higher kynurenine:tryptophan ratios (days 1-2), and fewer lymphocytes (days 1-4) than healthy volunteers (P < 0.05). Although patients with poor outcomes (i.e., BS, ARDS, MOF, and death) had significantly lower tryptophan levels and greater lymphopenia on several days after injury, the sample size was too small to draw any definitive conclusions. These data indicate that decreased plasma tryptophan levels and lymphopenia typically occur after major trauma. A concomitant increase in kynurenine suggests that the observed tryptophan deficiency is caused, in part, by IDO-mediated tryptophan degradation.

  5. Efficiency of n-octyl-acetate, 2-heptanone and citronellal in repelling bees from basil (Ocimum sellowii - Labiatae

    Directory of Open Access Journals (Sweden)

    Darclet Teresinha Malerbo-Souza

    2004-03-01

    Full Text Available The objective of this study was to test repellent substances for honey bees, Apis mellifera, for basil, Ocimum sellowii, and to study the most frequent insects in this crop as well as its behaviors. The frequency of honey bees did not decrease with the application of n.octyl.acetate, citronellal and 2.heptanone, used as repellents, in the concentrations 2.5, 5.0, 7.5 and 10.0% diluted in water. However, when the products (20% were diluted in water (75% and glycerine (5% were effective in repelling those bees of the basil flowers for a period of 20 minutes. The flower lasted, on average, 30 h from the bud phase until the flower withered. The flowers number opened by inflorescence was, on average, 5.65 flowers, and the inflorescence presented, on average, 160 flowers-buds. The basil was visited mainly for the honey bee (98.0%, followed by Augochloropsis electra bee - Halictidae (2.0% and visits sporadics of Diptera and Lepidoptera, collected only nectar. The honey bee frequency increased during the day to 14:00, decreasing soon after, accompanying the curve of the temperature sets registered in the experiment days.O objetivo do experimento foi estudar a polinização em manjericão (Ocimum sellowii, a fim de verificar sua atratividade para as abelhas Apis mellifera, os insetos mais freqüentes, bem como seus comportamentos e testar substâncias repelentes para as abelhas A. mellifera. A flor durou, em média, 30 horas, desde sua abertura até o murchamento. O número de flores abertas por inflorescência foi, em média, 5,65 flores, sendo que a inflorescência possuía, em média, 160 botões florais. O manjericão foi visitado quase que exclusivamente pela abelha A. mellifera africanizada (98,0%, seguida pela abelha Augochloropsis electra-Halictidae (2,0% e visitas esporádicas de dípteros e lepidópteros, sendo que todos coletavam apenas néctar. A freqüência da abelha africanizada aumentou no decorrer do dia até às 14 horas, diminuindo em

  6. A single β-octyl glucoside molecule induces HIV-1 Nef dimer formation in the absence of partner protein binding.

    Directory of Open Access Journals (Sweden)

    Mousheng Wu

    Full Text Available The HIV-1 Nef accessory protein is essential for viral pathogenicity and AIDS progression. Nef forms complexes with multiple host cell factors to facilitate viral replication and promote immune escape of HIV-infected cells. Previous X-ray crystal structures demonstrate that Nef forms homodimers, the orientation of which are influenced by host cell binding partners. In cell-based fluorescence complementation assays, Nef forms homodimers at the plasma membrane. However, recombinant Nef proteins often exist as monomers in solution, suggesting that membrane interaction may also trigger monomer to dimer transitions. In this study, we show that monomeric Nef core proteins can be induced to form dimers in the presence of low concentrations of the non-ionic surfactant, β-octyl glucoside (βOG. X-ray crystallography revealed that a single βOG molecule is present in the Nef dimer, with the 8-carbon acyl chain of the ligand binding to a hydrophobic pocket formed by the dimer interface. This Nef-βOG dimer interface involves helix αB, as observed in previous dimer structures, as well as a helix formed by N-terminal residues 54-66. Nef dimer formation is stabilized in solution by the addition of βOG, providing biochemical validation for the crystal structure. These observations together suggest that the interaction with host cell lipid mediators or other hydrophobic ligands may play a role in Nef dimerization, which has been previously linked to multiple Nef functions including host cell protein kinase activation, CD4 downregulation, and enhancement of HIV-1 replication.

  7. Photolysis of the organic UV filter, avobenzone, combined with octyl methoxycinnamate by nano-TiO2 composites.

    Science.gov (United States)

    Kim, E J; Kim, M J; Im, N R; Park, S N

    2015-08-01

    A protection of the skin from harmful UV rays is important in preventing the skin damage and skin aging when exposed to sunlight. Titanium dioxide composites are used as a UV filter in sunscreen products combined with organic compounds such as butyl methoxydibenzoyl methane (avobenzone) and octyl methoxycinnamate (OMC) to improve the function of the sunscreen. In this study, the photolysis of avobenzone and OMC caused by the photocatalytic TiO2 nano composites (NCs) is investigated. Three different types of oil/water (O/W) sunscreen formulations containing avobenzone and OMC were prepared. Each formulation contained one of three different types of surface modified TiO2 NCs, which were WP-S (small sized hydrophilic TiO2NCs, ~10nm), OP-S (small sized hydrophobic TiO2NCs, ~15nm), and OP-L (large sized hydrophobic TiO2NCs, ~200nm). The physicochemical properties of the NCs were analyzed using biophysical tools. Addition of a different size of TiO2NCs into O/W sunscreen formulations significantly increased the photolysis of OMC. Effect of quercetin on degradation of avobenzone and OMC by the NCs was also studied for all three formulations. Although the OP-S NCs showed the lowest photocatalytic ability and the highest UV blocking capability, the NCs promoted the photolysis of OMC to the greatest extent. These results can be utilized to design more effective sunscreens, which could potentially ensure optimal photo-protection. Copyright © 2015 Elsevier B.V. All rights reserved.

  8. Biochemical and genetic toxicity of the ionic liquid 1-octyl-3-methylimidazolium chloride on earthworms (Eisenia fetida).

    Science.gov (United States)

    Guo, Yingying; Liu, Tong; Zhang, Jun; Wang, Jinhua; Wang, Jun; Zhu, Lusheng; Yang, Jinhui

    2016-02-01

    Ionic liquids also known as "green solvents," are used in many fields. However, the dispersion of ionic liquids in soil systems is likely to cause damage to soil organisms. The objective of the present study was to investigate the toxicity of 1-octyl-3-methylimidazolium chloride ([C8 mim]Cl) on earthworms (Eisenia fetida). For this purpose, earthworms were exposed to different concentrations of [C8 mim]Cl (0 mg/kg, 5 mg/kg, 10 mg/kg, 20 mg/kg, and 40 mg/kg artificial soil) and sampled at 7 d, 14 d, 21 d, and 28 d. The results indicated that [C8 mim]Cl could cause an accumulation of reactive oxygen species (ROS) in earthworms, even at the lowest concentration (5 mg/kg). Compared with the controls, during the [C8 mim]Cl exposure period, the activities of superoxide dismutase (SOD) and catalase (CAT) decreased and then increased, whereas the activities of peroxidase (POD) and glutathione S-transferase (GST) increased. These changes in the activities of antioxidant enzymes and GST indicated that [C8 mim]Cl could induce oxidative damage in earthworms. The malondialdehyde content was increased by high levels of [C8 mim]Cl at 14 d and 28 d, indicating that [C8 mim]Cl could lead to lipid peroxidation in earthworms. In addition, the degree of DNA damage significantly increased with increasing [C8 mim]Cl concentrations and exposure time. The present study shows that [C8 mim]Cl caused biochemical and genetic toxicity in earthworms. © 2015 SETAC.

  9. Indolic substances in plasma, cerebrospinal fluid, and frontal cortex of human subjects infused with saline or tryptophan.

    Science.gov (United States)

    Gillman, P K; Bartlett, J R; Bridges, P K; Hunt, A; Patel, A J; Kantamaneni, B D; Curzon, G

    1981-08-01

    Psychiatric patients undergoing the psychosurgical operation of stereotactic subcaudate tractotomy were infused intravenously with either saline or L-tryptophan (15 mg/kg/h). Plasma, lumbar cerebrospinal fluid (CSF), ventricular CSF and a specimen of frontal cortex were collected. The relationships of plasma concentrations of substances claimed to influence brain tryptophan concentration (total tryptophan, free tryptophan, large neutral amino acids) with the concentration of tryptophan in the cortex and CSF were investigated. Tryptophan infusion resulted in plasma tryptophan values comparable to those found after oral doses used in treating depression or insomnia, and about sixfold increases of tryptophan in the cerebral cortex. Increased brain 5-hydroxytryptamine synthesis was indicated by significant rises of CSF 5-hydroxyindoleacetic acid. The concentration of plasma free tryptophan was a better predictor than plasma total tryptophan of cortex tryptophan concentration. As all correlation coefficients of plasma versus brain or plasma versus ventricular CSF tryptophan concentrations were decreased when allowance was made for differences of concentration of large neutral amino acids, the results suggest that the role of these substances within their physiological range as inhibitors of tryptophan transport to the brain may previously have been overemphasised.

  10. Antihypertensive and cardioprotective effects of the dipeptide isoleucine-tryptophan and whey protein hydrolysate.

    Science.gov (United States)

    Martin, M; Kopaliani, I; Jannasch, A; Mund, C; Todorov, V; Henle, T; Deussen, A

    2015-12-01

    Angiotensin-converting enzyme inhibitors are treatment of choice in hypertensive patients. Clinically used inhibitors exhibit a structural similarity to naturally occurring peptides. This study evaluated antihypertensive and cardioprotective effects of ACE-inhibiting peptides derived from food proteins in spontaneously hypertensive rats. Isoleucine-tryptophan (in vitro IC50 for ACE = 0.7 μm), a whey protein hydrolysate containing an augmented fraction of isoleucine-tryptophan, or captopril was given to spontaneously hypertensive rats (n = 60) over 14 weeks. Two further groups, receiving either no supplement (Placebo) or intact whey protein, served as controls. Systolic blood pressure age-dependently increased in the Placebo group, whereas the blood pressure rise was effectively blunted by isoleucine-tryptophan, whey protein hydrolysate and captopril (-42 ± 3, -38 ± 5, -55 ± 4 mm Hg vs. Placebo). At study end, myocardial mass was lower in isoleucine-tryptophan and captopril groups but only partially in the hydrolysate group. Coronary flow reserve (1 μm adenosine) was improved in isoleucine-tryptophan and captopril groups. Plasma ACE activity was significantly decreased in isoleucine-tryptophan, hydrolysate and captopril groups, but in aortic tissue only after isoleucine-tryptophan or captopril treatment. This was associated with lowered expression and activity of matrix metalloproteinase-2. Following isoleucine-tryptophan and captopril treatments, gene expression of renin was significantly increased indicating an active feedback within renin-angiotensin system. Whey protein hydrolysate and isoleucine-tryptophan powerfully inhibit plasma ACE resulting in antihypertensive effects. Moreover, isoleucine-tryptophan blunts tissue ACE activity, reduces matrix metalloproteinase-2 activity and improves coronary flow reserve. Thus, whey protein hydrolysate and particularly isoleucine-tryptophan may serve as innovative food additives with the goal of attenuating

  11. Dendritic biomimicry: microenvironmental hydrogen-bonding effects on tryptophan fluorescence.

    Science.gov (United States)

    Koenig, S; Müller, L; Smith, D K

    2001-03-02

    Two series of dendritically modified tryptophan derivatives have been synthesised and their emission spectra measured in a range of different solvents. This paper presents the syntheses of these novel dendritic structures and discusses their emission spectra in terms of both solvent and dendritic effects. In the first series of dendrimers, the NH group of the indole ring is available for hydrogen bonding, whilst in the second series, the indole NH group has been converted to NMe. Direct comparison of the emission wavelengths of analogous NH and NMe derivatives indicates the importance of the Kamlet-Taft solvent beta3 parameter, which reflects the ability of the solvent to accept a hydrogen bond from the NH group, an effect not possible for the NMe series of dendrimers. For the NH dendrimers, the attachment of a dendritic shell to the tryptophan subunit leads to a red shift in emission wavelength. This dendritic effect only operates in non-hydrogen-bonding solvents. For the NMe dendrimers, however, the attachment of a dendritic shell has no effect on the emission spectra of the indole ring. This proves the importance of hydrogen bonding between the branched shell and the indole NH group in causing the dendritic effect. This is the first time a dendritic effect has been unambiguously assigned to individual hydrogen-bonding interactions and indicates that such intramolecular interactions are important in dendrimers, just as they are in proteins. Furthermore, this paper sheds light on the use of tryptophan residues as a probe of the microenvironment within proteins--in particular, it stresses the importance of hydrogen bonds formed by the indole NH group.

  12. Gallium uptake in tryptophan-related pulmonary disease

    International Nuclear Information System (INIS)

    Kim, S.M.; Park, C.H.; Intenzo, C.M.; Patel, R.

    1991-01-01

    We describe a patient who developed fever, fatigue, muscle weakness, dyspnea, skin rash, and eosinophilia after taking high doses of tryptophan for insomnia for two years. A gallium-67 scan revealed diffuse increased uptake in the lung and no abnormal uptake in the muscular distribution. Bronchoscopy and biopsy confirmed inflammatory reactions with infiltration by eosinophils, mast cells, and lymphocytes. CT scan showed an interstitial alveolar pattern without fibrosis. EMG demonstrated diffuse myopathy. Muscle biopsy from the right thigh showed an inflammatory myositis with eosinophilic and lymphocytic infiltrations

  13. Chiral Discrimination of Tryptophan Enantiomers via (1R, 2R-2-Amino-1, 2-Diphenyl Ethanol Modified Interface

    Directory of Open Access Journals (Sweden)

    Juan Zhou

    2011-01-01

    Full Text Available The paper reported that a simple chiral selective interface constructed by (1R, 2R-2-amino-1, 2-diphenyl ethanol had been developed to discriminate tryptophan enantiomers. Cyclic voltammetry (CV and electrochemical impedance spectroscopy (EIS were used for the characteristic analysis of the electrode. The results indicated that the interface showed stable and sensitive property to determine the tryptophan enantiomers. Moreover, it exhibited the better stereoselectivity for L-tryptophan than that for D-tryptophan. The discrimination characteristics of the chiral selective interface for discriminating tryptophan enantiomers, including the response time, the effect of tryptophan enantiomers concentration, and the stability, were investigated in detail. In addition, the chiral selective interface was used to determine the enantiomeric composition of L- and D-tryptophan enantiomer mixtures by measuring the relative change of the peak current as well as in pure enantiomeric solutions. These results suggested that the chiral selective interface has the potential for enantiomeric discrimination of tryptophan enantiomers.

  14. Synthesis of Trimethylolpropane Esters of Calophyllum Methyl Esters : Effect of Temperature and Molar Ratio

    Directory of Open Access Journals (Sweden)

    Yeti Widyawati

    2014-12-01

    Full Text Available Trimethylolpropane esters were synthesized by transesterification of calophyllum methyl esters and trimethylolpropane using a calcium oxide as the catalyst. The results showed that the optimal reaction conditions (temperature: 130 0C, reaction time: 5 h, reactant molar ratio: 3.9:1, catalyst amount 3%w/w, and formed  trimethylolpropane ester of 79.0% were obtained. The basic physicochemical properties of the trimethylolpropane esters were the following : kinematic viscosities of 56.40 cSt and 8.8 cSt at 40 0C and 100 0C,  viscosity index 193, flash point 218 0C and pour point -3 0C. So Methyl esters of fatty acids of would callophylum  methyl ester is good raw material for the synthesis of lubricating oils.

  15. Results of correlation of values of individual behaviour of rats with liver tryptophan pyrrolase activity.

    Science.gov (United States)

    Tikal, K; Kunz, K

    1976-01-01

    A significant negative correlation was found between the individual animal's horizontal activity in an open field and liver tryptophan pyrrolase (LTP) activity. On the other hand, the duration of immobility in an open field correlated postively and significantly with liver tryptophan pyrrolase activity.

  16. Low plasma tryptophan in carcinoid patients is associated with increased urinary cortisol excretion

    NARCIS (Netherlands)

    Tanke, Marit A. C.; Kema, Ido P.; Dijck-Brouwer, Janneke; Doornbos, Bennard; De Vries, Elisabeth G. E.; Korf, Jakob

    2008-01-01

    Background: Previously we observed inpatients suffering from a metastatic carcinoid tumor that irritability, aggression and lack of impulse control are associated with Low levels of plasma tryptophan and presumably with low brain serotonin function. In rats we showed that a diet of low tryptophan

  17. Stereospecific effects of intraduodenal tryptophan on pyloric and duodenal motility in humans

    NARCIS (Netherlands)

    Edelbroek, M.; Sun, W. M.; Horowitz, M.; Dent, J.; Smout, A.; Akkermans, L.

    1994-01-01

    BACKGROUND: L-Tryptophan delays gastric emptying in animals to a greater extent than D-tryptophan, but none of the possible motor mechanisms responsible for this stereospecific effect have been evaluated. METHODS: In 11 healthy volunteers antropyloroduodenal pressures were recorded in the fasted

  18. Tryptophan end-tagging for promoted lipopolysaccharide interactions and anti-inflammatory effects

    DEFF Research Database (Denmark)

    Singh, Shalini; Datta, Aritreyee; Schmidtchen, Artur

    2017-01-01

    The objective of the present study is the investigation of possibilities for boosting peptide anti-inflammatory effects by tryptophan end-tagging, including identification of underlying mechanisms for this. In doing so, effects of tryptophan end-tagging of KYE21 (KYEITTIHNLFRKLTHRLFRR), a peptide...

  19. The association of sleep quality and insomnia with dietary intake of tryptophan and niacin

    NARCIS (Netherlands)

    Verster, J.; Fernstrand, A.; Bury, D.; Roth, T.; Garssen, J.

    2015-01-01

    Introduction: Dietary intake of tryptophan and niacin have been related to sleep. However, the sleep-promoting effects of these nutrients are still under investigation. The aim of the current study was to examine the relationship between daily dietary intake of tryptophan and niacin and sleep.

  20. Stochastic Resonance Activity Influences Serum Tryptophan Metabolism in Healthy Human Subjects

    Directory of Open Access Journals (Sweden)

    Berthold Kepplinger

    2011-01-01

    Full Text Available Background Stochastic resonance therapy (SRT is used for rehabilitation of patients with various neuropsychiatric diseases. An alteration in tryptophan metabolism along the kynurenine pathway has been identified in the central and peripheral nervous systems in patients with neuroinflammatory and neurodegenerative diseases and during the aging process. This study investigated the effect of SRT as an exercise activity on serum tryptophan metabolites in healthy subjects. Methods Serum L-tryptophan, L-kynurenine, kynurenic acid, and anthranilic acid levels were measured one minute before SRT and at one, 5, 15, 30, and 60 minutes after SRT. We found that SRT affected tryptophan metabolism. Serum levels of L-tryptophan, L-kynurenine, and kynurenic acid were significantly reduced for up to 60 minutes after SRT. Anthranilic acid levels were characterized by a moderate, non significant transient decrease for up to 15 minutes, followed by normalization at 60 minutes. Tryptophan metabolite ratios were moderately altered, suggesting activation of metabolism after SRT. Lowering of tryptophan would generally involve activation of tryptophan catabolism and neurotransmitter, protein, and bone biosynthesis. Lowering of kynurenic acid by SRT might be relevant for improving symptoms in patients with neuropsychiatric disorders, such as Parkinson's disease, Alzheimer's disease, schizophrenia, and depression, as well as certain pain conditions.

  1. L-Tryptophan Production by Auxotrophic and Analogue Resistant Mutants of

    Directory of Open Access Journals (Sweden)

    A. Roy

    2011-01-01

    Full Text Available A number of tyrosine plus phenylalanine double auxotrophic mutants were isolated by N-methyl-N-nitro-N-nitrosoguanidine (MNNG treatment of a locally isolated strain of Aureobacterium flavescens of which 11A 39 and 11A 17 were selected on the basis of their tryptophan production in a mineral salt medium over other isolated mutant strains. The mutational block in the aromatic amino acid biosynthetic pathway of the selected double auxotrophs were determined. By controlling pH of the production medium to near neutrality, the active growth period could be extended up to 72 h and more tryptophan was accumulated compared to pH unregulated culture where the active growth ceased after 48 h. Further improvement of the tryptophan production has been achieved by stepwise isolation of a mutant strain resistant to the tryptophan analogues p-fluorotryptophan (FT and 5-methyl tryptophan (MT from the 11A 39 . Demand for L-tryptophan as food additive and therapeutic agent is increasing day by day throughout the World, particularly in the underdeveloped and developing countries like India. Still to date India depends on other countries for L-tryptophan. The aim of this work is to develop a potent high yielding, feed back insensitive mutant strain and optimization of its medium pH for maximum production of tryptophan.

  2. Cobalt-catalyzed hydrogenation of esters to alcohols: unexpected reactivity trend indicates ester enolate intermediacy.

    Science.gov (United States)

    Srimani, Dipankar; Mukherjee, Arup; Goldberg, Alexander F G; Leitus, Gregory; Diskin-Posner, Yael; Shimon, Linda J W; Ben David, Yehoshoa; Milstein, David

    2015-10-12

    The atom-efficient and environmentally benign catalytic hydrogenation of carboxylic acid esters to alcohols has been accomplished in recent years mainly with precious-metal-based catalysts, with few exceptions. Presented here is the first cobalt-catalyzed hydrogenation of esters to the corresponding alcohols. Unexpectedly, the evidence indicates the unprecedented involvement of ester enolate intermediates. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  3. Ortho-substituent correlated retention of polychlorinated biphenyls on a 50% n-octyl-methylpolysiloxane stationary phase by HRGC/MSD

    Energy Technology Data Exchange (ETDEWEB)

    Fischer, R.; Ballschmiter, K.

    1988-11-01

    Polychlorinated biphenyls (PCB) have been known as ubiquitous environmental pollutants since the late 60s. They are found partitioned between all environmental compartments according to their physico-chemical properties. Investigation of their partitioning, degradation, and transport behaviour demands sensitive and selective analytical methods for this complex mixture of up to 209 theoretically possible compounds. Congener-specific separation by high-resolution gas chromatography coupled with mass-selective detection would be a suitable approach to this multi-compound problem. In this paper, the separation of PCB congeners by capillary gas chromatography (HRGC) on a 50% n-octyl-methylpolysiloxane phase is presented.

  4. Effects of pre- and postnatal exposure to the UV-filter Octyl Methoxycinnamate (OMC) on the reproductive, auditory and neurological development of rat offspring

    DEFF Research Database (Denmark)

    Petersen, Marta Axelstad; Boberg, Julie; Hougaard, Karin Sørig

    2011-01-01

    Octyl Methoxycinnamate (OMC) is a frequently used UV-filter in sunscreens and other cosmetics. The aim of the present study was to address the potential endocrine disrupting properties of OMC, and to investigate how OMC induced changes in thyroid hormone levels would be related to the neurological......, postnatal growth and timing of sexual maturation were assessed. On postnatal day 16, gene expression in prostate and testes, and weight and histopathology of the thyroid gland, liver, adrenals, prostate, testes, epididymis and ovaries were measured. After weaning, offspring were evaluated in a battery...... through usage of sunscreens and other cosmetics....

  5. 21 CFR 172.854 - Polyglycerol esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Polyglycerol esters of fatty acids. 172.854 Section... HUMAN CONSUMPTION Multipurpose Additives § 172.854 Polyglycerol esters of fatty acids. Polyglycerol esters of fatty acids, up to and including the decaglycerol esters, may be safely used in food in...

  6. Inhibiting tryptophan metabolism enhances interferon therapy in kidney cancer.

    Science.gov (United States)

    Trott, Josephine F; Kim, Jeffrey; Abu Aboud, Omran; Wettersten, Hiromi; Stewart, Benjamin; Berryhill, Grace; Uzal, Francisco; Hovey, Russell C; Chen, Ching-Hsien; Anderson, Katie; Graef, Ashley; Sarver, Aaron L; Modiano, Jaime F; Weiss, Robert H

    2016-10-11

    Renal cell carcinoma (RCC) is increasing in incidence, and a complete cure remains elusive. While immune-checkpoint antibodies are promising, interferon-based immunotherapy has been disappointing. Tryptophan metabolism, which produces immunosuppressive metabolites, is enhanced in RCC. Here we show indolamine-2,3-dioxygenase-1 (IDO1) expression, a kynurenine pathway enzyme, is increased not only in tumor cells but also in the microenvironment of human RCC compared to normal kidney tissues. Neither kynurenine metabolites nor IDO inhibitors affected the survival or proliferation of human RCC or murine renal cell adenocarcinoma (RENCA) cells in vitro. However, interferon-gamma (IFNγ) induced high levels of IDO1 in both RCC and RENCA cells, concomitant with enhanced kynurenine levels in conditioned media. Induction of IDO1 by IFNα was weaker than by IFNγ. Neither the IDO1 inhibitor methyl-thiohydantoin-DL-tryptophan (MTH-trp) nor IFNα alone inhibited RENCA tumor growth, however the combination of MTH-trp and IFNα reduced tumor growth compared to IFNα. Thus, the failure of IFNα therapy for human RCC is likely due to its inability to overcome the immunosuppressive environment created by increased IDO1. Based on our data, and given that IDO inhibitors are already in clinical trials for other malignancies, IFNα therapy with an IDO inhibitor should be revisited for RCC.

  7. Tryptophan-functionalized gold nanoparticles for deep UV imaging of microbial cells.

    Science.gov (United States)

    Pajović, Jelena D; Dojčilović, Radovan; Božanić, Dušan K; Kaščáková, Slavka; Réfrégiers, Matthieu; Dimitrijević-Branković, Suzana; Vodnik, Vesna V; Milosavljević, Aleksandar R; Piscopiello, Emanuela; Luyt, Adriaan S; Djoković, Vladimir

    2015-11-01

    Biocompatible fluorescent nanostructures were prepared by a functionalization of gold nanoparticles with the amino acid tryptophan. The gold-tryptophan bioconjugates were investigated by TEM and HRTEM and various spectroscopy methods (XPS, FTIR, UV-vis and photoluminescence). It was found that the gold nanoparticles, initially 8 nm in diameter, aggregate in the presence of the amino acid. From the XPS and FTIR spectroscopy results, it was concluded that the tryptophan gold interactions mainly take place via indole and carboxyl groups. Although the indole group is involved in the interaction with the gold surfaces, the tryptophan-gold hybrids showed strong fluorescence due to the presence of multilayers of tryptophan. Deep ultra violet (DUV) imaging performed at the SOLEIL synchrotron showed that it is possible to detect these hybrid nanostructures within Escherichia coli cells. Copyright © 2015 Elsevier B.V. All rights reserved.

  8. Lower Levels of Cervicovaginal Tryptophan Are Associated With Natural Clearance of Chlamydia in Women.

    Science.gov (United States)

    Jordan, Stephen J; Olson, Kristin M; Barnes, Stephen; Wilson, Landon S; Berryhill, Taylor F; Bakshi, Rakesh; Brown, LaDraka' T; Press, Christen G; Geisler, William M

    2017-06-15

    Chlamydiatrachomatis (Ct) infection causes significant morbidity. In vitro studies demonstrate that Ct growth inhibition occurs by interferon-gamma (IFN-γ)-mediated depletion of intracellular tryptophan, and some Ct strains utilize extracellular indole to restore tryptophan levels. Whether tryptophan levels are associated with Ct infection clearance in humans remains unknown. We evaluated tryptophan, indole, and IFN-γ levels in cervicovaginal lavages from women with either naturally cleared or persisting Ct infection. Women who cleared infection had significantly lower tryptophan levels and trended toward lower IFN-γ levels compared to women with persisting infection. Due to its volatility, indole was not measurable in either group. © The Author 2017. Published by Oxford University Press for the Infectious Diseases Society of America. All rights reserved. For permissions, e-mail: journals.permissions@oup.com.

  9. Pharmacokinetics of Ketorolac Pentyl Ester, a Novel Ester Derivative of Ketorolac, in Rabbits

    Directory of Open Access Journals (Sweden)

    Jann-Inn Tzeng

    2005-08-01

    Full Text Available Ketorolac is a potent nonsteroidal anti-inflammatory drug. Recently, a novel ester of ketorolac, ketorolac pentyl ester, was synthesized. When prepared in injectable oil, the new agent demonstrated a long duration of action. Ketorolac pentyl ester was synthesized using a prodrug design by esterification of ketorolac, and appeared to be a prodrug of ketorolac in vivo, which needed to be confirmed. The aim of the present study was to establish the prodrug's pharmacokinetics in vivo, and to confirm whether or not ketorolac pentyl ester was a prodrug of ketorolac. Pharmacokinetic profiles of intravenous ketorolac and its pentyl ester on an equal-molar basis in six rabbits were evaluated. A high-performance liquid chromatographic method was used to determine the plasma concentrations of ketorolac and its pentyl ester. We found that the plasma concentrations of ketorolac pentyl ester declined rapidly after injection and so did the conversion of ketorolac pentyl ester to ketorolac. Also, the conversion of ketorolac was proved complete when compared with intravenous ketorolac under an equi-molar basis. In conclusion, this in vivo pharmacokinetic study confirmed that keterolac pentyl ester was a prodrug of keterolac.

  10. Isolation and characterization of horridum toxin with arginine ester hydrolase activity from Heloderma horridum (beaded lizard) venom.

    Science.gov (United States)

    Nikai, T; Imai, K; Sugihara, H; Tu, A T

    1988-07-01

    A hemorrhagic toxin with lethal and arginine ester hydrolytic activities was isolated from Heloderma horridum (beaded lizard) venom by Sephadex G-75, DEAE-Sephacel, and Q-Sepharose column chromatography. The hemorrhagic toxin was shown to be homogeneous as demonstrated by a single band on acrylamide gel electrophoresis and immunodiffusion. Its molecular weight is approximately 31,000 with an isoelectric point of 3.9. Hemorrhagic, lethal, and benzoyl-L-arginine ethyl ester hydrolytic activities of this preparation were inhibited by diisopropyl fluorophosphate (DFP), N-bromosuccinimide, and beta-mercaptoethanol, suggesting that serine, tryptophan, and disulfide bonds are involved in these activities. Also there was an increase in creatine kinase activity in mice serum which is an indicator that the toxin is involved in muscle damage. This protein was stable to heat and pH ranges between 2 and 11. The Michaelis constant (Km), for benzoyl-L-arginine ethyl ester, and inhibition constant (Ki), for DFP, were found to be 6.9 X 10(-3) and 1.93 X 10(-4) M, respectively.

  11. Conversion of carbohydrates to levulinic acid esters

    DEFF Research Database (Denmark)

    2014-01-01

    The present invention relates to the field of converting carbohydrates into levulinic acid, a platform chemical for many chemical end products. More specifically the invention relates to a method for converting carbohydrates such as mono-, di- or polysaccharides, obtained from for example biomass...... production into a suitable levulinic acid ester in the presence of a zeolite or zeotype catalyst and a suitable alcohol, and the ester may be further converted into levulinic acid if desired....

  12. The influence of tri-n-octyl phosphine oxide and extraction stage on purification of Thorium concentrate

    International Nuclear Information System (INIS)

    M-V-Purwani; Moch-Setyadji

    2015-01-01

    The extraction of thorium oxalate concentrate as processing product of monazite using Tri Octyl Phosphine Oxide (TOPO) has been done. The most impurities contained in thorium oxalate concentrate are Ce (cerium) and La (lanthanum). The purpose of this study is to purify Th by separating Ce and La using extraction process. The extraction is done by batch and multistage. The solution of feed or water phase is 10 grams of Th oxalate concentrate dissolved in 10.08 M HNO 3 so that the volume becomes 100 mL and the organic phase is TOPO in kerosene. Stripping in each stage conducted three times, first stripping use water, second stripping use 5 % oxalic acid and the third stripping use water. Extraction time at every stage is 15 minutes and stripping time at every stage is 5 minutes with ratio of aqueous phase to organic phase = 1 : 1 . The parameters were studied % TOPO - kerosene and number of extraction stage. The optimum usage of TOPO in kerosene is 5 %. On extraction I obtained Ce concentrate and on extraction II and III obtained Th concentrates. The extraction II efficiency of Th is 39.76 % and extraction III efficiency of Th is 26.33 % . Coefficient of distribution (Kd) of Th in stage II is 0.7587 and Kd of Th in stage III is 1.0096. Total extraction efficiency of Th is 80.08 %, total extraction efficiency of Ce is 56.12 %, and total extraction efficiency of La is 1.54 %. The separation factor of Th – Ce in extraction I is 1.00 and separation factor of Th – La in extraction I is 92.0, separation factor of Th – Ce in extraction II is 250.24, and separation factor of Th – La in extraction II is ∞. Separation factor of Th – Ce in extraction III is 124.22 and separation factor of Th – La in extraction III is ∞. Total separation factor of Th – Ce is 1.4270 and total separation factor of Th – La is 4.0459. The content of Th oxalate in stripping product from the extraction II is 97.06 % and in stripping product from the extraction III is 98

  13. Allied, MGC link on cyanate esters

    International Nuclear Information System (INIS)

    Wood, A.

    1993-01-01

    In the latest of a line of joint ventures in its plastics business, Allied Signal has reached agreement with Mitsubishi Gas Chemical (MGC) to jointly develop thermoset cyanate ester resins and blends. The deal will involve further development of Allied Signal's Primaset phenol-formaldehyde cyanate ester resins, a new entrant in the thermoset arena. Although the Primaset resins were discovered in the 1960s, this would be the first time they are available commercially. The deal will marry Primaset technology with MGC's Skylex bisphenol A cyanate ester resins, says Fred DiAntonis, director/advanced materials at Allied Signal. The two firms are looking at marketing blends of the two materials. The potential market for these resins, used commercially by the electronics industry in printed circuit boards and by the aerospace industry in composites, is significant, says Robert P. Viarengo, Allied Signal president/performance materials. By aligning ourselves with MGC, the world leader in cyanate ester resin, we anticipate moving forward aggressively. The main competitor is Ciba, which acquired bisphenol A cyanate ester resins with its purchase of Rhone-Poulenc's high temperature resins business. DiAntonis estimates the market for cyanate ester resins could be worth $150 million by the end of the decade, although development costs have been in the tens of millions of dollars range

  14. Allenyl esters as quenching agents for ruthenium olefin metathesis catalysts.

    Science.gov (United States)

    Roy, Animesh; Silvestri, Maximilian A; Hall, Robert A; Lepore, Salvatore D

    2017-01-04

    In the attempt to synthesize substituted allenyl esters through a metathesis coupling of unsubstituted allenyl esters and alkenes using a variety of ruthenium catalysts, it was discovered that allenyl esters themselves cleanly arrested the activity of the catalysts. Further studies suggests possible utility of allene esters as general quenching agents for metathesis reactions. To explore this idea, several representative olefin metathesis reactions, including ring closing, were successfully terminated by the addition of simple allenyl esters for more convenient purification.

  15. Desorption of Lipases Immobilized on Octyl-Agarose Beads and Coated with Ionic Polymers after Thermal Inactivation. Stronger Adsorption of Polymers/Unfolded Protein Composites

    Directory of Open Access Journals (Sweden)

    Jose J. Virgen-Ortíz

    2017-01-01

    Full Text Available Lipases from Candida antarctica (isoform B and Rhizomucor miehei (CALB and RML have been immobilized on octyl-agarose (OC and further coated with polyethylenimine (PEI and dextran sulfate (DS. The enzymes just immobilized on OC supports could be easily released from the support using 2% SDS at pH 7, both intact or after thermal inactivation (in fact, after inactivation most enzyme molecules were already desorbed. The coating with PEI and DS greatly reduced the enzyme release during thermal inactivation and improved enzyme stability. However, using OC-CALB/RML-PEI-DS, the full release of the immobilized enzyme to reuse the support required more drastic conditions: a pH value of 3, a buffer concentration over 2 M, and temperatures above 45 °C. However, even these conditions were not able to fully release the thermally inactivated enzyme molecules from the support, being necessary to increase the buffer concentration to 4 M sodium phosphate and decrease the pH to 2.5. The formation of unfolded protein/polymers composites seems to be responsible for this strong interaction between the octyl and some anionic groups of OC supports. The support could be reused five cycles using these conditions with similar loading capacity of the support and stability of the immobilized enzyme.

  16. Experimental and theoretical study on the oxidation mechanism of dopamine in n-octyl pyridinium based ionic liquids–carbon paste modified electrodes

    International Nuclear Information System (INIS)

    Díaz, Carlos; García, Camilo; Iturriaga-Vásquez, Patricio; Aguirre, Maria Jesús; Muena, Juan Pablo; Contreras, Renato; Ormazábal-Toledo, Rodrigo; Isaacs, Mauricio

    2013-01-01

    This work describes the influence of n-octyl pyridinium cations based ionic liquids–carbon paste modified electrodes on the oxidation mechanism of dopamine. Ionic liquids formed by hexafluorophosphate anion and n-octyl pyridinium [R-OPy] + ; R = CH 3 , H, CF 3 , where ionic liquids containing CH 3 and CF 3 are new products, were synthesized and characterized. Modified carbon paste electrodes with these salts were characterized by electrochemical impedance spectroscopy and cyclic voltammetry. Electrochemical oxidation of dopamine was studied in PBS buffer solution at pH = 7.4. The influence of the ionic liquids in the oxidation of dopamine was studied by cyclic voltammetry and rotating disk electrode. The results show that typical carbon paste electrode presents an electrochemical/chemical mechanism; whereas [OPy]PF 6 and [CF 3 -OPy]PF 6 modified electrodes present an electrochemical/chemical/electrochemical mechanism. The experimental study is complemented with a theoretical analysis of substituent effects in terms of the molecular electrostatic potential, Mulliken population analysis and second order perturbation theory probed at the cation moiety of the IL. These indices consistently show an electron density accumulation at the ipso position of the pyridinium moiety of the IL that is in agreement with the electrochemical characterization

  17. Methyl esters from vegetable oils with hydroxy fatty acids: Comparison of lesquerella and castor methyl esters

    Science.gov (United States)

    The search for alternative feedstocks for biodiesel as partial replacement for petrodiesel has recently extended to castor oil. In this work, the castor oil methyl esters were prepared and their properties determined in comparison to the methyl esters of lesquerella oil, which in turn is seen as alt...

  18. Increased Tryptophan Metabolism Is Associated With Activity of Inflammatory Bowel Diseases.

    Science.gov (United States)

    Nikolaus, Susanna; Schulte, Berenice; Al-Massad, Natalie; Thieme, Florian; Schulte, Dominik M; Bethge, Johannes; Rehman, Ateequr; Tran, Florian; Aden, Konrad; Häsler, Robert; Moll, Natalie; Schütze, Gregor; Schwarz, Markus J; Waetzig, Georg H; Rosenstiel, Philip; Krawczak, Michael; Szymczak, Silke; Schreiber, Stefan

    2017-12-01

    Administration of tryptophan and some of its metabolites reduces the severity of colitis in mice, whereas removing tryptophan from the diet increases susceptibility to colitis. Transfer of the intestinal microbiome transfers the colitogenic phenotype from tryptophan starved animals to normally nourished mice. We aimed to systematically evaluate serum levels of tryptophan and its metabolites in patients with inflammatory bowel diseases (IBD), and study their association with clinical and serologic features. We studied 535 consecutive patients with IBD (211 with ulcerative colitis [UC], 234 with Crohn's disease [CD]; 236 male), enrolled in Germany from August 2013 through April 2014 and followed until July 2016. Serum samples were collected from patients and 291 matched individuals without IBD (controls); levels of tryptophan were measured using high-performance liquid chromatography. Metabolites of tryptophan were measured in serum from 148 patients and 100 controls by mass spectrometry. We measured levels of interleukin 22 in serum from 28 patients by enzyme-linked immunosorbent assay. Paired stool and serum samples were collected from a subset of patients with active UC (n = 10) or CD (n = 8) to investigate associations between serum levels of tryptophan and composition of the fecal microbiota, analyzed by 16S ribosomal DNA amplicon sequencing. We used real-time polymerase chain reaction to measure levels of messenger RNAs in colonic biopsies from 60 patients with UC, 50 with CD, and 30 controls. We collected information on patients' disease activity scores, medications, laboratory assessments, and clinical examinations during recruitment and follow-up visits. Serum levels of tryptophan were significantly lower in patients with IBD than in controls (P = 5.3 × 10 -6 ) with a stronger reduction in patients with CD (vs control; P = 1.1 × 10 -10 ) than UC (vs control; P = 2.8 × 10 -3 ). We found a negative correlation between serum levels of tryptophan and

  19. Tryptophan overloading activates brain regions involved with cognition, mood and anxiety.

    Science.gov (United States)

    Silva, Luana C A; Viana, Milena B; Andrade, José S; Souza, Melyssa A; Céspedes, Isabel C; D'Almeida, Vânia

    2017-01-01

    Tryptophan is the only precursor of serotonin and mediates serotonergic activity in the brain. Previous studies have shown that the administration of tryptophan or tryptophan depletion significantly alters cognition, mood and anxiety. Nevertheless, the neurobiological alterations that follow these changes have not yet been fully investigated. The aim of this study was to verify the effects of a tryptophan-enriched diet on immunoreactivity to Fos-protein in the rat brain. Sixteen male Wistar rats were distributed into two groups that either received standard chow diet or a tryptophan-enriched diet for a period of thirty days. On the morning of the 31st day, animals were euthanized and subsequently analyzed for Fos-immunoreactivity (Fos-ir) in the dorsal and median raphe nuclei and in regions that receive serotonin innervation from these two brain areas. Treatment with a tryptophan-enriched diet increased Fos-ir in the prefrontal cortex, nucleus accumbens, paraventricular hypothalamus, arcuate and ventromedial hypothalamus, dorsolateral and dorsomedial periaqueductal grey and dorsal and median raphe nucleus. These observations suggest that the physiological and behavioral alterations that follow the administration of tryptophan are associated with the activation of brain regions that regulate cognition and mood/anxiety-related responses.

  20. Was the Chlamydial Adaptative Strategy to Tryptophan Starvation an Early Determinant of Plastid Endosymbiosis?

    Science.gov (United States)

    Cenci, Ugo; Ducatez, Mathieu; Kadouche, Derifa; Colleoni, Christophe; Ball, Steven G

    2016-01-01

    Chlamydiales were recently proposed to have sheltered the future cyanobacterial ancestor of plastids in a common inclusion. The intracellular pathogens are thought to have donated those critical transporters that triggered the efflux of photosynthetic carbon and the consequent onset of symbiosis. Chlamydiales are also suspected to have encoded glycogen metabolism TTS (Type Three Secretion) effectors responsible for photosynthetic carbon assimilation in the eukaryotic cytosol. We now review the reasons underlying other chlamydial lateral gene transfers evidenced in the descendants of plastid endosymbiosis. In particular we show that half of the genes encoding enzymes of tryptophan synthesis in Archaeplastida are of chlamydial origin. Tryptophan concentration is an essential cue triggering two alternative modes of replication in Chlamydiales. In addition, sophisticated tryptophan starvation mechanisms are known to act as antibacterial defenses in animal hosts. We propose that Chlamydiales have donated their tryptophan operon to the emerging plastid to ensure increased synthesis of tryptophan by the plastid ancestor. This would have allowed massive expression of the tryptophan rich chlamydial transporters responsible for symbiosis. It would also have allowed possible export of this valuable amino-acid in the inclusion of the tryptophan hungry pathogens. Free-living single cell cyanobacteria are devoid of proteins able to transport this amino-acid. We therefore investigated the phylogeny of the Tyr/Trp transporters homologous to E. coli TyrP/Mre and found yet another LGT from Chlamydiales to Archaeplastida thereby considerably strengthening our proposal.

  1. Eosinophilia-myalgia syndrome associated with exposure to tryptophan from a single manufacturer.

    Science.gov (United States)

    Slutsker, L; Hoesly, F C; Miller, L; Williams, L P; Watson, J C; Fleming, D W

    1990-07-11

    Although eosinophilia-myalgia syndrome has been linked to use of tryptophan, it has been unclear whether tryptophan itself or a contaminant causes illness. In Oregon, we compared the brand and source of tryptophan used by 58 patients with eosinophilia-myalgia syndrome with the brand and source of tryptophan used by 30 asymptomatic controls identified through a random telephone survey and 63 asymptomatic controls who contacted the Oregon Health Division voluntarily. Although a single brand/retail lot of tryptophan was statistically associated with the development of eosinophilia-myalgia syndrome, there was no common importer, wholesaler, tablet maker, encapsulator, or distributor. However, 45 (98%) of 46 cases had taken a product made by one manufacturer, compared with three (30%) of 10 telephone survey controls and 15 (48%) of 31 volunteer controls. Retail lots of tryptophan from this manufacturer that were associated with cases were significantly more likely to have been produced from January through June 1989 than lots from this manufacturer that were taken by controls. These findings indicate that the recent epidemic of eosinophilia-myalgia syndrome was caused by a contaminant or an alteration in a subset of tryptophan manufactured by a single company in Japan shortly before the outbreak began.

  2. Tryptophan, Neurodegeneration and HIV-Associated Neurocognitive Disorder

    Directory of Open Access Journals (Sweden)

    Nicholas W.S. Davies

    2010-06-01

    Full Text Available This review presents an up-to-date assessment of the role of the tryptophan metabolic and catabolic pathways in neurodegenerative disease and HIV-associated neurocognitive disorder. The kynurenine pathway and the effects of each of its enzymes and products are reviewed. The differential expression of the kynurenine pathway in cells within the brain, including inflammatory cells, is explored given the increasing recognition of the importance of inflammation in neurodegenerative disease. An overview of common mechanisms of neurodegeneration is presented before a review and discussion of the evidence for a pathogenetic role of the kynurenine pathway in Alzheimer’s disease, HIV-associated neurocognitive disorder, Huntington’s disease, motor neurone disease, and Parkinson’s disease.

  3. Tryptophan, Neurodegeneration and HIV-Associated Neurocognitive Disorder

    Science.gov (United States)

    Davies, Nicholas W.S.; Guillemin, Gilles; Brew, Bruce J.

    2010-01-01

    This review presents an up-to-date assessment of the role of the tryptophan metabolic and catabolic pathways in neurodegenerative disease and HIV-associated neurocognitive disorder. The kynurenine pathway and the effects of each of its enzymes and products are reviewed. The differential expression of the kynurenine pathway in cells within the brain, including inflammatory cells, is explored given the increasing recognition of the importance of inflammation in neurodegenerative disease. An overview of common mechanisms of neurodegeneration is presented before a review and discussion of the evidence for a pathogenetic role of the kynurenine pathway in Alzheimer’s disease, HIV-associated neurocognitive disorder, Huntington’s disease, motor neurone disease, and Parkinson’s disease. PMID:22084594

  4. Distinct Contributions of Tryptophan Residues within the Dimerization Domain to Nanog Function.

    Science.gov (United States)

    Mullin, Nicholas P; Gagliardi, Alessia; Khoa, Le Tran Phuc; Colby, Douglas; Hall-Ponsele, Elisa; Rowe, Arthur J; Chambers, Ian

    2017-05-19

    The level of the transcription factor Nanog directly determines the efficiency of mouse embryonic stem cell self-renewal. Nanog protein exists as a dimer with the dimerization domain composed of a simple repeat region in which every fifth residue is a tryptophan, the tryptophan repeat (WR). Although WR is necessary to enable Nanog to confer LIF-independent self-renewal, the mechanism of dimerization and the effect of modulating dimerization strength have been unclear. Here we couple mutagenesis with functional and dimerization assays to show that the number of tryptophans within the WR is linked to the strength of homodimerization, Sox2 heterodimerization and self-renewal activity. A reduction in the number of tryptophan residues leads initially to a gradual reduction in activity before a precipitous reduction in activity occurs upon reduction in tryptophan number below eight. Further functional attrition follows subsequent tryptophan number reduction with substitution of all tryptophan residues ablating dimerization and self-renewal function completely. A strong positional influence of tryptophans exists, with residues at the WR termini contributing more to Nanog function, particularly at the N-terminal end. Limited proteolysis demonstrates that a structural core of Nanog encompassing the homeodomain and the tryptophan repeat can support LIF-independent colony formation. These results increase understanding of the molecular interactions occurring between transcription factor subunits at the core of the pluripotency gene regulatory network and will enhance our ability to control pluripotent cell self-renewal and differentiation. Copyright © 2016 The Authors. Published by Elsevier Ltd.. All rights reserved.

  5. Exogenous Tryptophan Promotes Cutaneous Wound Healing of Chronically Stressed Mice through Inhibition of TNF-α and IDO Activation

    Science.gov (United States)

    Bandeira, Luana Graziella; Bortolot, Beatriz Salari; Cecatto, Matheus Jorand; Monte-Alto-Costa, Andréa; Romana-Souza, Bruna

    2015-01-01

    Stress prolongs the inflammatory response compromising the dermal reconstruction and wound closure. Acute stress-induced inflammation increases indoleamine 2, 3-dioxygenase-stimulated tryptophan catabolism. To investigate the role of indoleamine 2, 3-dioxygenase expression and tryptophan administration in adverse effects of stress on cutaneous wound healing, mice were submitted to chronic restraint stress and treated with tryptophan daily until euthanasia. Excisional lesions were created on each mouse and 5 or 7 days later, the lesions were analyzed. In addition, murine skin fibroblasts were exposed to elevated epinephrine levels plus tryptophan, and fibroblast activity was evaluated. Tryptophan administration reversed the reduction of the plasma tryptophan levels and the increase in the plasma normetanephrine levels induced by stress 5 and 7 days after wounding. Five days after wounding, stress-induced increase in the protein levels of tumor necrosis factor-α and indoleamine 2, 3-dioxygenase, and this was inhibited by tryptophan. Stress-induced increase in the lipid peroxidation and the amount of the neutrophils, macrophages and T cells number was reversed by tryptophan 5 days after wounding. Tryptophan administration inhibited the reduction of myofibroblast density, collagen deposition, re-epithelialization and wound contraction induced by stress 5 days after wounding. In dermal fibroblast culture, the tryptophan administration increased the cell migration and AKT phosphorylation in cells treated with high epinephrine levels. In conclusion, tryptophan-induced reduction of inflammatory response and indoleamine 2, 3-dioxygenase expression may have accelerated cutaneous wound healing of chronically stressed mice. PMID:26057238

  6. Serotonin, tryptophan metabolism and the brain-gut-microbiome axis.

    Science.gov (United States)

    O'Mahony, S M; Clarke, G; Borre, Y E; Dinan, T G; Cryan, J F

    2015-01-15

    The brain-gut axis is a bidirectional communication system between the central nervous system and the gastrointestinal tract. Serotonin functions as a key neurotransmitter at both terminals of this network. Accumulating evidence points to a critical role for the gut microbiome in regulating normal functioning of this axis. In particular, it is becoming clear that the microbial influence on tryptophan metabolism and the serotonergic system may be an important node in such regulation. There is also substantial overlap between behaviours influenced by the gut microbiota and those which rely on intact serotonergic neurotransmission. The developing serotonergic system may be vulnerable to differential microbial colonisation patterns prior to the emergence of a stable adult-like gut microbiota. At the other extreme of life, the decreased diversity and stability of the gut microbiota may dictate serotonin-related health problems in the elderly. The mechanisms underpinning this crosstalk require further elaboration but may be related to the ability of the gut microbiota to control host tryptophan metabolism along the kynurenine pathway, thereby simultaneously reducing the fraction available for serotonin synthesis and increasing the production of neuroactive metabolites. The enzymes of this pathway are immune and stress-responsive, both systems which buttress the brain-gut axis. In addition, there are neural processes in the gastrointestinal tract which can be influenced by local alterations in serotonin concentrations with subsequent relay of signals along the scaffolding of the brain-gut axis to influence CNS neurotransmission. Therapeutic targeting of the gut microbiota might be a viable treatment strategy for serotonin-related brain-gut axis disorders. Copyright © 2014 Elsevier B.V. All rights reserved.

  7. Assessment of Tryptophan Uptake and Kinetics Using 1-(2-18F-Fluoroethyl)-l-Tryptophan and α-11C-Methyl-l-Tryptophan PET Imaging in Mice Implanted with Patient-Derived Brain Tumor Xenografts.

    Science.gov (United States)

    Michelhaugh, Sharon K; Muzik, Otto; Guastella, Anthony R; Klinger, Neil V; Polin, Lisa A; Cai, Hancheng; Xin, Yangchun; Mangner, Thomas J; Zhang, Shaohui; Juhász, Csaba; Mittal, Sandeep

    2017-02-01

    Abnormal tryptophan metabolism via the kynurenine pathway is involved in the pathophysiology of a variety of human diseases including cancers. α- 11 C-methyl-l-tryptophan ( 11 C-AMT) PET imaging demonstrated increased tryptophan uptake and trapping in epileptic foci and brain tumors, but the short half-life of 11 C limits its widespread clinical application. Recent in vitro studies suggested that the novel radiotracer 1-(2- 18 F-fluoroethyl)-l-tryptophan ( 18 F-FETrp) may be useful to assess tryptophan metabolism via the kynurenine pathway. In this study, we tested in vivo organ and tumor uptake and kinetics of 18 F-FETrp in patient-derived xenograft mouse models and compared them with 11 C-AMT uptake. Xenograft mouse models of glioblastoma and metastatic brain tumors (from lung and breast cancer) were developed by subcutaneous implantation of patient tumor fragments. Dynamic PET scans with 18 F-FETrp and 11 C-AMT were obtained for mice bearing human brain tumors 1-7 d apart. The biodistribution and tumoral SUVs for both tracers were compared. 18 F-FETrp showed prominent uptake in the pancreas and no bone uptake, whereas 11 C-AMT showed higher uptake in the kidneys. Both tracers showed uptake in the xenograft tumors, with a plateau of approximately 30 min after injection; however, 18 F-FETrp showed higher tumoral SUV than 11 C-AMT in all 3 tumor types tested. The radiation dosimetry for 18 F-FETrp determined from the mouse data compared favorably with the clinical 18 F-FDG PET tracer. 18 F-FETrp tumoral uptake, biodistribution, and radiation dosimetry data provide strong preclinical evidence that this new radiotracer warrants further studies that may lead to a broadly applicable molecular imaging tool to examine abnormal tryptophan metabolism in human tumors. © 2017 by the Society of Nuclear Medicine and Molecular Imaging.

  8. Plasma Tryptophan and the Kynurenine-Tryptophan Ratio are Associated with the Acquisition of Statural Growth Deficits and Oral Vaccine Underperformance in Populations with Environmental Enteropathy.

    Science.gov (United States)

    Kosek, Margaret N; Mduma, Estomih; Kosek, Peter S; Lee, Gwenyth O; Svensen, Erling; Pan, William K Y; Olortegui, Maribel Paredes; Bream, Jay H; Patil, Crystal; Asayag, Cesar Ramal; Sanchez, Graciela Meza; Caulfield, Laura E; Gratz, Jean; Yori, Pablo Peñataro

    2016-10-05

    Early childhood enteric infections have adverse impacts on child growth and can inhibit normal mucosal responses to oral vaccines, two critical components of environmental enteropathy. To evaluate the role of indoleamine 2,3-dioxygenase 1 (IDO1) activity and its relationship with these outcomes, we measured tryptophan and the kynurenine-tryptophan ratio (KTR) in two longitudinal birth cohorts with a high prevalence of stunting. Children in rural Peru and Tanzania (N = 494) contributed 1,251 plasma samples at 3, 7, 15, and 24 months of age and monthly anthropometrics from 0 to 36 months of age. Tryptophan concentrations were directly associated with linear growth from 1 to 8 months after biomarker assessment. A 1-SD increase in tryptophan concentration was associated with a gain in length-for-age Z-score (LAZ) of 0.17 over the next 6 months in Peru (95% confidence interval [CI] = 0.11-0.23, P tryptophan and kynurenine as biomarkers for this syndrome, particularly in identifying those at risk for hyporesponsivity to oral vaccines. © The American Society of Tropical Medicine and Hygiene.

  9. Effects of tryptophan supplementation on cashmere fiber characteristics, serum tryptophan, and related hormone concentrations in cashmere goats.

    Science.gov (United States)

    Ma, H; Zhang, W; Song, W H; Sun, P; Jia, Z H

    2012-10-01

    This study was designed to investigate the effects of tryptophan (Trp) supplementation on cashmere fiber characteristics and on serum Trp, melatonin (MEL), prolactin (PRL), insulin-like growth factor 1 (IGF-1), triiodothyronine (T3), and thyroxine (T4) concentrations in cashmere goats during the cashmere fast-growth period. Thirty-six Liaoning cashmere wether goats were stratified on the basis of body weight (28±0.8 kg) and assigned randomly to 1 of the following 4 rumen-protected Trp treatments: 0, 2.0, 4.0, and 6.0 g per goat per day. The experimental period lasted 137 d. Blood samples were collected monthly during the daytime (8:00 AM) and at night (8:00 PM). Tryptophan supplementation improved cashmere growth rates, cashmere weight, and body weight (P=0.001) and increased serum Trp levels, nighttime MEL concentrations, IGF-1, and T3 and T4 concentrations (Pcashmere growth rate and nighttime serum MEL concentrations was observed (r=0.879, P=0.001). A moderately negative correlation between cashmere growth rates and serum PRL concentrations during the day and at night (rday=-0.645, P=0.007; rnight=-0.583, P=0.018) was observed. A moderately positive correlation between the cashmere growth rate and the daytime serum IGF-1 concentration (r=0.536, P=0.032) was observed, and no correlation was found between the cashmere growth rate and the other serum hormone concentrations. These data indicate that changes in serum concentrations of MEL, IGF-1, and PRL are related to cashmere growth in Liaoning cashmere goats during the cashmere fast-growth period. Under the experimental conditions of the current trial, we suggest that Trp may promote cashmere growth by increasing daytime IGF-1 and nighttime MEL secretion. Copyright © 2012 Elsevier Inc. All rights reserved.

  10. Zero birefringence films of pullulan ester derivatives

    Science.gov (United States)

    Danjo, Takahiro; Enomoto, Yukiko; Shimada, Hikaru; Nobukawa, Shogo; Yamaguchi, Masayuki; Iwata, Tadahisa

    2017-04-01

    High-performance films with almost zero-birefringence and zero-wavelength dispersion were succeeded to prepare from pullulan esters derivatives (PLEs) without any additives. Optical transmittance analysis, birefringence measurement of PLE cast film and hot stretched films, and infrared dichroism analysis were conducted to characterize optical properties of PLE films comparing with cellulose triacetate which is commercially used as low-birefringence in optical devices. The aims of this study, characterization of optical properties of pullulan esters, can develop a deep understanding of the fundamental knowing and applicability of polysaccharides. Accordingly, authors believe this paper will open the gate for researches in the application of polysaccharides.

  11. Application conditions for ester cured alkaline phenolic resin sand

    Directory of Open Access Journals (Sweden)

    Ren-he Huang

    2016-07-01

    Full Text Available Five organic esters with different curing speeds: propylene carbonate (i.e. high-speed ester A; 1, 4-butyrolactone; glycerol triacetate (i.e. medium-speed ester B; glycerol diacetate; dibasic ester (DBE (i.e. low-speed ester C, were chosen to react with alkaline phenolic resin to analyze the application conditions of ester cured alkaline phenolic resin. The relationships between the curing performances of the resin (including pH value, gel pH value, gel time of resin solution, heat release rate of the curing reaction and tensile strength of the resin sand and the amount of added organic ester and curing temperature were investigated. The results indicated the following: (1 The optimal added amount of organic ester should be 25wt.%-30wt.% of alkaline phenolic resin and it must be above 20wt.%-50 wt.% of the organic ester hydrolysis amount. (2 High-speed ester A (propylene carbonate has a higher curing speed than 1, 4-butyrolactone, and they were both used as high-speed esters. Glycerol diacetate is not a high-speed ester in alkaline phenolic resin although it was used as a high-speed ester in ester cured sodium silicate sand; glycerol diacetate and glycerol triacetate can be used as medium-speed esters in alkaline phenolic resin. (3 High-speed ester A, medium-speed ester B (glycerol triacetate and low-speed ester C (dibasic ester, i.e., DBE should be used below 15 ìC, 35 ìC and 50 ìC, respectively. High-speed ester A or low-speed ester C should not be used alone but mixed with medium-speed ester B to improve the strength of the resin sand. (4 There should be a suitable solid content (generally 45wt.%-65wt.% of resin, alkali content (generally 10wt.%-15wt.% of resin and viscosity of alkaline phenolic resin (generally 50-300 mPa≤s in the preparation of alkaline phenolic resin. Finally, the technique conditions of alkaline phenolic resin preparation and the application principles of organic ester were discussed.

  12. Acute tryptophan depletion dose dependently impairs object memory in serotonin transporter knockout rats

    NARCIS (Netherlands)

    Olivier, J D A; Jans, L A W; Korte-Bouws, G A H; Korte, S M; Deen, P M T; Cools, A R; Ellenbroek, B A; Blokland, A

    2008-01-01

    RATIONALE: Acute tryptophan depletion (ATD) transiently lowers central serotonin levels and can induce depressive mood states and cognitive defects. Previous studies have shown that ATD impairs object recognition in rats. OBJECTIVES: As individual differences exist in central serotonin

  13. Acute tryptophan depletion in humans: a review of theoretical, practical and ethical aspects

    Science.gov (United States)

    Young, Simon N.

    2013-01-01

    The acute tryptophan depletion (ATD) technique has been used extensively to study the effect of low serotonin in the human brain. This review assesses the validity of a number of published criticisms of the technique and a number of previously unpublished potential criticisms. The conclusion is that ATD can provide useful information when results are assessed in conjunction with results obtained using other techniques. The best-established conclusion is that low serotonin function after tryptophan depletion lowers mood in some people. However, this does not mean that other variables, altered after tryptophan depletion, are necessarily related to low serotonin. Each aspect of brain function has to be assessed separately. Furthermore, a negative tryptophan depletion study does not mean that low serotonin cannot influence the variable studied. This review suggests gaps in knowledge that need to be filled and guidelines for carrying out ATD studies. PMID:23428157

  14. Linoleic acid, thymine, and tryptophan radiosensitization by protoporphyrin in presence of oxygene

    International Nuclear Information System (INIS)

    Champel, P.; Mignot, M.A.; Pillement, B.; Fontenil, L.; Rocquet, G.

    Sensitizing effect induced by protoporphyrin, an active molecule in photooxidation is studied. Studied substances are tryptophan, thymine, linoleic acid, each component representing one of the great groups of biological components, nucleic acid, proteins, lipids [fr

  15. Post-synthetic modification of tryptophan containing peptides via NIS mediation.

    Science.gov (United States)

    Gu, Chen-Xue; Bi, Qing-Wei; Gao, Chu-Kun; Wen, Jian; Zhao, Zhi-Gang; Chen, Zili

    2017-04-18

    A new efficient method was developed to provide modified tryptophan peptides through NIS (N-iodosuccinimide) mediated N 2 -selective coupling of a Trp unit with 1,2,3-triazoles, of which, the preliminary spectral properties were also studied.

  16. FLIM-FRET image analysis of tryptophan in prostate cancer cells

    Science.gov (United States)

    Periasamy, Ammasi; Alam, Shagufta R.; Svindrych, Zdenek; Wallrabe, Horst

    2017-07-01

    A region of interest (ROI) based quantitative FLIM-FRET image analysis is developed to quantitate the autofluorescence signals of the essential amino acid tryptophan as a biomarker to investigate the metabolism in prostate cancer cells.

  17. Effects of Tryptophan Content and Backbone Spacing on the Uptake Efficiency of Cell-Penetrating Peptides

    KAUST Repository

    Rydberg, Hanna A.

    2012-07-10

    Cell-penetrating peptides (CPPs) are able to traverse cellular membranes and deliver macromolecular cargo. Uptake occurs through both endocytotic and nonendocytotic pathways, but the molecular requirements for efficient internalization are not fully understood. Here we investigate how the presence of tryptophans and their position within an oligoarginine influence uptake mechanism and efficiency. Flow cytometry and confocal fluorescence imaging are used to estimate uptake efficiency, intracellular distribution and toxicity in Chinese hamster ovarian cells. Further, membrane leakage and lipid membrane affinity are investigated. The peptides contain eight arginine residues and one to four tryptophans, the tryptophans positioned either at the N-terminus, in the middle, or evenly distributed along the amino acid sequence. Our data show that the intracellular distribution varies among peptides with different tryptophan content and backbone spacing. Uptake efficiency is higher for the peptides with four tryptophans in the middle, or evenly distributed along the peptide sequence, than for the peptide with four tryptophans at the N-terminus. All peptides display low cytotoxicity except for the one with four tryptophans at the N-terminus, which was moderately toxic. This finding is consistent with their inability to induce efficient leakage of dye from lipid vesicles. All peptides have comparable affinities for lipid vesicles, showing that lipid binding is not a decisive parameter for uptake. Our results indicate that tryptophan content and backbone spacing can affect both the CPP uptake efficiency and the CPP uptake mechanism. The low cytotoxicity of these peptides and the possibilities of tuning their uptake mechanism are interesting from a therapeutic point of view. © 2012 American Chemical Society.

  18. Dietary tryptophan alleviates dextran sodium sulfate-induced colitis through aryl hydrocarbon receptor in mice.

    Science.gov (United States)

    Islam, Jahidul; Sato, Shoko; Watanabe, Kouichi; Watanabe, Takaya; Ardiansyah; Hirahara, Keisuke; Aoyama, Yukihide; Tomita, Shuhei; Aso, Hisashi; Komai, Michio; Shirakawa, Hitoshi

    2017-04-01

    Ulcerative colitis is the typical progression of chronic inflammatory bowel disease. Amino acids, particularly tryptophan, have been reported to exert a protective effect against colitis induced by dextran sodium sulfate (DSS), but the precise underlying mechanisms remain incompletely clarified. Tryptophan metabolites are recognized to function as endogenous ligands for aryl hydrocarbon receptor (Ahr), which is a critical regulator of inflammation and immunity. Thus, we conducted this study to investigate whether dietary tryptophan supplementation protects against DSS-induced colitis by acting through Ahr. Female wild-type (WT) and Ahr-deficient (knockout; KO) mice (10-12 weeks old) were divided into four groups and fed either a control or 0.5% tryptophan diet. The tryptophan diet ameliorated DSS-induced colitis symptoms and severity in WT mice but not in KO mice, and the diet reduced the mRNA expression of Il-6, Tnfα, Il-1β and the chemokines Ccl2, Cxcl1 and Cxcl2 in the WT groups. Furthermore, Il-22 and Stat3 mRNA expression in the colon was elevated in WT mice fed with the tryptophan diet, which mainly protected epithelial layer integrity, and Ahr also modulated immune homeostasis by regulating Foxp3 and Il-17 mRNA expression. These data suggest that tryptophan-containing diet might ameliorate DSS-induced acute colitis and regulate epithelial homeostasis through Ahr. Thus, tryptophan could serve as a promising preventive agent in the treatment of ulcerative colitis. Copyright © 2017 Elsevier Inc. All rights reserved.

  19. Effects of dietary L-tryptophan supplementation on intestinal response to chronic unpredictable stress in broilers.

    Science.gov (United States)

    Yue, Yunshuang; Guo, Yuming; Yang, Ying

    2017-07-01

    Stress has been recognized as a critical risk factor for gastrointestinal diseases in both humans and animals. However, nutritional strategies to attenuate stress-induced intestinal barrier function and underlying mechanisms remain largely unknown. This study tested the hypothesis that L-tryptophan enhanced intestinal barrier function by regulating mucosal serotonin metabolism in chronic unpredictable stress-exposed broilers. One-day-old male broilers (Arbor Acres) were fed a basal diet supplemented with or without L-tryptophan in the absence or presence of chronic unpredictable stress. Feed intake, body weight gain, plasma corticosterone and 5-hydroxytryptamine (5-HT), intestinal permeability, mucosal secretory IgA (sIgA), and mRNA levels for tryptophan hydroxylase 1 (TPH1), IL-1β, IL-6, TNF-α, IL-10, protein abundance for claudin-1, occludin, and ZO-1 were determined. Stress exposure led to elevated plasma corticosterone (P tryptophan supplementation. Western blot analysis showed that stress exposure resulted in decreased protein abundance for occludin, claudin-1, and ZO-1, which was attenuated by L-tryptophan. mRNA levels for IL-1β, IL-6, and TNF-α were increased, but those for IL-10 were decreased, in the jejunal tissue of broilers subjected to stress. This effect of stress on cytokine expression was abolished by L-tryptophan treatment. The effects of stress were associated with decreased plasma concentration of 5-HT (P Tryptophan supplementation markedly attenuated stress-induced alterations in 5-HT and TPH1 mRNA level in jejunal tissues of broilers. Collectively, these results indicate that L-tryptophan supplementation alleviates chronic unpredictable stress-induced intestinal barrier dysfunction by regulating 5-HT metabolism in broilers.

  20. Changes of intermediary taurine and tryptophan metabolism after combined radiation-thermal injury

    International Nuclear Information System (INIS)

    Konnova, L.A.; Novoselova, G.S.

    1986-01-01

    The dynamics of changes of the taurine and tryptophane concentration in blood serum of rats has been studied during 30 days after 3b degree burn of 15% of body surface after total even exposure to radiation in doses of 3 and 6 Gy, and after combined radiation thermal injury. Combined radiation-thermal injury was found to be characterized by reduced concentration of taurine but an increase of the tryptophane level from the second-third day after the injury

  1. Nutritional tryptophan restriction impairs plasticity of retinotectal axons during the critical period.

    Science.gov (United States)

    Penedo, Letícia Abel; Oliveira-Silva, Priscilla; Gonzalez, Ericka M C; Maciel, Rafaela; Jurgilas, Patricia B; Melibeu, Adriana da Cunha Faria; Campello-Costa, Paula; Serfaty, Claudio Alberto

    2009-05-01

    The use-dependent specification of neural circuits occurs during post-natal development with a conspicuous influence of environmental factors, such as malnutrition that interferes with the major steps of brain maturation. Serotonin (5-HT), derived exclusively from the essential aminoacid tryptophan, is involved in mechanisms of development and use-dependent plasticity of the central nervous system. We studied the effects of the nutritional restriction of tryptophan in the plasticity of uncrossed retinotectal axons following a retinal lesion to the contralateral retina during the critical period in pigmented rats. Litters were fed through their mothers with a low tryptophan content diet, based on corn and gelatin, a complemented diet with standard tryptophan requirements for rodents or standard laboratory diet. The results suggest a marked reduction in the plasticity of intact axons into denervated territories in the tryptophan restricted group in comparison to control groups. Tryptophan complementation between PND10-21 completely restored retinotectal plasticity. However, the re-introduction of tryptophan after the end of the critical period (between PND28-P41) did not restore the sprouting ability of uncrossed axons suggesting a time-dependent effect to the reversion of plasticity deficits. Tryptophan-restricted animals showed a reduced activity of matrix metalloproteinase-9 and altered expressions of phosphorylated forms of ERK1/2 and AKT. Our results demonstrate the influence of this essential aminoacid as a modulator of neural plasticity during the critical period through the reduction of serotonin content which alters plasticity-related signaling pathways and matrix degradation.

  2. Effects of Exhaustive Aerobic Exercise on Tryptophan-Kynurenine Metabolism in Trained Athletes.

    Directory of Open Access Journals (Sweden)

    Barbara Strasser

    Full Text Available Exhaustive exercise can cause a transient depression of immune function. Data indicate significant effects of immune activation cascades on the biochemistry of monoamines and amino acids such as tryptophan. Tryptophan can be metabolized through different pathways, a major route being the kynurenine pathway, which is often systemically up-regulated when the immune response is activated. The present study was undertaken to examine the effect of exhaustive aerobic exercise on biomarkers of immune activation and tryptophan metabolism in trained athletes. After a standardized breakfast 2 h prior to exercise, 33 trained athletes (17 women, 16 men performed an incremental cycle ergometer exercise test at 60 rpm until exhaustion. After a 20 min rest phase, the participants performed a 20 min maximal time-trial on a cycle ergometer (RBM Cyclus 2, Germany. During the test, cyclists were strongly encouraged to choose a maximal pedalling rate that could be maintained for the respective test duration. Serum concentrations of amino acids tryptophan, kynurenine, phenylalanine, and tyrosine were determined by HPLC and immune system biomarker neopterin by ELISA at rest and immediately post exercise. Intense exercise was associated with a strong increase in neopterin concentrations (p<0.001, indicating increased immune activation following intense exercise. Exhaustive exercise significantly reduced tryptophan concentrations by 12% (p<0.001 and increased kynurenine levels by 6% (p = 0.022. Also phenylalanine to tyrosine ratios were lower after exercise as compared with baseline (p<0.001. The kynurenine to tryptophan ratio correlated with neopterin (r = 0.560, p<0.01. Thus, increased tryptophan catabolism by indoleamine 2,3-dioxygenase appears likely. Peak oxygen uptake correlated with baseline tryptophan and kynurenine concentrations (r = 0.562 and r = 0.511, respectively, both p<0.01. Findings demonstrate that exhaustive aerobic exercise is associated with

  3. Product study of 1-adamantyl and 1-bicyclo[2.2.2]octyl radicals in hydrocarbon solvents. An unusually large hydrogen isotope effect

    International Nuclear Information System (INIS)

    Engel, P.S.; Chae, W.K.; Baughman, S.A.; Marschke, G.E.; Lewis, E.S.; Timberlake, J.W.; Luedtke, A.E.

    1983-01-01

    1-Adamantyl (ada.) and 1-bicyclo[2.2.2]octyl (bo.) radicals have been generated by photolysis of the corresponding azoalkanes in various hydrocarbon solvents. Both radicals abstract hydrogen readily from saturated hydrocarbons and they add to aromatic rings much faster than tert-butyl. does. Despite its reactivity, ada. is remarkably selective in hydrogen atom abstraction, preferring a benzylic hydrogen 25:1 over a cyclohexane hydrogen. The effect of solvent viscosity indicates that formation of the radical dimers biada and bibo occurs in the solvent cage. The most striking result of this work is a deuterium isotope effect of 25 for hydrogen transfer from cyclohexane to ada. at 65 0 C. Steric compression in the transition state is postulated to cause an unusually large tunnel correction and hence a large k/sub H//k/sub D/. 6 tables

  4. Modifier-free separation of trivalent actinides and lanthanides from fast reactor simulated high-level liquid waste using N,N-di-octyl-2-hydroxyacetamide

    International Nuclear Information System (INIS)

    Prathibha, T.; Antony, M.P.; Homi Bhabha National Institute, Mumbai; Kumaresan, R.; Nayak, P.K.; Venkatesan, K.A.; Subramanian, G.G.S.; Rajeswari, S.; Kalaiyarasu, T.; Karunakaran, R.

    2017-01-01

    The extraction behaviour of Am(III) and other metal ions present in the fast reactor simulated high- level liquid waste (FR-SHLLW) was studied using a modifier-free solvent phase composed of N,N-di-octyl-2-hydroxyacetamide (DOHyA) in n-dodecane. Quantitative extraction of Am(III) was achieved with the co-extraction of all lanthanides, Y(III) and Mo(VI) in the first five stages of a 20-stage mixer-settler. During the stripping run with 0.5 M HNO 3 , Am(III), Ln(III) and Y(III) were quantitatively transferred to the aqueous product in three stages. The other extracted metal ions were retained in organic phase. The results showed that the extraction performance of DOHyA was superior to other amide extractant systems reported in the literature. (author)

  5. In vitro effect of octyl - methoxycinnamate (OMC) on the release of Gn-RH and amino acid neurotransmitters by hypothalamus of adult rats.

    Science.gov (United States)

    Carbone, S; Szwarcfarb, B; Reynoso, R; Ponzo, O J; Cardoso, N; Ale, E; Moguilevsky, J A; Scacchi, P

    2010-05-01

    OMC (octyl-methoxycinnamate), an endocrine disruptor having estrogenic activity, is used in sunscreen creams as UV filter. We studied its "in vitro" effects on the hypothalamic release of Gn-RH as well as on the amino acid neurotransmitter system. OMC significantly decreased Gn-RH release in normal male and female rats as well as in castrated rats with substitutive therapy. No effects were observed in castrated rats without substitutive therapy. In males OMC increases the release of GABA, decreasing the production of glutamate (GLU) while in the female decreases the excitatory amino acid aspartate (ASP) and GLU without modifications in the hypothalamic GABA release. These results suggest that OMC acting as endocrine disruptor could alter the sex hormone-neurotransmitter-Gn-RH axis relationships in adult rats.

  6. Spectroscopy and computational studies on the interaction of octyl, dodecyl, and hexadecyl derivatives of anionic and cationic surfactants with adenosine deaminase.

    Science.gov (United States)

    Ajloo, Davood; Mahmoodabadi, Najmeh; Ghadamgahi, Maryam; Saboury, Ali Akbar

    2016-07-01

    Effects of sodium (octyl, dodecyl, hexadecyl) sulfate and their cationic analogous on the structure of adenosine deaminase (ADA) were investigated by fluorescence and circular dichroism spectroscopy as well as molecular dynamics simulation and docking calculation. Root-mean-square derivations, radius of gyration, solvent accessible surface area, and radial distribution function were obtained. The results showed that anionic and cationic surfactants reduce protein stability. Cationic surfactants have more effect on the ADA structure in comparison with anionic surfactants. More concentration and longer surfactants are parallel to higher denaturation. Furthermore, aggregation in the presence of anionic surfactants is more than cationic surfactants. Docking data showed that longer surfactants have more interaction energy and smaller ones bound to the active site.

  7. Separation of Cu, In, Fe and Sn from nuclear grade thorium by tri-n-octyl amine-5 M HCI and their determination by atomic absorption spectrophotometry

    International Nuclear Information System (INIS)

    Moraes, S. de; Cipriani, M.; Abrao, A.

    1976-01-01

    The results of solvent extraction separation of a group of metal traces in high pure thorium with the aid of tri-n-octyl amine-benzene from ThCL 4 HCI are summarized. ThCl 4 HCI-KI solutions Cu,In,Fe and Sn are extracted together and determined by atomic absoprtion spectrophotometry, burning directly the organic phase. The behavior of Cu,In,Fe and Sn toward direct burn of the organic phase using hydrogen-air mixture was studied, and an absorption enhancement was observed. The procedure is being used ot perform the quality control of nuclear grade thorium and its compounds. The calibration curves have provided precisions in the range 1 to 10% in analysis of thorium

  8. Preparation of a chitosan-coated C(18)-functionalized magnetite nanoparticle sorbent for extraction of phthalate ester compounds from environmental water samples.

    Science.gov (United States)

    Zhang, Xiao Le; Niu, Hong Yun; Zhang, Sheng Xiao; Cai, Ya Qi

    2010-05-01

    Novel superparamagnetic chitosan-coated C(18)-functionalized magnetite nanoparticles (MNPs) were successfully synthesized and applied as an effective sorbent for the preconcentration of several typical phthalate ester compounds from environmental water samples. The MNPs were 20 nm in diameter and had a high magnetic saturation value (52 emu g(-1)), which endowed the sorbent with a large surface area and the convenience of isolation from water samples. Phthalate esters could be extracted by the interior octadecyl groups through hydrophobic interaction. The hydrophilic porous chitosan polymer coating promoted the dispersion of MNPs in water samples, and improved the anti-interference ability of the sorbent without influencing the adsorption of analytes. The main factors affecting the adsorption of phthalate esters, including the pH of the solution, humic acid, sample loading volume, adsorption time, and desorption conditions, were investigated and optimized. Under the conditions selected (pH 11, adsorption time 20 min, elution with 10 mL of acetonitrile, and concentration to 0.5 mL), concentration factors of 1,000 were achieved by extracting 500 mL of several environmental water samples with 0.1 g of MNP sorbent. The method detection limits obtained for di-n-propyl phthalate, di-n-butyl phthalate, dicyclohexyl phthalate, and di-n-octyl phthalate were 12.3, 18.7, 36.4, and 15.6 ng L(-1), respectively. The recoveries of spiked samples ranged from 60 to 100%, with a low relative standard deviation (1-8%), which indicated good method precision.

  9. Influence of tryptophan and related compounds on ergot alkaloid formation in Claviceps purpurea (FR.) Tul.

    Science.gov (United States)

    Erge, D; Schumann, B; Gröger, D

    1984-01-01

    L-Tryptophan did not exert any influence on peptide alkaloid formation in an ergotamine and in an ergosine-accumulating C. purpurea strain. A different picture was observed in a series of related C. purpurea strains. Tryptophan showed a slight stimulatory effect on the ergotoxine producer Pepty 695/S. A blocked mutant of it, designated as Pepty 695/ch which was able to accumulate secoclavines gave similar results. In a high-yielding elymoclavine strain Pepty 695/e, the progeny of the former one, tryptophan up to a concentration of 25 mM stimulated remarkably clavine biosynthesis. Furthermore, tryptophan could overcome the block of synthesis by inorganic phosphate. Increased specific activities of chanoclavine cyclase but not DMAT synthetase were observed in cultures of strain Pepty 695/e supplemented with tryptophan. 5-Methyltryptophan and bioisosteres of tryptophan were ineffective in alkaloid stimulation. These results are compared with those obtained with the grass ergot strain SD 58 and discussed with the relation to other induction phenomena.

  10. L-Tryptophan Production in Escherichia coli Improved by Weakening the Pta-AckA Pathway.

    Science.gov (United States)

    Liu, Lina; Duan, Xuguo; Wu, Jing

    2016-01-01

    Acetate accumulation during the fermentation process of Escherichia coli FB-04, an L-tryptophan production strain, is detrimental to L-tryptophan production. In an initial attempt to reduce acetate formation, the phosphate acetyltransferase gene (pta) from E. coli FB-04 was deleted, forming strain FB-04(Δpta). Unfortunately, FB-04(Δpta) exhibited a growth defect. Therefore, pta was replaced with a pta variant (pta1) from E. coli CCTCC M 2016009, forming strain FB-04(pta1). Pta1 exhibits lower catalytic capacity and substrate affinity than Pta because of a single amino acid substitution (Pro69Leu). FB-04(pta1) lacked the growth defect of FB-04(Δpta) and showed improved fermentation performance. Strain FB-04(pta1) showed a 91% increase in L-tryptophan yield in flask fermentation experiments, while acetate production decreased by 35%, compared with its parent FB-04. Throughout the fed-batch fermentation process, acetate accumulation by FB-04(pta1) was slower than that by FB-04. The final L-tryptophan titer of FB-04(pta1) reached 44.0 g/L, representing a 15% increase over that of FB-04. Metabolomics analysis showed that the pta1 genomic substitution slightly decreased carbon flux through glycolysis and significantly increased carbon fluxes through the pentose phosphate and common aromatic pathways. These results indicate that this strategy enhances L-tryptophan production and decreases acetate accumulation during the L-tryptophan fermentation process.

  11. Tryptophan biosynthesis is important for resistance to replicative stress in Saccharomyces cerevisiae.

    Science.gov (United States)

    Godin, Stephen K; Lee, Alison G; Baird, Jared M; Herken, Benjamin W; Bernstein, Kara A

    2016-05-01

    Acute tryptophan depletion is used to induce low levels of serotonin in the brain. This method has been widely used in psychiatric studies to evaluate the effect of low levels of serotonin, and is generally considered a safe and reversible procedure. Here we use the budding yeast Saccharomyces cerevisiae to study the effects of tryptophan depletion on growth rate upon exposure to DNA-damaging agents. Surprisingly, we found that budding yeast undergoing tryptophan depletion were more sensitive to DNA-damaging agents such as methyl methanesulphonate (MMS) and hydroxyurea (HU). We found that this defect was independent of several DNA repair pathways, such as homologous recombination, base excision repair and translesion synthesis, and that this damage sensitivity was not due to impaired S-phase signalling. Upon further analysis, we found that the DNA-damage sensitivity of tryptophan depletion was likely due to impaired protein synthesis. These studies describe an important source of variance in budding yeast when using tryptophan as an auxotrophic marker, particularly on studies focusing on DNA repair, and suggest that further testing of the effect of tryptophan depletion on DNA repair in mammalian cells is warranted. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

  12. Role of decreased Plasma Tryptophan in memory deficits observed in Type-I diabetes

    International Nuclear Information System (INIS)

    Ahmad, S.; Tabassum, S.; Haider, S.

    2013-01-01

    Objective: To investigate the relationship between plasma tryptophan and the occurrence of memory dysfunctions in male and female type 1 diabetics. Methods: The case-control study was conducted at two urban healthcare facilities in Karachi from January to June 2009, and comprised 100 diabetic subjects of among whom were 50 men and 50 women. The controls were also similar in number and gender. A questionnaire was used to evaluate the memory impairment in the subjects. Plasma tryptophan was determined by high performance liquid chromatography with ultra-violet method. Students t-test was used to analyse tryptophan data. Results: There was considerable memory impairment in the cases (n=40) compared to the controls (n=5). Results also showed a significant (p<0.01) decrease in plasma tryptophan levels in both male and female diabetic patients. Conclusions: Diabetic subjects exhibited occurrence of memory impairment with concomitant decline in plasma tryptophan levels. The findings indicate that decreased brain uptake of tryptophan and lowered brain 5-hydroxytryptamine levels may be responsible for the memory deficits seen in diabetics. (author)

  13. Room temperature phosphorescence study on the structural flexibility of single tryptophan containing proteins

    Science.gov (United States)

    Kowalska-Baron, Agnieszka; Gałęcki, Krystian; Wysocki, Stanisław

    2015-01-01

    In this study, we have undertaken efforts to find correlation between phosphorescence lifetimes of single tryptophan containing proteins and some structural indicators of protein flexibility/rigidity, such as the degree of tryptophan burial or its exposure to solvent, protein secondary and tertiary structure of the region of localization of tryptophan as well as B factors for tryptophan residue and its immediate surroundings. Bearing in mind that, apart from effective local viscosity of the protein/solvent matrix, the other factor that concur in determining room temperature tryptophan phosphorescence (RTTP) lifetime in proteins is the extent of intramolecular quenching by His, Cys, Tyr and Trp side chains, the crystallographic structures derived from the Brookhaven Protein Data Bank were also analyzed concentrating on the presence of potentially quenching amino acid side chains in the close proximity of the indole chromophore. The obtained results indicated that, in most cases, the phosphorescence lifetimes of tryptophan containing proteins studied tend to correlate with the above mentioned structural indicators of protein rigidity/flexibility. This correlation is expected to provide guidelines for the future development of phosphorescence lifetime-based method for the prediction of structural flexibility of proteins, which is directly linked to their biological function.

  14. Synthesis and stability of new spiroaminoborate esters

    OpenAIRE

    Stepanenko, Viatcheslav; de Jesús, Melvin; Garcia, Carmelo; Barnes, Charles L.; Ortiz-Marciales, Margarita

    2012-01-01

    New spiroaminoborate esters derived from 1,1-diphenylprolinol, ephedrine and dihydroquinine with different alkoxy substituents were prepared as stable crystalline compounds and characterized by spectroscopical analysis and specific rotation. The structure of the spiroborate 4 derived from 1,1-diphenylprolinol and dicyclohexyl-1,1′-diol was confirmed by X-ray analysis.

  15. 1347-IJBCS-Article-Dr Innocent Ester

    African Journals Online (AJOL)

    KODJIO NORBERT

    Say (Culicidae: Diptera). Ester INNOCENT 1*, Eliangiringa KAALE 2 and Zakaria H. MBWAMBO 1. 1 Institute of Traditional Medicine, Muhimbili University of Health and Allied Sciences,. P.O. Box 65001, Dar es Salaam, Tanzania. 2Department of Medicinal Chemistry, School of Pharmacy, Muhimbili University of Health and ...

  16. Two New Phorbol Esters from Euphorbia bothae

    African Journals Online (AJOL)

    NICO

    Euphorbias of South Africa: Two New Phorbol Esters from. Euphorbia bothae. Wendy L. Popplewell,1 Eloise A. Marais,1 Linda Brand,2. Brian H. Harvey2 and Michael T. Davies-Coleman1*. 1Department of Chemistry, Rhodes University, Grahamstown, 6140 South Africa. 2Unit for Drug Research and Development, Division ...

  17. Naturally Occurring Cinnamic Acid Sugar Ester Derivatives

    Directory of Open Access Journals (Sweden)

    Yuxin Tian

    2016-10-01

    Full Text Available Cinnamic acid sugar ester derivatives (CASEDs are a class of natural product with one or several phenylacrylic moieties linked with the non-anomeric carbon of a glycosyl skeleton part through ester bonds. Their notable anti-depressant and brains protective activities have made them a topic of great interest over the past several decades. In particular the compound 3′,6-disinapoylsucrose, the index component of Yuanzhi (a well-known Traditional Chinese Medicine or TCM, presents antidepressant effects at a molecular level, and has become a hotspot of research on new lead drug compounds. Several other similar cinnamic acid sugar ester derivatives are reported in traditional medicine as compounds to calm the nerves and display anti-depression and neuroprotective activity. Interestingly, more than one third of CASEDs are distributed in the family Polygalaceae. This overview discusses the isolation of cinnamic acid sugar ester derivatives from plants, together with a systematic discussion of their distribution, chemical structures and properties and pharmacological activities, with the hope of providing references for natural product researchers and draw attention to these interesting compounds.

  18. Avocado and olive oil methyl esters

    Science.gov (United States)

    Biodiesel, the mono-alkyl esters of vegetable oils, animal fats or other triacylglycerol-containing materials and an alternative to conventional petroleum-based diesel fuel, has been derived from a variety of feedstocks. Numerous feedstocks have been investigated as potential biodiesel sources, incl...

  19. Temporary occlusion of the inferior lacrimal punctum and canaliculi of dogs with n-butyl-cyanoacrylate and 2-octyl-cyanoacrylate

    Directory of Open Access Journals (Sweden)

    Cristiane dos Santos Honsho

    2014-09-01

    Full Text Available The occlusion of the inferior lacrimal punctum limits tear drainage and thus keeps it over the ocular surface, prolongs lubrication and minimizes the need of ocular lubricants. The aim of this study was to evaluate the effectiveness of n-butyl-cyanoacrylate and 2-octyl-cyanoacrylate adhesives in the occlusion of the inferior lacrimal punctum and canaliculi of dogs and their clinical repercussions over 180 days. Eleven dogs, were divided into two groups: occlusion with n-butyl-cyanoacrylate (GB, n=6 and with 2-octyl-cyanoacrylate (GO, n=5. Tear production, blepharospasm, ocular discharge, epiphora and conjunctival hyperemia were analyzed before the procedure and on days (T 3,7,15, 30, 45, 60, 90, 120, 150 and 180 after the procedure. Tear production of GB was significantly higher at T90 (P=0.0282 than its control. Variations between days showed that T7 (P=0.0069 and T180 (P=0.0207 varied significantly from T0. In the GO group, when treatment was compared to control, T15 (P<0.001 was significantly different from the rest. Variations between days showed that T15 was significantly different than T0 (P=0.0044, T3 (P=0.0234, T60 (P=0.0207 and T90 (P=0.0482. No significant difference was observed between the treatment groups at any given time. It was concluded that both adhesives were effective in occluding lacrimal drainage for long periods and could thus be considered as therapeutic options in treating animals with lacrimal deficiency

  20. Ester Tuiksoo - Eesti esimene naissoost põllumajandusminister / Ester Tuiksoo ; interv. Toomas Verrev

    Index Scriptorium Estoniae

    Tuiksoo, Ester, 1965-

    2007-01-01

    Ametist lahkuv põllumajandusminister Ester Tuiksoo räägib saadud juhtimiskogemusest, Euroopa Liidu ühise põllumajanduspoliitika juurutamisest, rahvuskala valimisest, Rahvaliidu käekäigust parlamendivalimistel

  1. QSAR for cholinesterase inhibition by organophosphorus esters and CNDO/2 calculations for organophosphorus ester hydrolysis

    Science.gov (United States)

    Johnson, H.; Kenley, R. A.; Rynard, C.; Golub, M. A.

    1985-01-01

    Quantitative structure-activity relationships were derived for acetyl- and butyrylcholinesterase inhibition by various organophosphorus esters. Bimolecular inhibition rate constants correlate well with hydrophobic substituent constants, and with the presence or absence of catonic groups on the inhibitor, but not with steric substituent constants. CNDO/2 calculations were performed on a separate set of organophosphorus esters, RR'P(O)X, where R and R' are alkyl and/or alkoxy groups and X is fluorine, chlorine or a phenoxy group. For each subset with the same X, the CNDO-derived net atomic charge at the central phosphorus atom in the ester correlates well with the alkaline hydrolysis rate constant. For the whole set of esters with different X, two equations were derived that relate either charge and leaving group steric bulk, or orbital energy and bond order to the hydrogen hydrolysis rate constant.

  2. Euphorbias of South Africa: Two New Phorbol Esters from ...

    African Journals Online (AJOL)

    Euphorbias of South Africa: Two New Phorbol Esters from Euphorbia bothae. ... WL Popplewell, EA Marais, L Brand, BH Harvey, MT Davies-Coleman. Abstract. Two known phorbol esters, 12-deoxyphorbol-13-isobutyrate-20-acetate (1) and 12-deoxyphorbol-13-(2-methylbutyrate)-20-acetate (2), and two new phorbol esters, ...

  3. Biocatalytic synthesis and antioxidant capacities of ascorbyl esters ...

    African Journals Online (AJOL)

    ajl yemi

    2011-11-28

    Nov 28, 2011 ... available on the comparison of antioxidant activities of ascorbyl esters biosynthesized using alkyl ester, fatty acid and triglyceride as acyl donors. Therefore, this study focused on the enzymatic synthesis of L-ascorbyl acid fatty acid esters catalyzed by immobilized lipase from C. antarctica (Novozym 435) in.

  4. 21 CFR 172.848 - Lactylic esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Lactylic esters of fatty acids. 172.848 Section 172... CONSUMPTION Multipurpose Additives § 172.848 Lactylic esters of fatty acids. Lactylic esters of fatty acids... prepared from lactic acid and fatty acids meeting the requirements of § 172.860(b) and/or oleic acid...

  5. 21 CFR 172.859 - Sucrose fatty acid esters.

    Science.gov (United States)

    2010-04-01

    ... solvents which may be used in the preparation of sucrose fatty acid esters are those generally recognized... preparation of sucrose fatty acid esters. (b) Sucrose fatty acid esters meet the following specifications: (1..., 5100 Paint Branch Pkwy., College Park, MD 20740, or available for inspection at the National Archives...

  6. 21 CFR 175.210 - Acrylate ester copolymer coating.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Acrylate ester copolymer coating. 175.210 Section... COATINGS Substances for Use as Components of Coatings § 175.210 Acrylate ester copolymer coating. Acrylate ester copolymer coating may safely be used as a food-contact surface of articles intended for packaging...

  7. Activated Sludge Biodegradation of 12 Commercial Phthalate Esters

    OpenAIRE

    O'Grady, Dean P.; Howard, Philip H.; Werner, A. Frances

    1985-01-01

    The activated sludge biodegradability of 12 commercial phthalate esters was evaluated in two test systems: (i) a semicontinuous activated sludge test and (ii) an acclimated 19-day die-away procedure. Both procedures demonstrated that phthalate esters are rapidly biodegraded under activated sludge conditions when loss of the parent phthalate ester (primary degradation) is measured.

  8. Celorbicol, isocelorbicol, and their esters: new sesquiterpenoids from Celastrus orbiculatus

    Energy Technology Data Exchange (ETDEWEB)

    Smith, C.R. Jr. (Dept. of Agriculture, Peoria, IL); Miller, R.W.; Weisleder, D.; Rohwedder, W.K.; Eickman, N.; Clardy, J.

    1976-10-01

    Esters of two new sesquiterpenoid polyalcohols - celorbicol and isocelorbicol - have been isolated from Celastrus orbiculatus. Structures of the parent alcohols have been established by x-ray crystallography, and those of the derived esters have been assigned by NMR spectroscopy. These compounds are structurally related to other polyesters and ester alkaloids from the Celastraceae, all of which are based on the dihydroagarofuran ring system.

  9. Poly(ester-anhydride):poly(beta-amino ester) micro- and nanospheres: DNA encapsulation and cellular transfection.

    Science.gov (United States)

    Pfeifer, Blaine A; Burdick, Jason A; Little, Steve R; Langer, Robert

    2005-11-04

    Poly(ester-anhydride) delivery devices allow flexibility regarding carrier dimensions (micro- versus nanospheres), degradation rate (anhydride versus ester hydrolysis), and surface labeling (through the anhydride functional unit), and were therefore tested for DNA encapsulation and transfection of a macrophage P388D1 cell line. Poly(l-lactic acid-co-sebacic anhydride) and poly(l-lactic acid-co-adipic anhydride) were synthesized through melt condensation, mixed with 25 wt.% poly(beta-amino ester), and formulated with plasmid DNA (encoding firefly luciferase) into micro- and nanospheres using a double emulsion/solvent evaporation technique. The micro- and nanospheres were then characterized (size, morphology, zeta potential, DNA release) and assayed for DNA encapsulation and cellular transfection over a range of poly(ester-anhydride) copolymer ratios. Poly(ester-anhydride):poly(beta-amino ester) composite microspheres (6-12 microm) and nanospheres (449-1031 nm), generated with copolymers containing between 0 and 25% total polyanhydride content, encapsulated plasmid DNA (>or=20% encapsulation efficiency). Within this polyanhydride range, poly(adipic anhydride) copolymers provided DNA encapsulation at an increased anhydride content (10%, microspheres; 10-25%, nanospheres) compared to poly(sebacic anhydride) copolymers (1%, microspheres and nanospheres) with cellular transfection correlating with the observed DNA encapsulation.

  10. Rearrangement of beta,gamma-unsaturated esters with thallium trinitrate: synthesis of indans bearing a beta-keto ester moiety

    Directory of Open Access Journals (Sweden)

    Silva Jr. Luiz F.

    2006-01-01

    Full Text Available The rearrangement of beta,gamma-unsaturated esters, such as 2-(3,4-dihydronaphthalen-1-yl-propionic acid ethyl ester, with thallium trinitrate (TTN in acetic acid leads to 3-indan-1-yl-2-methyl-3-oxo-propionic acid ethyl ester in good yield, through a ring contraction reaction. The new indans thus obtained feature a beta-keto ester moiety, which would be useful for further functionalization.

  11. Updates on the biology of serotonin and tryptophan hydroxylase.

    Science.gov (United States)

    Swami, Tara; Weber, H Christian

    2018-02-01

    To summarize the most recent findings relevant to the biology of serotonin (5-hydroxytryptamine; 5-HT) and the enzyme tryptophan hydroxylase (TPH) in human gastrointestinal disease. Serotonin is synthesized in the central nervous system (CNS) and the gastrointestinal tract where it is secreted from enteroendocrine cells. Its biosynthesis is regulated by two isoforms of the enzyme TPH of which TPH1 is localized predominantly in gastrointestinal enteroendocrine cells. Serotonin activates the peristaltic reflexes, regulates gastrointestinal motility, and has a role in intestinal inflammation. Inhibition of TPH with novel molecules represents a new pharmacological tool in the successful management of carcinoid syndrome in patients with gastrointestinal neuroendocrine tumors (GI-NETs). Certain 5-HT receptor subtype agonists and antagonists are useful in the treatment of functional gastrointestinal disorders. The gastrointestinal tract is the largest storage organ for serotonin where its biosynthesis is regulated by TPH1. It has several important functions in gastrointestinal motility, secretion, and inflammation. Furthermore, TPH represents a target for inhibitory pharmacological therapy of serotonin access states such as the carcinoid syndrome.

  12. Tryptophan Hydroxylase 2 Gene and Alcohol Use among College Students

    Science.gov (United States)

    Gacek, Paul; Conner, Tamlin S.; Tennen, Howard; Kranzler, Henry R.; Covault, Jonathan

    2009-01-01

    Objective Genes that regulate serotonin activity are regarded as promising predictors of heavy alcohol use. Tryptophan Hydroxylase (TPH2) plays an important role in serotonergic neurotransmission by serving as the rate-limiting enzyme for serotonin biosynthesis in the midbrain and serotonergic neurons. Despite the link between TPH2 and serotonergic function, TPH2’s role in the pathogenesis of alcohol use disorders remains unclear. The goal of this study was to examine whether variation in the TPH2 gene is associated with risky alcohol consumption. Specifically, this study examined whether the TPH2 G-703T polymorphism predicted alcohol consumption among college students. Methods In two successive years, 351 undergraduates were asked to record their alcohol use each day for 30 days using an internet-based electronic diary. Participants’ DNA was collected and polymerase chain reaction genotyping was performed. Results Alcohol consumption was not associated with the TPH2 G-703T polymorphism alone, or the interaction of TPH2 with two other candidate polymorphisms (TPH1 C218A, and the SLC6A4 tri-allelic 5-HTTLPR) or negative life events. Conclusions This study supports recent null findings relating TPH2 to drinking outcomes. It also extends these findings by showing null interactions with the TPH1 C218A polymorphism, the SLC6A4 tri-allelic 5-HTTLPR polymorphism, and environmental stressors in predicting sub-clinical alcohol use among Caucasian American young adults. PMID:18782386

  13. Antitumour agents as inhibitors of tryptophan 2,3-dioxygenase

    Energy Technology Data Exchange (ETDEWEB)

    Pantouris, Georgios; Mowat, Christopher G., E-mail: C.G.Mowat@ed.ac.uk

    2014-01-03

    Highlights: •∼2800 National Cancer Institute USA compounds have been screened as potential inhibitors of TDO and/or IDO. •Seven compounds with anti-tumour properties have been identified as potent inhibitors. •NSC 36398 (taxifolin, dihydroquercetin) is selective for TDO with a K{sub i} of 16 M. •This may help further our understanding of the role of TDO in cancer. -- Abstract: The involvement of tryptophan 2,3-dioxygenase (TDO) in cancer biology has recently been described, with the enzyme playing an immunomodulatory role, suppressing antitumour immune responses and promoting tumour cell survival and proliferation. This finding reinforces the need for specific inhibitors of TDO that may potentially be developed for therapeutic use. In this work we have screened ∼2800 compounds from the library of the National Cancer Institute USA and identified seven potent inhibitors of TDO with inhibition constants in the nanomolar or low micromolar range. All seven have antitumour properties, killing various cancer cell lines. For comparison, the inhibition potencies of these compounds were tested against IDO and their inhibition constants are reported. Interestingly, this work reveals that NSC 36398 (dihydroquercetin, taxifolin), with an in vitro inhibition constant of ∼16 μM, is the first TDO-selective inhibitor reported.

  14. Tryptophanase-Catalyzed L-Tryptophan Synthesis from D-Serine in the Presence of Diammonium Hydrogen Phosphate

    Directory of Open Access Journals (Sweden)

    Fujii Noriko

    2009-06-01

    Full Text Available Tryptophanase, an enzyme with extreme absolute stereospecificity for optically active stereoisomers, catalyzes the synthesis of L-tryptophan from L-serine and indole through a β-substitution mechanism of the ping-pong type, and has no activity on D-serine. We previously reported that tryptophanase changed its stereospecificity to degrade D-tryptophan in highly concentrated diammonium hydrogen phosphate, (NH42HPO4 solution. The present study provided the same stereospecific change seen in the D-tryptophan degradation reaction also occurs in tryptophan synthesis from D-serine. Tryptophanase became active to D-serine to synthesize L-tryptophan in the presence of diammonium hydrogen phosphate. This reaction has never been reported before. D-serine seems to undergo β-replacement via an enzyme-bonded α-aminoacylate intermediate to yield L-tryptophan.

  15. Photoinduced Intramolecular Tryptophan Oxidation and Excited-State Behavior of [Re(L-AA)(CO)3(r-diimine)] þ (L = Pyridine or Imidazole, AA = Tryptophan, Tyrosine, Phenylalanine)

    Czech Academy of Sciences Publication Activity Database

    Blanco-Rodríguez, A. M.; Towrie, M.; Sýkora, Jan; Záliš, Stanislav; Vlček, Antonín

    2011-01-01

    Roč. 50, č. 13 (2011), s. 6122-6134 ISSN 0020-1669 R&D Projects: GA MŠk(CZ) LD11082 Institutional research plan: CEZ:AV0Z40400503 Keywords : tryptophan * tyrosine * phenylalanine Subject RIV: CF - Physical ; Theoretical Chemistry Impact factor: 4.601, year: 2011

  16. 13C-tryptophan breath test detects increased catabolic turnover of tryptophan along the kynurenine pathway in patients with major depressive disorder

    Science.gov (United States)

    Teraishi, Toshiya; Hori, Hiroaki; Sasayama, Daimei; Matsuo, Junko; Ogawa, Shintaro; Ota, Miho; Hattori, Kotaro; Kajiwara, Masahiro; Higuchi, Teruhiko; Kunugi, Hiroshi

    2015-01-01

    Altered tryptophan–kynurenine (KYN) metabolism has been implicated in major depressive disorder (MDD). The l-[1-13C]tryptophan breath test (13C-TBT) is a noninvasive, stable-isotope tracer method in which exhaled 13CO2 is attributable to tryptophan catabolism via the KYN pathway. We included 18 patients with MDD (DSM-IV) and 24 age- and sex-matched controls. 13C-tryptophan (150 mg) was orally administered and the 13CO2/12CO2 ratio in the breath was monitored for 180 min. The cumulative recovery rate during the 180-min test (CRR0–180; %), area under the Δ13CO2-time curve (AUC; %*min), and the maximal Δ13CO2 (Cmax; %) were significantly higher in patients with MDD than in the controls (p = 0.004, p = 0.008, and p = 0.002, respectively). Plasma tryptophan concentrations correlated negatively with Cmax in both the patients and controls (p = 0.020 and p = 0.034, respectively). Our results suggest that the 13C-TBT could be a novel biomarker for detecting a subgroup of MDD with increased tryptophan–KYN metabolism. PMID:26524975

  17. Tryptophan pathway alterations in the postpartum period and in acute postpartum psychosis and depression.

    Science.gov (United States)

    Veen, Cato; Myint, Aye Mu; Burgerhout, Karin M; Schwarz, Markus J; Schütze, Gregor; Kushner, Steven A; Hoogendijk, Witte J; Drexhage, Hemmo A; Bergink, Veerle

    2016-01-01

    Women are at very high risk for the first onset of acute and severe mood disorders the first weeks after delivery. Tryptophan breakdown is increased as a physiological phenomenon of the postpartum period and might lead to vulnerability for affective psychosis (PP) and severe depression (PD). The aim of the current study was to investigate alterations in tryptophan breakdown in the physiological postpartum period compared to patients with severe postpartum mood disorders. We included 52 patients (29 with PP, 23 with PD), 52 matched healthy postpartum women and 29 healthy non-postpartum women. Analyzes of serum tryptophan metabolites were performed using LC-MS/MS system for tryptophan, kynurenine, 3-hydroxykynurenine, kynurenic acid and 5-hydroxyindoleacetic acid. The first two months of the physiological postpartum period were characterized by low tryptophan levels, increased breakdown towards kynurenine and a downstream shift toward the 3-OH-kynurenine arm, away from the kynurenic acid arm. Kynurenine was significantly lower in patients with PP and PD as compared to healthy postpartum women (p=0.011 and p=0.001); the remaining tryptophan metabolites demonstrated few differences between patients and healthy postpartum women. Low prevalence of the investigated disorders and strict exclusion criteria to obtain homogenous groups, resulted in relatively small sample sizes. The high kynurenine levels and increased tryptophan breakdown as a phenomenon of the physiological postpartum period was not present in patients with severe postpartum mood disorders. No differences were observed in the levels of the 'neurotoxic' 3-OH-kynurenine and the 'neuroprotective' kynurenic acid arms between patients and healthy postpartum women. Copyright © 2015 Elsevier B.V. All rights reserved.

  18. The tryptophan/kynurenine pathway, systemic inflammation, and long-term outcome after kidney transplantation.

    Science.gov (United States)

    de Vries, Laura V; Minović, Isidor; Franssen, Casper F M; van Faassen, Martijn; Sanders, Jan-Stephan F; Berger, Stefan P; Navis, Gerjan; Kema, Ido P; Bakker, Stephan J L

    2017-08-01

    Tryptophan is metabolized along the kynurenine pathway, initially to kynurenine, and subsequently to cytotoxic 3-hydroxykynurenine. There is increasing interest in this pathway because of its proinflammatory nature, and drugs interfering in it have received increasing attention. We aimed to investigate whether serum and urinary parameters of the tryptophan/kynurenine pathway, and particularly cytotoxic 3-hydroxykynurenine, are associated with systemic inflammation and long-term outcome in renal transplant recipients (RTR). Data were collected in outpatient RTR with a functioning graft for >1 yr. Tryptophan, kynurenine, and 3-hydroxykynurenine in serum and urine were measured using LC-MS/MS. A total of 561 RTR (age: 51 ± 12 yr; 56% male) were included at a median of 6.0 (2.6-11.6) yr posttransplantation. Baseline median serum tryptophan was 40.0 (34.5-46.0) µmol/l, serum kynurenine was 1.8 (1.4-2.2) µmol/l, and serum 3-hydroxykynurenine was 42.2 (31.0-61.7) nmol/l. Serum kynurenine and 3-hydroxykynurenine were strongly associated with parameters of systemic inflammation. During follow-up for 7.0 (6.2-7.5) yr, 51 RTR (9%) developed graft failure and 120 RTR (21%) died. Both serum kynurenine and 3-hydroxykynurenine were independently associated with graft failure [HR 1.72 (1.23-2.41), P = 0.002; and HR 2.03 (1.42-2.90), P tryptophan/kynurenine pathway parameters were not associated with outcome. Of tryptophan metabolites, serum 3-hydroxykynurenine is cross-sectionally most strongly and consistently associated with systemic inflammation and prospectively with adverse long-term outcome after kidney transplantation. Serum 3-hydroxykynurenine may be an interesting biomarker and target for the evaluation of drugs interfering in the tryptophan/kynurenine pathway. Copyright © 2017 the American Physiological Society.

  19. Molecular imaging correlates of tryptophan metabolism via the kynurenine pathway in human meningiomas.

    Science.gov (United States)

    Bosnyák, Edit; Kamson, David O; Guastella, Anthony R; Varadarajan, Kaushik; Robinette, Natasha L; Kupsky, William J; Muzik, Otto; Michelhaugh, Sharon K; Mittal, Sandeep; Juhász, Csaba

    2015-09-01

    Increased tryptophan metabolism via the kynurenine pathway (KP) is a key mechanism of tumoral immune suppression in gliomas. However, details of tryptophan metabolism in meningiomas have not been elucidated. In this study, we evaluated in vivo tryptophan metabolism in meningiomas and compared it with gliomas using α-[(11)C]-methyl-L-tryptophan (AMT)-PET. We also explored expression patterns of KP enzymes in resected meningiomas. Forty-seven patients with MRI-detected meningioma (n = 16) and glioma (n = 31) underwent presurgical AMT-PET scanning. Tumoral AMT uptake and tracer kinetic parameters (including K and k3' evaluating unidirectional uptake and trapping, respectively) were measured, correlated with meningioma grade, and compared between meningiomas and gliomas. Patterns of KP enzyme expression were assessed by immunohistochemistry in all meningiomas. Meningioma grade showed a positive correlation with AMT k3' tumor/cortex ratio (r = 0.75, P = .003), and this PET parameter distinguished grade I from grade II/III meningiomas with 92% accuracy. Kinetic AMT parameters could differentiate meningiomas from both low-grade gliomas (97% accuracy by k3' ratios) and high-grade gliomas (83% accuracy by K ratios). Among 3 initial KP enzymes (indoleamine 2,3-dioxygenase 1/2, and tryptophan 2,3-dioxygenase 2 [TDO2]), TDO2 showed the strongest immunostaining, particularly in grade I meningiomas. TDO2 also showed a strong negative correlation with AMT k3' ratios (P = .001). PET imaging of tryptophan metabolism can provide quantitative imaging markers for differentiating grade I from grade II/III meningiomas. TDO2 may be an important driver of in vivo tryptophan metabolism in these tumors. These results can have implications for pharmacological targeting of the KP in meningiomas. © The Author(s) 2015. Published by Oxford University Press on behalf of the Society for Neuro-Oncology. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.

  20. Serum Analysis of Tryptophan Catabolism Pathway: Correlation with Crohn’s Disease Activity

    Science.gov (United States)

    Gupta, Nitin K; Thaker, Ameet I; Kanuri, Navya; Riehl, Terrence E; Rowley, Christopher W; Stenson, William F; Ciorba, Matthew A

    2011-01-01

    BACKGROUND Indoleamine 2,3 dioxygenase 1 (IDO1) is a tryptophan catabolizing enzyme with immunotolerance promoting functions. We sought to determine if increased gut expression of IDO1 in Crohn’s disease (CD) would result in detectable changes in serum levels of tryptophan and the initial IDO1 pathway catabolite, kynurenine. METHODS Individuals were prospectively enrolled through the Washington University Digestive Diseases Research Center. Montreal classification was used for disease phenotyping. Disease severity was categorized by physician’s global assessment. Serum tryptophan and kynurenine were measured by high pressure liquid chromatography. IDO1 immunohistochemical staining was performed on formalin-fixed tissue blocks. RESULTS 25 CD patients and 11 controls were enrolled. 8 CD patients had serum collected at two different time points and levels of disease activity. Strong IDO1 expression exists in both the lamina propria and epithelium during active CD compared to controls. Suppressed serum tryptophan levels and an elevated kynurenine/tryptophan (K/T) ratio were found in individuals with active CD as compared to those in remission or the control population. K/T ratios correlated positively with disease activity as well as with C-reactive protein and erythrocyte sedimentation rate. In the subgroup of CD patients with two serum measurements, tryptophan levels elevated while kynurenine levels and the K/T ratio lowered as the disease activity lessened. CONCLUSIONS IDO1 expression in Crohn’s disease is associated with lower serum tryptophan and an elevated K/T ratio. These levels may serve a reasonable objective marker of gut mucosal immune activation and surrogate for Crohn’s Disease activity. PMID:21823214

  1. Real-Time monitoring of intracellular wax ester metabolism

    Directory of Open Access Journals (Sweden)

    Karp Matti

    2011-09-01

    Full Text Available Abstract Background Wax esters are industrially relevant molecules exploited in several applications of oleochemistry and food industry. At the moment, the production processes mostly rely on chemical synthesis from rather expensive starting materials, and therefore solutions are sought from biotechnology. Bacterial wax esters are attractive alternatives, and especially the wax ester metabolism of Acinetobacter sp. has been extensively studied. However, the lack of suitable tools for rapid and simple monitoring of wax ester metabolism in vivo has partly restricted the screening and analyses of potential hosts and optimal conditions. Results Based on sensitive and specific detection of intracellular long-chain aldehydes, specific intermediates of wax ester synthesis, bacterial luciferase (LuxAB was exploited in studying the wax ester metabolism in Acinetobacter baylyi ADP1. Luminescence was detected in the cultivation of the strain producing wax esters, and the changes in signal levels could be linked to corresponding cell growth and wax ester synthesis phases. Conclusions The monitoring system showed correlation between wax ester synthesis pattern and luminescent signal. The system shows potential for real-time screening purposes and studies on bacterial wax esters, revealing new aspects to dynamics and role of wax ester metabolism in bacteria.

  2. Synthesis of Estolide 2-ethylhexyl Ester from Ricinus communis

    International Nuclear Information System (INIS)

    Nazrizawati Ahmad Tajuddin; Nor Habibah Rosli

    2013-01-01

    Estolide 2-ethylhexyl ester synthesized through condensation reaction between ricinoleic acid from castor oil (Ricinus communis) and lauric acid, and then capped with 2-ethylhexyl alcohol. The reaction was continuously conducted under vacuum for 24 hours. Product of 2-ethylhexyl ester was characterized by using Fourier Transform Infrared (FTIR) to determine functional group and Nuclear Magnetic Resonans (NMR) for structure's determination. The presence of ester group at 1738.23 cm -1 wavenumber indicates that the formation of estolide ester has occurred. The vibration peak of C-O at 1174.60 cm -1 and 1117.10 cm -1 support the formation of ester. The presence of CH 2 bending indicated the long-chain compound. The ester methine signal at 3.8669 ppm indicated the estolide linkage in the 1 H-NMR spectrum while the 13 C-NMR showed two carbonyl signals at 173.41 ppm for acid and 173.56 ppm for ester. (author)

  3. Plasma Tryptophan and the Kynurenine–Tryptophan Ratio Are Associated with the Acquisition of Statural Growth Deficits and Oral Vaccine Underperformance in Populations with Environmental Enteropathy

    Science.gov (United States)

    Kosek, Margaret N.; Mduma, Estomih; Kosek, Peter S.; Lee, Gwenyth O.; Svensen, Erling; Pan, William K. Y.; Olortegui, Maribel Paredes; Bream, Jay H.; Patil, Crystal; Asayag, Cesar Ramal; Sanchez, Graciela Meza; Caulfield, Laura E.; Gratz, Jean; Yori, Pablo Peñataro

    2016-01-01

    Early childhood enteric infections have adverse impacts on child growth and can inhibit normal mucosal responses to oral vaccines, two critical components of environmental enteropathy. To evaluate the role of indoleamine 2,3-dioxygenase 1 (IDO1) activity and its relationship with these outcomes, we measured tryptophan and the kynurenine–tryptophan ratio (KTR) in two longitudinal birth cohorts with a high prevalence of stunting. Children in rural Peru and Tanzania (N = 494) contributed 1,251 plasma samples at 3, 7, 15, and 24 months of age and monthly anthropometrics from 0 to 36 months of age. Tryptophan concentrations were directly associated with linear growth from 1 to 8 months after biomarker assessment. A 1-SD increase in tryptophan concentration was associated with a gain in length-for-age Z-score (LAZ) of 0.17 over the next 6 months in Peru (95% confidence interval [CI] = 0.11–0.23, P < 0.001) and a gain in LAZ of 0.13 Z-scores in Tanzania (95% CI = 0.03–0.22, P = 0.009). Vaccine responsiveness data were available for Peru only. An increase in kynurenine by 1 μM was associated with a 1.63 (95% CI = 1.13–2.34) increase in the odds of failure to poliovirus type 1, but there was no association with tetanus vaccine response. A KTR of 52 was 76% sensitive and 50% specific in predicting failure of response to serotype 1 of the oral polio vaccine. KTR was associated with systemic markers of inflammation, but also interleukin-10, supporting the association between IDO1 activity and immunotolerance. These results strongly suggest that the activity of IDO1 is implicated in the pathophysiology of environmental enteropathy, and demonstrates the utility of tryptophan and kynurenine as biomarkers for this syndrome, particularly in identifying those at risk for hyporesponsivity to oral vaccines. PMID:27503512

  4. N-acetyl-l-tryptophan, but not N-acetyl-d-tryptophan, rescues neuronal cell death in models of amyotrophic lateral sclerosis.

    Science.gov (United States)

    Sirianni, Ana C; Jiang, Jiying; Zeng, Jiang; Mao, Lilly L; Zhou, Shuanhu; Sugarbaker, Peter; Zhang, Xinmu; Li, Wei; Friedlander, Robert M; Wang, Xin

    2015-09-01

    Amyotrophic lateral sclerosis (ALS) is a neurodegenerative disease characterized by progressive motor neuron loss. Evidence suggests that mitochondrial dysfunction, apoptosis, oxidative stress, inflammation, glutamate excitotoxicity, and proteasomal dysfunction are all responsible for ALS pathogenesis. N-acetyl-tryptophan has been identified as an inhibitor of mitochondrial cytochrome c release and therefore is a potential neuroprotective agent. By quantifying cell death, we demonstrate that N-acetyl-l-tryptophan (L-NAT) and N-acetyl-DL-tryptophan are neuroprotective in NSC-34 motor neuron-like cells and/or primary motor neurons, while their isomer N-acetyl-d-tryptophan has no protective effect. These findings are consistent with energy minimization and molecular modeling analysis, confirming that L-NAT generates the most stable complex with the neurokinin-1 receptor (NK-1R). L-NAT inhibits the secretion of Substance P and IL-1β (Enzyme-Linked Immunosorbent Assay and/or dot blots) and mitochondrial dysfunction by effectively inhibiting the release of cytochrome c/Smac/AIF from mitochondria into the cytoplasm and activation of apoptotic pathways, including the activation of caspase-1, -9, and -3, as well as proteasomal dysfunction through restoring chymotrypsin-like, trypsin-like, and caspase-like proteasome activity. These data provide insight into the molecular mechanisms by which L-NAT offers neuroprotection in models of ALS and suggest its potential as a novel therapeutic strategy for ALS. We demonstrate that L-NAT (N-acetyl-l-tryptophan), but not D-NAT, rescues NSC-34 cells and primary motor neurons from cell death. L-NAT inhibits the secretion of Substance P and IL-1β, and caspase-1 activation, the release of cytochrome c/Smac/AIF, and the activation of caspase -9, and -3, as well as proteasomal dysfunction. The data suggest the potential of L-NAT as a novel therapeutic strategy for amyotrophic lateral sclerosis (ALS). AIF, apoptosis-inducing factor. © 2015

  5. Enzymatic synthesizing of phytosterol oleic esters.

    Science.gov (United States)

    Pan, Xinxin; Chen, Biqiang; Wang, Juan; Zhang, Xinzhi; Zhul, Biyun; Tan, Tianwei

    2012-09-01

    A method of synthesizing the phytosterol esters from oleic acid and sterols was studied, using immobilized lipase Candida sp. 99-125 as catalyst. Molar ratio (oleic acid/phytosterols), temperature, reaction period, organic solvents, catalyst, and silica-gel drier were optimized, and the result showed that 93.4% of the sterols had been esterified under the optimal synthetic condition: the molar ratio of oleic acid/phytosterol is 1:1 in 10 mL iso-octane, immobilized lipase (w, 140% of the sterols), incubated in an orbital shaker (200 rpm) at a temperature of 45 °C for 24 h. The immobilized lipase could be reused for at least 13 times with limited loss of esterification activity. The conversion still maintained up to 86.6%. Hence, this developed process for synthesizing phytosterol esters could be considered as simple and low-energy consumption compared to existing chemical processes.

  6. Atmospheric oxidation of selected alcohols and esters

    Energy Technology Data Exchange (ETDEWEB)

    Becker, K.H.; Cavalli, F.

    2001-03-01

    The decision whether it is appropriate and beneficial for the environment to deploy specific oxygenated organic compounds as replacements for traditional solvent types requires a quantitative assessment of their potential atmospheric impacts including tropospheric ozone and other photooxidant formation. This involves developing chemical mechanisms for the gasphase atmospheric oxidation of the compounds which can be reliably used in models to predict their atmospheric reactivity under a variety of environmental conditions. Until this study, there was very little information available concerning the atmospheric fate of alcohols and esters. The objectives of this study were to measure the atmospheric reaction rates and to define atmospheric reaction mechanisms for the following selected oxygenated volatile organic compounds: the alcohols, 1-butanol and 1-pentanol, and the esters, methyl propionate and dimethyl succinate. The study has successfully addressed these objectives. (orig.)

  7. Naturally occurring antifungal aromatic esters and amides

    International Nuclear Information System (INIS)

    Ali, M.S.; Shahnaz; Tabassum, S.; Ogunwande, I.A.; Pervez, M.K.

    2010-01-01

    During the search of antifungal natural products from terrestrial plants, a new long chained aromatic ester named grandiflorate along with spatazoate from Portulaca grandiflora and N-[2-methoxy-2-(4-methoxyphenyl) ethyl]-trans-cinnamide and aegeline from Solanum erianthum of Nigeria were isolated and tested against six fungal species. The known constituents have not been reported so far from mentioned investigated plants. Structures of the isolated compounds were elucidated with the aid of spectroscopic techniques including two dimensional NMR experiments. Among the compounds, the esters found more potent than amides against Candida albicans and Aspergillus flavus. The new compound grandiflorate gave response against all tested fungal species while aegeline was found to give lowest inhibition during this study. (author)

  8. Clinical and physiological consequences of rapid tryptophan depletion.

    Science.gov (United States)

    Moore, P; Landolt, H P; Seifritz, E; Clark, C; Bhatti, T; Kelsoe, J; Rapaport, M; Gillin, J C

    2000-12-01

    We review here the rapid tryptophan depletion (RTD) methodology and its controversial association with depressive relapse. RTD has been used over the past decade to deplete serotonin (5-hydroxy-tryptamine, or 5-HT) in humans and to probe the role of the central serotonin system in a variety of psychiatric conditions. Its current popularity was stimulated by reports that RTD reversed the antidepressant effects of selective serotonin reuptake inhibitors (SSRIs) and monoamine oxidase inhibitors (MAOIs) in remitted patients with a history of depression but not in patients treated with antidepressants which promote catecholaminergic rather than serotonergic neurotransmission (such as tricyclic antidepressants or buproprion). However, RTD has inconsistent effects in terms of full clinical relapse in depressed patients. Pooling the data from all published reports, patients who are either unmedicated and/or fully remitted are much less likely to experience relapse (7 of 61, or approximately 9%) than patients who are recently medicated and partially remitted (63 of 133, or approximately 47%; although, the numbers here may reflect patient overlap between reports). Recently remitted patients who have been treated with non-pharmacological therapies such as total sleep deprivation, electroconvulsive therapy, or bright light therapy also do not commonly show full clinical relapse with RTD. We briefly review RTD effects in other psychiatric disorders, many of which are treated with SSRIs. There is accumulating evidence to suggest that RTD affects central serotonergic neurotransmission. Nevertheless, many questions remain about the ability of RTD to reverse the beneficial effects of SSRIs or MAOIs, or to induce symptoms in unmedicated symptomatic or asymptomatic patients.

  9. Synthetic Methods for Ester Bond Formation and Conformational Analysis of Ester-Containing Carbohydrates

    Science.gov (United States)

    Hackbusch, Sven

    This dissertation encompasses work related to synthetic methods for the formation of ester linkages in organic compounds, as well as the investigation of the conformational influence of the ester functional group on the flexibility of inter-saccharide linkages, specifically, and the solution phase structure of ester-containing carbohydrate derivatives, in general. Stereoselective reactions are an important part of the field of asymmetric synthesis and an understanding of their underlying mechanistic principles is essential for rational method development. Here, the exploration of a diastereoselective O-acylation reaction on a trans-2-substituted cyclohexanol scaffold is presented, along with possible reasons for the observed reversal of stereoselectivity dependent on the presence or absence of an achiral amine catalyst. In particular, this work establishes a structure-activity relationship with regard to the trans-2-substituent and its role as a chiral auxiliary in the reversal of diastereoselectivity. In the second part, the synthesis of various ester-linked carbohydrate derivatives, and their conformational analysis is presented. Using multidimensional NMR experiments and computational methods, the compounds' solution-phase structures were established and the effect of the ester functional group on the molecules' flexibility and three-dimensional (3D) structure was investigated and compared to ether or glycosidic linkages. To aid in this, a novel Karplus equation for the C(sp2)OCH angle in ester-linked carbohydrates was developed on the basis of a model ester-linked carbohydrate. This equation describes the sinusoidal relationship between the C(sp2)OCH dihedral angle and the corresponding 3JCH coupling constant that can be determined from a J-HMBC NMR experiment. The insights from this research will be useful in describing the 3D structure of naturally occurring and lab-made ester-linked derivatives of carbohydrates, as well as guiding the de novo-design of

  10. Methyl and ethyl soybean esters production

    Energy Technology Data Exchange (ETDEWEB)

    Pighinelli, Anna Leticia Montenegro Turtelli; Park, Kil Jin; Zorzeto, Thais Queiroz [Universidade Estadual de Campinas (FEAGRI/UNICAMP), SP (Brazil). Fac. de Engenharia Agricola], E-mail: annalets@feagri.unicamp.br; Bevilaqua, Gabriela [Universidade Estadual de Campinas (IQ/UNICAMP), SP (Brazil). Inst. de Quimica

    2008-07-01

    Biodiesel is a fuel obtained from triglycerides found in nature, like vegetable oils and animal fats. Nowadays it has been the subject of many researches impulses by the creation of the Brazilian law that determined the blend of 2% of biodiesel with petrodiesel. Basically, there are no limitations on the oilseed type for chemical reaction, but due to high cost of this major feedstock, it is important to use the grain that is available in the region of production. Soybean is the oilseed mostly produced in Brazil and its oil is the only one that is available in enough quantity to supply the current biodiesel demand. The objective of this work was to study the effects of reaction time and temperature on soybean oil transesterification reaction with ethanol and methanol. A central composite experimental design with five variation levels was used and response surface methodology applied for the data analysis. The statistical analysis of the results showed that none of the factors affected the ethyl esters production. However, the methyl esters production suffered the influence of temperature (linear effect), reaction time (linear and quadratic) and interaction of these two variables. None of the generated models showed significant regression consequently it was not possible to build the response surface. The experiments demonstrated that methanol is the best alcohol for transesterification reactions and the ester yield was up to 85%. (author)

  11. Lignans from Carthamus tinctorius suppress tryptophan breakdown via indoleamine 2,3-dioxygenase

    Science.gov (United States)

    Kuehnl, Susanne; Schroecksnadel, Sebastian; Temml, Veronika; Gostner, Johanna M.; Schennach, Harald; Schuster, Daniela; Schwaiger, Stefan; Rollinger, Judith M.; Fuchs, Dietmar; Stuppner, Hermann

    2013-01-01

    Seed extracts of Carthamus tinctorius L. (Asteraceae), safflower, have been traditionally used to treat coronary disease, thrombotic disorders, and menstrual problems but also against cancer and depression. A possible effect of C. tinctorius compounds on tryptophan-degrading activity of enzyme indoleamine 2,3-dioxygenase (IDO) could explain many of its activities. To test for an effect of C. tinctorius extracts and isolated compounds on cytokine-induced IDO activity in immunocompetent cells in vitro methanol and ethylacetate seed extracts were prepared from cold pressed seed cakes of C. tinctorius and three lignan derivatives, trachelogenin, arctigenin and matairesinol were isolated. The influence on tryptophan breakdown was investigated in peripheral blood mononuclear cells (PBMCs). Effects were compared to neopterin production in the same cellular assay. Both seed extracts suppressed tryptophan breakdown in stimulated PBMC. The three structurally closely related isolates exerted differing suppressive activity on PBMC: arctigenin (IC50 26.5 μM) and trachelogenin (IC50 of 57.4 μM) showed higher activity than matairesinol (IC50 >200 μM) to inhibit tryptophan breakdown. Effects on neopterin production were similar albeit generally less strong. Data show an immunosuppressive property of compounds which slows down IDO activity. The in vitro results support the view that some of the anti-inflammatory, anti-cancer and antidepressant properties of C. tinctorius lignans might relate to their suppressive influence on tryptophan breakdown. PMID:23867649

  12. Selective Oxidation of Methionine and Tryptophan Residues in a Therapeutic IgG1 Molecule.

    Science.gov (United States)

    Folzer, Emilien; Diepold, Katharina; Bomans, Katrin; Finkler, Christof; Schmidt, Roland; Bulau, Patrick; Huwyler, Jörg; Mahler, Hanns-Christian; Koulov, Atanas V

    2015-09-01

    Oxidation of methionine and tryptophan are common degradation pathways for monoclonal antibodies and present major analytical challenges in biotechnology. Generally, protein oxidation is detectable in stability and/or stressed samples (e.g., exposed to hydrogen peroxide, UV light, or metal ions). The induced chemical modifications may impact the biological activity of antibodies and may have biological consequences. However, these effects and the contribution of individual protein modifications are difficult to delineate as different amino acids are often oxidized simultaneously and accompanied by other degradants such as aggregates, especially in forced degradation studies. Here, we report a new method to obtain selective oxidation of methionine or tryptophan by using oxidation reagents combined with large excess of free tryptophan or methionine, correspondingly. More specifically, using hydrogen peroxide or tert-butyl hydroperoxide in combination with addition of free tryptophan allowed for selective oxidation of methionine. Conversely, the use of 2,2-azobis(2-amidinopropane) dihydrochloride in combination with free methionine resulted in selective tryptophan oxidation, whereas methionine oxidation was not significantly altered. This novel stress model system may prove to be valuable tool in future mechanistic studies of oxidative degradation of protein therapeutics. © 2015 Wiley Periodicals, Inc. and the American Pharmacists Association.

  13. Model of Tryptophan Metabolism, Readily Scalable Using Tissue-specific Gene Expression Data*

    Science.gov (United States)

    Stavrum, Anne-Kristin; Heiland, Ines; Schuster, Stefan; Puntervoll, Pål; Ziegler, Mathias

    2013-01-01

    Tryptophan is utilized in various metabolic routes including protein synthesis, serotonin, and melatonin synthesis and the kynurenine pathway. Perturbations in these pathways have been associated with neurodegenerative diseases and cancer. Here we present a comprehensive kinetic model of the complex network of human tryptophan metabolism based upon existing kinetic data for all enzymatic conversions and transporters. By integrating tissue-specific expression data, modeling tryptophan metabolism in liver and brain returned intermediate metabolite concentrations in the physiological range. Sensitivity and metabolic control analyses identified expected key enzymes to govern fluxes in the branches of the network. Combining tissue-specific models revealed a considerable impact of the kynurenine pathway in liver on the concentrations of neuroactive derivatives in the brain. Moreover, using expression data from a cancer study predicted metabolite changes that resembled the experimental observations. We conclude that the combination of the kinetic model with expression data represents a powerful diagnostic tool to predict alterations in tryptophan metabolism. The model is readily scalable to include more tissues, thereby enabling assessment of organismal tryptophan metabolism in health and disease. PMID:24129579

  14. The effect of acute tryptophan depletion on mood and impulsivity in polydrug ecstasy users.

    Science.gov (United States)

    Young, Simon N; Regoli, Martine; Leyton, Marco; Pihl, Robert O; Benkelfat, Chawki

    2014-02-01

    Several studies suggest users of 3,4-methylenedioxymethamphetamine (ecstasy) have low levels of serotonin. Low serotonin may make them susceptible to lowered mood. This work aims to study the acute effects on mood and impulsivity of lowering serotonin levels with acute tryptophan depletion in polydrug ecstasy users and to determine whether effects were different in men and women. In a double-blind cross-over study, participants who had used ecstasy at least 25 times (n = 13) and nonuser controls (n = 17) received a tryptophan-deficient amino acid mixture and a control amino acid mixture containing tryptophan, at least 1 week apart. Mood was measured using the profile of mood states, and impulsivity was measured with the Go/No-Go task. The main result shows that a lowering of mood after acute tryptophan depletion occurred only in female polydrug ecstasy users (n = 7), relative to controls (n = 9). Results from the Go/No-Go task suggested that impulsivity was not increased by acute tryptophan depletion in polydrug ecstasy users. The group sizes were small, when males and females were considered separately. Women polydrug ecstasy users appear to be more susceptible than men to the effects of lowered serotonin levels. If use of ecstasy alone or in conjunction with other drugs causes progressive damage of serotonin neurons, women polydrug ecstasy users may become susceptible to clinical depression.

  15. Judgment of pure fermented soy sauce by fluorescence resonance energy transfer of OPA-tryptophan adduct.

    Science.gov (United States)

    Gao, You-Syuan; Hsieh, Bo-Chuan; Cheng, Tzong-Jih; Chen, Richie L C

    2015-07-01

    Tryptophan was detected with a flow-injection manifold after reacting with mM order of fluorogenic o-phthalaldehyde (OPA)/thiol reagent (pH 10.0) in the carrier stream (0.63 mL/min). Based on the intra-molecular fluorescence resonance energy transfer of OPA-tryptophan adduct, the difference in fluorescence intensity obtained at 280 and 300 nm excitation was used to detect tryptophan content with satisfactory precision (CV<6.5% for concentration higher than 0.5 μM), linearity (0.1-10 μM, R(2)=0.9893) and sensitivity (≈10 nM). Since tryptophan will decompose during manufacturing non-fermented soy sauce by acid-hydrolysis procedure, the method was used to discriminate pure fermented soy sauces, adulterated soy sauces and chemical soy sauces in less than 5 min. The ratio of tryptophan to total amino acid content served as the index for the judgment, and the results were validated by capillary electrophoresis. Copyright © 2015 Elsevier Ltd. All rights reserved.

  16. Glycine as a regulator of tryptophan-dependent pigment synthesis in Malassezia furfur.

    Science.gov (United States)

    Barchmann, Thorsten; Hort, Wiebke; Krämer, Hans-Joachim; Mayser, Peter

    2011-01-01

    The effects of the addition of different amino nitrogens on growth, morphology and secondary metabolism of Malassezia furfur were investigated. After primary culture on Dixon agar, M. furfur CBS 1878 was transferred into a fluid medium together with the nitrogen sources, glycine (Gly) or tryptophan (Trp), or a combination of both. Growth was measured by means of a direct cell counting method and pigment synthesis was photometrically assessed. Addition of glycine resulted in an exponential increase in biomass, but not in pigment production. Tryptophan as the sole nitrogen source caused distinct brown staining of the medium, without increasing biomass. Simultaneous equimolar addition of both amino acids resulted in an initial increase in biomass as a sign of preferential metabolism of glycine, followed by a growth plateau and pigment production which, caused by higher biomass, occurred more rapidly than after addition of tryptophan alone. The yeast-cell morphology changed from round to oval. Addition of glycine to the tryptophan-containing liquid culture stopped pigment formation with simultaneous growth induction. These in vitro on-off phenomena depending on the nitrogen source might be significant in the pathogenesis of pityriasis versicolor: hyperhidrosis followed by preferential consumption of individual nitrogen sources such as glycine with exponential growth and thereafter transamination of tryptophan and TRP-dependent pigment synthesis. © 2009 Blackwell Verlag GmbH.

  17. GPR142 Controls Tryptophan-Induced Insulin and Incretin Hormone Secretion to Improve Glucose Metabolism.

    Directory of Open Access Journals (Sweden)

    Hua V Lin

    Full Text Available GPR142, a putative amino acid receptor, is expressed in pancreatic islets and the gastrointestinal tract, but the ligand affinity and physiological role of this receptor remain obscure. In this study, we show that in addition to L-Tryptophan, GPR142 signaling is also activated by L-Phenylalanine but not by other naturally occurring amino acids. Furthermore, we show that Tryptophan and a synthetic GPR142 agonist increase insulin and incretin hormones and improve glucose disposal in mice in a GPR142-dependent manner. In contrast, Phenylalanine improves in vivo glucose disposal independently of GPR142. Noteworthy, refeeding-induced elevations in insulin and glucose-dependent insulinotropic polypeptide are blunted in Gpr142 null mice. In conclusion, these findings demonstrate GPR142 is a Tryptophan receptor critically required for insulin and incretin hormone regulation and suggest GPR142 agonists may be effective therapies that leverage amino acid sensing pathways for the treatment of type 2 diabetes.

  18. New insights into biodrying mechanism associated with tryptophan and tyrosine degradations during sewage sludge biodrying.

    Science.gov (United States)

    Cai, Lu; Krafft, Thomas; Chen, Tong-Bin; Lv, Wen-Zhou; Gao, Ding; Zhang, Han-Yan

    2017-11-01

    Sewage sludge biodrying is a treatment that uses bio-heat generated from organic degradation to remove water from sewage sludge. Dewatering is still limited during biodrying, due to the presence of extracellular polymeric substances (EPS) in sludge. To study the biodrying mechanism associated with EPS compositions tryptophan and tyrosine degradations, this study investigated the microbial function in sludge biodrying material. This study conducted a taxonomic analysis of biodrying material; determined the most abundant genetic functions; analyzed the functional microorganisms involved in the degradations of tryptophan and tyrosine; and summarized the metabolic pathways. The results indicated efficient degradations of tryptophan and tyrosine were observed during the initial thermophilic phase; functional microorganisms were mainly from the phyla Firmicutes, Actinobacteria, and Proteobacteria, enriched with genes involved in amino acid transport and metabolism. These findings highlight the potentially important microorganisms and typical pathways that may help improve dewaterability during biodegradation. Copyright © 2017 Elsevier Ltd. All rights reserved.

  19. Photosensitizer-conjugated tryptophan-containing peptide ligands as new dual-targeted theranostics for cancers.

    Science.gov (United States)

    Kim, Jisu; Chae, Jihyun; Kim, Jun Soo; Goh, Sung-Ho; Choi, Yongdoo

    2016-11-20

    Here we report that new dual-targeted theranostic anti-cancer agents can be produced by simple conjugation of photosensitizers with tryptophan-containing peptide ligands via cyclic disulfide linkages. In the proof-of-concept study, photosensitizers conjugated with EGFR-targeting peptide GE11 (C-EGFR) were in close proximity with tryptophan residues in the conjugate, resulting in quenching of its fluorescence and singlet oxygen generation. C-EGFR specifically binds to target receptors on the cancer cell surface, after which it is internalized via receptor-mediated endocytosis. Intracellular cleavage of cyclic disulfide bonds allows separation of the photosensitizers from the tryptophan residue, after which they emit near-infrared (NIR) fluorescence and produce a phototoxic effect in the target cells. This strategy enabled us to accomplish simultaneous real-time NIR fluorescence imaging of EGFR-overexpressing cancer cells with high contrast and selective photodynamic therapy. Copyright © 2016 Elsevier B.V. All rights reserved.

  20. Twenty-four-hour plasma tryptophan concentrations and ratios are below normal in obese subjects and are not normalized by substantial weight reduction

    DEFF Research Database (Denmark)

    Breum, Leif; Rasmussen, Michael H; Hilsted, Jannik

    2003-01-01

    BACKGROUND: Plasma tryptophan concentrations and the ratio of tryptophan to other large neutral amino acids (plasma tryptophan ratio) are reportedly low in obese subjects. The plasma tryptophan ratio predicts brain tryptophan uptake and serotonin production. If this ratio is low in obese subjects...... subjects. Blood samples were drawn frequently throughout the 24-h period. An insulin tolerance test was also used to determine whether weight loss altered the ability of insulin to modify plasma concentrations of tryptophan and of the other large neutral amino acids. RESULTS: Plasma tryptophan...... concentrations and ratios in obese subjects were low at all times; these effects persisted after weight reduction. Plasma concentrations of all the large neutral amino acids decreased during insulin infusion in all the groups. CONCLUSIONS: The low 24-h plasma tryptophan ratios in obese and formerly obese...

  1. Aspirin down-regulates tryptophan degradation in stimulated human peripheral blood mononuclear cells in vitro.

    Science.gov (United States)

    Schroecksnadel, K; Winkler, C; Wirleitner, B; Schennach, H; Fuchs, D

    2005-04-01

    Acetylsalicylic acid (aspirin) is one of the most widely used drugs worldwide, due mainly to its broad therapeutic spectrum with anti-inflammatory, antipyretic, antithrombotic and analgesic effects. However, the exact mechanisms by which aspirin influences inflammation, pain and immune system activation are only partly understood. Within activation of the cellular immune system, Th1-type cytokine interferon (IFN)-gamma induces enzyme indoleamine-2,3-dioxygenase (IDO) which converts tryptophan to kynurenine. In parallel, IFN-gamma induces enzyme GTP-cyclohydrolase I, which gives rise to neopterin production by activated human macrophages. Similarly, tryptophan degradation and neopterin formation increase during several disease states involving Th1-type immune activation. Using stimulated human peripheral blood mononuclear cells (PBMC), the effect of aspirin on tryptophan degradation and neopterin production was investigated. Stimulation of PBMC with mitogens concanavalin A, phytohaemagglutinin and pokeweed mitogen induced significant tryptophan catabolism as was reflected by a decline in tryptophan levels and a parallel increase in kynurenine concentrations compared with unstimulated cells. In parallel, neopterin production was enhanced. Treatment of stimulated PBMC with increasing doses of 1-5 mM aspirin significantly decreased stimulation-induced tryptophan degradation and neopterin production as well. All the effects of aspirin were dose-dependent. The parallel influence of aspirin on both biochemical pathways implies that there was no direct inhibitory effect of aspirin on IDO; rather, it inhibits production of IFN-gamma in mitogen-treated PBMC. The influence of aspirin on biochemical pathways induced by IFN-gamma may represent an important part of its broad pharmacological effect.

  2. Non-invasive tryptophan fluorescence measurements as a novel method of grading cataract.

    Science.gov (United States)

    Erichsen, Jesper Høiberg; Mensah, Aurore; Kessel, Line

    2017-12-01

    Development of non-invasive treatments for cataract calls for a sensitive diagnostic assay. We conducted a study to test whether the ratio of folded tryptophan to non-tryptophan fluorescence emission (F-factor) may be used for grading cataracts in human lenses. The F-factor was measured on aspirated lens material from eyes undergoing femtosecond laser assisted cataract surgery (FLACS) and was compared to a preoperative optical grading of cataract using Scheimpflug imaging. The preoperative optical grading allocated the cataracts to 1 of 4 categories according to the density of the cataract. All cataracts were age-related. Lens material from 16 eyes of 14 patients was included in the study. Cataracts were preoperatively graded in categories 1, 2 and 3. No lenses were category 4. For nuclear cataracts mean values of F-factor were 52.9 (SD 12.2), 61.7 (SD 5.3) and 75.7 (SD 8.9) for categories 1, 2 and 3 respectively. Linear regression on F-factor as a function of preoperative grading category showed increasing values of F-factor with increasing preoperative grading category, R 2  = 0.515. Our experiment showed that preoperative optical grading of cataracts by Scheimpflug imaging may correlate to measures of tryptophan and non-tryptophan fluorescence in human lenses. Based on our results we find that measuring the ratio between tryptophan- and non-tryptophan fluorescence may be a future tool for grading cataracts, but further research is needed. Copyright © 2017 Elsevier Ltd. All rights reserved.

  3. Pigment production on L-tryptophan medium by Cryptococcus gattii and Cryptococcus neoformans.

    Science.gov (United States)

    Chaskes, Stuart; Cammer, Michael; Nieves, Edward; Casadevall, Arturo

    2014-01-01

    In recent years strains previously grouped within Cryptococcus neoformans have been divided into two species C. neoformans and C. gattii, with Cryptococcus neoformans comprising serotypes A, D, and AD and C. gattii comprising serotypes B and C. Cryptococcus neoformans have also been subdivided into two varieties C. neoformans var. grubii, serotype A, and C. neoformans var. neoformans, serotype D. We analyzed the growth and pigment production characteristics of 139 strains of Cryptococcus spp. in L-tryptophan containing media. Nearly all strains of Cryptococcus, including each variety and serotype tested produced a pink water-soluble pigment (molecular weight of 535.2 Da) from L-tryptophan. Consequently, the partial separation of the species was based on whether the pink pigment was secreted into the medium (extracellular) or retained as an intracellular pigment. On L-tryptophan medium C. neoformans var. grubii and serotype AD produced a pink extracellular pigment. In contrast, for C. gattii, the pink pigment was localized intracellularly and masked by heavy production of brown pigments. Pigment production by C. neoformans var. neoformans was variable with some strains producing the pink extracellular pigment and others retained the pink pigment intracellularly. The pink intracellular pigment produced by strains of C. neoformans var. neoformans was masked by production of brown pigments. Cryptococcus laccase mutants failed to produce pigments from L-tryptophan. This is the first report that the enzyme laccase is involved in tryptophan metabolism. Prior to this report Cryptococcus laccase produced melanin or melanin like-pigments from heterocyclic compounds that contained ortho or para diphenols, diaminobenzenes and aminophenol compounds. The pigments produced from L-tryptophan were not melanin.

  4. Pigment Production on L-Tryptophan Medium by Cryptococcus gattii and Cryptococcus neoformans

    Science.gov (United States)

    Chaskes, Stuart; Cammer, Michael; Nieves, Edward; Casadevall, Arturo

    2014-01-01

    In recent years strains previously grouped within Cryptococcus neoformans have been divided into two species C. neoformans and C. gattii, with Cryptococcus neoformans comprising serotypes A, D, and AD and C. gattii comprising serotypes B and C. Cryptococcus neoformans have also been subdivided into two varieties C. neoformans var. grubii, serotype A, and C. neoformans var. neoformans, serotype D. We analyzed the growth and pigment production characteristics of 139 strains of Cryptococcus spp. in L-tryptophan containing media. Nearly all strains of Cryptococcus, including each variety and serotype tested produced a pink water-soluble pigment (molecular weight of 535.2 Da) from L-tryptophan. Consequently, the partial separation of the species was based on whether the pink pigment was secreted into the medium (extracellular) or retained as an intracellular pigment. On L-tryptophan medium C. neoformans var. grubii and serotype AD produced a pink extracellular pigment. In contrast, for C. gattii, the pink pigment was localized intracellularly and masked by heavy production of brown pigments. Pigment production by C. neoformans var. neoformans was variable with some strains producing the pink extracellular pigment and others retained the pink pigment intracellularly. The pink intracellular pigment produced by strains of C. neoformans var. neoformans was masked by production of brown pigments. Cryptococcus laccase mutants failed to produce pigments from L-tryptophan. This is the first report that the enzyme laccase is involved in tryptophan metabolism. Prior to this report Cryptococcus laccase produced melanin or melanin like-pigments from heterocyclic compounds that contained ortho or para diphenols, diaminobenzenes and aminophenol compounds. The pigments produced from L-tryptophan were not melanin. PMID:24736553

  5. Western diet-induced anxiolytic effects in mice are associated with alterations in tryptophan metabolism.

    Science.gov (United States)

    Ohland, Christina L; Pankiv, Evelina; Baker, Glen; Madsen, Karen L

    2016-10-01

    Western-style diets high in saturated fat and refined carbohydrate have been shown to alter gut microbiota as well as being associated with altered behaviour and learning ability. The objective of this study was to determine the effects of short-term intake of a Western-style diet on intestinal cytokine expression, tryptophan metabolism, and levels of neurotransmitters in the brain. At 7 weeks of age, 129S1/SvImJ mice were placed on a standard chow or Western-style diet (fat 33%, refined carbohydrates 49%) for 3 weeks. Anxiety-like behaviour was assessed by the latency to step-down test and exploration assessed in a Barnes maze. Neurotransmitter levels in forebrains were analysed by high-pressure liquid chromatography. Liver metabolism was examined by 1 H nuclear magnetic resonance (NMR). Cytokine expression in the intestine was measured using MesoScale discovery platform. mRNA levels of tryptophan hydroxylase (Tph) and indoleamine 2,3-dioxygenase (IDO) in the brain and intestine were measured using qPCR. Results showed that mice fed the Western diet displayed reduced exploratory and anxiety-like behaviour. Anxiolytic effects correlated with increased hippocampal brain-derived neurotrophic factor (BDNF) and tryptophan levels. Brain serotonin was not altered. These changes were associated with reduced expression of small intestinal indoleamine 2,3-dioxygenase, a tryptophan-processing enzyme. Western diet-fed mice exhibited low-grade systemic and intestinal inflammation along with altered liver metabolic profiles. In conclusion, diets high in fat and refined sugar are associated with increased levels of brain BDNF and tryptophan and decreased exploratory and anxiety-like behaviour. These behavioural changes correlated with altered intestinal tryptophan metabolism and liver metabolic profiles.

  6. Quinine interactions with tryptophan and tyrosine in malaria patients, and implications for quinine responses in the clinical setting.

    Science.gov (United States)

    Islahudin, Farida; Pleass, Richard J; Avery, Simon V; Ting, Kang-Nee

    2012-10-01

    Recent work with the yeast model revealed that the antiprotozoal drug quinine competes with tryptophan for uptake via a common transport protein, causing cellular tryptophan starvation. In the present work, it was hypothesized that similar interactions may occur in malaria patients receiving quinine therapy. A direct observational study was conducted in which plasma levels of drug and amino acids (tryptophan, tyrosine and phenylalanine) were monitored during quinine treatment of malaria patients with Plasmodium falciparum infections. Consistent with competition for uptake from plasma into cells, plasma tryptophan and tyrosine levels increased ≥2-fold during quinine therapy. Plasma quinine levels in individual plasma samples were significantly and positively correlated with tryptophan and tyrosine in the same samples. Control studies indicated no effect on phenylalanine. Chloroquine treatment of Plasmodium vivax-infected patients did not affect plasma tryptophan or tyrosine. During quinine treatment, plasma tryptophan was significantly lower (and quinine significantly higher) in patients experiencing adverse drug reactions. Plasma quinine levels during therapy are related to patient tryptophan and tyrosine levels, and these interactions can determine patient responses to quinine. The study also highlights the potential for extrapolating insights directly from the yeast model to human malaria patients.

  7. Liquid chromatography-fluorescence and liquid chromatography-mass spectrometry detection of tryptophan degradation products of a recombinant monoclonal antibody.

    Science.gov (United States)

    Nowak, Christine; Ponniah, Gomathinayagam; Cheng, Guilong; Kita, Adriana; Neill, Alyssa; Kori, Yekaterina; Liu, Hongcheng

    2016-03-01

    Light exposure is one of several conditions used to study the degradation pathways of recombinant monoclonal antibodies. Tryptophan is of particular interest among the 20 amino acids because it is the most photosensitive. Tryptophan degradation forms several products, including an even stronger photosensitizer and several reactive oxygen species. The current study reports a specific peptide mapping procedure to monitor tryptophan degradation. Instead of monitoring peptides using UV 214 nm, fluorescence detection with an excitation wavelength of 295 nm and an emission wavelength of 350 nm was used to enable specific detection of tryptophan-containing peptides. Peaks that decreased in area over time are likely to contain susceptible tryptophan residues. This observation can allow further liquid chromatography-mass spectrometry (LC-MS) analysis to focus only on those peaks to confirm tryptophan degradation products. After confirmation of tryptophan degradation, susceptibility of tryptophan residues can be compared based on the peak area decrease. Copyright © 2015 Elsevier Inc. All rights reserved.

  8. /sup 13/C NMR evidence of the slow exchange of tryptophans in dihydrofolate reductase between stable conformations

    Energy Technology Data Exchange (ETDEWEB)

    London, R.E. (Univ. of California, Los Alamos, NM); Groff, J.P.; Blakley, R.L.

    1979-01-01

    /sup 13/C NMR spectra are reported for dihydrofolate reductase of Streptococcus faecium labeled with (..gamma..-/sup 13/C)tryptophan. Two of the four tryptophans generate unusual resonances indicating slow exchange of the residues between alternative stable conformations. Since 3', 5'-dichloromethotrexate sharpens two of the resonances, it apparently locks the corresponding residues into one conformation.

  9. Environmentally friendly properties of vegetable oil methyl esters

    Directory of Open Access Journals (Sweden)

    Gateau Paul

    2005-07-01

    Full Text Available Measurements were carried out on Vegetable Oil Methyl Esters (VOME or FAME answering the most recent specifications. The products tested are RME (Rapeseed oil Methyl Ester, ERME (Erucic Rapeseed oil Methyl Esters, SME (Sunflower oil Methyl Esters, and HOSME (High Oleic Sunflower oil Methyl Esters. They contain more than 99.5% of fatty acid mono esters. The compositions are given. VOME are not volatile and they are not easily flammable. They are not soluble in water and they are biodegradable. According to the methods implemented for the determination of the German classification of substances hazardous to waters WGK, they are not toxic on mammals and unlike diesel fuel they are not toxic on fish, daphnia, algae and bacteria. The RME is not either toxic for shrimps. According to tests on rabbits, RME and SME are not irritating for the skin and the eyes. VOME display particularly attractive environmental properties.

  10. Role of tryptophan repeats and flanking amino acids in Myb-DNA interactions.

    OpenAIRE

    Saikumar, P; Murali, R; Reddy, E P

    1990-01-01

    The c-myb protooncogene codes for a sequence-specific DNA-binding protein that appears to act as a transcriptional regulator and is highly conserved through evolution. The DNA-binding domain of Myb has been shown to contain three imperfectly conserved repeats of 52 amino acids that constitute the amino-terminal end. Within each repeat, there are three tryptophans that are separated by 18 or 19 amino acids and are flanked by basic amino acids. To determine the role of tryptophans and the flank...

  11. The crystal structure of tryptophan hydroxylase with bound amino acid substrate

    DEFF Research Database (Denmark)

    Windahl, Michael Skovbo; Petersen, Charlotte Rode; Christensen, Hans Erik Mølager

    2008-01-01

    of the neurotransmitter and hormone serotonin (5-hydroxytryptamine). We have determined the 1.9 Å resolution crystal structure of the catalytic domain (Δ1−100/Δ415−445) of chicken TPH isoform 1 (TPH1) in complex with the tryptophan substrate and an iron-bound imidazole. This is the first structure of any aromatic amino...... acid hydroxylase with bound natural amino acid substrate. The iron coordination can be described as distorted trigonal bipyramidal coordination with His273, His278, and Glu318 (partially bidentate) and one imidazole as ligands. The tryptophan stacks against Pro269 with a distance of 3.9 Å between...

  12. Don't panic. A guide to tryptophan depletion with disorder-specific anxiety provocation.

    Science.gov (United States)

    Hood, S D; Bell, C J; Argyropoulos, S V; Nutt, D J

    2016-11-01

    The 2002 paper "Does 5-HT restrain panic? A tryptophan depletion study in panic disorder patients recovered on paroxetine" by Bell and colleagues - reprinted in this issue of the Journal - reports on a study undertaken in the halcyon days of David Nutt's Psychopharmacology Unit at the University of Bristol, England. In this invited commentary authors of the original work discuss the impact of this paper on the field of acute tryptophan depletion research (especially in the field of clinical anxiety disorders) and the development of disorder-specific anxiogenic provocations over the past decade. © The Author(s) 2016.

  13. Probing the Aggregation Behavior of Neat Imidazolium-Based Alkyl Sulfate (Alkyl = Ethyl, Butyl, Hexyl, and Octyl) Ionic Liquids through Time Resolved Florescence Anisotropy and NMR and Fluorescence Correlation Spectroscopy Study.

    Science.gov (United States)

    Majhi, Debashis; Pabbathi, Ashok; Sarkar, Moloy

    2016-01-14

    Aggregation behavior of a series of neat 1-ethyl 3-methylimidazolium alkyl sulfate (alkyl = ethyl, butyl, hexyl, and octyl) ionic liquids has been investigated through combined time-resolved fluorescence spectroscopy, 1-D and 2-D NMR spectroscopy, and fluorescence correlation spectroscopy (FCS). Interestingly, experimentally measured rotational relaxation times (τr) for ethyl, butyl, hexyl and octyl systems are measured to be 2.25, 1.64, 1.36, and 1.32 times higher than the estimated (from Stokes-Einstein-Debye theory) values for the same respective systems. This indicates that the emitting species is not the monomeric imidazolium moiety rather an associated species, and volume of the rotating fluorescing species decreases even though the length of the alkyl moiety on the anions is increased. The shift in the (1)H proton signal as well as a change in the width of the same signal upon dilution of the neat ionic liquids indicates that ionic liquids exist in the aggregated form. Further investigation through the 2D-ROESY experiment shows that interaction between imidazolium and sulfate is relatively stronger in the ethyl system than that of the longer octyl system. FCS measurements independently show that the hydrodynamic volume decreases with an increase in the anion chain length. The NMR and FCS results are consistent with the findings of the fluorescence anisotropy study.

  14. Ingestion of branched-chain amino acids and tryptophan during sustained exercise in man: failure to affect performance

    DEFF Research Database (Denmark)

    Van Hall, Gerrit; Raaymakers, J S; Saris, W H

    1995-01-01

    1. An increased uptake of tryptophan in the brain may increase serotoninergic activity and recently has been suggested to be a cause of fatigue during prolonged exercise. The present study, therefore, investigates whether ingestion of tryptophan or the competing branched-chain amino acids (BCAAs...... tryptophan ingestion caused a 7- to 20-fold increase. Exercise time to exhaustion was not different between treatments (122 +/- 3 min). 3. The data suggest that manipulation of tryptophan supply to the brain either has no additional effect upon serotoninergic activity during prolonged exhaustive exercise......) affect performance. Ten endurance-trained male athletes were studied during cycle exercise at 70-75% maximal power output, while ingesting, ad random and double-blind, drinks that contained 6% sucrose (control) or 6% sucrose supplemented with (1) tryptophan (3 g l-1), (2) a low dose of BCAA (6 g l-1...

  15. Parameters affecting ethyl ester production by Saccharomyces cerevisiae during fermentation.

    Science.gov (United States)

    Saerens, S M G; Delvaux, F; Verstrepen, K J; Van Dijck, P; Thevelein, J M; Delvaux, F R

    2008-01-01

    Volatile esters are responsible for the fruity character of fermented beverages and thus constitute a vital group of aromatic compounds in beer and wine. Many fermentation parameters are known to affect volatile ester production. In order to obtain insight into the production of ethyl esters during fermentation, we investigated the influence of several fermentation variables. A higher level of unsaturated fatty acids in the fermentation medium resulted in a general decrease in ethyl ester production. On the other hand, a higher fermentation temperature resulted in greater ethyl octanoate and decanoate production, while a higher carbon or nitrogen content of the fermentation medium resulted in only moderate changes in ethyl ester production. Analysis of the expression of the ethyl ester biosynthesis genes EEB1 and EHT1 after addition of medium-chain fatty acid precursors suggested that the expression level is not the limiting factor for ethyl ester production, as opposed to acetate ester production. Together with the previous demonstration that provision of medium-chain fatty acids, which are the substrates for ethyl ester formation, to the fermentation medium causes a strong increase in the formation of the corresponding ethyl esters, this result further supports the hypothesis that precursor availability has an important role in ethyl ester production. We concluded that, at least in our fermentation conditions and with our yeast strain, the fatty acid precursor level rather than the activity of the biosynthetic enzymes is the major limiting factor for ethyl ester production. The expression level and activity of the fatty acid biosynthetic enzymes therefore appear to be prime targets for flavor modification by alteration of process parameters or through strain selection.

  16. Isolation and identification of an ester from a crude oil

    Science.gov (United States)

    Phillips, H.F.; Breger, I.A.

    1958-01-01

    A dioctylphthalate has been isolated from a crude oil by means of adsorption column chromatography. The ester was identified by means of elemental analysis, refractive index, and its infra-red absorption spectrum. Saponification of the isolate and examination of the resultant alcohol by means of infrared absorption spectra led to the conclusion that the ester is a branched chain dioctylphthalate. This is the first reported occurrence of an ester in crude petroleum. ?? 1958.

  17. Nanoemulsions containing octyl methoxycinnamate and solid particles of TiO₂: preparation, characterization and in vitro evaluation of the solar protection factor.

    Science.gov (United States)

    Silva, Flavia F F; Ricci-Júnior, Eduardo; Mansur, Claudia R E

    2013-09-01

    The objective of this work was to develop and evaluate the physical-chemical properties of oil-in-water nanoemulsions for application as nanocosmetics for sun protection. Oil-in-water dispersions were processed by ultrasound (US) to obtain small emulsion droplets. These emulsions were obtained in the presence of commercial nonionic surfactants based on polyoxides and avocado oil as the oil phase. The US generated small but unstable droplets. This problem was solved by using a different surfactant, with a longer ethylene oxide chain, able to promote stabilization by steric mechanisms. The light scattering technique was used to characterize the nanoemulsions by their dispersed droplets' size, size distribution and variation of distribution with time (stability). Chemical and physical sunscreens - octyl methoxycinnamate (OMC) and titanium dioxide (TiO₂), respectively - were added to the stable system. The anti-UVB activity of the nanoemulsions and their components were evaluated by the method of Mansur et al. (1986) and spectral transmittance. The solar protection factor (SPF) was proportional to the OMC and TiO₂ concentrations. The in vitro OMC release was evaluated, and the presence of TiO₂ in the nanoemulsion did not affect the release profile, which showed the diffusion-dependent kinetics of the active ingredient in the formulation.

  18. Microbial corrosion resistance of galvanized coatings with 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one as a biocidal ingredient in electrolytes

    International Nuclear Information System (INIS)

    Zhai, Xiaofan; Myamina, Maria; Duan, Jizhou; Hou, Baorong

    2013-01-01

    Highlights: •Addition of DCOIT to zinc electrolyte increases current efficiency. •Zn deposited from electrolytes with DCOIT inhibits growth and metabolism of SRB. •DCOIT on coating surfaces influences the coating structure and morphology. •EIS and polarization results show good microbial-corrosion resistance in SRB. -- Abstract: Electrodeposition of galvanized coatings from electrolyte containing 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) can increase microbial corrosion resistance. Coatings were found to inhibit the growth and metabolism of sulphate-reducing bacteria (SRB). Open circuit potentials and corrosion rates of coupons revealed DCOIT effectively influences the coating property. Energy diffraction spectrum and infrared absorption spectra were used to detect DCOIT on the coating surface. Scanning electron microscopy and X-ray diffraction revealed morphological and structural modifications. Electrochemical impedance spectroscopy and polarization techniques determined the corrosion behaviour of coatings in SRB. Results showed coatings formed from electrolytes with DCOIT have improved microbial corrosion resistance and bactericidal action

  19. 1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

    Directory of Open Access Journals (Sweden)

    Norma Wrobel

    2017-03-01

    Full Text Available The title compound, 2C36H39N3O4·H2O, is a linear π-conjugated ladder oligomer with an alkyl chain on the central nitrogen atom. This diindolocarbazole, prepared via a twofold Cadogan reaction, adopts a sligthly convex shape, anti to the disordered octyl group. The unit cell contains nine molecules of the title compound and half a water molecule per main molecule. The water molecule forms hydrogen bridges, connecting the carbazole-NH and methoxy groups of different molecules. The crystal contains solvent molecules which are located in a channel parallel to the c axis. It was not possible to determine the position and nature of the solvent (a mixure of choroform, n-pentane and DMSO. The SQUEEZE [Spek (2015. Acta Cryst. C71, 9–18] option of PLATON was used to model the missing electron density. The given chemical formula and other crystal data do not take into account these solvent molecules.

  20. Skin absorption studies of octyl-methoxycinnamate loaded poly(D,L-lactide) nanoparticles: estimation of the UV filter distribution and release behaviour in skin layers.

    Science.gov (United States)

    Vettor, M; Bourgeois, S; Fessi, H; Pelletier, J; Perugini, P; Pavanetto, F; Bolzinger, M A

    2010-05-01

    New formulation strategies have to be developed to limit the skin penetration of UV-filter. Nanoparticles (NP) are very suitable for that purpose. In this study, the skin distribution, at different times (1, 2 and 3 h), of octyl-methoxycinnamate (OMC) from loaded PLA-nanoparticles was compared to a classical formulation containing non-encapsulated OMC, using the Franz cell method. The results showed that the OMC penetration was clearly impeded by stratum corneum and that the major part of the OMC-NP was accumulated at the skin surface (> 80%). A significant lower OMC amount was quantified in viable skin with NP compared to the OMC emulgel. To accurately determine the real OMC amount in close contact with viable skin layers two solvents were used to extract OMC from the skin compartments. Acetone (ACET) allowed quantifying both OMC in NP and OMC released from the particles, while isopropylmyristate (IPM), a non-solvent of the NP polymer (PLA), allowed quantifying only OMC released from the particles. Using IPM as an extraction solvent, it appeared that the OMC released from NP, in contact with viable skin, was 3-fold lower than free OMC diffused from the emulgel. Lastly, a sustained release was observed when nanoparticles were used.

  1. Octyl gallate reduces ATP levels and Ki67 expression leading HepG2 cells to cell cycle arrest and mitochondria-mediated apoptosis.

    Science.gov (United States)

    Lima, Kelly Goulart; Krause, Gabriele Catyana; da Silva, Elisa Feller Gonçalves; Xavier, Léder Leal; Martins, Léo Anderson Meira; Alice, Laura Manzoli; da Luz, Luiza Bueno; Gassen, Rodrigo Benedetti; Filippi-Chiela, Eduardo Cremonese; Haute, Gabriela Viegas; Garcia, Maria Claudia Rosa; Funchal, Giselle Afonso; Pedrazza, Leonardo; Reghelin, Camille Kirinus; de Oliveira, Jarbas Rodrigues

    2018-04-01

    Octyl gallate (OG) is an antioxidant that has shown anti-tumor, anti-diabetic and anti-amyloidogenic activities. Mitochondria play an important role in hepatocellular carcinoma, mainly by maintaining accelerated cellular proliferation through the production of ATP. Thus, the mitochondria may be a target for antitumor therapies. Here, we investigated the effects of OG in the hepatocarcinoma cell line (HepG2) and the mechanisms involved. We report, for the first time, that treatment with OG for 24h inhibited HepG2 cell growth by decreasing mitochondrial activity and mass, which led to the reduction of ATP levels. This reduction in the energy supply triggered a decrease in Ki67 protein expression, leading cells to cycle arrest. In addition, treatment with two doses of OG for 48h induced loss of mitochondrial functionality, mitochondrial swelling and apoptosis. Finally, we report that HepG2 cells had no resistance to treatment after multiple doses. Collectively, our findings indicate that metabolic dysregulation and Ki67 protein reduction are key events in the initial anti-proliferative action of OG, whereas mitochondrial swelling and apoptosis induction are involved in the action mechanism of OG after prolonged exposure. This suggests that OG targets mitochondria, thus representing a candidate for further research on therapies for hepatocarcinoma. Copyright © 2017 Elsevier Ltd. All rights reserved.

  2. Biotransformation--XXXIV. Metabolism of testosterone esters in fungi cultures.

    Science.gov (United States)

    Brzezowska, E; Dmochowska-Gładysz, J; Kołek, T; Nobilec, E

    1993-08-01

    Seven esters of testosterone: acetate, propionate, enanthate, caprate, undecanoate, isobutyrate and isocaproate (some of them are used as drugs) were transformed by microorganisms: Absidia coerulea, Acremonium roseum, Aphanocladium album and Rhodotorula mucilaginosa to obtain some information about their metabolism. It was observed that the presence and structure of the acyl group mainly influenced the degree of transformation. The first step of the reaction was probably hydrolysis of ester, followed by testosterone transformation. Only the branched chain esters were transformed by R. mucilaginosa without hydrolysis of the ester bond.

  3. Emission and Mechanical Evaluations of Vinyl-Ester Resin Systems

    National Research Council Canada - National Science Library

    Sands, James

    2003-01-01

    Vinyl-ester resins (VE) are frequently used in liquid molding of composite materials for several applications including naval and army structures, commercial boat manufacturing, and building construction...

  4. A novel thermooxidatively stable poly(ester-imide-benzoxazole)

    Energy Technology Data Exchange (ETDEWEB)

    Sundar, R.A.; Mathias, L.J. [Univ. of Sothern Mississippi, Hattiesburg, MS (United States)

    1993-12-31

    A poly(ester-amide-imide) was synthesized by the low temperature solution polycondensation of 4-amino-5-hydroxy-N,4{prime}-hydroxyphenyl phthalimide with isophthaloyl chloride. Subsequent thermal cyclodehydration of the poly(ester-amide-imide) at 320{degrees}C in vacuum afforded the poly(ester-imide-benzoxazole). This polymer was only soluble in sulfuric acid. FTIR and NMR spectra confirmed structure. The poly(ester-imide-benzoxazole) had no detectable thermal transitions up to 500{degrees}C in nitrogen, and was reasonably stable in air and nitrogen, with weight retentions of 95% at 500{degrees}C.

  5. Investigation of bifunctional ester additives for methanol-gasoline system

    International Nuclear Information System (INIS)

    Zhang, J.; Yang, C.; Tang, Y.; Du, Q.; Song, N.; Zhang, Z.

    2014-01-01

    To explore new and multifunctional additives for methanol-gasoline, tartaric ester were synthesized and screened as phase stabilizer and saturation vapor pressure depressor for methanol-gasoline. The effect of the esters structure on the efficiency was discussed. The results show that the stabilities of the blends depend on the length of the glycolic esters alkoxy group. In addition, the tartaric esters also can depress the saturation vapor pressure of methanol-gasoline effectively in M15. Effect of the structure on the efficiency was also discussed. (author)

  6. Tandem transformation of glycerol to esters.

    Science.gov (United States)

    Sotenko, Maria V; Rebroš, Martin; Sans, Victor S; Loponov, Konstantin N; Davidson, Matthew G; Stephens, Gill; Lapkin, Alexei A

    2012-12-31

    Tandem transformation of glycerol via microbial fermentation and enzymatic esterification is presented. The reaction can be performed with purified waste glycerol from biodiesel production in a continuous mode, combining continuous fermentation with membrane-supported enzymatic esterification. Continuous anaerobic fermentation was optimized resulting in the productivity of 2.4 g L⁻¹ h⁻¹ of 1,3-propanediol. Biphasic esterification of 1,3-propanediol was optimized to achieve ester yield of up to 75%. A hollow fibre membrane contactor with immobilized Rhizomucor miehei lipase was demonstrated for the continuous tandem fermentation-esterification process. Copyright © 2012 Elsevier B.V. All rights reserved.

  7. Palladium-catalysed arylation of acetoacetate esters to yield 2-arylacetic acid esters

    CSIR Research Space (South Africa)

    Zeevaart, JG

    2004-05-24

    Full Text Available The coupling reaction between ethyl acetoacetate and a number of aryl halides in the presence of palladium acetate, a bulky and electron rich phosphine and K3PO4 is described. The arylated acetoacetate ester is de-acylated under the reaction...

  8. Neutral Lipid Biosynthesis in Engineered Escherichia coli: Jojoba Oil-Like Wax Esters and Fatty Acid Butyl Esters

    OpenAIRE

    Kalscheuer, Rainer; Stöveken, Tim; Luftmann, Heinrich; Malkus, Ursula; Reichelt, Rudolf; Steinbüchel, Alexander

    2006-01-01

    Wax esters are esters of long-chain fatty acids and long-chain fatty alcohols which are of considerable commercial importance and are produced on a scale of 3 million tons per year. The oil from the jojoba plant (Simmondsia chinensis) is the main biological source of wax esters. Although it has a multitude of potential applications, the use of jojoba oil is restricted, due to its high price. In this study, we describe the establishment of heterologous wax ester biosynthesis in a recombinant E...

  9. Does dietary tryptophan around farrowing affect sow behavior and piglet mortality

    Science.gov (United States)

    Piglet mortality remains a serious welfare and economic problem. Much of the early mortality is due to crushing by the sow. Tryptophan has been shown to reduce aggression and have a calming effect on behaviour, which may reduce the number and type of posture changes, thereby altering risk of crushin...

  10. Internal Energies of Ion-Sputtered Neutral Tryptophan and Thymine Molecules Determined by Vacuum Ultraviolet Photoionization

    Energy Technology Data Exchange (ETDEWEB)

    Zhou, Jia; Takahashi, Lynelle; Wilson, Kevin R.; Leone, Stephen R.; Ahmed, Musahid

    2010-03-11

    Vacuum ultraviolet photoionization coupled to secondary neutral mass spectrometry (VUV-SNMS) of deposited tryptophan and thymine films are performed at the Chemical Dynamics Beamline. The resulting mass spectra show that while the intensity of the VUV-SNMS signal is lower than the corresponding secondary ion mass spectroscopy (SIMS) signal, the mass spectra are significantly simplified in VUV-SNMS. A detailed examination of tryptophan and thymine neutral molecules sputtered by 25 keV Bi3 + indicates that the ion-sputtered parent molecules have ~;;2.5 eV of internal energy. While this internal energy shifts the appearance energy of the photofragment ions for both tryptophan and thymine, it does not change the characteristic photoionizaton efficiency (PIE) curves of thymine versus photon energy. Further analysis of the mass spectral signals indicate that approximately 80 neutral thymine molecules and 400 tryptophan molecules are sputtered per incident Bi3 + ion. The simplified mass spectra and significant characteristic ion contributions to the VUV-SNMS spectra indicate the potential power of the technique for organic molecule surface analysis.

  11. Mutation of tryptophan residues in lipoprotein lipase. Effects on stability, immunoreactivity, and catalytic properties

    NARCIS (Netherlands)

    Lookene, A.; Groot, N. B.; Kastelein, J. J.; Olivecrona, G.; Bruin, T.

    1997-01-01

    Previous studies had pointed to an important function of a putative exposed loop in the C-terminal domain of lipoprotein lipase for activity against emulsified lipid substrates. This loop contains 3 tryptophan residues (Trp390, Trp393, and Trp394). We have expressed and characterized lipase mutants

  12. No Tryptophan, Tyrosine and Phenylalanine Abnormalities in Children with Attention-Deficit/Hyperactivity Disorder

    NARCIS (Netherlands)

    Bergwerff, C.E.; Luman, M.; Blom, H.J.; Oosterlaan, J.

    2016-01-01

    Background The aim of the current study was to explore the role of aromatic amino acids (AAAs) in blood in relation to attention-deficit/hyperactivity disorder (ADHD). Given their impact on the synthesis of serotonin and dopamine, decreased concentrations of the AAAs tryptophan, tyrosine and

  13. Reprint of 'pH tuning of Nafion for selective detection of tryptophan'

    Energy Technology Data Exchange (ETDEWEB)

    Frith, K.-A. [Department of Biochemistry, Microbiology and Biotechnology, Rhodes University, Grahamstown, 6140 (South Africa); Limson, J.L., E-mail: j.limson@ru.ac.z [Department of Biochemistry, Microbiology and Biotechnology, Rhodes University, Grahamstown, 6140 (South Africa)

    2010-05-30

    Selective and sensitive detection of the amino acid tryptophan is of importance in food processing, pharmaceutical formulations and in biological fluids. Electrochemical methods of detection of tryptophan are hampered by sluggish electron transfer kinetics and in complex matrices through overlapping peaks from interferents. This study examines the potential of the cation exchange membrane Nafion to enhance selectivity and sensitivity of this analyte through a seldom explored feature of this membrane: pH manipulation. A detailed examination of the effect of pH on the selectivity afforded by Nafion as a function of the analyte charge is presented. Selective detection of tryptophan and significant increases in sensitivity of its detection was observed in the presence of melatonin, dopamine and other interferents present in a pharmaceutical formulation through manipulation of the pH of the solution. At pH 3.0 at a Nafion-modified electrode, changes in the protonation of melatonin and tryptophan lowered the anodic potential of the analytes in a non-uniform manner increasing the peak resolution and permitting analyses with detection limits of 1.6 +- 0.1 nM and 1.6 +- 0.2 nM, respectively.

  14. pH tuning of Nafion for selective detection of tryptophan

    Energy Technology Data Exchange (ETDEWEB)

    Frith, K.-A. [Department of Biochemistry, Microbiology and Biotechnology, Rhodes University, Grahamstown, 6140 (South Africa); Limson, J.L. [Department of Biochemistry, Microbiology and Biotechnology, Rhodes University, Grahamstown, 6140 (South Africa)], E-mail: j.limson@ru.ac.za

    2009-05-01

    Selective and sensitive detection of the amino acid tryptophan is of importance in food processing, pharmaceutical formulations and in biological fluids. Electrochemical methods of detection of tryptophan are hampered by sluggish electron transfer kinetics and in complex matrices through overlapping peaks from interferents. This study examines the potential of the cation exchange membrane Nafion to enhance selectivity and sensitivity of this analyte through a seldom explored feature of this membrane: pH manipulation. A detailed examination of the effect of pH on the selectivity afforded by Nafion as a function of the analyte charge is presented. Selective detection of tryptophan and significant increases in sensitivity of its detection was observed in the presence of melatonin, dopamine and other interferents present in a pharmaceutical formulation through manipulation of the pH of the solution. At pH 3.0 at a Nafion-modified electrode, changes in the protonation of melatonin and tryptophan lowered the anodic potential of the analytes in a non-uniform manner increasing the peak resolution and permitting analyses with detection limits of 1.6 {+-} 0.1 nM and 1.6 {+-} 0.2 nM, respectively.

  15. Direct fluorination of melatonin and 5-hydroxy-L-tryptophan with [18F]F2

    International Nuclear Information System (INIS)

    Chirakal, R.; Firnau, G.; Garnett, E.S.

    1986-01-01

    In order that melatonin receptors may be studied in man with positron emission tomography, melatonin labelled with a positron emitting isotope is needed. The preparation of 6-fluoro-melatonin labelled with F-18 is described. Using the same fluorination method, 5-hydroxy-6-(F-18)fluorotryptophan and 4-(F-18)fluoro-5-hydroxy-tryptophan were also prepared. (UK)

  16. Enrichment of cellulose acetate nanofibre assemblies for therapeutic delivery of l-tryptophan.

    Science.gov (United States)

    Ghorani, Behrouz; Goswami, Parikshit; Blackburn, Richard S; Russell, Stephen J

    2018-03-01

    The essential amino acid l-tryptophan is naturally present in the body, and is also available as a water soluble dietary supplement. The feasibility of preparing enriched cellulose acetate (CA)-based fibres as a vehicle for therapeutic delivery of such biomolecules was investigated. A new ternary solvent system consisting of acetone: N,N-dimethylacetamide: methanol (2:1:2) has been demonstrated to permit the solution blending of CA with the water soluble l-tryptophan. Nanofibrous webs substantially free of structural defects were continuously produced with mean fibre diameters in the range of 520-1010nm, dependent on process parameters. Morphology and diameter of fibres were influenced by concentration of CA spinning solution, applied voltage and flow rates. The kinetic release profile of l-tryptophan from electrospun CA nanofibres was described by the pseudo-second order kinetic model. Fibres with mean diameter of 720nm provide both the highest initial desorption rate and rate constant, which was partially attributed to the low fibre diameter and high relative surface area, but also the fact that the 720nm fibres produced were the most bead-free, providing diffusion advantages over the fibres with lowest mean diameter (520nm). The feasibility of combining l-tryptophan within fibres provides a promising route for manufacture of transdermal delivery devices. Copyright © 2017 Elsevier B.V. All rights reserved.

  17. Formation and detection of oxidant-generated tryptophan dimers in peptides and proteins

    DEFF Research Database (Denmark)

    Carroll, Luke; Pattison, David I; Davies, Justin B

    2017-01-01

    and function. Due to its low oxidation potential, the indole ring of tryptophan (Trp) is a major target, with this resulting in the formation of indolyl radicals (Trp•). These undergo multiple reactions including ring opening and dimerization which can result in protein aggregation. The factors that govern Trp...

  18. Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

    Directory of Open Access Journals (Sweden)

    Michele Mari

    2014-08-01

    Full Text Available The reaction of 3-substituted indoles with dehydroalanine (Dha derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization–cyclization followed by C3- to C2-alkyl migration and rearomatization.

  19. Comprehensive analysis of the tryptophan metabolome in urine of patients with acute intermittent porphyria.

    Science.gov (United States)

    Gomez-Gomez, Alex; Marcos, Josep; Aguilera, Paula; To-Figueras, Jordi; Pozo, Oscar J

    2017-08-15

    Acute intermittent porphyria (AIP) is a rare metabolic disorder due to a deficiency of porphobilinogen deaminase, the third enzyme of the heme biosynthetic pathway. This low enzymatic activity may predispose to the appearance of acute neurological attacks. Seminal studies suggested that AIP was associated with changes in tryptophan homeostasis with inconclusive results. Therefore, the aim of this study was to analyze the urinary metabolome of AIP patients focusing on tryptophan metabolism using state-of-the-art technology. This was a case-control study including a group of 25 AIP patients with active biochemical disease and increased excretion of heme-precursors and 25 healthy controls. Tryptophan and related compounds and metabolites including: large neutral amino acids (LNAAs), serotonin, kynurenine, kynurenic acid and anthranilic acid were quantified in urine by liquid chromatography tandem-mass spectrometry (LC-MS/MS). Twenty-nine biological markers (including metabolic ratios and absolute concentrations) were compared between patients and controls. Significant differences were found in the tryptophan-kynurenine metabolic pathway. Compared to controls, AIP patients showed: (a) increased urinary excretion of kynurenine and anthranilic acid (Ptryptophan ratio (Ptryptophan ratio in urine and a reduction of the kynurenic acid/kynurenine ratio. The modified ratios suggest induction of indoleamine 2,3-deoxygenase and decreased activity of kynurenine aminotransferase in the liver. The results confirm that LC-MS/MS is useful for the characterization of the urinary metabolome of hepatic porphyrias. Copyright © 2017. Published by Elsevier B.V.

  20. Stabilization of Tryptophan Hydroxylase 2 by L-Phenylalanine Induced Dimerization

    DEFF Research Database (Denmark)

    Tidemand, Kasper Damgaard; Christensen, Hans Erik Mølager; Hoeck, Niclas

    2016-01-01

    Tryptophan hydroxylase 2 (TPH2) catalyses the initial and rate-limiting step in the biosynthesis of serotonin, which is associated with a variety of disorders such as depression, obsessive compulsive disorder, and schizophrenia. Full length TPH2 is poorly characterized due to low purification...

  1. Problem-Solving Test: Attenuation--A Mechanism to Regulate Bacterial Tryptophan Biosynthesis

    Science.gov (United States)

    Szeberenyi, Jozsef

    2010-01-01

    Terms to be familiar with before you start to solve the test: tryptophan, transcription unit, operon, "trp" repressor, corepressor, operator, promoter, palindrome, initiation, elongation, and termination of transcription, open reading frame, coupled transcription/translation, chromosome-polysome complex. (Contains 2 figures and 1 footnote.)

  2. Quenching of Tryptophan Fluorescence in Unfolded Cytochrome "c": A Biophysics Experiment for Physical Chemistry Students

    Science.gov (United States)

    Schlamadinger, Diana E.; Kats, Dina I.; Kim, Judy E.

    2010-01-01

    Laboratory experiments that focus on protein folding provide excellent opportunities for undergraduate students to learn important topics in the expanding interdisciplinary field of biophysics. Here, we describe the use of Stern-Volmer plots to determine the extent of solvent accessibility of the single tryptophan residue (trp-59) in unfolded and…

  3. The Tryptophan-Kynurenine Pathway, Systemic Inflammation, and Long-Term Outcome after Kidney Transplantation

    NARCIS (Netherlands)

    de Vries, Laura V; Minovic, Isidor; Franssen, Casper Fm; van Faassen, Martijn; Sanders, Jan-Stephan F.; Berger, Stefan P; Navis, Gerjan; Kema, Ido P; Bakker, Stephan Jl

    2017-01-01

    BACKGROUND: Tryptophan is metabolized along the kynurenine pathway, initially to kynurenine, and subsequently to cytotoxic 3-hydroxykynurenine. There is increasing interest in this pathway, because of its pro-inflammatory nature, and drugs interfering in it receive increasing attention. We aimed to

  4. A Relay Pathway between Arginine and Tryptophan Metabolism Confers Immunosuppressive Properties on Dendritic Cells

    NARCIS (Netherlands)

    G. Mondanelli (Giada); R. Bianchi (Roberta); M.T. Pallotta (Maria Teresa); C. Orabona (Ciriana); E. Albini (Elisa); A. Iacono (Alberta); M.L. Belladonna (Maria Laura); C. Vacca (Carmine); F. Fallarino (Francesca); A. Macchiarulo (Antonio); S. Ugel (Stefano); V. Bronte (Vincenzo); F. Gevi (Federica); L. Zolla (Lello); A.P. Verhaar (Auke); M.P. Peppelenbosch (Maikel); E.M.C. Mazza (Emilia Maria Cristina); S. Bicciato (Silvio); Y. Laouar (Yasmina); L. Santambrogio (Laura); P. Puccetti (Paolo); C. Volpi (Claudia); U. Grohmann (Ursula)

    2017-01-01

    textabstractArginase 1 (Arg1) and indoleamine 2,3-dioxygenase 1 (IDO1) are immunoregulatory enzymes catalyzing the degradation of l-arginine and l-tryptophan, respectively, resulting in local amino acid deprivation. In addition, unlike Arg1, IDO1 is also endowed with non-enzymatic signaling activity

  5. Converging evidence for central 5-HT effects in acute tryptophan depletion

    DEFF Research Database (Denmark)

    Crockett, Molly; Clark, Luke; Roiser, Jonathan

    2012-01-01

    Acute tryptophan depletion (ATD), a dietary technique for manipulating brain serotonin (5-HT) function, has advanced our understanding of 5-HT mechanisms in the etiology and treatment of depression and other affective disorders.1 A recent review article in Molecular Psychiatry questioned the vali...

  6. Cross-linking of lens crystallin proteins induced by tryptophan metabolites and metal ions

    DEFF Research Database (Denmark)

    Tweeddale, Helen J; Hawkins, Clare Louise; Janmie, Joane F

    2016-01-01

    Long-wavelength solar UV radiation is implicated in photodamage to the human eye. The human lens contains multiple tryptophan-derived compounds that have significant absorbance bands in the UVA region (λ 315-400 nm) that act as efficient physical filters for these wavelengths. The concentrations ...

  7. PYROLYTIC PRODUCTS FROM TRYPTOPHAN AND GLUTAMIC-ACID ARE POSITIVE IN THE MAMMALIAN SPOT-TEST

    DEFF Research Database (Denmark)

    Jensen, Niels Juul

    1983-01-01

    Pyrolysates of tryptophan (Trp-P-2) and glutamic acid (Glu-P-1) are known mutagens in in vitro short term mutagenicity tests, and have also shown carcinogenic effects in long term animal studies. The present study demonstrates that they also produce mutations in somatic cells. This result...

  8. Effect of diet on plasma tryptophan and serotonin in trained mares and geldings

    NARCIS (Netherlands)

    Alberghina, D.; Giannetto, C.; Visser, E.K.; Ellis, A.D.

    2010-01-01

    Concentrations of tryptophan (TRP) and serotonin (5-HT) in plasma were measured in 36 moderately trained Dutch warmblood horses after eight weeks on a high fibre (n=18) or high starch (n=18) diet. Samples were taken three hours after feeding, when the horse was at rest, either at 11.00 or 14.00

  9. Surplus dietary tryptophan inhibits stress hormone kinetics and induces insulin resistance in pigs

    NARCIS (Netherlands)

    Koopmans, S.J.; Ruis, M.A.W.; Dekker, R.A.; Korte, M.

    2009-01-01

    Recently we have shown that surplus dietary tryptophan (TRP) reduced the plasma concentrations of cortisol and noradrenaline in pigs. Stress hormones are known to affect insulin sensitivity and metabolism. We now investigated the long-term effects of surplus dietary TRP on 1) plasma and urinary

  10. Tryptophan biosynthesis in stramenopiles: eukaryotic winners in the diatom complex chloroplast

    Czech Academy of Sciences Publication Activity Database

    Jiroutová, Kateřina; Horák, Aleš; Bowler, C.; Oborník, Miroslav

    2007-01-01

    Roč. 65, č. 5 (2007), s. 496-511 ISSN 0022-2844 R&D Projects: GA AV ČR IAA500220502 Institutional research plan: CEZ:AV0Z60220518 Keywords : tryptophan synthesis * mosaic origin * diatom * Oomycetes Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 3.234, year: 2007

  11. Central fatigue and nycthemeral change of serum tryptophan and serotonin in the athletic horse

    Directory of Open Access Journals (Sweden)

    Percipalle Maurizio

    2005-04-01

    Full Text Available Abstract Background The serotonergic system is associated with numerous brain functions, including the resetting of the mammalian circadian clock. The synthesis and metabolism of 5-HT in the brain increases in response to exercise and is correlated with high levels of blood-borne tryptophan (TRP. The present investigation was aimed at testing the existence of a daily rhythm of TRP and 5-HT in the blood of athletic horses. Methods Blood samples from 5 Thoroughbred mares were collected at 4-hour intervals for 48 hours (starting at 08:00 hours on day 1 and finishing at 4:00 on day 2 via an intravenous cannula inserted into the jugular vein. Tryptophan and serotonin concentrations were assessed by HPLC. Data analysis was conducted by one-way repeated measures analysis of variance (ANOVA and by the single cosinor method. Results ANOVA showed a highly significant influence of time both on tryptophan and on serotonin, in all horses, on either day, with p values Conclusion The results showed that serotonin and tryptophan blood levels undergo nycthemeral variation with typical evening acrophases. These results enhance the understanding of the athlete horse's chronoperformance and facilitate the establishment of training programs that take into account the nycthemeral pattern of aminoacids deeply involved in the onset of central fatigue.

  12. D-tryptophan from probiotic bacteria influences the gut microbiome and allergic airway disease.

    Science.gov (United States)

    Kepert, Inge; Fonseca, Juliano; Müller, Constanze; Milger, Katrin; Hochwind, Kerstin; Kostric, Matea; Fedoseeva, Maria; Ohnmacht, Caspar; Dehmel, Stefan; Nathan, Petra; Bartel, Sabine; Eickelberg, Oliver; Schloter, Michael; Hartmann, Anton; Schmitt-Kopplin, Philippe; Krauss-Etschmann, Susanne

    2017-05-01

    Chronic immune diseases, such as asthma, are highly prevalent. Currently available pharmaceuticals improve symptoms but cannot cure the disease. This prompted demands for alternatives to pharmaceuticals, such as probiotics, for the prevention of allergic disease. However, clinical trials have produced inconsistent results. This is at least partly explained by the highly complex crosstalk among probiotic bacteria, the host's microbiota, and immune cells. The identification of a bioactive substance from probiotic bacteria could circumvent this difficulty. We sought to identify and characterize a bioactive probiotic metabolite for potential prevention of allergic airway disease. Probiotic supernatants were screened for their ability to concordantly decrease the constitutive CCL17 secretion of a human Hodgkin lymphoma cell line and prevent upregulation of costimulatory molecules of LPS-stimulated human dendritic cells. Supernatants from 13 of 37 tested probiotic strains showed immunoactivity. Bioassay-guided chromatographic fractionation of 2 supernatants according to polarity, followed by total ion chromatography and mass spectrometry, yielded C 11 H 12 N 2 O 2 as the molecular formula of a bioactive substance. Proton nuclear magnetic resonance and enantiomeric separation identified D-tryptophan. In contrast, L-tryptophan and 11 other D-amino acids were inactive. Feeding D-tryptophan to mice before experimental asthma induction increased numbers of lung and gut regulatory T cells, decreased lung T H 2 responses, and ameliorated allergic airway inflammation and hyperresponsiveness. Allergic airway inflammation reduced gut microbial diversity, which was increased by D-tryptophan. D-tryptophan is a newly identified product from probiotic bacteria. Our findings support the concept that defined bacterial products can be exploited in novel preventative strategies for chronic immune diseases. Copyright © 2016. Published by Elsevier Inc.

  13. Acute tryptophan depletion attenuates brain-heart coupling following external feedback

    Directory of Open Access Journals (Sweden)

    Erik M Mueller

    2012-04-01

    Full Text Available External and internal performance feedback triggers neural and visceral modulations such as reactions in the medial prefrontal cortex and insulae or changes of heart period (HP. The functional coupling of neural and cardiac responses following feedback (cortico-cardiac connectivity is not well understood. While linear time-lagged within-subjects correlations of single-trial EEG and HP (cardio-electroencephalographic covariance-tracing, CECT indicate a robust negative coupling of EEG magnitude 300 ms after presentation of an external feedback stimulus with subsequent alterations of heart period (the so-called N300H phenomenon, the neurotransmitter systems underlying feedback-evoked cortico-cardiac connectivity are largely unknown. Because it has been shown that acute tryptophan depletion (ATD, attenuating brain serotonin (5-HT, decreases cardiac but not neural correlates of feedback processing, we hypothesized that 5-HT may be involved in feedback-evoked cortico-cardiac connectivity. In a placebo-controlled double-blind crossover design, twelve healthy participants received a tryptophan-free amino-acid drink at one session and a balanced amino-acid control-drink on another and twice performed a time-estimation task with feedback presented after each trial. N300H magnitude and plasma tryptophan levels were assessed. Results indicated a robust N300H after the control drink, which was significantly attenuated following ATD. Moreover, plasma tryptophan levels during the control session were correlated with N300H amplitude such that individuals with lower tryptophan levels showed reduced N300H. Together, these findings indicate that 5-HT is important for feedback-induced covariation of cortical and cardiac activity. Because individual differences in anxiety have previously been linked to 5-HT, cortico-cardiac coupling and feedback processing, the present findings may be particularly relevant for futures studies linking 5-HT to anxiety.

  14. The role of two Pseudomonas aeruginosa anthranilate synthases in tryptophan and quorum signal production

    Science.gov (United States)

    Palmer, Gregory C.; Jorth, Peter A.

    2013-01-01

    Pseudomonas aeruginosa is a Gram-negative, opportunistic pathogen that causes infections in the lungs of individuals with the genetic disease cystic fibrosis. Density-dependent production of toxic factors regulated by the Pseudomonas quinolone signal (2-heptyl-3-hydroxy-4-quinolone; PQS) have been proposed to be involved in P. aeruginosa virulence. PQS biosynthesis requires conversion of the central metabolite chorismate to anthranilate by anthranilate synthase. This reaction is also the first step in tryptophan biosynthesis. P. aeruginosa possesses two functional anthranilate synthases, TrpEG and PhnAB, and these enzymes are not functionally redundant, as trpEG mutants are tryptophan auxotrophs but produce PQS while mutants in phnAB are tryptophan prototrophs but do not produce PQS in minimal media. The goal of the work described in this paper was to determine the mechanism for this lack of functional complementation of TrpEG and PhnAB. Our results reveal that overexpression of either enzyme compensates for tryptophan auxotrophy and PQS production in the trpEG and phnAB mutants respectively, leading to the hypothesis that differential regulation of these genes is responsible for the lack of functional complementation. In support of this hypothesis, trpEG was shown to be expressed primarily during low-density growth while phnAB was expressed primarily at high density. Furthermore, dysregulation of phnAB expression eliminated tryptophan auxotrophy in the P. aeruginosa trpEG mutant. Based on these data, we propose a model for anthranilate sequestration by differential transcriptional regulation of the two P. aeruginosa anthranilate synthase enzymes. PMID:23449919

  15. Disturbed tryptophan metabolism correlating to progression and metastasis of esophageal squamous cell carcinoma.

    Science.gov (United States)

    Cheng, Jing; Jin, Hai; Hou, Xiaobei; Lv, Jie; Gao, Xianfu; Zheng, Guangyong

    2017-05-06

    Esophageal squamous cell carcinoma (ESCC) is one of the most frequent malignancies worldwide. Lymph node metastasis is the leading cause of death in ESCC patients. To identify early diagnostic and prognostic biomarkers of ESCC and elucidate underlying pathogenesis of the disease, a targeted metabolomics strategy based on liquid chromatography combined with tandem mass spectrometry was applied to explore tryptophan metabolism between ESCC patients, metastatic ESCC patients (mESCC), and healthy controls. Statistical analysis on metabolite expression abundance and compound concentration ratio was conducted to discriminate patients from healthy controls. The concentration ratio of kynurenine, 5-hydroxytryptophan, 5-hydroxyindole-3-acetic acid, 5-hydroxytryptamine to their precursor tryptophan were identified as potential biomarkers, presenting high diagnostic capacity for distinguishing ESCC and mESCC patients from healthy controls. Moreover, a prognostic prediction model was also built on these ratios to distinguish metastasis patients from non-metastasis patients successfully. The high performance of ESCC prediction models suggest that concentration ratios of compounds may be used as biomarkers for early diagnosis and prognosis of the disease. In addition, concentration ratios of compounds show a progressively increased trend from non-metastasis to metastasis patients compared with healthy controls, which is in accordance with process of malignant transformation of ESCC. This interested finding suggests that disturbed tryptophan metabolism is correlated to progression and metastasis of ESCC since concentration ratios of compounds reflect activity of enzymes involved in tryptophan metabolism. This study reveals the impact of tryptophan metabolism to tumorigenesis and metastasis of ESCC, which help biologists investigate mechanism of the disease. Copyright © 2017 Elsevier Inc. All rights reserved.

  16. L-tryptophan and dipeptide derivatives for supercoiled plasmid DNA purification.

    Science.gov (United States)

    Santos, Tiago; Carvalho, Josué; Corvo, Marta C; Cabrita, Eurico J; Queiroz, J A; Cruz, C

    2016-06-01

    The present study focus on the preparation of chromatography supports for affinity-based chromatography of supercoiled plasmid purification. Three l-tryptophan based supports are prepared through immobilization on epoxy-activated Sepharose and characterized by HR-MAS NMR. The SPR is employed for a fast screening of l-tryptophan derivatives, as potential ligands for the biorecognition of supercoiled isoform, as well as, to establish the suitable experimental conditions for the chromatography. The results reveal that the overall affinity is high (KD=10(-9) and 10(-8)M) and the conditions tested show that the use of HEPES 100mM enables the separation and purification of supercoiled at T=10°C. The STD-NMR is performed to accomplish the epitope mapping of the 5'-mononucleotides bound to l-tryptophan derivatives supports. The data shows that the interactions between the three supports and the 5'-mononucleotides are mainly hydrophobic and π-π stacking. The chromatography experiments are performed with l-tryptophan support and plasmids pVAX-LacZ and pPH600. The supercoiled isoform separation is achieved at T=10°C by decreasing the concentration of (NH4)2SO4 from 2.7 to 0M in HEPES for pVAX-LacZ and 2.65M to 0M in HEPES for pPH600. Overall, l-tryptophan derivatives can be a promising strategy to purify supercoiled for pharmaceutical applications. Copyright © 2016 Elsevier B.V. All rights reserved.

  17. Regulating the balance between the kynurenine and serotonin pathways of tryptophan metabolism.

    Science.gov (United States)

    Li, Yang; Hu, Nan; Yang, Dan; Oxenkrug, Gregory; Yang, Qing

    2017-03-01

    Tryptophan is metabolized along the kynurenine and serotonin pathways, resulting in formation of kynurenine metabolites, neuroactive serotonin and melatonin. Each pathway is critical for maintaining healthy homeostasis. However, the two pathways are extremely unequal in their ability to degrade tryptophan, and little is known about the mechanisms maintaining the balance between them. Here, we demonstrated that in PC12 cells, a change of expression of key genes of one pathway resulted in a change of expression of key genes of the other. Melatonin, the end product of the serotonin pathway, played an important role in tryptophan metabolism by affecting both key enzymes of the two pathways. Melatonin treatment induced the expression of indole-2,3-dioxygenase 1 (IDO1) and enhanced the activity of the IDO1 promoter while decreasing the expression of arylalkylamine N-acetyl transferase. Melatonin treatment up-regulated the expression of forkhead box protein O1 (FoxO1) and enhanced the binding of FoxO1 to the IDO1 promoter. FoxO1 was shown to be a new regulator for IDO1 expression. Melatonin treatment decreased the phosphorylation of FoxO1 by extracellular signal-regulated kinases 1 and 2 and protein kinase B (Akt) and increased the phosphorylation of binding protein 14-3-3 by c-Jun N-terminal kinase (JNK), and thus the complex of FoxO1-14-3-3 in the cytoplasm was disassembled and FoxO1 was relocated to the nucleus to induce IDO1 expression. The JNK signaling pathway played an important role in melatonin-induced IDO1 up-regulation. In conclusion, this study suggests a link between melatonin, JNK, FoxO1 and IDO1 that acts as a potential balance regulator of tryptophan metabolism, and offers a new approach to treat diseases related to dysregulation of tryptophan metabolism. © 2017 Federation of European Biochemical Societies.

  18. Modulating short tryptophan- and arginine-rich peptides activity by substitution with histidine.

    Science.gov (United States)

    Bacalum, Mihaela; Janosi, Lorant; Zorila, Florina; Tepes, Ana-Maria; Ionescu, Cristina; Bogdan, Elena; Hadade, Niculina; Craciun, Liviu; Grosu, Ion; Turcu, Ioan; Radu, Mihai

    2017-07-01

    High antimicrobial efficacy of short tryptophan-and arginine-rich peptides makes them good candidates in the fight against pathogens. Substitution of tryptophan and arginine by histidine could be used to modulate the peptides efficacy by optimizing their structures. The peptide (RRWWRWWRR), reported to showed good antimicrobial efficacy, was used as template, seven new analogs being designed substituting tryptophan or arginine with histidine. The peptides' efficacy was tested against E. coli, B. subtilis and S. aureus. The cytotoxicity and hemolytic effect were evaluated and the therapeutic index was inferred for each peptide. Atomic force microscopy and molecular simulation were used to analyze the effects of peptides on bacterial membrane. The substitution of tryptophan by histidine proved to strongly modulate the antimicrobial activity, mainly by changing the peptide-to-membrane binding energy. The substitution of arginine has low effect on the antimicrobial efficacy. The presence of histidine residue reduced the cytotoxic and hemolytic activity of the peptides in some cases maintaining the same efficacy against bacteria. The peptides' antimicrobial activity was correlated to the 3D-hydrophobic moment and to a simple structure-based packing parameter. The results show that some of these peptides have the potential to become good candidates to fight against bacteria. The substitution by histidine proved to fine tune the therapeutic index allowing the optimization of the peptide structure mainly by changing its binding energy and 3D-hydrophobic moment. The short tryptophan reach peptides therapeutic index can be maximized using the histidine substitution to optimize their structure. Copyright © 2017 Elsevier B.V. All rights reserved.

  19. Promoting effect of saccharin and DL-tryptophan in urinary bladder carcinogenesis.

    Science.gov (United States)

    Cohen, S M; Arai, M; Jacobs, J B; Friedell, G H

    1979-04-01

    The existence of at least two stages in bladder carcinogenesis was evaluated in male Fischer rats using N-[14-(5-nitro-2-furyl)-2-thiazolyl]formamide (FANFT) fed for six weeks at a level of 0.2% of the diet as the initiator. Sodium saccharin and DL-tryptophan were fed at levels of 5 and 2% of the diet, respectively, as possible promoting chemicals, and they were fed either immediately after FANFT administration or after six weeks of FANFT plus six weeks of control diet. All surviving rats were killed at the end of two years. Both chemicals significantly increased the incidence of bladder tumors following FANFT feeding compared to six weeks of FANFT feeding followed by control diet, and the results were similar whether saccharin or tryptophan feeding was started immediately after FANFT feeding was concluded or after a six-week delay. Saccharin was considerably more potent as a promoting agent than was tryptophan, inducing higher incidences of bladder tumors and having a shorter latent period. Long-term administration of FANFT induced a 100% incidence of bladder cancer. Sequential epithelial changes were observed by scanning and transmission electron microscopy as well as by light microscopy. Pleomorphic microvilli were present on the superficial cells of all tumors examined and on the surface cells of hyperplastic bladder epithelium after six weeks of FANFT plus six weeks of saccharin, but not after six weeks of FANFT and six weeks of control diet. Rats fed only saccharin tryptophan, or control diet did not have bladder tumors or pleomorphic microvilli on bladder epithelium. These data suggest that saccharin and tryptophan might act as tumor-promoting agents during bladder carcinogenesis.

  20. Preparation of esters of gallic acid with higher primary alcohols

    NARCIS (Netherlands)

    Kerk, G.J.M. van der; Verbeek, J.H.; Cleton, J.C.F.

    1951-01-01

    The esters of gallic acid and higher primary alcohols, especially fatty alcohols, have recently gained considerable interest as possible antioxidants for fats. Two independent methods for the preparation of these esters are described. In the first method the hitherto unknown compound galloyl

  1. Production of both esters and biogas from Mexican poppy

    African Journals Online (AJOL)

    AJL

    esters, use oils of plant origin like vegetable oils and tree born oil seeds are ... Usage of ester will allow a balance to be sought between agriculture .... Sci. Technol. Plastic tube. Stopper. Glass bottle. (1 liter capacity). Rubber cap. Gas collector. Digester. Displaced water. Figure 1. Reactor design (see experimental set up).

  2. Alternative Production of Fatty Acid Methyl Esters from Triglycerides ...

    African Journals Online (AJOL)

    The catalysts activity was tested in thermocatalytic cracking of triglyceride; a direct conversion process for fatty acid methyl esters (biodiesel). The SZ1 not only exhibited higher conversion of triglycerides but higher fatty acid methyl esters (FAMEs) yields of approximately 59% after 3h as compared to SZ2 (32%). In addition ...

  3. Effect of Sucrose Esters on the Physicochemical Properties of Wheat ...

    African Journals Online (AJOL)

    HP

    modified starch were analyzed by Fourier transform infrared spectroscopy (FITR), scanning electron microscopy (SEM) and differential scanning calorimetry (DSC). Results: The properties of wheat starch changed greatly by adding different sucrose esters to their structures. Starch containing 0.30 % sucrose esters had the ...

  4. Phthalic acid esters found in municipal organic waste

    DEFF Research Database (Denmark)

    Hartmann, Hinrich; Ahring, Birgitte Kiær

    2003-01-01

    Contamination of the organic fraction of municipal solid waste (OFMSW) with xenobiotic compounds and their fate during anaerobic digestion was investigated. The phthalic acid ester di-(2- ethylhexyl)phthalate (DEHP) was identified as the main contaminant in OFMSW in concentrations more than half...... matter with high biogas yields and efficient reduction of the phthalic acid ester contamination....

  5. Determination of Phthalate Esters in the Aquatic Environment ...

    African Journals Online (AJOL)

    The use of solid phase extraction and capillary GLC provides the basis for selective determination of phthalate ester plasticizers in rivers and marine water samples. Of the several solvent ratios (methanol in dichloromethane) that were tried for selective elution of phthalate esters from the C18 solid phase glass catridge, the ...

  6. Protective effect of glucosamine cyclohexyl ester on osteoarthritis in ...

    African Journals Online (AJOL)

    Purpose: To investigate the therapeutic effect of glucosamine cyclohexyl ester on osteoarthritis (OA) in a rat model. Methods: Reverse transcription-quantitative polymerase chain reaction (RT-qPCR) and western blot assays were used to analyze the effect of glucosamine cyclohexyl ester on changes in mRNA and protein ...

  7. Effect of Sucrose Esters on the Physicochemical Properties of Wheat ...

    African Journals Online (AJOL)

    HP

    International Pharmaceutical Abstract, Chemical Abstracts, Embase, Index Copernicus, EBSCO, African Index. Medicus, JournalSeek .... Table 1: Rapid visco-analyzer parameters for wheat starch modified with sucrose esters. Content of sucrose esters δ%ε. Peak. (cP). Trough. (cP). Breakdown. (cP). Final. (cP). Setback.

  8. Distribution of phthalate esters in underground water from power ...

    African Journals Online (AJOL)

    This study investigates the distribution of phthalateacid esters (PAEs) in groundwater from some power stations in Delta State. Groundwater samples were collected from eight power transmission and distribution stations. Concentrations (μg/L) of six phthalate acid esters compounds in the groundwater ranged from ...

  9. Protective effect of glucosamine cyclohexyl ester on osteoarthritis in ...

    African Journals Online (AJOL)

    Purpose: To investigate the therapeutic effect of glucosamine cyclohexyl ester on osteoarthritis (OA) in a rat model. Methods: Reverse transcription-quantitative polymerase chain reaction (RT-qPCR) and western blot assays were used to analyze the effect of glucosamine cyclohexyl ester on changes in mRNA and.

  10. N-acetyl-L-tryptophan, a substance-P receptor antagonist attenuates aluminum-induced spatial memory deficit in rats.

    Science.gov (United States)

    Fernandes, Joylee; Mudgal, Jayesh; Rao, Chamallamudi Mallikarjuna; Arora, Devinder; Basu Mallik, Sanchari; Pai, K S R; Nampoothiri, Madhavan

    2018-06-01

    Neuroinflammation plays an important role in the pathophysiology of Alzheimer's disease. Neurokinin substance P is a key mediator which modulates neuroinflammation through neurokinin receptor. Involvement of substance P in Alzheimer's disease is still plausible and various controversies exist in this hypothesis. Preventing the deleterious effects of substance P using N-acetyl-L-tryptophan, a substance P antagonist could be a promising therapeutic strategy. This study was aimed to evaluate the effect of N-acetyl-L-tryptophan on aluminum induced spatial memory alterations in rats. Memory impairment was induced using aluminum chloride (AlCl 3 ) at a dose of 10 mg/kg for 42 d. After induction of dementia, rats were exposed to 30 and 50 mg/kg of N-acetyl-L-tryptophan for 28 d. Spatial memory alterations were measured using Morris water maze. Acetylcholinesterase activity and antioxidant enzyme glutathione level were assessed in hippocampus, frontal cortex and striatum. The higher dose of N-acetyl-L-tryptophan (50 mg/kg) significantly improved the aluminum induced memory alterations. N-acetyl-L-tryptophan exposure resulted in significant increase in acetylcholinesterase activity and glutathione level in hippocampus. The neuroprotective effect of N-acetyl-L-tryptophan could be due to its ability to block substance P mediated neuroinflammation, reduction in oxidative stress and anti-apoptotic properties. To conclude, N-acetyl-L-tryptophan may be considered as a novel neuroprotective therapy in Alzheimer's disease.

  11. Effect of dietary protein content and tryptophan supplementation on dominance aggression, territorial aggression, and hyperactivity in dogs.

    Science.gov (United States)

    DeNapoli, J S; Dodman, N H; Shuster, L; Rand, W M; Gross, K L

    2000-08-15

    To evaluate the effect of high- and low-protein diets with or without tryptophan supplementation on behavior of dogs with dominance aggression, territorial aggression, and hyperactivity. Prospective crossover study. 11 dogs with dominance aggression, 11 dogs with territorial aggression, and 11 dogs with hyperactivity. In each group, 4 diets were fed for 1 weeks each in random order with a transition period of not diet. Two diets had low protein content (approximately 18%), and 2 diets had high protein content (approximately 30%). Two of the diets (1 low-protein and 1 high-protein) were supplemented with tryptophan. Owners scored their dog's behavior daily by use of customized behavioral score sheets. Mean weekly values of 5 behavioral measures and serum concentrations of serotonin and tryptophan were determined at the end of each dietary period. For dominance aggression, behavioral scores were highest in dogs fed unsupplemented high-protein rations. For territorial aggression, [corrected] tryptophan-supplemented low-protein diets were associated with significantly lower behavioral scores than low-protein diets without tryptophan supplements. For dogs with dominance aggression, the addition of tryptophan to high-protein diets or change to a low-protein diet may reduce aggression. For dogs with territorial aggression, tryptophan supplementation of a low-protein diet may be helpful in reducing aggression.

  12. Relation of plasma tryptophan concentrations during pregnancy to maternal sleep and mental well-being: The GUSTO cohort.

    Science.gov (United States)

    van Lee, Linde; Cai, Shirong; Loy, See Ling; Tham, Elaine K H; Yap, Fabian K P; Godfrey, Keith M; Gluckman, Peter D; Shek, Lynette P C; Teoh, Oon Hoe; Goh, Daniel Y T; Tan, Kok Hian; Chong, Yap Seng; Meaney, Michael J; Chen, Helen; Broekman, Birit F P; Chong, Mary F F

    2018-01-01

    Evidence suggests a relation between plasma tryptophan concentrations and sleep and mental well-being. As no studies have been performed in pregnant women, we studied the relation of plasma tryptophan concentrations during pregnancy with sleep quality, and mood during and after pregnancy. Pregnant women (n = 572) from the Growing Up in Singapore Towards healthy Outcomes study completed the Pittsburgh Sleep Quality Index (PSQI), the Edinburgh Postnatal Depression Scale (EPDS) and the State-Trait Anxiety Inventory (STAI) at 26-28 weeks gestation and three months post-delivery. Plasma tryptophan concentrations were measured at 26-28 weeks gestation. Poisson regressions estimated prevalence ratios (PR) for the association between tryptophan and poor sleep quality (PSQI global score > 5), probable antenatal depression (EPDS ≥ 15) and probable anxiety (STAI-state ≥ 41) were calculated adjusting for covariates. Mean plasma tryptophan concentrations was 48.0µmol/L (SD: 8.09). Higher plasma tryptophan concentrations were associated with a lower prevalence of antenatal poor sleep quality adjusting for covariates [PR: 0.88 (95% CI 0.80, 0.97) per 10µmol/L], especially in those participants who also suffered from anxiety symptoms [PR: 0.80 (95% CI 0.67, 0.95)]. No associations were observed between tryptophan concentrations during pregnancy and postnatal sleep quality or mental well-being. Subjective measures were used to assess sleep and mental well-being. We observed that higher plasma tryptophan concentrations were associated with a 12% lower prevalence of poor sleep quality during pregnancy, in particular among those with anxiety symptoms. These findings suggest the importance of having adequate tryptophan concentrations during pregnancy. Copyright © 2017 Elsevier B.V. All rights reserved.

  13. The Effects of Tryptophan on Everyday Interpersonal Encounters and Social Cognitions in Individuals with a Family History of Depression

    Science.gov (United States)

    Schoevers, Robert A.; aan het Rot, Marije

    2015-01-01

    Background: Individuals with a family history of depression show subtle abnormalities in the processing of social stimuli. This could negatively affect their interpersonal functioning and contribute to their depression risk. Repeated administration of the serotonin precursor tryptophan has previously been shown to increase agreeable behavior and reduce quarrelsome behavior in irritable people, who are also considered at risk for depression. Methods: To examine the effects of tryptophan on social functioning in individuals with a family history of depression, 40 men and women with at least one first-degree relative with depression received tryptophan (1g three times a day) and placebo for 14 days each in a double-blind crossover design and recorded their social behavior and mood during everyday interpersonal encounters. Participants also provided daily ratings of their positive and negative cognitions concerning their social functioning. Results: Tryptophan improved mood. Unexpectedly, tryptophan increased quarrelsome behavior and reduced agreeable behavior, specifically during interactions at home. The behavioral effects of tryptophan were not moderated by mood or by the interaction partner. Negative social cognitions were lower when tryptophan was given second and lower during placebo when placebo was given second. Conclusion: Overall, tryptophan may not alter social behavior in individuals with a family history of depression as it does in irritable people. However, the behavioral effects of tryptophan at home might be seen as a way for individuals with a family history of depression to achieve more control. Over time, this may positively influence the way they feel and think about themselves in a social context. PMID:25733537

  14. Acute tryptophan depletion in C57BL/6 mice does not induce central serotonin reduction or affective behavioural changes.

    Science.gov (United States)

    van Donkelaar, Eva L; Blokland, Arjan; Lieben, Cindy K J; Kenis, Gunter; Ferrington, Linda; Kelly, Paul A T; Steinbusch, Harry W M; Prickaerts, Jos

    2010-01-01

    Acute tryptophan depletion is extensively used to investigate the implication of serotonin in the onset of depressive disorders. In rats, it lowers peripheral tryptophan and decreases central serotonin concentrations. We aimed to establish the rat model of acute tryptophan depletion in the mouse for potential application as serotonin challenge tool in genetic mouse models of depression. Pharmacokinetic and behavioural effects of a tryptophan-free diet were examined in Swiss and C57BL/6 mice. Peripheral amino acids were measured and central tryptophan and serotonin concentrations were compared with anxiety and depression-like behaviour in the elevated zero-maze, forced swimming test or tail suspension test. While acute tryptophan depletion resulted in a 74% reduction of the plasma ratio tryptophan to the sum of other large neutral amino acids in Swiss mice 1h after administration (2x10 ml/kg, 30 min interval), there was only a 40% reduction in C57BL/6 mice. The latter did not show anxiety in the elevated zero-maze or increased immobility in the forced swimming test or tail suspension test. A higher dose (2x20 ml/kg) with a longer interval (60 min) reduced the ratio with 68% in C57BL/6 mice, lowered hippocampal serotonin turnover and had no functional effect when tested in the elevated zero-maze and forced swimming test. These findings have important implications for the use of acute tryptophan depletion in general and in particular for its application in mice. Although in healthy mice no clear central serotonin or functional effects were observed, further research is indicated using mice with pre-existing serotonin dysfunction, as they might be more vulnerable to acute tryptophan depletion. 2009 Elsevier Ltd. All rights reserved.

  15. Rapid NIR determination of alkyl esters in virgin olive oil

    International Nuclear Information System (INIS)

    Cayuela, J.A.

    2017-01-01

    The regulation of The European Union for olive oil and olive pomace established the limit of 35 mg·kg-1 for fatty acids ethyl ester contents in extra virgin olive oils, from grinding seasons after 2016. In this work, predictive models have been established for measuring fatty acid ethyl and methyl esters and to measure the total fatty acid alkyl esters based on near infrared spectroscopy (NIRS), and used successfully for this purpose. The correlation coefficients from the external validation exercises carried out with these predictive models ranged from 0.84 to 0.91. Different classification tests using the same models for the thresholds 35 mg·kg-1 for fatty acid ethyl esters and 75 mg·kg-1 for fatty acid alkyl esters provided success percentages from 75.0% to 95.2%. [es

  16. Evaluation of octyl p-methoxycinnamate included in liposomes and cyclodextrins in anti-solar preparations: preparations, characterizations and in vitro penetration studies.

    Science.gov (United States)

    Monteiro, Mariana Sato de Souza de Bustamante; Ozzetti, Rafael Antonio; Vergnanini, André Luiz; de Brito-Gitirana, Lycia; Volpato, Nadia Maria; de Freitas, Zaida Maria Faria; Ricci-Júnior, Eduardo; dos Santos, Elisabete Pereira

    2012-01-01

    Awareness of the harmful effects of ultraviolet radiation has led to the increasing use of sunscreens, thus, the development of safe and effective antisolar preparations is important. The inclusion of sunscreen molecules in different release systems, like liposomes (lipo) and cyclodextrins (CD) is therefore required. The in vivo sun protection factor (SPF), water resistance, and in vitro transdermal penetration test of octyl p-methoxycinnamate (OMC) in different dispersions, such as OMC encapsulated in liposomes (lipo/OMC), OMC encapsulated in β-cyclodextrins (β-CD/OMC), OMC encapsulated in both release systems (lipo/OMC and β-CD/OMC), and an OMC-free formulation were determined. Although the formulation containing only the lipo/OMC system revealed high value of in vivo SPF (11.0 ± 1.3) and water resistance (SPF = 10.3 ± 2.2), the formulation containing both release systems (lipo/OMC + β-cyclodextrin/OMC) showed the best result in the in vivo SPF test (11.6 ± 1.6). In the penetration test, the formulation containing the lipo/OMC system had better performance, since a high amount of OMC in the epidermis (18.04 ± 1.17 μg) and a low amount of OMC in the dermis (9.4 ± 2.36 μg) were observed. These results suggest that liposomes interact with the cells of the stratum corneum, promoting retention of OMC in this layer. According to our study, the lipo/OMC system is the most advantageous release system, due to its ability to both increase the amount of OMC in the epidermis and decrease the risk of percutaneous absorption.

  17. An ultra-high performance liquid chromatography method to determine the skin penetration of an octyl methoxycinnamate-loaded liquid crystalline system.

    Science.gov (United States)

    Prado, A H; Borges, M C; Eloy, J O; Peccinini, R G; Chorilli, M

    2017-10-01

    Cutaneous penetration is a critical factor in the use of sunscreen, as the compounds should not reach systemic circulation in order to avoid the induction of toxicity. The evaluation of the skin penetration and permeation of the UVB filter octyl methoxycinnamate (OMC) is essential for the development of a successful sunscreen formulation. Liquid-crystalline systems are innovative and potential carriers of OMC, which possess several advantages, including controlled release and protection of the filter from degradation. In this study, a new and effective method was developed using ultra-high performance liquid chromatography (UPLC) with ultraviolet detection (UV) for the quantitative analysis of penetration of OMC-loaded liquid crystalline systems into the skin. The following parameters were assessed in the method: selectivity, linearity, precision, accuracy, robustness, limit of detection (LOD), and limit of quantification (LOQ). The analytical curve was linear in the range from 0.25 to 250 μg.m-1, precise, with a standard deviation of 0.05-1.24%, with an accuracy in the range from 96.72 to 105.52%, and robust, with adequate values for the LOD and LOQ of 0.1 and 0.25 μg.mL -1, respectively. The method was successfully used to determine the in vitro skin permeation of OMC-loaded liquid crystalline systems. The results of the in vitro tests on Franz cells showed low cutaneous permeation and high retention of the OMC, particularly in the stratum corneum, owing to its high lipophilicity, which is desirable for a sunscreen formulation.

  18. Effects of a 5-day treatment with the UV-filter octyl-methoxycinnamate (OMC) on the function of the hypothalamo-pituitary-thyroid function in rats.

    Science.gov (United States)

    Klammer, Holger; Schlecht, Christiane; Wuttke, Wolfgang; Schmutzler, Cornelia; Gotthardt, Inka; Köhrle, Josef; Jarry, Hubertus

    2007-09-05

    Octyl-methoxycinnamate (OMC) is one of the most frequently used UV-filters in sunscreens to protect the skin against the noxious influence of UV radiation. Recently, OMC was suspected to act as an "endocrine active chemical" (EAC) with estrogenic actions. While EACs have been investigated thoroughly for interference with reproductive function in mammalians, surprisingly little efforts have been made to investigate an interference of EACs with the hypothalamo-pituitary-thyroid (HPT) axis despite the expression of estrogen receptors in all parts of this axis. Therefore, we conducted an in vivo study with ovariectomised rats treated for 5 days with different doses of OMC or 17beta-estradiol (E2) as a control. Determined parameters comprised serum levels of TSH, T4 and T3, hypothalamic TRH mRNA expression, protein-expression of the sodium-iodide-symporter (NIS) and the TSH receptor and the activities of thyroid peroxidase (TPO) in the thyroid and the T3-responsive hepatic type I 5'deiodinase (Dio1) in the liver. While E2 did not affect TSH-, T4- or T3-levels, OMC caused a dose-dependent decrease of serum concentrations of all of these hormones. TRH expression remained unaffected, while in the thyroid, expression of the TSH receptor but not of NIS was stimulated by OMC. TPO activity was unaltered but Dio1 activity was reduced by OMC. Thus, our results demonstrate a non-estrogenic interference of OMC within the rodent HPT axis with inadequate feedback response to impaired thyroid hormone status, indicated by decreased serum thyroid hormone and hepatic Dio1 levels.

  19. Effects of a 5-day treatment with the UV-filter octyl-methoxycinnamate (OMC) on the function of the hypothalamo-pituitary-thyroid function in rats

    International Nuclear Information System (INIS)

    Klammer, Holger; Schlecht, Christiane; Wuttke, Wolfgang; Schmutzler, Cornelia; Gotthardt, Inka; Koehrle, Josef; Jarry, Hubertus

    2007-01-01

    Octyl-methoxycinnamate (OMC) is one of the most frequently used UV-filters in sunscreens to protect the skin against the noxious influence of UV radiation. Recently, OMC was suspected to act as an 'endocrine active chemical' (EAC) with estrogenic actions. While EACs have been investigated thoroughly for interference with reproductive function in mammalians, surprisingly little efforts have been made to investigate an interference of EACs with the hypothalamo-pituitary-thyroid (HPT) axis despite the expression of estrogen receptors in all parts of this axis. Therefore, we conducted an in vivo study with ovariectomised rats treated for 5 days with different doses of OMC or 17β-estradiol (E2) as a control. Determined parameters comprised serum levels of TSH, T4 and T3, hypothalamic TRH mRNA expression, protein-expression of the sodium-iodide-symporter (NIS) and the TSH receptor and the activities of thyroid peroxidase (TPO) in the thyroid and the T3-responsive hepatic type I 5'deiodinase (Dio1) in the liver. While E2 did not affect TSH-, T4- or T3-levels, OMC caused a dose-dependent decrease of serum concentrations of all of these hormones. TRH expression remained unaffected, while in the thyroid, expression of the TSH receptor but not of NIS was stimulated by OMC. TPO activity was unaltered but Dio1 activity was reduced by OMC. Thus, our results demonstrate a non-estrogenic interference of OMC within the rodent HPT axis with inadequate feedback response to impaired thyroid hormone status, indicated by decreased serum thyroid hormone and hepatic Dio1 levels

  20. Structure and Activity of an Aminoacyl-tRNA Synthetase that Charges tRNA with Nitro-Tryptophan

    Energy Technology Data Exchange (ETDEWEB)

    Buddha,M.; Crane, B.

    2005-01-01

    The most divergent of two tryptophanyl tRNA synthetases (TrpRS II) found in Deinococcus radiodurans interacts with a nitric oxide synthase protein that produces 4-nitro-tryptophan (4-NRP). TrpRS II efficiently charges transfer RNATrp with 4-NRP and 5-hydroxy-tryptophan (5-HRP). The crystal structures of TrpRS II bound to tryptophan and 5-HRP reveal residue substitutions that accommodate modified indoles. A class of auxiliary bacterial TrpRSs conserve this capacity to charge tRNA with nonstandard amino acids.

  1. A Brief Historic Overview of Clinical Disorders Associated with Tryptophan: The Relevance to Chronic Fatigue Syndrome (CFS and Fibromyalgia (FM.

    Directory of Open Access Journals (Sweden)

    Adele Blankfield

    2012-01-01

    Full Text Available Last century there was a short burst of interest in the tryptophan related disorders of pellagra and related abnormalities that are usually presented in infancy. 1 , 2 Nutritional physiologists recognized that a severe human dietary deficiency of either tryptophan or the B group vitamins could result in central nervous system (CNS sequelae such as ataxia, cognitive dysfunction and dysphoria, accompanied by skin hyperpigmentation. 3 , 4 The current paper will focus on the emerging role of tryptophan in chronic fatigue syndrome (CFS and fibromyalgia (FM.

  2. Methods of refining and producing dibasic esters and acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E.; Cohen, Steven A.; Gildon, Demond L.

    2016-06-14

    Methods and systems for making dibasic esters and/or dibasic acids using metathesis are generally disclosed. In some embodiments, the methods comprise reacting a terminal olefin ester with an internal olefin ester in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In some embodiments, the terminal olefin ester or the internal olefin ester are derived from a renewable feedstock, such as a natural oil feedstock. In some such embodiments, the natural oil feedstock, or a transesterified derivative thereof, is metathesized to make the terminal olefin ester or the internal olefin ester.

  3. Activated sludge degradation of adipic acid esters.

    Science.gov (United States)

    Saeger, V W; Kalley, R G; Hicks, O; Tucker, E S; Mieure, J P

    1976-01-01

    The biodegradability of three aliphatic adipic acid diesters and a 1,3-butylene glycol adipic acid polyester was determined in acclimated, activated sludge systems. Rapid primary biodegradation from 67 to 99+% was observed at 3- and 13-mg/liter feed levels for di-n-hexyl adipate, di(2-ethylhexyl) adipate, and di(heptyl, nonyl) adipate in 24 h. When acclimated, activated sludge microorganisms were employed as the seed for two carbon dioxide evolution procedures, greater than 75% of the theoretical carbon dioxide was evolved for the three diesters and the polyester in a 35-day test period. The essentially complete biodegradation observed in these studies suggests that these esters would not persist when exposed to similar mixed microbial populations in the environment. PMID:1275494

  4. Ketone ester effects on metabolism and transcription.

    Science.gov (United States)

    Veech, Richard L

    2014-10-01

    Ketosis induced by starvation or feeding a ketogenic diet has widespread and often contradictory effects due to the simultaneous elevation of both ketone bodies and free fatty acids. The elevation of ketone bodies increases the energy of ATP hydrolysis by reducing the mitochondrial NAD couple and oxidizing the coenzyme Q couple, thus increasing the redox span between site I and site II. In contrast, metabolism of fatty acids leads to a reduction of both mitochondrial NAD and mitochondrial coenzyme Q causing a decrease in the ΔG of ATP hydrolysis. In contrast, feeding ketone body esters leads to pure ketosis, unaccompanied by elevation of free fatty acids, producing a physiological state not previously seen in nature. The effects of pure ketosis on transcription and upon certain neurodegenerative diseases make approach not only interesting, but of potential therapeutic value.

  5. Organophosphorus ester-induced chronic neurotoxicity.

    Science.gov (United States)

    Abou-Donia, Mohamed B

    2003-08-01

    Organophosphorus compounds are potent neurotoxic chemicals that are widely used in medicine, industry, and agriculture. The neurotoxicity of these chemicals has been documented in accidental human poisoning, epidemiological studies, and animal models. Organophosphorus compounds have 3 distinct neurotoxic actions. The primary action is the irreversible inhibition of acetylcholinesterase, resulting in the accumulation of acetylcholine and subsequent overstimulation of the nicotinic and muscarinic acetylcholine receptors, resulting in cholinergic effects. Another action of some of these compounds, arising from single or repeated exposure, is a delayed onset of ataxia, accompanied by a Wallerian-type degeneration of the axon and myelin in the most distal portion of the longest tracts in both the central and peripheral nervous systems, and is known as organophosphorus ester-induced delayed neurotoxicity (OPIDN). In addition, since the introduction and extensive use of synthetic organophosphorus compounds in agriculture and industry half a century ago, many studies have reported long-term, persistent, chronic neurotoxicity symptoms in individuals as a result of acute exposure to high doses that cause acute cholinergic toxicity, or from long-term, low-level, subclinical doses of these chemicals. The author attempts to define the neuronal disorder that results from organophosphorus ester-induced chronic neurotoxicity (OPICN), which leads to long-term neurological and neurobehavioral deficits. Although the mechanisms of this neurodegenerative disorder have yet to be established, the sparse available data suggest that large toxic doses of organophosphorus compounds cause acute necrotic neuronal cell death in the brain, whereas sublethal or subclinical doses produce apoptotic neuronal cell death and involve oxidative stress.

  6. Short-chain fluorescent tryptophan tags for on-line detection of functional recombinant proteins

    Directory of Open Access Journals (Sweden)

    Siepert Eva-Maria

    2012-09-01

    Full Text Available Abstract Background Conventional fluorescent proteins, such as GFP, its derivatives and flavin mononucleotide based fluorescent proteins (FbFPs are often used as fusion tags for detecting recombinant proteins during cultivation. These reporter tags are state-of-the-art; however, they have some drawbacks, which can make on-line monitoring challenging. It is discussed in the literature that the large molecular size of proteins of the GFP family may stress the host cell metabolism during production. In addition, fluorophore formation of GFP derivatives is oxygen-dependent resulting in a lag-time between expression and fluorescence detection and the maturation of the protein is suppressed under oxygen-limited conditions. On the contrary, FbFPs are also applicable in an oxygen-limited or even anaerobic environment but are still quite large (58% of the size of GFP. Results As an alternative to common fluorescent tags we developed five novel tags based on clustered tryptophan residues, called W-tags. They are only 5-11% of the size of GFP. Based on the property of tryptophan to fluoresce in absence of oxygen it is reasonable to assume that the functionality of our W-tags is also given under anaerobic conditions. We fused these W-tags to a recombinant protein model, the anti-CD30 receptor single-chain fragment variable antibody (scFv Ki-4(scFv and the anti-MucI single-chain fragment variable M12(scFv. During cultivation in Microtiter plates, the overall tryptophan fluorescence intensity of all cultures was measured on-line for monitoring product formation via the different W-tags. After correlation of the scattered light signal representing biomass concentration and tryptophan fluorescence for the uninduced cultures, the fluorescence originating from the biomass was subtracted from the overall tryptophan signal. The resulting signal, thus, represents the product fluorescence of the tagged and untagged antibody fragments. The product fluorescence signal

  7. Evening intake of α-lactalbumin increases plasma tryptophan availability and improves morning alertness and brain measures of attention

    NARCIS (Netherlands)

    Markus, C.R.; Jonkman, L.M.; Lammers, J.H.C.M.; Deutz, N.E.P.; Messer, M.H.; Rigtering, N.

    2005-01-01

    Background: Brain serotonin function is thought to promote sleep regulation and cognitive processes, whereas sleep abnormalities and subsequent behavioral decline are often attributed to deficient brain serotonin activity. Brain uptake of the serotonin precursor tryptophan is dependent on nutrients

  8. The Effects of Tryptophan on Everyday Interpersonal Encounters and Social Cognitions in Individuals with a Family History of Depression

    NARCIS (Netherlands)

    Hogenelst, Koen; Schoevers, Robert A.; Rot, Marije Aan Het

    2015-01-01

    Background: Individuals with a family history of depression show subtle abnormalities in the processing of social stimuli. This could negatively affect their interpersonal functioning and contribute to their depression risk. Repeated administration of the serotonin precursor tryptophan has

  9. Differences in the association of inflammation and tryptophan with depressive symptoms between white and non-white chronic dialysis patients

    NARCIS (Netherlands)

    Haverkamp, Gertrud L; Loosman, Wim L; Schouten, Robbert W; Franssen, Casper F; Kema, Ido P; van Diepen, Merel; Dekker, Friedo W; Siegert, Carl E; Honig, Adriaan

    Objective: Possibly, different biochemical parameters are involved in the development of depressive symptoms in white and non-white dialysis patients. We examined whether the association between inflammation and depressive symptoms and between tryptophan and depressive symptoms differs between white

  10. Thermal and mechanical properties of fatty acid starch esters.

    Science.gov (United States)

    Winkler, H; Vorwerg, W; Rihm, R

    2014-02-15

    The current study examined thermal and mechanical properties of fatty acid starch esters (FASEs). All highly soluble esters were obtained by the sustainable, homogeneous transesterification of fatty acid vinyl esters in dimethylsulfoxide (DMSO). Casted films of products with a degree of substitution (DS) of 1.40-1.73 were compared with highly substituted ones (DS 2.20-2.63). All films were free of any plasticizer additives. Hydrophobic surfaces were characterized by contact angle measurements. Dynamic scanning calorimetry (DSC) and dynamic mechanical thermal analysis (DMTA) revealed thermal transitions (T(g), T(m)) which were influenced by the internal plasticizing effect of the ester groups. Thermal gravimetric analysis (TGA) measurements showed the increased thermal stability toward native starch. Tensile tests revealed the decreasing strength and stiffness of the products with increasing ester-group chain length while the elongation increased up to the ester group laurate and after that decreased. Esters of the longest fatty acids, palmitate and stearate turned out to be brittle materials due to super molecular structures of the ester chains such as confirmed by X-ray. Summarized products with a DS 1.40-1.73 featured more "starch-like" properties with tensile strength up to outstanding 43 MPa, while products with a DS >2 behaved more "oil-like". Both classes of esters should be tested as a serious alternative to commercial starch blends and petrol-based plastics. The term Cnumber is attributed to the number of total C-Atoms of the fatty acid (e.g. C6=Hexanoate). Copyright © 2013 Elsevier Ltd. All rights reserved.

  11. Boric Ester-Type Molten Salt via Dehydrocoupling Reaction

    OpenAIRE

    Noriyoshi Matsumi; Yoshiyuki Toyota; Prerna Joshi; Puhup Puneet; Raman Vedarajan; Toshihiro Takekawa

    2014-01-01

    Novel boric ester-type molten salt was prepared using 1-(2-hydroxyethyl)-3-methylimidazolium chloride as a key starting material. After an ion exchange reaction of 1-(2-hydroxyethyl)-3-methylimidazolium chloride with lithium (bis-(trifluoromethanesulfonyl) imide) (LiNTf2), the resulting 1-(2-hydroxyethyl)-3-methylimidazolium NTf2 was reacted with 9-borabicyclo[3.3.1]nonane (9-BBN) to give the desired boric ester-type molten salt in a moderate yield. The structure of the boric ester-type molt...

  12. Catalytic Oxidation of Allylic Alcohols to Methyl Esters

    DEFF Research Database (Denmark)

    Gallas-Hulin, Agata; Kotni, Rama Krishna; Nielsen, Martin

    2017-01-01

    Aerobic oxidation of allylic alcohols to methyl esters using gold nanoparticles supported on different metal oxide carriers has been performed successfully under mild conditions (room temperature, 0.1 MPa O2) without significant loss of catalytic activity. The effects of different reaction...... parameters are studied to find the suitable reaction conditions. All catalysts are characterised by XRD, XRF and TEM. Among these catalysts, Au/TiO2 showed the most efficient catalytic activity towards the selective oxidation of allylic alcohols to the corresponding esters. Moreover, the same Au/TiO2...... to synthesize methyl esters from allylic alcohols....

  13. Sugar ester surfactants: enzymatic synthesis and applications in food industry.

    Science.gov (United States)

    Neta, Nair S; Teixeira, José A; Rodrigues, Lígia R

    2015-01-01

    Sugar esters are non-ionic surfactants that can be synthesized in a single enzymatic reaction step using lipases. The stability and efficiency of lipases under unusual conditions and using non-conventional media can be significantly improved through immobilization and protein engineering. Also, the development of de novo enzymes has seen a significant increase lately under the scope of the new field of synthetic biology. Depending on the esterification degree and the nature of fatty acid and/or sugar, a range of sugar esters can be synthesized. Due to their surface activity and emulsifying capacity, sugar esters are promising for applications in food industry.

  14. Acyl-lupeol esters from Parahancornia amapa (Apocynaceae

    Directory of Open Access Journals (Sweden)

    Carvalho Mário G. de

    2001-01-01

    Full Text Available From the roots of Parahancornia amapa, family Apocynaceae, the following compounds were isolated and identified nine new and ten known 3beta-O-acyl lupeol esters, beta-sitosterol, stigmasterol, beta-sitosterone, the triterpenoids beta-amyrin, alpha-amyrin, lupeol and their acetyl derivatives. The structures of these compounds were established by spectroscopic data, mainly ¹H and 13C (HBBD and DEPT NMR spectra. The methyl esters obtained by hydrolysis of acyl lupeol esters and methylation of the corresponding acids were characterized by MS-GC analysis.

  15. Effect of deletion and overexpression of tryptophan metabolism genes on growth and fermentation capacity at low temperature in wine yeast

    OpenAIRE

    Martí-Raga, M.; Guillamon, J.M.; Chiva, R.; García-Rios, E.; López-Malo, M.

    2014-01-01

    10.1002/btpr.1915 Low-temperature fermentations produce wines with greater aromatic complexity, but the success of these fermentations greatly depends on the adaptation of yeast cells to cold. Tryptophan has been previously reported to be a limiting amino acid during Saccharomyces cerevisiae growth at low temperature. The objective of this study was to determine the influence of the tryptophan metabolism on growth and fermentation performance during low-temperature wine fermentation. To t...

  16. Tryptophan-enriched antioxidant cereals improve sleep in children with autistic spectrum and attention deficit hyperactivity disorders

    OpenAIRE

    Galán, Carmen; Sánchez, Soledad; Franco, Lourdes; Bravo, Rafael; Rivero, Montserrat; Rodríguez, Ana Beatriz; Barriga, Carmen

    2017-01-01

    Theintake of foods rich in tryptophan produces beneficial effects on sleep. Themajority of children with neurological disorders like autistic spectrum disorder(ASD), cerebral palsy or attention deficit hyperactivity disorder (ADHD) havesleep problems. To evaluate the effect of tryptophan-enriched cereal intake onsleep of children with neurological disorders. Involving 7 children with ASD, 9children with cerebral palsy and 6 children with ADHD. They carried a wrist actimeterto record activity....

  17. Tryptophan-Assisted Synthesis Reduces Bimetallic Gold/Silver Nanoparticle Cytotoxicity and Improves Biological Activity

    Directory of Open Access Journals (Sweden)

    Igor O. Shmarakov

    2014-10-01

    Full Text Available Aiming to reduce the potential in vivo hepato-and nephrotoxicity of Ag/Au bimetallic nanoparticles (NPs stabilized by sodium dodecyl sulphate (SDS, an approach involving a simultaneous reduction of silver nitrate and tetrachlorauratic acid using tryptophan (Trp as a reducing/stabilizing agent was applied during NP synthesis. The obtained Ag/Au/Trp NPs (5–15 nm sized were able to form stable aggregates with an average size of 370–450 nm and were potentially less toxic than Ag/Au/SDS in relation to a mouse model system based on clinical biochemical parameters and oxidative damage product estimation. Ag/Au/Trp NPs were shown to exhibit anticancer activity in relation to a Lewis lung carcinoma model. The data generated from the present study support the fact that the use of tryptophan in NP synthesis is effective in attenuating the potential hepatotoxicity and nephrotoxicity of NPs during their in vivo application.

  18. Tryptophan metabolism: entering the field of aging and age-related pathologies.

    Science.gov (United States)

    van der Goot, Annemieke T; Nollen, Ellen A A

    2013-06-01

    Aging is an important risk factor for many debilitating diseases, including cancer and neurodegeneration. In model organisms, interfering with metabolic signaling pathways, including the insulin/insulin-like growth factor (IGF) 1 (IIS) and TOR pathways, can protect against age-related pathologies and increase lifespan. Recent studies in multiple organisms have implicated tryptophan metabolism as a powerful regulator of age-related diseases and lifespan. Its high conservation throughout evolution has enabled studies that begin to dissect the contribution of individual enzymes and metabolites. Here, we focus on the emerging view of tryptophan metabolism as a pathway that integrates environmental and metabolic signals to regulate animal biology and health. Copyright © 2013 Elsevier Ltd. All rights reserved.

  19. L-Tryptophan on Cu(111): engineering a molecular labyrinth driven by indole groups

    Energy Technology Data Exchange (ETDEWEB)

    Yitamben, E. N.; Clayborne, A.; Darling, Seth B.; Guisinger, N. P.

    2015-05-21

    The present article investigates the adsorption and molecular orientation of L-Tryptophan, which is both an essential amino acid important for protein synthesis and of particular interest for the development of chiral molecular electronics and biocompatible processes and devices, on Cu(111) using scanning tunneling microscopy and spectroscopy at 55 K and at room temperature. The arrangement of chemisorbed L-Tryptophan on the copper surface varies with both temperature and surface coverage. At low coverage, small clusters form on the surface irrespective of temperature, while at high coverage an ordered chain structure emerges at room temperature, and a tightly packed structure forms a molecular labyrinth at low temperature. The dominating superstructure of the adsorbates arises from intermolecular hydrogen bonding, and pi-bonding interactions between the indole groups of neighboring molecules and the Cu surface.

  20. Synthesis and fungicidal activity of tryptophan analogues - the unexpected calycanthaceous alkaloid derivatives.

    Science.gov (United States)

    Zheng, Shaojun; Gu, Yongdong; Li, Longbo; Zhu, Rui; Cai, Xingwei; Bai, Hongjin; Zhang, Jiwen

    2017-05-01

    A series of 21 N-protected tryptophan derivatives were synthesised from tryptophan in good yields. Their structures were characterised by IR, 1 H NMR, 13 C NMR, DEPT (90° and 135°) and MS analysis. The synthesised compounds were evaluated against a wide variety of plant pathogen fungi. Compounds a19 and a21 displayed activity against Fusarium oxysporum (F. oxysporum), and compound a21 showed high activity against F. oxysporum and Eggplant Verticillium, with EC 50 values of 58.27 and 77.39 μg mL -1 , respectively. Considering that the bioassay of the title compounds was evaluated, effects of the chain alkyl substituents may contribute to the significant variations in fungicidal potency. Their structure-antifungal activity relationships were also discussed. These results will pave the way for further design, structural modification and development of calycanthaceous alkaloids as antimicrobial agents.

  1. Stochastic thermodynamics of a chemical nanomachine: The channeling enzyme tryptophan synthase.

    Science.gov (United States)

    Loutchko, Dimitri; Eisbach, Maximilian; Mikhailov, Alexander S

    2017-01-14

    The enzyme tryptophan synthase is characterized by a complex pattern of allosteric interactions that regulate the catalytic activity of its two subunits and opening or closing of their ligand gates. As a single macromolecule, it implements 13 different reaction steps, with an intermediate product directly channeled from one subunit to another. Based on experimental data, a stochastic model for the operation of tryptophan synthase has been earlier constructed [D. Loutchko, D. Gonze, and A. S. Mikhailov, J. Phys. Chem. B 120, 2179 (2016)]. Here, this model is used to consider stochastic thermodynamics of such a chemical nanomachine. The Gibbs energy landscape of the internal molecular states is determined, the production of entropy and its flow within the enzyme are analyzed, and the information exchange between the subunits resulting from allosteric cross-regulations and channeling is discussed.

  2. l-Tryptophan Radical Cation Electron Spin Resonance Studies: Connecting Solution-derived Hyperfine Coupling Constants with Protein Spectral Interpretations

    Science.gov (United States)

    Connor, Henry D.; Sturgeon, Bradley E.; Mottley, Carolyn; Sipe, Herbert J.; Mason, Ronald P.

    2009-01-01

    Fast-flow electron spin resonance (ESR) spectroscopy has been used to detect a free radical formed from the reaction of l-tryptophan with Ce4+ in an acidic aqueous environment. Computer simulations of the ESR spectra from l-tryptophan and several isotopically modified forms strongly support the conclusion that the l-tryptophan radical cation has been detected by ESR for the first time. The hyperfine coupling constants (HFCs) determined from the well-resolved isotropic ESR spectra support experimental and computational efforts to understand l-tryptophan's role in protein catalysis of oxidation-reduction processes. l-tryptophan HFCs facilitated the simulation of fast-flow ESR spectra of free radicals from two related compounds, tryptamine and 3-methylindole. Analysis of these three compounds' β-methylene hydrogen HFC data along with equivalent l-tyrosine data has led to a new computational method that can distinguish between these two amino acid free radicals in proteins without dependence on isotope labeling, electron nuclear double resonance or high-field ESR. This approach also produces geometric parameters (dihedral angles for the β-methylene hydrogens) which should facilitate protein site assignment of observed l-tryptophan radicals as has been done for l-tyrosine radicals. PMID:18433127

  3. Gonadal hormone levels and platelet tryptophan and serotonin concentrations in perimenopausal women with or without depressive symptoms.

    Science.gov (United States)

    Flores-Ramos, Mónica; Moreno, Julia; Heinze, Gerhard; Aguilera-Pérez, Rafael; Pellicer Graham, Francisco

    2014-03-01

    The etiology of depressive symptoms associated with the transition to menopause is still unknown; hormonal changes, serotonergic system or insomnia, could be a trigger to depressive symptomatology. The aim of the present study was to evaluate gonadal hormonal levels, platelet serotonin concentrations and platelet tryptophan concentrations in a group of depressed perimenopausal women and their healthy counterparts. A total of 63 perimenopausal women between 45 and 55 years old were evaluated; of these, 44 were depressed patients, and 19 were perimenopausal women without depression. The instruments that were applied included the Center for Epidemiologic Studies Depression Scale (CES-D), the Hamilton Depression Rating Scale (HDRS) and the Green Climacteric Scale (GCS); gonadal hormone levels and platelet tryptophan and serotonin concentrations were measured in all participants. Differences in hormonal levels and tryptophan and serotonin concentrations were evaluated with respect to specific symptoms, such as insomnia, hot flashes, nervousness, depressed mood and loss of interest. No differences between groups were observed with respect to hormonal levels and tryptophan and serotonin concentrations; mean sleep hours and insomnia were significantly correlated with platelet tryptophan concentrations. In this sample, all symptoms of depression could not be explained by platelet tryptophan and serotonin concentrations and hormonal levels; differences were observed only when we evaluated insomnia and hot flashes.

  4. Tripping up Trp: Modification of protein tryptophan residues by reactive oxygen species, modes of detection, and biological consequences.

    Science.gov (United States)

    Ehrenshaft, Marilyn; Deterding, Leesa J; Mason, Ronald P

    2015-12-01

    Proteins comprise a majority of the dry weight of a cell, rendering them a major target for oxidative modification. Oxidation of proteins can result in significant alterations in protein molecular mass such as breakage of the polypeptide backbone and/or polymerization of monomers into dimers, multimers, and sometimes insoluble aggregates. Protein oxidation can also result in structural changes to amino acid residue side chains, conversions that have only a modest effect on protein size but can have widespread consequences for protein function. There are a wide range of rate constants for amino acid reactivity, with cysteine, methionine, tyrosine, phenylalanine, and tryptophan having the highest rate constants with commonly encountered biological oxidants. Free tryptophan and tryptophan protein residues react at a diffusion-limited rate with hydroxyl radical and also have high rate constants for reactions with singlet oxygen and ozone. Although oxidation of proteins in general and tryptophan residues specifically can have effects detrimental to the health of cells and organisms, some modifications are neutral, whereas others contribute to the function of the protein in question or may act as a signal that damaged proteins need to be replaced. This review provides a brief overview of the chemical mechanisms by which tryptophan residues become oxidized, presents both the strengths and the weaknesses of some of the techniques used to detect these oxidative interactions, and discusses selected examples of the biological consequences of tryptophan oxidation in proteins from animals, plants, and microbes. Published by Elsevier Inc.

  5. Tryptophan Scanning Reveals Dense Packing of Connexin Transmembrane Domains in Gap Junction Channels Composed of Connexin32*

    Science.gov (United States)

    Brennan, Matthew J.; Karcz, Jennifer; Vaughn, Nicholas R.; Woolwine-Cunningham, Yvonne; DePriest, Adam D.; Escalona, Yerko; Perez-Acle, Tomas; Skerrett, I. Martha

    2015-01-01

    Tryptophan was substituted for residues in all four transmembrane domains of connexin32. Function was assayed using dual cell two-electrode voltage clamp after expression in Xenopus oocytes. Tryptophan substitution was poorly tolerated in all domains, with the greatest impact in TM1 and TM4. For instance, in TM1, 15 substitutions were made, six abolished coupling and five others significantly reduced function. Only TM2 and TM3 included a distinct helical face that lacked sensitivity to tryptophan substitution. Results were visualized on a comparative model of Cx32 hemichannel. In this model, a region midway through the membrane appears highly sensitive to tryptophan substitution and includes residues Arg-32, Ile-33, Met-34, and Val-35. In the modeled channel, pore-facing regions of TM1 and TM2 were highly sensitive to tryptophan substitution, whereas the lipid-facing regions of TM3 and TM4 were variably tolerant. Residues facing a putative intracellular water pocket (the IC pocket) were also highly sensitive to tryptophan substitution. Although future studies will be required to separate trafficking-defective mutants from those that alter channel function, a subset of interactions important for voltage gating was identified. Interactions important for voltage gating occurred mainly in the mid-region of the channel and focused on TM1. To determine whether results could be extrapolated to other connexins, TM1 of Cx43 was scanned revealing similar but not identical sensitivity to TM1 of Cx32. PMID:25969535

  6. The tryptophan synthetase gene TRP1 of Nodulisporium sp.: molecular characterization and its relation to nodulisporic acid A production.

    Science.gov (United States)

    Ireland, C; Peekhaus, N; Lu, P; Sangari, R; Zhang, A; Masurekar, P; An, Z

    2008-06-01

    Nodulisporic acid A (NAA), an insecticidal indole diterpene, is produced by the fungus Nodulisporium sp. Since indole-3-glycerolphosphate is the precursor of the indole moiety of NAA, it is suggested that the activity of tryptophan synthetase may play a role in NAA biosynthesis. To investigate this hypothesis, the tryptophan synthetase gene TRP1 of Nodulisporium sp. was cloned and characterized. The gene consists of three introns of 146, 68, and 57 bp. The four exons encode a protein of 712 amino acids, the sequence of which is highly homologous to that of other fungal tryptophan synthetase proteins. The transcription initiation site was mapped 66 bp upstream to the ATG, and the polyA tail attachment site is 169 bp downstream to the translation stop codon. Replacement of the N-terminal half of the gene with a hygromycin selection marker yielded mutants with the tryptophan auxotroph/hygromycin-resistance (trp(-)/hyr) phenotype. The TRP1 mutants required a high concentration of tryptophan supplement in solid medium (10 mM) to sustain minimal growth and failed to produce NAA in the production medium (FFL-CAM) supplemented with high concentrations of tryptophan.

  7. Multiresponse optimization of a UPLC method for the simultaneous determination of tryptophan and 15 tryptophan-derived compounds using a Box-Behnken design with a desirability function.

    Science.gov (United States)

    Setyaningsih, Widiastuti; Saputro, Irfan E; Carrera, Ceferino A; Palma, Miguel; Barroso, Carmelo G

    2017-06-15

    A Box-Behnken design was used in conjunction with multiresponse optimization based on the desirability function to carry out the simultaneous separation of tryptophan and 15 derivatives by Ultra Performance Liquid Chromatography. The gradient composition of the mobile phase and the flow rate were optimized with respect to the resolution of severely overlapping chromatographic peaks and the total run time. Two different stationary phases were evaluated (hybrid silica and a solid-core-based C 18 column). The methods were validated and a suitable sensitivity was found for all compounds in the concentration range 1-100μgL -1 (R 2 >0.999). High levels of repeatability and intermediate precision (CV less than 0.25% and 1.7% on average for the retention time and the signal area, respectively) were obtained. The new method was applied to the determination tryptophan and its derivatives in black pigmented glutinous and non-glutinous rice grain samples. Copyright © 2016 Elsevier Ltd. All rights reserved.

  8. Serum Levels of Tryptophan, 5-Hydroxytryptophan and Serotonin in Patients Affected with Different Forms of Amenorrhea

    Directory of Open Access Journals (Sweden)

    S. Comai

    2010-01-01

    Full Text Available Tryptophan (Trp is present in the serum, partly bound to albumine and in the free form. The unbound portion of circulating tryptophan has the property of crossing the hematoencephalic barrier and being converted within the brain into serotonin (5-HT through the enzymatic processes of hydroxylation and decarboxylation. The serotoninergic system plays an important role in neuroendocrine control of reproductive hormone secretion, and in particular, it may influence GnRH pulsatility, a function essential for reproductive processes. In this study, we analysed serum levels of tryptophan, serotonin and 5-hydroxytryptophan (5-HTP in women with three different forms of amenorrhea: 16 patients were diagnosed with anorexia nervosa, 60 patients with functional hypothalamic amenorrhea, and 14 patients with hyperprolactinemia. Data were compared with those of a group of 25 healthy women. Serum Trp levels were significantly (P ≤ 0.05 lower in the anorexic (11.64 ± 0.53 μg/ml, mean ± S.E. than in the control (12.98 ± 0.37 μg/ml groups. In addition, in the anorexic group a statistical dispersion of Trp values was shown indicating a bimodal data distribution suggesting the existence of two different subgroups of patients. Regarding 5-HTP, an increase of its serum level was observed in all the groups with amenorrhea with the highest value in hyperprolactinemic patients. On the contrary, no statistical differences in serum 5-HT levels among the four analyzed groups were observed. This study shows that women affected by various forms of amenorrhea present an altered metabolism of tryptophan via serotonin and, in particular, markedly high differences are observed between the two subgroups of anorexic patients.

  9. Serum Levels of Tryptophan, 5-Hydroxytryptophan and Serotonin in Patients Affected with Different Forms of Amenorrhea

    Directory of Open Access Journals (Sweden)

    S. Comai

    2010-06-01

    Full Text Available Tryptophan (Trp is present in the serum, partly bound to albumine and in the free form. The unbound portion of circulating tryptophan has the property of crossing the hematoencephalic barrier and being converted within the brain into serotonin (5-HT through the enzymatic processes of hydroxylation and decarboxylation. The serotoninergic system plays an important role in neuroendocrine control of reproductive hormone secretion, and in particular, it may influence GnRH pulsatility, a function essential for reproductive processes. In this study, we analysed serum levels of tryptophan, serotonin and 5-hydroxytryptophan (5-HTP in women with three different forms of amenorrhea: 16 patients were diagnosed with anorexia nervosa, 60 patients with functional hypothalamic amenorrhea, and 14 patients with hyperprolactinemia. Data were compared with those of a group of 25 healthy women. Serum Trp levels were significantly (P ≤ 0.05 lower in the anorexic (11.64 ± 0.53 µg/ml, mean ± S.E. than in the control (12.98 ± 0.37 µg/ml groups. In addition, in the anorexic group a statistical dispersion of Trp values was shown indicating a bimodal data distribution suggesting the existence of two different subgroups of patients. Regarding 5-HTP, an increase of its serum level was observed in all the groups with amenorrhea with the highest value in hyperprolactinemic patients. On the contrary, no statistical differences in serum 5-HT levels among the four analyzed groups were observed. This study shows that women affected by various forms of amenorrhea present an altered metabolism of tryptophan via serotonin and, in particular, markedly high differences are observed between the two subgroups of anorexic patients.

  10. Drugs with antidepressant properties affect tryptophan metabolites differently in rodent models with depression-like behavior.

    Science.gov (United States)

    Eskelund, Amanda; Li, Yan; Budac, David P; Müller, Heidi K; Gulinello, Maria; Sanchez, Connie; Wegener, Gregers

    2017-07-01

    The metabolism of tryptophan through kynurenine and serotonin pathways is linked to depression. Here, effects of different drugs with antidepressant properties (vortioxetine, fluoxetine, and ketamine) on various tryptophan metabolites in different brain regions and plasma were examined using tandem mass spectrometry (LC-MS/MS), in Flinders Sensitive Line rats, a genetic rat model of depression, and its controls: Flinders Sensitive Line and Sprague-Dawley rats. Protein levels of kynurenine pathway enzymes were measured in the brains and livers of these rat strains. Furthermore, effects of vortioxetine on tryptophan metabolites were assessed in the cortical regions of lupus mice (MRL/MpJ-Fas Ipr ), a murine model of increased depression-like behavior associated with inflammation. Sustained vortioxetine or fluoxetine (at doses aimed to fully occupy serotonin transporter via food or drinking water for at least 14 days) reduced levels of the excitotoxin quinolinic acid (QUIN) in various brain regions in all rats. Furthermore, chronic vortioxetine reduced levels of QUIN in MRL/MpJ-Fas Ipr mice. Acute i.p. administration of fluoxetine (10 mg/kg) or vortioxetine (10 mg/kg) led to reduced brain 5-hydroxyindoleacetic acid in Sprague-Dawley rats (2, 4, 6, and 8 h) and a similar trend was evident in Flinders Sensitive Line and Flinders Sensitive Line rats after 4 h. In contrast, single or repeated administration of ketamine (15 mg/kg i.p.) did not induce significant changes in metabolite levels. In conclusion, sustained vortioxetine and fluoxetine administration decreased QUIN independent of species, while ketamine was ineffective. These results support the hypothesis that modulating tryptophan metabolism may be part of the mechanism of action for some antidepressants. © 2017 International Society for Neurochemistry.

  11. Dynamic Allostery Mediated by a Conserved Tryptophan in the Tec Family Kinases.

    Directory of Open Access Journals (Sweden)

    Nikita Chopra

    2016-03-01

    Full Text Available Bruton's tyrosine kinase (Btk is a Tec family non-receptor tyrosine kinase that plays a critical role in immune signaling and is associated with the immunological disorder X-linked agammaglobulinemia (XLA. Our previous findings showed that the Tec kinases are allosterically activated by the adjacent N-terminal linker. A single tryptophan residue in the N-terminal 17-residue linker mediates allosteric activation, and its mutation to alanine leads to the complete loss of activity. Guided by hydrogen/deuterium exchange mass spectrometry results, we have employed Molecular Dynamics simulations, Principal Component Analysis, Community Analysis and measures of node centrality to understand the details of how a single tryptophan mediates allostery in Btk. A specific tryptophan side chain rotamer promotes the functional dynamic allostery by inducing coordinated motions that spread across the kinase domain. Either a shift in the rotamer population, or a loss of the tryptophan side chain by mutation, drastically changes the coordinated motions and dynamically isolates catalytically important regions of the kinase domain. This work also identifies a new set of residues in the Btk kinase domain with high node centrality values indicating their importance in transmission of dynamics essential for kinase activation. Structurally, these node residues appear in both lobes of the kinase domain. In the N-lobe, high centrality residues wrap around the ATP binding pocket connecting previously described Catalytic-spine residues. In the C-lobe, two high centrality node residues connect the base of the R- and C-spines on the αF-helix. We suggest that the bridging residues that connect the catalytic and regulatory architecture within the kinase domain may be a crucial element in transmitting information about regulatory spine assembly to the catalytic machinery of the catalytic spine and active site.

  12. Urinary metabolomics of young Italian autistic children supports abnormal tryptophan and purine metabolism.

    Science.gov (United States)

    Gevi, Federica; Zolla, Lello; Gabriele, Stefano; Persico, Antonio M

    2016-01-01

    Autism spectrum disorder (ASD) is still diagnosed through behavioral observation, due to a lack of laboratory biomarkers, which could greatly aid clinicians in providing earlier and more reliable diagnoses. Metabolomics on human biofluids provides a sensitive tool to identify metabolite profiles potentially usable as biomarkers for ASD. Initial metabolomic studies, analyzing urines and plasma of ASD and control individuals, suggested that autistic patients may share some metabolic abnormalities, despite several inconsistencies stemming from differences in technology, ethnicity, age range, and definition of "control" status. ASD-specific urinary metabolomic patterns were explored at an early age in 30 ASD children and 30 matched controls (age range 2-7, M:F = 22:8) using hydrophilic interaction chromatography (HILIC)-UHPLC and mass spectrometry, a highly sensitive, accurate, and unbiased approach. Metabolites were then subjected to multivariate statistical analysis and grouped by metabolic pathway. Urinary metabolites displaying the largest differences between young ASD and control children belonged to the tryptophan and purine metabolic pathways. Also, vitamin B 6 , riboflavin, phenylalanine-tyrosine-tryptophan biosynthesis, pantothenate and CoA, and pyrimidine metabolism differed significantly. ASD children preferentially transform tryptophan into xanthurenic acid and quinolinic acid (two catabolites of the kynurenine pathway), at the expense of kynurenic acid and especially of melatonin. Also, the gut microbiome contributes to altered tryptophan metabolism, yielding increased levels of indolyl 3-acetic acid and indolyl lactate. The metabolic pathways most distinctive of young Italian autistic children largely overlap with those found in rodent models of ASD following maternal immune activation or genetic manipulations. These results are consistent with the proposal of a purine-driven cell danger response, accompanied by overproduction of epileptogenic and

  13. Predictive and prognostic role of serum neopterin and tryptophan breakdown in prostate cancer.

    Science.gov (United States)

    Pichler, Renate; Fritz, Josef; Heidegger, Isabel; Steiner, Eberhard; Culig, Zoran; Klocker, Helmut; Fuchs, Dietmar

    2017-04-01

    The γ-interferon-induced enzymes indoleamine 2,3-dioxygenase and GTP-cyclohydrolase are key players in tumor immune escape mechanisms. We quantified serum levels of neopterin and tryptophan breakdown (tryptophan, kynurenine, and kynurenine-to-tryptophan ratio) in addition to prostate-specific antigen (PSA) in newly diagnosed prostate cancer (PCa) patients (n = 100) before radical prostatectomy (RP) as well as at time of biochemical recurrence (BCR) after RP (n = 50) in comparison to healthy men (n = 49). Effects of biomarkers on the risk of PCa diagnosis on transrectal biopsy, worse histopathological characteristics of the RP specimens, and cancer-specific survival (CSS) after BCR were investigated. Neopterin (hazard ratio [HR], 2.46; 95% confidence interval [CI], 1.08-5.61; P = 0.032) and kynurenine (HR, 2.93; 95% CI, 1.26-6.79; P = 0.012) levels were univariately associated with CSS. When adjusted for other biomarkers, only neopterin remained an independent predictor of CSS (HR, 2.56; 95% CI, 1.07-6.12; P = 0.035). Only PSA was associated with an increased risk of PCa diagnosis on biopsy, univariately (odds ratio, 3.14; 95% CI, 1.68-5.88; P tryptophan breakdown cannot be considered as biomarkers in detecting PCa or in predicting worse final pathological findings, neopterin levels are useful for stratifying patients into different prognostic groups after BCR. © 2017 The Authors Cancer Science published by John Wiley & Sons Australia, Ltd on behalf of Japanese Cancer Association.

  14. Effect of tryptophan enriched diets on aggression in hierarchical groups of juvenile Atlantic salmon (Salmo salar)

    OpenAIRE

    Vindas Alvarado, Marco Antonio

    2010-01-01

    Aggression in fish hierarchies often leads to one dominant individual monopolizing resources (food/shelter), thus increasing their fitness. Meanwhile individuals in subordinate ranks, endure high stressful conditions, which often lead to disease and higher mortality rates. Levels of serotonin have been linked to agonistic behavior. Enriching fish diets with tryptophan (TRP), the natural precursor for serotonin, has been used in several vertebrate species in order to control agg...

  15. Physiological roles of tryptophan in teleosts: current knowledge and perspectives for future studies

    DEFF Research Database (Denmark)

    Hoseini, Seyyed Morteza; Pérez-Jiménez, Amelia; Costas, Benjamin

    2017-01-01

    from the neuroendocrine to the immune system in vertebrates. In aquaculture, extensive research has been performed to optimize the levels of tryptophan in the commercial diets for many fish species. Providing adequate levels of this amino acid is critically important for fish growth but also for fish......- mediated functions, along with its participation in the regulation of the immune system and its role as an antioxidant and antitoxic agent in fish....

  16. Dynamic Allostery Mediated by a Conserved Tryptophan in the Tec Family Kinases.

    Science.gov (United States)

    Chopra, Nikita; Wales, Thomas E; Joseph, Raji E; Boyken, Scott E; Engen, John R; Jernigan, Robert L; Andreotti, Amy H

    2016-03-01

    Bruton's tyrosine kinase (Btk) is a Tec family non-receptor tyrosine kinase that plays a critical role in immune signaling and is associated with the immunological disorder X-linked agammaglobulinemia (XLA). Our previous findings showed that the Tec kinases are allosterically activated by the adjacent N-terminal linker. A single tryptophan residue in the N-terminal 17-residue linker mediates allosteric activation, and its mutation to alanine leads to the complete loss of activity. Guided by hydrogen/deuterium exchange mass spectrometry results, we have employed Molecular Dynamics simulations, Principal Component Analysis, Community Analysis and measures of node centrality to understand the details of how a single tryptophan mediates allostery in Btk. A specific tryptophan side chain rotamer promotes the functional dynamic allostery by inducing coordinated motions that spread across the kinase domain. Either a shift in the rotamer population, or a loss of the tryptophan side chain by mutation, drastically changes the coordinated motions and dynamically isolates catalytically important regions of the kinase domain. This work also identifies a new set of residues in the Btk kinase domain with high node centrality values indicating their importance in transmission of dynamics essential for kinase activation. Structurally, these node residues appear in both lobes of the kinase domain. In the N-lobe, high centrality residues wrap around the ATP binding pocket connecting previously described Catalytic-spine residues. In the C-lobe, two high centrality node residues connect the base of the R- and C-spines on the αF-helix. We suggest that the bridging residues that connect the catalytic and regulatory architecture within the kinase domain may be a crucial element in transmitting information about regulatory spine assembly to the catalytic machinery of the catalytic spine and active site.

  17. Comparative safety of the antifouling compound butenolide and 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) to the marine medaka (Oryzias melastigma)

    Energy Technology Data Exchange (ETDEWEB)

    Chen, Lianguo [Division of Life Science, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong Special Administrative Region (Hong Kong); Ye, Rui [State Key Laboratory in Marine Pollution, Department of Biology and Chemistry, City University of Hong Kong, Kowloon, Hong Kong Special Administrative Region (Hong Kong); Xu, Ying; Gao, Zhaoming [Division of Life Science, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong Special Administrative Region (Hong Kong); Au, Doris W.T. [State Key Laboratory in Marine Pollution, Department of Biology and Chemistry, City University of Hong Kong, Kowloon, Hong Kong Special Administrative Region (Hong Kong); Qian, Pei-Yuan, E-mail: boqianpy@ust.hk [Division of Life Science, Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong Special Administrative Region (Hong Kong)

    2014-04-01

    Highlights: • Adverse effects of antifouling compound butenolide were studied using marine medaka. • The active ingredient in SeaNine 211, DCOIT, was employed as positive control. • Butenolide induced transient, reversible biological effects on marine medaka. • Lower toxicity of butenolide on marine biota highlights its promising application. • The increased sensitivity of male medaka addresses the gender difference. - Abstract: This study evaluated the potential adverse effects of butenolide, a promising antifouling compound, using the marine medaka (Oryzias melastigma), a model fish for marine ecotoxicology. The active ingredient used in the commercial antifoulant SeaNine 211, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) was employed as the positive control. Adult marine medaka (4-month-old) were exposed to various concentrations of butenolide or DCOIT for 28 days and then depurated in clean seawater for 14 days (recovery). A suite of sensitive biomarkers, including hepatic oxidative stress, neuronal signal transmission, endocrine disruption, and reproductive function, was used to measure significant biological effects induced by the chemicals. Compared to DCOIT, chronic exposure to butenolide induced a lower extent of oxidative stress in the liver of male and female medaka. Furthermore, butenolide-exposed fish could recover faster from oxidative stress than fish exposed to DCOIT. Regarding neurotransmission, DCOIT significantly inhibited acetylcholinesterase (AChE) activity in the brain of both male and female medaka, whereas this was not significant for butenolide. In addition, plasma estradiol (E{sub 2}) level was elevated and testosterone (T) level was decreased in male medaka exposed to DCOIT. This greatly imbalanced sex hormones ratio (E{sub 2}/T) in exposed males, indicating that DCOIT is a potent endocrine disruptive chemical. In contrast, butenolide induced only moderate effects on sex hormone levels in exposed males, which could be

  18. Comparative safety of the antifouling compound butenolide and 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) to the marine medaka (Oryzias melastigma)

    International Nuclear Information System (INIS)

    Chen, Lianguo; Ye, Rui; Xu, Ying; Gao, Zhaoming; Au, Doris W.T.; Qian, Pei-Yuan

    2014-01-01

    Highlights: • Adverse effects of antifouling compound butenolide were studied using marine medaka. • The active ingredient in SeaNine 211, DCOIT, was employed as positive control. • Butenolide induced transient, reversible biological effects on marine medaka. • Lower toxicity of butenolide on marine biota highlights its promising application. • The increased sensitivity of male medaka addresses the gender difference. - Abstract: This study evaluated the potential adverse effects of butenolide, a promising antifouling compound, using the marine medaka (Oryzias melastigma), a model fish for marine ecotoxicology. The active ingredient used in the commercial antifoulant SeaNine 211, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) was employed as the positive control. Adult marine medaka (4-month-old) were exposed to various concentrations of butenolide or DCOIT for 28 days and then depurated in clean seawater for 14 days (recovery). A suite of sensitive biomarkers, including hepatic oxidative stress, neuronal signal transmission, endocrine disruption, and reproductive function, was used to measure significant biological effects induced by the chemicals. Compared to DCOIT, chronic exposure to butenolide induced a lower extent of oxidative stress in the liver of male and female medaka. Furthermore, butenolide-exposed fish could recover faster from oxidative stress than fish exposed to DCOIT. Regarding neurotransmission, DCOIT significantly inhibited acetylcholinesterase (AChE) activity in the brain of both male and female medaka, whereas this was not significant for butenolide. In addition, plasma estradiol (E 2 ) level was elevated and testosterone (T) level was decreased in male medaka exposed to DCOIT. This greatly imbalanced sex hormones ratio (E 2 /T) in exposed males, indicating that DCOIT is a potent endocrine disruptive chemical. In contrast, butenolide induced only moderate effects on sex hormone levels in exposed males, which could be gradually

  19. Comparative safety of the antifouling compound butenolide and 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) to the marine medaka (Oryzias melastigma)

    KAUST Repository

    Chen, Lianguo

    2014-04-01

    This study evaluated the potential adverse effects of butenolide, a promising antifouling compound, using the marine medaka (Oryzias melastigma), a model fish for marine ecotoxicology. The active ingredient used in the commercial antifoulant SeaNine 211, 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOIT) was employed as the positive control. Adult marine medaka (4-month-old) were exposed to various concentrations of butenolide or DCOIT for 28 days and then depurated in clean seawater for 14 days (recovery). A suite of sensitive biomarkers, including hepatic oxidative stress, neuronal signal transmission, endocrine disruption, and reproductive function, was used to measure significant biological effects induced by the chemicals. Compared to DCOIT, chronic exposure to butenolide induced a lower extent of oxidative stress in the liver of male and female medaka. Furthermore, butenolide-exposed fish could recover faster from oxidative stress than fish exposed to DCOIT. Regarding neurotransmission, DCOIT significantly inhibited acetylcholinesterase (AChE) activity in the brain of both male and female medaka, whereas this was not significant for butenolide. In addition, plasma estradiol (E2) level was elevated and testosterone (T) level was decreased in male medaka exposed to DCOIT. This greatly imbalanced sex hormones ratio (E2/T) in exposed males, indicating that DCOIT is a potent endocrine disruptive chemical. In contrast, butenolide induced only moderate effects on sex hormone levels in exposed males, which could be gradually recovered during depuration. Moreover, the endocrine disruptive effect induced by butenolide did not affect normal development of offspring. In contrast, DCOIT-exposed fish exhibited a decrease of egg production and impaired reproductive success. Overall, the above findings demonstrated that chronic exposure to butenolide induced transient, reversible biological effect on marine medaka, while DCOIT could impair reproductive success of fish, as

  20. Effects of pre- and postnatal exposure to the UV-filter octyl methoxycinnamate (OMC) on the reproductive, auditory and neurological development of rat offspring.

    Science.gov (United States)

    Axelstad, Marta; Boberg, Julie; Hougaard, Karin Sørig; Christiansen, Sofie; Jacobsen, Pernille Rosenskjold; Mandrup, Karen Riiber; Nellemann, Christine; Lund, Søren Peter; Hass, Ulla

    2011-02-01

    Octyl Methoxycinnamate (OMC) is a frequently used UV-filter in sunscreens and other cosmetics. The aim of the present study was to address the potential endocrine disrupting properties of OMC, and to investigate how OMC induced changes in thyroid hormone levels would be related to the neurological development of treated offspring. Groups of 14-18 pregnant Wistar rats were dosed with 0, 500, 750 or 1000 mg OMC/kg bw/day during gestation and lactation. Serum thyroxine (T(4)), testosterone, estradiol and progesterone levels were measured in dams and offspring. Anogenital distance, nipple retention, postnatal growth and timing of sexual maturation were assessed. On postnatal day 16, gene expression in prostate and testes, and weight and histopathology of the thyroid gland, liver, adrenals, prostate, testes, epididymis and ovaries were measured. After weaning, offspring were evaluated in a battery of behavioral and neurophysiological tests, including tests of activity, startle response, cognitive and auditory function. In adult animals, reproductive organ weights and semen quality were investigated. Thyroxine (T(4)) levels showed a very marked decrease during the dosing period in all dosed dams, but were less severely affected in the offspring. On postnatal day 16, high dose male offspring showed reduced relative prostate and testis weights, and a dose-dependent decrease in testosterone levels. In OMC exposed female offspring, motor activity levels were decreased, while low and high dose males showed improved spatial learning abilities. The observed behavioral changes were probably not mediated solely by early T(4) deficiencies, as the observed effects differed from those seen in other studies of developmental hypothyroxinemia. At eight months of age, sperm counts were reduced in all three OMC-dosed groups, and prostate weights were reduced in the highest dose group. Taken together, these results indicate that perinatal OMC-exposure can affect both the reproductive and

  1. Effects of pre- and postnatal exposure to the UV-filter Octyl Methoxycinnamate (OMC) on the reproductive, auditory and neurological development of rat offspring

    International Nuclear Information System (INIS)

    Axelstad, Marta; Boberg, Julie; Hougaard, Karin Sorig; Christiansen, Sofie; Jacobsen, Pernille Rosenskjold; Mandrup, Karen Riiber; Nellemann, Christine; Lund, Soren Peter; Hass, Ulla

    2011-01-01

    Octyl Methoxycinnamate (OMC) is a frequently used UV-filter in sunscreens and other cosmetics. The aim of the present study was to address the potential endocrine disrupting properties of OMC, and to investigate how OMC induced changes in thyroid hormone levels would be related to the neurological development of treated offspring. Groups of 14-18 pregnant Wistar rats were dosed with 0, 500, 750 or 1000 mg OMC/kg bw/day during gestation and lactation. Serum thyroxine (T 4 ), testosterone, estradiol and progesterone levels were measured in dams and offspring. Anogenital distance, nipple retention, postnatal growth and timing of sexual maturation were assessed. On postnatal day 16, gene expression in prostate and testes, and weight and histopathology of the thyroid gland, liver, adrenals, prostate, testes, epididymis and ovaries were measured. After weaning, offspring were evaluated in a battery of behavioral and neurophysiological tests, including tests of activity, startle response, cognitive and auditory function. In adult animals, reproductive organ weights and semen quality were investigated. Thyroxine (T 4 ) levels showed a very marked decrease during the dosing period in all dosed dams, but were less severely affected in the offspring. On postnatal day 16, high dose male offspring showed reduced relative prostate and testis weights, and a dose-dependent decrease in testosterone levels. In OMC exposed female offspring, motor activity levels were decreased, while low and high dose males showed improved spatial learning abilities. The observed behavioral changes were probably not mediated solely by early T 4 deficiencies, as the observed effects differed from those seen in other studies of developmental hypothyroxinemia. At eight months of age, sperm counts were reduced in all three OMC-dosed groups, and prostate weights were reduced in the highest dose group. Taken together, these results indicate that perinatal OMC-exposure can affect both the reproductive and

  2. Evaluating the use of PAO (4 cSt polyalphaoelfin) oil instead of DOP (di-octyl phthalate) oil for measuring the aerosol capture of nuclear canister filters

    Energy Technology Data Exchange (ETDEWEB)

    Moore, Murray E. [Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

    2014-07-18

    This document details the distinction between using PAO (4 cSt polyalphaoelfin) oil instead of DOP (di-octyl phthalate) oil for measuring the aerosol capture of filters. This document is developed to justify the use of PAO rather than DOP for evaluating the performance of filters in the SAVY 4000 and Hagan containers. The design criteria (Anderson et al, 2012) for purchasing SAVY 4000 containers and the Safety Analysis Report for the SAVY 4000 Container Series specified that the filter must “capture greater than 99.97% of 0.45 μm mean diameter dioctyl phthalate (DOP) aerosol at the rated flow with a DOP concentration of 65±15 micrograms per liter.”This corresponds to a leakage percent of 0.03% (3.0x10-2). The density of DOP oil is 985 kg/m3 and the density of PAO oil is 819 kg/m3. ATI Test Inc measured the mass mean diameter of aerosol distributions produced by a single Laskin type III-A nozzle operating at a 20 psig air pressure as 0.563 μm for DOP oil and 0.549 μm for PAO oil. (See Appendix A.) For both types of oil in this document, the single fiber method calculated the leakage percent to be 4.4x10-5 for DOP oil and 4.7x10-5 for PAO oil. Although the percent error between these two quantities is 7.7%, these calculated leakage percent values are more than two orders of magnitude less than the criterion specified in the SAVY canister SAR. As a point of reference, the photometer used to measure the SAVY canister filter performance cannot resolve values for the leakage percent below 1.0x10-5. Additionally, over a range of particle sizes from 0.01 μm to 3.0 μm, there was less than 4.0x10-5 error between the calculated filter efficiency for the two types of oil at any particular particle size diameter. In conclusion, the difference between using DOP and PAO for testing SAVY canister filters is of inconsequential concern.

  3. Synergistic activation of protein kinase Calpha, -betaI, and -gamma isoforms induced by diacylglycerol and phorbol ester: roles of membrane association and activating conformational changes.

    Science.gov (United States)

    Slater, S J; Milano, S K; Stagliano, B A; Gergich, K J; Ho, C; Mazurek, A; Taddeo, F J; Kelly, M B; Yeager, M D; Stubbs, C D

    1999-03-23

    Protein kinase Calpha (PKCalpha) has been shown to contain two discrete activator sites with differing binding affinities for phorbol esters and diacylglycerols. The interaction of diacylglycerol with a low-affinity phorbol ester binding site leads to enhanced high-affinity phorbol ester binding and to a potentiated level of activity [Slater, S. J., Ho, C., Kelly, M. B., Larkin, J. D. , Taddeo, F. J., Yeager, M. D., and Stubbs, C. D. (1996) J. Biol. Chem. 271, 4627-4631]. In this study, the mechanism of this enhancement of activity was examined with respect to the Ca2+ dependences of membrane association and accompanying conformational changes that lead to activation. The association of PKCalpha with membranes containing 12-O-tetradecanoylphorbol 13-acetate (TPA) or 1, 2-dioleoylglycerol (DAG), determined from tryptophan to dansyl-PE resonance energy transfer (RET) measurements, was found to occur at relatively low Ca2+ levels (tryptophan fluorescence anisotropy. Coaddition of DAG and TPA resulted in a reduction in the Ca2+ levels required for both the conformational change and enzyme activation. Also, it was found that incubation of the enzyme with TPA alone resulted in a time-dependent increase in the Ca2+-independent PKCalpha activity, the rate and extent of which was further enhanced upon coaddition with DAG. Tauhe results suggest that the enhanced level of activity induced by coaddition of DAG and TPA involves both Ca2+-dependent and Ca2+-independent activating conformational changes which result in active conformers of PKCalpha distinct

  4. Microbiota control of a tryptophan-AhR pathway in disease tolerance to fungi.

    Science.gov (United States)

    Romani, Luigina; Zelante, Teresa; De Luca, Antonella; Iannitti, Rossana G; Moretti, Silvia; Bartoli, Andrea; Aversa, Franco; Puccetti, Paolo

    2014-11-01

    An increased understanding of the importance of microbiota in shaping the host's immune and metabolic activities has rendered fungal interactions with their hosts more complex than previously appreciated. The aryl hydrocarbon receptor (AhR) has a pivotal role in connecting tryptophan catabolism by microbial communities and the host's own pathway of tryptophan metabolite production with the orchestration of T-cell function. AhR activation by a Lactobacillus-derived AhR ligand leads to the production of IL-22 to the benefit of mucosal defense mechanisms, an activity upregulated in the absence of the host tryptophan catabolic enzyme, indoleamine 2,3-dioxygenase 1 (IDO1), which is required for protection from fungal diseases ("disease tolerance"). As AhR activation in turn leads to the activation-in a feedback fashion-of IDO1, the regulatory loop involving AhR and IDO1 may have driven the coevolution of commensal fungi with the mammalian immune system and the microbiota, to the benefit of host survival and fungal commensalism. This review will discuss the essential help the microbiota provides in controlling the balance between the dual nature of the fungal-host relationship, namely, commensalism vs. infection. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  5. The Potential Role of Cannabinoids in Modulating Serotonergic Signaling by Their Influence on Tryptophan Metabolism

    Directory of Open Access Journals (Sweden)

    Dietmar Fuchs

    2010-08-01

    Full Text Available Phytocannabinoids present in Cannabis plants are well known to exert potent anti-inflammatory and immunomodulatory effects. Previously, we have demonstrated that the psychoactive D9-tetrahydrocannabinol (THC and the non-psychotropic cannabidiol (CBD modulate mitogen-induced Th1-type immune responses in peripheral blood mononuclear cells (PBMC. The suppressive effect of both cannabinoids on mitogen-induced tryptophan degradation mediated by indoleamine-2,3-dioxygenase (IDO, suggests an additional mechanism by which antidepressive effects of cannabinoids might be linked to the serotonergic system. Here, we will review the role of tryptophan metabolism in the course of cell mediated immune responses and the relevance of cannabinoids in serotonergic signaling. We conclude that in particular the non-psychotropic CBD might be useful for the treatment of mood disorders in patients with inflammatory diseases, since this cannabinoid seems to be safe and its effects on activation-induced tryptophan degradation by CBD were more potent as compared to THC.

  6. Tryptophan PET Imaging of the Kynurenine Pathway in Patient-Derived Xenograft Models of Glioblastoma.

    Science.gov (United States)

    Guastella, Anthony R; Michelhaugh, Sharon K; Klinger, Neil V; Kupsky, William J; Polin, Lisa A; Muzik, Otto; Juhász, Csaba; Mittal, Sandeep

    2016-01-01

    Increasing evidence demonstrates the immunosuppressive kynurenine pathway's (KP) role in the pathophysiology of human gliomas. To study the KP in vivo, we used the noninvasive molecular imaging tracer α-[(11)C]-methyl-l-tryptophan (AMT). The AMT-positron emission tomography (PET) has shown high uptake in high-grade gliomas and predicted survival in patients with recurrent glioblastoma (GBM). We generated patient-derived xenograft (PDX) models from dissociated cells, or tumor fragments, from 5 patients with GBM. Mice bearing subcutaneous tumors were imaged with AMT-PET, and tumors were analyzed to detect the KP enzymes indoleamine 2,3-dioxygenase (IDO) 1, IDO2, tryptophan 2,3-dioxygenase, kynureninase, and kynurenine 3-monooxygenase. Overall, PET imaging showed robust tumoral AMT uptake in PDX mice with prolonged tracer accumulation over 60 minutes, consistent with AMT trapping seen in humans. Immunostained tumor tissues demonstrated positive detection of multiple KP enzymes. Furthermore, intracranial implantation of GBM cells was performed with imaging at both 9 and 14 days postimplant, with a marked increase in AMT uptake at 14 days and a corresponding high level of tissue immunostaining for KP enzymes. These results indicate that our PDX mouse models recapitulate human GBM, including aberrant tryptophan metabolism, and offer an in vivo system for development of targeted therapeutics for patients with GBM. © The Author(s) 2016.

  7. Candida glabrata tryptophan-based pigment production via the Ehrlich pathway.

    Science.gov (United States)

    Brunke, Sascha; Seider, Katja; Almeida, Ricardo Sergio; Heyken, Antje; Fleck, Christian Benjamin; Brock, Matthias; Barz, Dagmar; Rupp, Steffen; Hube, Bernhard

    2010-04-01

    Pigments contribute to the pathogenicity of many fungi, mainly by protecting fungal cells from host defence activities. Here, we have dissected the biosynthetic pathway of a tryptophan-derived pigment of the human pathogen Candida glabrata, identified key genes involved in pigment production and have begun to elucidate the possible biological function of the pigment. Using transcriptional analyses and a transposon insertion library, we have identified genes associated with pigment production. Targeted deletion mutants revealed that the pigment is a by-product of the Ehrlich pathway of tryptophan degradation: a mutant lacking a tryptophan-upregulated aromatic aminotransferase (Aro8) displayed significantly reduced pigmentation and a recombinantly expressed version of this protein was sufficient for pigment production in vitro. Pigment production is tightly regulated as the synthesis is affected by the presence of alternative nitrogen sources, carbon sources, cyclic AMP and oxygen. Growth of C. glabrata on pigment inducing medium leads to an increased resistance to hydrogen peroxide, an effect which was not observed with a mutant defective in pigmentation. Furthermore, pigmented yeast cells had a higher survival rate when exposed to human neutrophils and caused increased damage in a monolayer model of human epithelia, indicating a possible role of pigmentation during interactions with host cells.

  8. Effect of sodium saccharin and L-tryptophan on rat urine during bladder carcinogenesis.

    Science.gov (United States)

    Demers, D M; Fukushima, S; Cohen, S M

    1981-01-01

    We examined several parameters of urine excretion during a two-year initiation-promotion experiment in male Fischer rats using four weeks of N-[4-(5-nitro-2-furyl)-2-thiazoly]formamide at 0.2% of the diet as the initiating agent and either 5% sodium saccharin or 2% L-tryptophan in the diet as promoting agents. Rats fed sodium saccharin increased their intake of water; this was accompanied by diarrhea and an increased urinary volume. Osmolality was decreased slightly. The total amount of sodium excreted was increased, although the concentration in the urine was similar to that of the controls or slightly increased. No abnormalities were observed in urinary potassium, calcium, urea, or other parameters measured except for the pH, which was slightly increased during the first three months of the experiment. There was no increase in the size or concentration of crystals in the urine of rats fed sodium saccharin, and no calculi were observed. Hypoglycemia and hypoglycosuria were present in sodium saccharin-fed rats and to a lesser extent in L-tryptophan-fed rats. No other abnormalities were seen in the urine of rats fed L-tryptophan. These data suggest that none of the urinary factors measured in our experiment, including crystal and calculus formation, correlated with the induction of urinary bladder lesions by sodium saccharin.

  9. PROCESS FOR HYDROGENOLYSIS OF ALPHA-HYDROXY ESTERS OR ACIDS USING A HETEROGENEOUS CATALYST

    DEFF Research Database (Denmark)

    2017-01-01

    The present invention relates to a method for hydrogenolysis of alpha-hydroxy esters or acids, comprising reacting the alpha-hydroxy ester or acid in the presence of a heterogeneous catalyst. The present invention also relates to a method for producing propionic acid ester, and the use of any...... of the methods for the production of propionic acid esters, such as alkyl propionate....

  10. Complex formation of technetium with the methyl esters of MAG2 and MAG1

    International Nuclear Information System (INIS)

    Noll, B.; Noll, S.; Grosse, B.; Johannsen, B.; Spies, H.

    1993-01-01

    Mercaptoacetylglycine methyl ester (MAG 2 ester) and mercaptoacetyldiglycine methyl ester (MAG 1 ester) were included to investigate complex formation of SH/amide ligands with technetium. The studies are aimed at finding out how blocking the carboxylic groups influences the complexation reaction, with a view to finding an approach to new lipophilic species. (orig./BBR)

  11. 21 CFR 172.852 - Glyceryl-lacto esters of fatty acids.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Glyceryl-lacto esters of fatty acids. 172.852... HUMAN CONSUMPTION Multipurpose Additives § 172.852 Glyceryl-lacto esters of fatty acids. Glyceryl-lacto esters of fatty acids (the lactic acid esters of mono- and diglycerides) may be safely used in food in...

  12. Chemoenzymatic Synthesis and Chemical Recycling of Poly(ester-urethanes

    Directory of Open Access Journals (Sweden)

    Hiroto Hayashi

    2011-08-01

    Full Text Available Novel poly(ester-urethanes were prepared by a synthetic route using a lipase that avoids the use of hazardous diisocyanate. The urethane linkage was formed by the reaction of phenyl carbonate with amino acids and amino alcohols that produced urethane-containing diacids and hydroxy acids, respectively. The urethane diacid underwent polymerization with polyethylene glycol and a,w-alkanediols and also the urethane-containing hydroxy acid monomer was polymerized by the lipase to produce high-molecular-weight poly(ester-urethanes. The periodic introduction of ester linkages into the polyurethane chain by the lipase-catalyzed polymerization afforded chemically recyclable points. They were readily depolymerized in the presence of lipase into cyclic oligomers, which were readily repolymerized in the presence of the same enzyme. Due to the symmetrical structure of the polymers, poly(ester-urethanes synthesized in this study showed higher Tm, Young’s modulus and tensile strength values.

  13. Space-Qualifiable Cyanate Ester Elastomer, Phase I

    Data.gov (United States)

    National Aeronautics and Space Administration — Cornerstone Research Group, Inc. (CRG) proposes to design and develop a space-qualifiable cyanate ester elastomer for application in self-deployable space structures...

  14. Biocatalytic synthesis and antioxidant capacities of ascorbyl esters ...

    African Journals Online (AJOL)

    ajl yemi

    2011-11-28

    , 2009). Lipases, especially that from Candida antarctica, have been successfully used to catalyze the synthesis of ascorbyl esters in tertiary alcohols, acetone and even in ionic liquids, employing saturated and unsaturated ...

  15. [Exposure to vegetal esters based metal cutting fluids: health effects].

    Science.gov (United States)

    Riva, M M; Bellini, M; Leghissa, P; Gambini, D; Mosconi, G

    2012-01-01

    The aim of our research is to study respiratory and dermatologic diseases (irritative and allergic) in a cohort of workers exposed to vegetal esters based metal cutting fluids of the latest generation. A cohort of 81 workers (mean age 34.5 years, seniority 17.4 years), with mean exposure to vegetal esters based metal cutting fluids of 2.8 years, has been subjected to clinical evaluations. The investigation did not reveal any disease or disorder of the respiratory system, any folluculitis or any allergic contact dermatitis caused by sensitization to vegetal esters based metal cutting fluids. On the contrary we documented 5 cases of irritant contact dermatitis, even if favored by an improper use of protection devices. According to early results, the introduction of vegetal esters based metal cutting fluids seems to reduce the risk to the worker's health. A longitudinal surveillance is still needed to confirm that even in the medium and long-term sensitizations will not occur.

  16. Diterpene esters of aristolochic acids from Aristolochia pubescens.

    Science.gov (United States)

    Nascimento, Isabele R; Lopes, Lucia M X

    2003-08-01

    From the acetone and ethanol extracts of the tubercula of Aristolochia pubescens, two diterpene esters of aristolochic acids were isolated, together with 23 known compounds. The structures of the compounds were determined on the basis of spectroscopic analysis.

  17. Space-Qualifiable Cyanate Ester Elastomer, Phase II

    Data.gov (United States)

    National Aeronautics and Space Administration — In Phase 1, CRG demonstrated the feasibility of a novel approach to prepare cyanate ester based elastomers. This approach polymerizes in-situ siloxane within a...

  18. Incorporation of Epicatechin Esters into Lignin Enhances Cell Wall Fermentability

    Science.gov (United States)

    Polyphenolic catechin esters are potentially attractive targets for lignin bioengineering because their copolymerization with monolignols could reduce lignin hydrophobicity and cross-linking to polysaccharides, or facilitate delignification by biomass pretreatments. To test this hypothesis, we biomi...

  19. Baker's yeast: production of D- and L-3-hydroxy esters

    DEFF Research Database (Denmark)

    Dahl, Allan Carsten; Madsen, Jørgen Øgaard

    1998-01-01

    Baker's yeast grown under oxygen limited conditions and used in the reduction of 3-oxo esters results in a shift of the stereoselectivity of the yeast towards D-hydroxy esters as compared with ordinary baker's yeast. The highest degree of stereoselectivity was obtained with growing yeast or yeast...... harvested while growing. In contrast, the stereoselectivity was shifted towards L-hydroxy esters when the oxo esters were added slowly to ordinary baker's yeast supplied with gluconolactone as co-substrate. The reduction rate with gluconolactone was increased by active aeration. Ethyl L-(S)-3......-hydroxybutanoate was afforded in >99% ee. Both enantiomers of ethyl 3-hydroxypentanoate, D-(R) in 96% ee and L-(S) in 93% ee, and of ethyl 4-chloro-3-hydroxybutanoate, D-(S) in 98% ee and L-(R) in 94% ee, were obtained. The results demonstrate that the stereoselectivity of baker's yeast can be controlled...

  20. Combustion characteristics of the mustard methyl esters

    International Nuclear Information System (INIS)

    Bannikov, M.G.; Vasilev, I.P.

    2011-01-01

    Mustard Methyl Esters (further bio diesel) and regular diesel fuel were tested in direct injection diesel engine. Analysis of experimental data was supported by an analysis of fuel injection and combustion characteristics. Engine fuelled with bio diesel had increased brake specific fuel consumption, reduced nitrogen oxides emission and smoke opacity, moderate increase in carbon monoxide emission with essentially unchanged unburned hydrocarbons emission. Increase in fuel consumption was attributed to lesser heating value of bio diesel and partially to decreased fuel conversion efficiency. Analysis of combustion characteristics revealed earlier start of injection and shorter ignition delay period of bio diesel. Resulting decrease in maximum rate of heat release and cylinder pressure was the most probable reason for reduced emission of nitrogen oxides. Analysis of combustion characteristics also showed that cetane index determined by ASTM Method D976 is not a proper measure of ignition quality of bio diesel. Conclusion was made on applicability of mustard oil as a source for commercial production of bio diesel in Pakistan. Potentialities of on improving combustion and emissions characteristics of diesel engine by reformulating bio diesel were discussed. (author)

  1. Sulfur deactivation of fatty ester hydrogenolysis catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Brands, D.S.; U-A-Sai, G.; Poels, E.K.; Bliek, A. [Univ. of Amsterdam (Netherlands). Dept. of Chemical Engineering

    1999-08-15

    Trace organosulfur compounds present as natural impurities in oleochemical feedstocks may lead to activation of copper-containing catalysts applied for hydrogenolysis of esters toward fatty alcohols. In this paper, the sulfur deactivation of Cu/SiO{sub 2} and Cu/ZnO/SiO{sub 2} catalysts was studied in the liquid-phase hydrogenolysis of methyl palmitate. The rate of deactivation is fast and increases as a function of the sulfur-containing compound present: octadecanethiol {approx} dihexadecyl disulfide < benzyl isothiocyanate < methyl p-toluene sulfonate < dihexadecyl sulfide < dibenzothiophene. The rapid deactivation is caused by the fact that sulfur is quantitatively removed from the reaction mixture and because mainly surface sulfides are formed under hydrogenolysis conditions. The life time of a zinc-promoted catalyst is up to two times higher than that of the Cu/SiO{sub 2} catalyst, most likely due to zinc surface sulfide formation. The maximum sulfur coverage obtained after full catalyst deactivation with dibenzothiophene and dihexadecyl sulfide--the sulfur compounds that cause the fastest deactivation--may be as low as 0.07. This is due to the fact that decomposition of these compounds as well as the hydrogenolysis reaction itself proceeds on ensembles of copper atoms. Catalyst regeneration studies reveal that activity cannot be regained by reduction or combined oxidation/reduction treatments. XRD, TPR, and TPO results confirm that no distinct bulk copper or zinc sulfide or sulfate phases are present.

  2. Solid state crystallisation of oligosaccharide ester derivatives

    CERN Document Server

    Wright, E A

    2002-01-01

    An investigation of the solid state properties of oligosaccharide ester derivatives (OEDs) with potential applications in drug delivery has been carried out. The amorphous form of two OEDs, trehalose octa-acetate (TOAC) and 6:6'-di-(beta-tetraacetyl glucuronyl)-hexaacetyl trehalose (TR153), was investigated as a matrix for the sustained release of active ingredients. The matrices showed a tendency to crystallise and so polymorph screens were performed to provide crystalline samples for structural analysis. The crystal structures of TOAC methanolate and TR153 acetonitrile solvate have been determined by single-crystal laboratory X-ray diffraction. TOAC methanolate crystallises in the orthorhombic space group P2 sub 1 2 sub 1 2 sub 1 with a = 15.429(18) A, b = 17.934(19) A and c = 13.518(4) A at 123 K. The structure is isomorphous with the previously reported structure of TOAC monohydrate form II. TR153 acetonitrile solvate crystallises in the monoclinic spacegroup C2 with a = 30:160(6) A, b = 11.878(3) A, c 20...

  3. How Well Does BODIPY-Cholesteryl Ester Mimic Unlabeled Cholesteryl Esters in High Density Lipoprotein Particles?

    DEFF Research Database (Denmark)

    Karilainen, Topi; Vuorela, Timo; Vattulainen, Ilpo

    2015-01-01

    We compare the behavior of unlabeled and BODIPY-labeled cholesteryl ester (CE) in high density lipoprotein by atomistic molecular dynamics simulations. We find through replica exchange umbrella sampling and unbiased molecular dynamics simulations that BODIPY labeling has no significant effect...... on the partitioning of CE between HDL and the water phase. However, BODIPY-CE was observed to diffuse more slowly and locate itself closer to the HDL-water interface than CE due to the BODIPY probe that is constrained to the surface region, and because the CE body in BODIPY-CE prefers to align itself away from...

  4. Methods of refining and producing dibasic esters and acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E.; Cohen, Steven A.; Gildon, Demond L.

    2016-03-15

    Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

  5. Methods of refining and producing dibasic esters and acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E; Cohen, Steven A; Gildon, Demond L

    2015-04-07

    Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.

  6. Natural fiber reinforced composites with moringa and vnyl ester matrix

    OpenAIRE

    Sundara, Babu Jagannathan

    2015-01-01

    In this research work an attempt is carried out for producing a Natural Plant Based fiber Reinforced Composites using the Moringa Resins and Vinyl Ester by utilizing the wastage of natural plant based fiber as Reinforcement material and Matrix material as Natural Resin and Vinyl Ester. The objective of the work is Utilization of Natural Plant Based Bio- degardable wastage into an alternative materials in the industrial applications by analyzing, Various Manufacturing and testing. Initially th...

  7. RAFT Polymerization of Vinyl Esters: Synthesis and Applications

    OpenAIRE

    Simon Harrisson; Xuan Liu; Jean-Noël Ollagnier; Olivier Coutelier; Jean-Daniel Marty; Mathias Destarac

    2014-01-01

    This article is the first comprehensive review on the study and use of vinyl ester monomers in reversible addition fragmentation chain transfer (RAFT) polymerization. It covers all the synthetic aspects associated with the definition of precision polymers comprising poly(vinyl ester) building blocks, such as the choice of RAFT agent and reaction conditions in order to progress from simple to complex macromolecular architectures. Although vinyl acetate was by far the most studied monomer of th...

  8. The enantioselective b-keto ester reductions by Saccharomyces cerevisiae

    Directory of Open Access Journals (Sweden)

    HASSAN TAJIK

    2006-09-01

    Full Text Available The enantioselective yeast reduction of aromatic b-keto esters, by use of potassium dihydrogen phosphate, calcium phosphate (monobasic, magnesium sulfate and ammonium tartrate (diammonium salt (10:1:1:50 in water at pH 7 as a buffer for 72–120 h with 45–90 % conversion to the corresponding aromatic -hydroxy esters was achieved by means of Saccharomyces cerevisiae.

  9. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks

    Energy Technology Data Exchange (ETDEWEB)

    Snead, Thomas E.; Cohen, Steven A.; Gildon, Demond L.; Beltran, Leslie V.; Kunz, Linda A.; Pals, Tessa M.; Quinn, Jordan R; Behrends, Jr., Raymond T.; Bernhardt, Randal J.

    2016-07-05

    Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.

  10. [Effect of pps and aroGfbr overexpression on L-tryptophan production in Corynebacterium pekinense].

    Science.gov (United States)

    Zang, Chuangang; Zhao, Zhi; Wang, Yu; Zhang, Yingzi; Ding, Jiuyuan

    2014-01-04

    In order to redirect carbon flows into aromatic amino acids biosynthesis pathway and further improve the production of L-tryptophan in Corynebacterium pekinense PD-67, two schemes were implemented. First, the supply of phosphoenolpyruvate (PEP), one of precursors of L-tryptophan biosynthesis, was increased. Second, the feedback inhibition of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase (DS), a key enzyme in the aromatic amino acids biosynthesis, was relieved and the activity of DS was increased. The phosphoenolpyruvate synthase gene (pps) was cloned from C. pekinense PD-67 chromosome by PCR and inserted into expression vector to construct a recombinant plasmid pXPPS; the aroG gene encoding DS isozymes was cloned from Escherichia coli chromosome by PCR and the mutation of Leu175Asp was introduced by site-directed mutagenesis using sequence-overlap extension PCR. The mutated gene named as aroGfbr was cloned to expression vector to construct a recombinant plasmid pXA; and the recombinant plasmid pXAPS co-expressing pps and aroGfbr was constructed. The three recombinant plasmids were transformed into PD-67 to generate the engineering strains PD-67/pXPS, PD-67/pXA and PD-67/pXAPS, respectively. The fermentation characteristics of the three engineering strains were investigated. The expression of pps and aroGfbr was confirmed by enzyme activity assays. The deregulation of feedback inhibition of AroGfbr was confirmed by determining DS activity in the presence of three aromatic amino acids. The overexpression of pps and aroGfbr resulted in an increase of L-tryptophan biosynthesis by 12.1% and 26.8%, respectively, while the co-expression of two genes increased the production of L-tryptophan by 35.9% in the engineering strain PD-67/pXAPS. Both of the overexpressions of the pps gene and aroGfbr gene can increase L-tryptophan biosynthesis, while the production was further improved by the co-expression of the two genes.

  11. Nutritional Stress Induced by Tryptophan-Degrading Enzymes Results in ATF4-Dependent Reprogramming of the Amino Acid Transporter Profile in Tumor Cells.

    Science.gov (United States)

    Timosenko, Elina; Ghadbane, Hemza; Silk, Jonathan D; Shepherd, Dawn; Gileadi, Uzi; Howson, Lauren J; Laynes, Robert; Zhao, Qi; Strausberg, Robert L; Olsen, Lars R; Taylor, Stephen; Buffa, Francesca M; Boyd, Richard; Cerundolo, Vincenzo

    2016-11-01

    Tryptophan degradation is an immune escape strategy shared by many tumors. However, cancer cells' compensatory mechanisms remain unclear. We demonstrate here that a shortage of tryptophan caused by expression of indoleamine 2,3-dioxygenase (IDO) and tryptophan 2,3-dioxygenase (TDO) resulted in ATF4-dependent upregulation of several amino acid transporters, including SLC1A5 and its truncated isoforms, which in turn enhanced tryptophan and glutamine uptake. Importantly, SLC1A5 failed to be upregulated in resting human T cells kept under low tryptophan conditions but was enhanced upon cognate antigen T-cell receptor engagement. Our results highlight key differences in the ability of tumor and T cells to adapt to tryptophan starvation and provide important insights into the poor prognosis of tumors coexpressing IDO and SLC1A5. Cancer Res; 76(21); 6193-204. ©2016 AACR. ©2016 American Association for Cancer Research.

  12. Ester Tuiksoo võitleb viina puhtuse eest / Ester Tuiksoo ; interv. Silja Lättemäe

    Index Scriptorium Estoniae

    Tuiksoo, Ester, 1965-

    2006-01-01

    Põllumajandusminister Ester Tuiksoo lubab Euroopa Liidu piiritusjookide määruse eelnõu arutusel kaitsta seisukohta, et viinaks tuleb pidada üksnes teraviljast või kartulist valmistatud piiritusjooki

  13. ESTIMATION OF HYDROLYSIS RATE CONSTANTS OF CARBOXYLIC ACID ESTER AND PHOSPHATE ESTER COMPOUNDS IN AQUEOUS SYSTEMS FROM MOLECULAR STRUCTURE BY SPARC

    Science.gov (United States)

    SPARC (SPARC Performs Automated Reasoning in Chemistry) chemical reactivity models were extended to calculate hydrolysis rate constants for carboxylic acid ester and phosphate ester compounds in aqueous non- aqueous and systems strictly from molecular structure. The energy diffe...

  14. Neutral lipid biosynthesis in engineered Escherichia coli: jojoba oil-like wax esters and fatty acid butyl esters.

    Science.gov (United States)

    Kalscheuer, Rainer; Stöveken, Tim; Luftmann, Heinrich; Malkus, Ursula; Reichelt, Rudolf; Steinbüchel, Alexander

    2006-02-01

    Wax esters are esters of long-chain fatty acids and long-chain fatty alcohols which are of considerable commercial importance and are produced on a scale of 3 million tons per year. The oil from the jojoba plant (Simmondsia chinensis) is the main biological source of wax esters. Although it has a multitude of potential applications, the use of jojoba oil is restricted, due to its high price. In this study, we describe the establishment of heterologous wax ester biosynthesis in a recombinant Escherichia coli strain by coexpression of a fatty alcohol-producing bifunctional acyl-coenzyme A reductase from the jojoba plant and a bacterial wax ester synthase from Acinetobacter baylyi strain ADP1, catalyzing the esterification of fatty alcohols and coenzyme A thioesters of fatty acids. In the presence of oleate, jojoba oil-like wax esters such as palmityl oleate, palmityl palmitoleate, and oleyl oleate were produced, amounting to up to ca. 1% of the cellular dry weight. In addition to wax esters, fatty acid butyl esters were unexpectedly observed in the presence of oleate. The latter could be attributed to solvent residues of 1-butanol present in the medium component, Bacto tryptone. Neutral lipids produced in recombinant E. coli were accumulated as intracytoplasmic inclusions, demonstrating that the formation and structural integrity of bacterial lipid bodies do not require specific structural proteins. This is the first report on substantial biosynthesis and accumulation of neutral lipids in E. coli, which might open new perspectives for the biotechnological production of cheap jojoba oil equivalents from inexpensive resources employing recombinant microorganisms.

  15. Side-chain crystallization in alkyl-substituted cellulose esters and hydroxypropyl cellulose esters.

    Science.gov (United States)

    Chen, Xi; Zheng, Nan; Wang, Qiao; Liu, Lingzhi; Men, Yongfeng

    2017-04-15

    The differences in side chain crystallization behavior between cellulose esters (CEs) and hydroxypropyl cellulose esters (HPCEs) were systematically investigated by a combination of differential scanning calorimetry (DSC) and small and wide-angle X-ray scattering techniques. DSC investigation indicated that under the same side chain length, the fusion enthalpy and the number of crystallized CH 2 of CEs were smaller than HPCEs. At the same time, their d-spacing and molecular arrangements were also different from each other. For the CEs, the side chains are perpendicular to the main chain, while the side chains most probably tend to tilt to main chain in the HPCEs as was evidenced by X-ray scattering results. The phenomenon can be understood as a consequence of different flexibility of attachment bridges in both kinds of side chain polymers and the steric hindrance of methyl group in the hydroxypropyl group in HPCEs. In addition, the added hydroxypropyl substituents make the side chain length increasing. Copyright © 2017 Elsevier Ltd. All rights reserved.

  16. Extraction and Liquid Chromatography-Tandem Mass Spectrometry Detection of 3-Monochloropropanediol Esters and Glycidyl Esters in Infant Formula.

    Science.gov (United States)

    Leigh, Jessica K; MacMahon, Shaun

    2016-12-14

    A method was developed for the extraction of fatty acid esters of 3-chloro-1,2-propanediol (3-MCPD) and glycidol from infant formula, followed by quantitative analysis of the extracts using liquid chromatography-tandem mass spectrometry (LC-MS/MS). These process-induced chemical contaminants are found in refined vegetable oils, and studies have shown that they are potentially carcinogenic and/or genotoxic, making their presence in edible oils (and processed foods containing these oils) a potential health risk. The extraction procedure involves a liquid-liquid extraction, where powdered infant formula is dissolved in water and extracted with ethyl acetate. Following shaking, centrifugation, and drying of the organic phase, the resulting fat extract is cleaned-up using solid-phase extraction and analyzed by LC-MS/MS. Method performance was confirmed by verifying the percent recovery of each 3-MCPD and glycidyl ester in a homemade powdered infant formula reference material. Average ester recoveries in the reference material ranged from 84.9 to 109.0% (0.6-9.5% RSD). The method was also validated by fortifying three varieties of commercial infant formulas with a 3-MCPD and glycidyl ester solution. Average recoveries of the esters across all concentrations and varieties of infant formula ranged from 88.7 to 107.5% (1.0-9.5% RSD). Based on the validation results, this method is suitable for producing 3-MCPD and glycidyl ester occurrence data in all commercially available varieties of infant formula.

  17. Studies on novel interpenetrating networks of urethane modified poly(ester-amide and vinyl ester of bisphenol-C

    Directory of Open Access Journals (Sweden)

    Pragnesh N. Dave

    2016-05-01

    Full Text Available Bisphthalamic acids were prepared by reaction of maleic anhydride and aromatic diamines. Novel poly(ester-amides (PEAs were prepared by reaction of DGEBF with bisphthalamic acids. Acrylation of PEAs was carried out using acryloyl chloride; products are called acrylated poly(ester-amides (APEAs. Epoxy resin based unsaturated poly(ester-amide resins (UPEAs can be prepared by many methods but here these were prepared by reported method. These UPEAs were then treated with acryloyl chloride to afford acrylated UPEAs resin (i.e. AUPEAs. Interpenetrating networks of equal proportional urethane modified poly(ester-amide and acrylated poly(ester-amide and vinyl ester of biaphenol c (VE resin were prepared. Urethane modified APEAs and AUPEAs were characterized by elemental analysis, molecular weight was determined by vapor pressure osmometer and by IR spectral study and by thermogravimetry. Based on DSC data in situ glass reinforced composites of the resultant blends have been prepared and characterized for mechanical, electrical and chemical properties. Unreinforced blends were characterized by thermogravimetry (TGA.

  18. Dysbiosis of the Vaginal Microbiota and Higher Vaginal Kynurenine/Tryptophan Ratio Reveals an Association with Chlamydia trachomatis Genital Infections

    Directory of Open Access Journals (Sweden)

    Noa Ziklo

    2018-01-01

    Full Text Available The natural course of Chlamydia trachomatis urogenital tract infections varies between individuals. While protective immunity can occur, some women can become reinfected, contributing to the development of severe pathology. While the reasons for these differences are unknown, an individual's response to induced interferon-γ (IFN-γ is suggested to be critical. IFN-γ induction of the enzyme indoleamine 2,3-dioxygenase, which depletes tryptophan, may be the key. One hypothesis suggests that indole-producing bacteria in the vaginal microbiota can provide a substrate for the Chlamydia to synthesize tryptophan, rescuing the Chlamydia from host IFN-γ attack. We studied a cohort of 25 women who were either, Chlamydia negative, Chlamydia positive with a single infection, or Chlamydia positive with repeated infection, to test our hypothesis. We characterized their vaginal microbiota, cytokine response, as well as their tryptophan, kynurenine and indole concentrations directly in vaginal secretions. We found that C. trachomatis urogenital tract infections either initial or repeat infections, were associated with elevated vaginal kynurenine/tryptophan ratios, primarily as a result of elevated kynurenine levels. In addition, vaginal microbiota of community state type (CST IV showed significantly lower vaginal tryptophan levels compared to CST I and III, which might be related to a higher abundance of indole producers found within this group. Furthermore, we found a higher abundance of indole producers in women who cleared their Chlamydia infection post antibiotic treatment. This study demonstrates for the first time in vivo, the association between high vaginal kynurenine/tryptophan ratios and C. trachomatis infections. In addition, tryptophan depletion was associated with vaginal microbiota of CST IV.

  19. Tryptophan degradation in irritable bowel syndrome: evidence of indoleamine 2,3-dioxygenase activation in a male cohort

    Directory of Open Access Journals (Sweden)

    Cryan John F

    2009-01-01

    Full Text Available Abstract Background Irritable bowel syndrome (IBS is a common disorder that affects 10–15% of the population. Although characterised by a lack of reliable biological markers, the disease state is increasingly viewed as a disorder of the brain-gut axis. In particular, accumulating evidence points to the involvement of both the central and peripheral serotonergic systems in disease symptomatology. Furthermore, altered tryptophan metabolism and indoleamine 2,3-dioxygenase (IDO activity are hallmarks of many stress-related disorders. The kynurenine pathway of tryptophan degradation may serve to link these findings to the low level immune activation recently described in IBS. In this study, we investigated tryptophan degradation in a male IBS cohort (n = 10 and control subjects (n = 26. Methods Plasma samples were obtained from patients and healthy controls. Tryptophan and its metabolites were measured by high performance liquid chromatography (HPLC and neopterin, a sensitive marker of immune activation, was measured using a commercially available ELISA assay. Results Both kynurenine levels and the kynurenine:tryptophan ratio were significantly increased in the IBS cohort compared with healthy controls. Neopterin was also increased in the IBS subjects and the concentration of the neuroprotective metabolite kynurenic acid was decreased, as was the kynurenic acid:kynurenine ratio. Conclusion These findings suggest that the activity of IDO, the immunoresponsive enzyme which is responsible for the degradation of tryptophan along this pathway, is enhanced in IBS patients relative to controls. This study provides novel evidence for an immune-mediated degradation of tryptophan in a male IBS population and identifies the kynurenine pathway as a potential source of biomarkers in this debilitating condition.

  20. Twins labeling-liquid chromatography/mass spectrometry based metabolomics for absolute quantification of tryptophan and its key metabolites.

    Science.gov (United States)

    Guo, Huimin; Jiao, Yu; Wang, Xu; Lu, Tao; Zhang, Zunjian; Xu, Fengguo

    2017-06-30

    Tryptophan metabolism plays a crucial role in mediating gastrointestinal function. Here, in order to absolutely quantify tryptophan and its metabolites, a liquid chromatography-mass spectrometry (LC-MS) based targeted metabolomics approach was developed using N-dimethyl-/N-diethyl-amino naphthalene-1-sulfonyl chloride (Dns/Dens-Cl) as twins labeling (TL) reagents. Dns-Cl is famous in amine and phenol derivations, and structure is similar with Dens-Cl. The introduction of easily protonated moiety of tertiary ammonium-containing part in the derivatives from Dns to tryptophan and its metabolites not only improved the LC separation but also enhanced their MS response. In addition, the Dens labeled standards were used as internal standards to compensate for matrix effects and ensure accurate quantifications. With the proposed method, twelve metabolites in tryptophan pathway could be detected at sub-ng/mL levels using only 20μL rat serum (the limit of detection could reach 3pg/mL for tryptamine, N-acetyl-serotonin and 6-hydroxymelatonin). The sensitivity was enhanced about 1-2 orders of magnitude compared with non-derivatization method. Focusing on tryptophan pathway, the method was successfully applied to determine the absolute serum concentrations of twelve tryptophan metabolites in a vincristine-induced ileus rat model. A significant down-regulation of the tryptophan metabolism along the kynurenine pathway and up-regulation of serotonin pathway were uncovered. Our findings provide a deeper insight into the mechanism of gastrointestinal dysfunction. Copyright © 2017 Elsevier B.V. All rights reserved.

  1. Tryptophan-enriched cereal intake improves nocturnal sleep, melatonin, serotonin, and total antioxidant capacity levels and mood in elderly humans.

    Science.gov (United States)

    Bravo, R; Matito, S; Cubero, J; Paredes, S D; Franco, L; Rivero, M; Rodríguez, A B; Barriga, C

    2013-08-01

    Melatonin and serotonin rhythms, which exhibit a close association with the endogenous circadian component of sleep, are attenuated with increasing age. This decrease seems to be linked to sleep alterations in the elderly. Chrononutrition is a field of chronobiology that establishes the principle of consuming foodstuffs at times of the day when they are more useful for health, improving, therefore, biorhythms and physical performance. Our aim was to analyze whether the consumption of cereals enriched with tryptophan, the precursor of both serotonin and melatonin, may help in the reconsolidation of the sleep/wake cycle and counteract depression and anxiety in 35 middle-aged/elderly (aged 55-75 year) volunteers in a simple blind assay. Data were collected for 3 weeks according to the following schedule: The control week participants consumed standard cereals (22.5 mg tryptophan in 30 g cereals per dose) at breakfast and dinner; for the treatment week, cereals enriched with a higher dose of tryptophan (60 mg tryptophan in 30 g cereals per dose) were eaten at both breakfast and dinner; the posttreatment week volunteers consumed their usual diet. Each participant wore a wrist actimeter that logged activity during the whole experiment. Urine was collected to analyze melatonin and serotonin urinary metabolites and to measure total antioxidant capacity. The consumption of cereals containing the higher dose in tryptophan increased sleep efficiency, actual sleep time, immobile time, and decreased total nocturnal activity, sleep fragmentation index, and sleep latency. Urinary 6-sulfatoxymelatonin, 5-hydroxyindoleacetic acid levels, and urinary total antioxidant capacity also increased respectively after tryptophan-enriched cereal ingestion as well as improving anxiety and depression symptoms. Cereals enriched with tryptophan may be useful as a chrononutrition tool for alterations in the sleep/wake cycle due to age.

  2. Peripheral Serotonin 1B Receptor Transcription Predicts the Effect of Acute Tryptophan Depletion on Risky Decision-Making.

    Science.gov (United States)

    Faulkner, Paul; Mancinelli, Federico; Lockwood, Patricia L; Matarin, Mar; Dolan, Raymond J; Wood, Nick W; Dayan, Peter; Roiser, Jonathan P

    2017-01-01

    The effects of acute tryptophan depletion on human decision-making suggest that serotonin modulates the processing of rewards and punishments. However, few studies have assessed which of the many types of serotonin receptors are responsible. Using a within-subject, double-blind, sham-controlled design in 26 subjects, we examined whether individual differences in serotonin system gene transcription, measured in peripheral blood, predicted the effect of acute tryptophan depletion on decision-making. Participants performed a task in which they chose between successive pairs of fixed, lower-stakes (control) and variable, higher-stakes (experimental) gambles, each involving wins or losses. In 21 participants, mRNA from 9 serotonin system genes was measured in whole blood prior to acute tryptophan depletion: 5-HT1B, 5-HT1F, 5-HT2A, 5-HT2B, 5-HT3A, 5-HT3E, 5-HT7 (serotonin receptors), 5-HTT (the serotonin transporter), and tryptophan hydroxylase 1. Acute tryptophan depletion did not significantly influence participants' sensitivity to probability, wins, or losses, although there was a trend for a lower tendency to choose experimental gambles overall following depletion. Significant positive correlations, which survived correction for multiple comparisons, were detected between baseline 5-HT1B mRNA levels and acute tryptophan depletion-induced increases in both the overall tendency to choose the experimental gamble and sensitivity to wins. No significant relationship was observed with any other peripheral serotonin system markers. Computational analyses of decision-making data provided results consistent with these findings. These results suggest that the 5-HT1B receptor may modulate the effects of acute tryptophan depletion on risky decision-making. Peripheral levels of serotonin markers may predict response to treatments that act upon the serotonin system, such as selective serotonin reuptake inhibitors. © The Author 2016. Published by Oxford University Press on behalf

  3. Sorption of organophosphate esters by carbon nanotubes

    Energy Technology Data Exchange (ETDEWEB)

    Yan, Wei; Yan, Li [State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085 (China); Duan, Jinming [School of Environmental and Municipal Engineering, Xi’an University of Architecture and Technology, Xi’an 710055 (China); Jing, Chuanyong, E-mail: cyjing@rcees.ac.cn [State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085 (China)

    2014-05-01

    Graphical abstract: The interfacial interactions between the OPE molecules and CNTs. - Highlights: • Oxygen-containing groups on CNTs change the sorption property for OPEs. • Molecular configuration of OPEs has insignificant impact on their sorption. • Hydrophobic, π–π EDA and Brønsted acid–base interaction occurred between the CNTs and OPEs. - Abstract: Insights from the molecular-level mechanism of sorption of organophosphate esters (OPEs) on carbon nanotubes (CNTs) can further our understanding of the fate and transport of OPEs in the environment. The motivation for our study was to explore the sorption process of OPEs on multi-walled CNTs (MWCNTs), single-walled CNTs (SWCNTs) and their oxidized counterparts (O-MWCNTs and O-SWCNTs), and its molecular mechanism over a wide concentration range. The sorption isotherm results revealed that the hydrophobicity of OPEs dominated their affinities on a given CNT and the π–π electron donor–acceptor (EDA) interaction also played an important role in the sorption of aromatic OPEs. This π–π EDA interaction, verified with Raman and FT-IR spectroscopy, could restrict the radial vibration of SWCNTs and affect the deformation vibration γ(CH) bands of OPE molecules. The OPE surface coverage on CNTs, estimated using the nonlinear Dubinin–Ashtakhov model, indicated that the oxygen-containing functional groups on CNTs could interact with water molecules by H-bonding, resulting in a decrease in effective sorption sites. In addition, FTIR analysis also confirmed the occurrence of Brønsted acid–base interactions between OPEs and surface OH groups of SWCNTs. Our results should provide mechanistic insights into the sorption mechanism of OPE contaminants on CNTs.

  4. A simple two step procedure for purification of the catalytic domain of chicken tryptophan hydroxylase 1 in a form suitable for crystallization

    DEFF Research Database (Denmark)

    Windahl, Michael Skovbo; Petersen, Charlotte R.; Munch, Astrid

    2008-01-01

    Tryptophan hydroxylase (TPH) [EC 1.14.16.4] catalyzes the conversion of tryptophan to 5-hydroxytryptophan, which is the first and rate-determining step in the biosynthesis of the neurotransmitter serotonin. We have expressed the catalytic domain of chicken (Gallus gallus) TPH isoform 1 in Escheri......Tryptophan hydroxylase (TPH) [EC 1.14.16.4] catalyzes the conversion of tryptophan to 5-hydroxytryptophan, which is the first and rate-determining step in the biosynthesis of the neurotransmitter serotonin. We have expressed the catalytic domain of chicken (Gallus gallus) TPH isoform 1...

  5. Frontline Science: Tryptophan restriction arrests B cell development and enhances microbial diversity in WT and prematurely agingErcc1-/Δ7mice.

    Science.gov (United States)

    van Beek, Adriaan A; Hugenholtz, Floor; Meijer, Ben; Sovran, Bruno; Perdijk, Olaf; Vermeij, Wilbert P; Brandt, Renata M C; Barnhoorn, Sander; Hoeijmakers, Jan H J; de Vos, Paul; Leenen, Pieter J M; Hendriks, Rudi W; Savelkoul, Huub F J

    2017-04-01

    With aging, tryptophan metabolism is affected. Tryptophan has a crucial role in the induction of immune tolerance and the maintenance of gut microbiota. We, therefore, studied the effect of dietary tryptophan restriction in young wild-type (WT) mice (118-wk life span) and in DNA-repair deficient, premature-aged ( Ercc1 -/Δ7 ) mice (20-wk life span). First, we found that the effect of aging on the distribution of B and T cells in bone marrow (BM) and in the periphery of 16-wk-old Ercc1 -/Δ7 mice was comparable to that in 18-mo-old WT mice. Dietary tryptophan restriction caused an arrest of B cell development in the BM, accompanied by diminished B cell frequencies in the periphery. In general, old Ercc1 -/Δ7 mice showed similar responses to tryptophan restriction compared with young WT mice, indicative of age-independent effects. Dietary tryptophan restriction increased microbial diversity and made the gut microbiota composition of old Ercc1 -/Δ7 mice more similar to that of young WT mice. The decreased abundances of Alistipes and Akkermansia spp. after dietary tryptophan restriction correlated significantly with decreased B cell precursor numbers. In conclusion, we report that dietary tryptophan restriction arrests B cell development and concomitantly changes gut microbiota composition. Our study suggests a beneficial interplay between dietary tryptophan, B cell development, and gut microbial composition on several aspects of age-induced changes. © Society for Leukocyte Biology.

  6. Growth inhibitory properties of lactose fatty acid esters

    Directory of Open Access Journals (Sweden)

    Seung-Min Lee

    2017-11-01

    Full Text Available Sugar esters are biodegradable, nonionic surfactants which have microbial inhibitory properties. The influence of the fatty acid chain length on the microbial inhibitory properties of lactose esters was investigated in this study. Specifically, lactose monooctanoate (LMO, lactose monodecanoate (LMD, lactose monolaurate (LML and lactose monomyristate (LMM were synthesized and dissolved in both dimethyl sulfoxide (DMSO and ethanol. Minimum inhibitory concentrations (MIC and minimum bactericidal concentrations (MBC were determined in growth media. LML was the most effective ester, exhibiting MIC values of <0.05 to <5 mg/ml for each Gram-positive bacteria tested (Bacillus cereus, Mycobacterium KMS, Streptococcus suis, Listeria monocytogenes, Enterococcus faecalis, and Streptococcus mutans and MBC values of <3 to <5 mg/ml for B. cereus, M. KMS, S. suis, and L. monocytogenes. LMD showed MIC and MBC values of <1 to <5 mg/ml for B. cereus, M. KMS, S. suis, L. monocytogenes, and E. faecalis, with greater inhibition when dissolved in ethanol. LMM showed MIC and MBC values of <1 to <5 mg/ml for B. cereus, M. KMS, and S. suis. LMO was the least effective showing a MBC value of <5 mg/ml for only B. cereus, though MIC values for S. suis and L. monocytogenes were observed when dissolved in DMSO. B. cereus and S. suis were the most susceptible to the lactose esters tested, while S. mutans and E. faecalis were the most resilient and no esters were effective on Escherichia coli O157:H7. This research showed that lactose esters esterified with decanoic and lauric acids exhibited greater microbial inhibitory properties than lactose esters of octanoate and myristate against Gram-positive bacteria.

  7. Regular moderate or intense exercise prevents depression-like behavior without change of hippocampal tryptophan content in chronically tryptophan-deficient and stressed mice.

    Directory of Open Access Journals (Sweden)

    Hosung Lee

    Full Text Available Regular exercise has an antidepressant effect in human subjects. Studies using animals have suggested that the antidepressant effect of exercise is attributable to an increase of brain 5-hydroxytryptamine (5-HT; however, the precise mechanism underlying the antidepressant action via exercise is unclear. In contrast, the effect of 5-HT on antidepressant activity has not been clarified, in part because the therapeutic response to antidepressant drugs has a time lag in spite of the rapid increase of brain 5-HT upon administration of these drugs. This study was designed to investigate the contribution of brain 5-HT to the antidepressant effect of exercise. Mice were fed a tryptophan-deficient diet and stressed using chronic unpredictable stress (CUS for 4 weeks with or without the performance of either moderate or intense exercise on a treadmill 3 days per week. The findings demonstrated that the onset of depression-like behavior is attributable not to chronic reduction of 5-HT but to chronic stress. Regular exercise, whether moderate or intense, prevents depression-like behavior with an improvement of adult hippocampal cell proliferation and survival and without the recovery of 5-HT. Concomitantly, the mice that exercised showed increased hippocampal noradrenaline. Regular exercise prevents the impairment of not long-term memory but short-term memory in a 5-HT-reduced state. Together, these findings suggest that: (1 chronic reduction of brain 5-HT may not contribute to the onset of depression-like behavior; (2 regular exercise, whether moderate or intense, prevents the onset of chronic stress-induced depression-like behavior independent of brain 5-HT and dependent on brain adrenaline; and (3 regular exercise prevents chronic tryptophan reduction-induced impairment of not long-term but short-term memory.

  8. Application of ethyl esters and d3-methyl esters as internal standards for the gas chromatographic quantification of transesterified fatty acid methyl esters in food.

    Science.gov (United States)

    Thurnhofer, Saskia; Vetter, Walter

    2006-05-03

    Ethyl esters (FAEE) and trideuterium-labeled methyl esters (d3-FAME) of fatty acids were prepared and investigated regarding their suitability as internal standards (IS) for the determination of fatty acids as methyl esters (FAME). On CP-Sil 88, ethyl esters of odd-numbered fatty acids eluted approximately 0.5 min after the respective FAME, and only coelutions with minor FAME were observed. Depending on the problem, one or even many FAEE can be added as IS for the quantification of FAME by both GC-FID and GC-MS. By contrast, d3-FAME coeluted with FAME on the polar GC column, and the use of the former as IS requires application of GC-MS. In the SIM mode, m/z 77 and 90 are suggested for d3-methyl esters of saturated fatty acids, whereas m/z 88 and 101 are recommended for ethyl esters of saturated fatty acids. These m/z values give either no or very low response for FAME and can thus be used for the analysis of FAME in food by GC-MS in the SIM mode. Fatty acids in sunflower oil and mozzarella cheese were quantified using five saturated FAEE as IS. Gravimetric studies showed that the transesterification procedure could be carried out without of loss of fatty acids. GC-EI/MS full scan analysis was suitable for the quantitative determination of all unsaturated fatty acids in both food samples, whereas GC-EI/MS in the SIM mode was particularly valuable for quantifying minor fatty acids. The novel GC-EI/MS/SIM method using fatty acid ethyl esters as internal standards can be used to quantify individual fatty acids only, that is, without determination of all fatty acids (the common 100% method), although this is present. This was demonstrated by the exclusive quantification of selected fatty acids including methyl-branched fatty acids, erucic acid (18:1n-9trans), and polyunsaturated fatty acids in cod liver oil and goat's milk fat.

  9. Meal pattern of male rats maintained on amino acid supplemented diets: the effect of tryptophan, lysine, arginine, proline and threonine.

    Science.gov (United States)

    Ayaso, Raghad; Ghattas, Hala; Abiad, Mohamad; Obeid, Omar

    2014-07-01

    The macronutrient composition of the diet has been shown to affect food intake, with proteins having distinct effects. The present study investigated the effect of diet supplementation with individual amino acids (tryptophan, lysine, arginine, proline and threonine) on meal pattern among male rats. Meal pattern and body weight were monitored for two weeks. Proline and threonine had minimal effects on meal pattern, while the most pronounced changes were observed in the tryptophan group. Both tryptophan and lysine decreased overall food intake, which was translated into a reduction in body weight. The reduced food intake of the tryptophan group was associated with an increase in meal size, intermeal intervals (IMI) and meal time and a decrease in meal number. The decrease in the food intake of the lysine group was associated with a reduction in both IMI and meal number, and this was accompanied by an increase in meal time. Arginine increased meal number, while decreasing IMI. Proline and threonine had a minimal effect on meal pattern. Lysine seems to increase satiety, and arginine seems to decrease it, while tryptophan seems to increase satiety and decrease satiation. Accordingly, changes in meal patterns are associated with the type of amino acid added to the diet.

  10. Meal Pattern of Male Rats Maintained on Amino Acid Supplemented Diets: The Effect of Tryptophan, Lysine, Arginine, Proline and Threonine

    Directory of Open Access Journals (Sweden)

    Raghad Ayaso

    2014-07-01

    Full Text Available The macronutrient composition of the diet has been shown to affect food intake, with proteins having distinct effects. The present study investigated the effect of diet supplementation with individual amino acids (tryptophan, lysine, arginine, proline and threonine on meal pattern among male rats. Meal pattern and body weight were monitored for two weeks. Proline and threonine had minimal effects on meal pattern, while the most pronounced changes were observed in the tryptophan group. Both tryptophan and lysine decreased overall food intake, which was translated into a reduction in body weight. The reduced food intake of the tryptophan group was associated with an increase in meal size, intermeal intervals (IMI and meal time and a decrease in meal number. The decrease in the food intake of the lysine group was associated with a reduction in both IMI and meal number, and this was accompanied by an increase in meal time. Arginine increased meal number, while decreasing IMI. Proline and threonine had a minimal effect on meal pattern. Lysine seems to increase satiety, and arginine seems to decrease it, while tryptophan seems to increase satiety and decrease satiation. Accordingly, changes in meal patterns are associated with the type of amino acid added to the diet.

  11. Effects of Tranilast on the Urinary Excretion of Kynurenic and Quinolinic Acid under Conditions of L Tryptophan Loading

    Directory of Open Access Journals (Sweden)

    Rowland R. Noakes

    2013-01-01

    Full Text Available The pathogenesis of morphea and other cutaneous sclerosing disorders remain poorly understood. Although they are considered to be autoimmune disorders, abnormal tryptophan metabolism may be involved. Current therapy is directed to supressing the autoimmune response. Demonstration of a therapeutic response to manipulation of the kynurenine pathway would both support a role for abnormal tryptophan metabolism and offer additional targets for therapy. Tranilast is a 3-hydroxyanthranilic acid derivative known to target the kynurenine pathway. The aim of this study was to see if tranilast lowered the urinary excretion of the kynurenine metabolites kynurenic and quinolinic acid under condition of L tryptophan loading in a volunteer. Mean baseline value for kynurenic acid and quinolinic acid were 1.1 and 2.1 mmol/mol creatinine, respectively. This rose to 5.6 and 3.8 mmol/mol creatinine respectively under conditions of L tryptophan loading 2 grams daily. Adding 1 g of tranilast daily lowered the values to 2.0 and 2.9 mmol/mol creatinine, respectively. These data suggest that tranilast acts as a competitive inhibitor of either indoleamine 2, 3-dioxygenase (IDO, tryptophan 2, 3 di-oxygenase (TDO or both. As it involved only 1 subject, the results may not be representative of the larger population and must be considered preliminary.

  12. Phytosterol ester constituents affect micellar cholesterol solubility in model bile.

    Science.gov (United States)

    Brown, Andrew W; Hang, Jiliang; Dussault, Patrick H; Carr, Timothy P

    2010-09-01

    Plant sterols and stanols (phytosterols) and their esters are nutraceuticals that lower LDL cholesterol, but the mechanisms of action are not fully understood. We hypothesized that intact esters and simulated hydrolysis products of esters (phytosterols and fatty acids in equal ratios) would differentially affect the solubility of cholesterol in model bile mixed micelles in vitro. Sodium salts of glycine- and taurine-conjugated bile acids were sonicated with phosphatidylcholine and either sterol esters or combinations of sterols and fatty acids to determine the amount of cholesterol solubilized into micelles. Intact sterol esters did not solubilize into micelles, nor did they alter cholesterol solubility. However, free sterols and fatty acids altered cholesterol solubility independently (no interaction effect). Equal contents of cholesterol and either campesterol, stigmasterol, sitosterol, or stigmastanol (sitostanol) decreased cholesterol solubility in micelles by approximately 50% compared to no phytosterol present, with stigmasterol performing slightly better than sitosterol. Phytosterols competed with cholesterol in a dose-dependent manner, demonstrating a 1:1 M substitution of phytosterol for cholesterol in micelle preparations. Unsaturated fatty acids increased the micelle solubility of sterols as compared with saturated or no fatty acids. No differences were detected in the size of the model micelles. Together, these data indicate that stigmasterol combined with saturated fatty acids may be more effective at lowering cholesterol micelle solubility in vivo.

  13. Development of continuous deglycerolisation reactor for ethyl ester production

    Directory of Open Access Journals (Sweden)

    Ruamporn Nikhom

    2014-12-01

    Full Text Available In this work, the development of continuous deglycerolisation (CD reactor for ethyl ester production was investigated to improve the ethyl ester conversion. The device to assist separation of glycerol, in the CD unit, integrates transesterification (mixing zone and separation (settling zone into one unit. For reversible transesterification, removing glycerol during reaction can drive the equilibrium to the product side in order to achieve high conversion. Two models of device to assist separation of glycerol have been carried out to investigate the suitable conditions for ethyl ester production. Results showed that the fin-type model could separate higher amount of glycerol from the reaction system in order to achieve high transesterification conversion. The suitable conditions found in this study were: molar ratio of oil to ethanol of 1:5, KOCH3 concentration of 1.6 %wt. retention time of 15 min and reaction temperature of 70°C. At these conditions, ethyl ester’s purity and yield were 97.3%wt. and 92.0%wt., respectively. In addition, the fuel properties of the final ethyl ester product met the biodiesel standard for methyl ester which specified by Department of Energy Business.

  14. Determination of testosterone esters and estradiol esters in bovine and porcine blood serum.

    Science.gov (United States)

    Rejtharová, Martina; Rejthar, Libor; Čačková, Katarína

    2017-04-01

    Monitoring of steroid esters in blood serum is desirable in order to detect the possible illegal use of natural hormones as growth promoters. A method for the determination of testosterone propionate, testosterone benzoate, testosterone isocaproate, testosterone decanoate and estradiol benzoate in bovine and porcine blood serum was developed. The procedure consists of protein precipitation and removal of phospholipids using a HybridSPE®-Phospholipid column followed by clean-up on a hydrophilic modified styrene polymer Supel TM -Select HLB column and LC-MS/MS measurement. The method was validated according to Commission Decision 2002/657/EC. Decision limits for all analytes were observed in the range 5-30 pg ml - 1 . The method was shown to be robust for bovine and porcine serum analyses and can be applied for both screening and confirmatory determination in routine residue monitoring.

  15. Magnetic covalent triazine framework for rapid extraction of phthalate esters in plastic packaging materials followed by gas chromatography-flame ionization detection.

    Science.gov (United States)

    Yan, Zijun; He, Man; Chen, Beibei; Gui, Bo; Wang, Cheng; Hu, Bin

    2017-11-24

    Covalent triazine frameworks (CTFs), featuring with high surface area, good thermal, chemical and mechanical stability, are good adsorbents in sample pretreatment. Herein, magnetic CTFs/Ni composite was prepared by in situ reduction of nickel ions on CTFs matrix with a solvothermal method. The prepared CTFs/Ni composite exhibited good preparation reproducibility, high chemical stability, and high extraction efficiency for targeted phthalate esters (PAEs) due to π-π interaction and hydrophobic effect. The porous structure of CTFs/Ni composite benefited the fast transfer of target PAEs from aqueous solution to the adsorbents, and the integrated magnetism contributed to the rapid separation of adsorbents from sample and elution solution. Based on it, a novel method of magnetic solid phase extraction (MSPE) combined with gas chromatography-flame ionization detector (GC-FID) was developed for the analysis of PAEs including dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), benzyl butyl phthalate (BBP), di-2-ethylhexl phthalate (DEHP), and di-n-octyl phthalate (DNOP) in plastic packaging materials. Under the optimal experimental conditions, the limits of detection (LODs, S/N=3) for six PAEs were found to be in the range of 0.024-0.085mg/kg. The linear range was 0.32-16mg/kg for DMP, DEP, 0.08-80mg/kg for DBP, 0.16-32mg/kg for BBP, DEHP, and 0.32-32mg/kg for DNOP, respectively. The enrichment factors ranged from 59 to 88-fold (theoretical enrichment factor was 133-fold). The proposed method was successfully applied to the analysis of PAEs in various plastic packaging materials with recoveries in the range of 70.6-119% for the spiked samples. This method is characterized with short operation time, high sensitivity, low consumption of harmful organic solvents and can be extended to the analysis of other trace aromatic compounds. Copyright © 2017 Elsevier B.V. All rights reserved.

  16. Tryptophan Intake in the US Adult Population Is Not Related to Liver or Kidney Function but Is Associated with Depression and Sleep Outcomes.

    Science.gov (United States)

    Lieberman, Harris R; Agarwal, Sanjiv; Fulgoni, Victor L

    2016-12-01

    Tryptophan is an indispensable amino acid and is a precursor of the neurotransmitter serotonin. Tryptophan metabolites, such as serotonin and melatonin, are thought to participate in the regulation of mood and sleep and tryptophan is used to treat insomnia, sleep apnea, and depression. This study examined the intake of tryptophan and its associations with biochemical, behavioral, sleep, and health and safety outcomes in adults in a secondary analysis of a large, publicly available database of the US population. Data from the NHANES 2001-2012 (n = 29,687) were used to determine daily intakes of tryptophan and its associations with biochemical markers of health- and safety-related outcomes, self-reported depression, and sleep-related variables. Data were adjusted for demographic factors and protein intake. Linear trends were computed across deciles of intake for each outcome variable, and P-trends were determined. The usual tryptophan intake by US adults was 826 mg/d, severalfold higher than the Estimated Average Requirement for adults of 4 mg/(kg ⋅ d) (∼280 mg/d for a 70-kg adult). Most health- and safety-related biochemical markers of liver function, kidney function, and carbohydrate metabolism were not significantly (P-trend > 0.05) associated with deciles of tryptophan intake and were well within normal ranges, even for individuals in the 99th percentile of intake. Usual intake deciles of tryptophan were inversely associated with self-reported depression measured by the Patient Health Questionnaire raw score (0-27; P-trend Tryptophan intake was not related to most markers of liver function, kidney function or carbohydrate metabolism. Levels of tryptophan intake in the US population appear to be safe as shown by the absence of abnormal laboratory findings. Tryptophan intake was inversely associated with self-reported level of depression and positively associated with sleep duration. © 2016 American Society for Nutrition.

  17. Enhanced synthesis of 5-hydroxy-l-tryptophan through tetrahydropterin regeneration.

    Science.gov (United States)

    Hara, Ryotaro; Kino, Kuniki

    2013-12-09

    5-Hydroxy-l-tryptophan (5-HTP) is a naturally occurring aromatic amino acid present in the seeds of the African plant Griffonia simplicifolia. Although 5-HTP has therapeutic effects in various symptoms, efficient method of producing 5-HTP has not been established. In this study, we developed a novel cofactor regeneration process to achieve enhanced synthesis of 5-HTP by using modified l-phenylalanine 4-hydroxylase of Chromobacterium violaceum. For the synthesis of 5-HTP using Escherichia coli whole cell bioconversion, l-tryptophan and 5-HTP degradation by E. coli endogenous catabolic enzymes should be considered. The tryptophanase gene was disrupted using the λ red recombination system, since tryptophanase is postulated as an initial enzyme for the degradation of l-tryptophan and 5-HTP in E. coli. For regeneration of the cofactor pterin, we screened and investigated several key enzymes, including dihydropteridine reductase from E. coli, glucose dehydrogenase from Bacillus subtilis, and pterin-4α-carbinolamine dehydratase from Pseudomonas syringae. Genes encoding these three enzymes were overexpressed in an E. coli tryptophanase-deficient host, resulting in the synthesis of 0.74 mM 5-HTP in the presence of 0.1 mM pterin and the synthesis of 0.07 mM 5-HTP in the absence of regeneration of pterin. These results clearly indicated the successful regeneration of pterin. Following optimization of the reaction conditions, 2.5 mM 5-HTP was synthesized with cofactor regeneration, while 0.8 mM 5-HTP was recovered without cofactor regeneration under the same reaction conditions, suggesting that the principle described here provides a new method for cofactor regeneration.

  18. Proton-coupled electron transfer from tryptophan: a concerted mechanism with water as proton acceptor.

    Science.gov (United States)

    Zhang, Ming-Tian; Hammarström, Leif

    2011-06-15

    The mechanism of proton-coupled electron transfer (PCET) from tyrosine in enzymes and synthetic model complexes is under intense discussion, in particular the pH dependence of the PCET rate with water as proton acceptor. Here we report on the intramolecular oxidation kinetics of tryptophan derivatives linked to [Ru(bpy)(3)](2+) units with water as proton acceptor, using laser flash-quench methods. It is shown that tryptophan oxidation can proceed not only via a stepwise electron-proton transfer (ETPT) mechanism that naturally shows a pH-independent rate, but also via another mechanism with a pH-dependent rate and higher kinetic isotope effect that is assigned to concerted electron-proton transfer (CEP). This is in contrast to current theoretical models, which predict that CEP from tryptophan with water as proton acceptor can never compete with ETPT because of the energetically unfavorable PT part (pK(a)(Trp(•)H(+)) = 4.7 ≫ pK(a)(H(3)O(+)) ≈ -1.5). The moderate pH dependence we observe for CEP cannot be explained by first-order reactions with OH(-) or the buffers and is similar to what has been demonstrated for intramolecular PCET in [Ru(bpy)(3)](3+)-tyrosine complexes (Sjödin, M.; et al. J. Am. Chem. Soc.2000, 122, 3932. Irebo, T.; et al. J. Am. Chem. Soc.2007, 129, 15462). Our results suggest that CEP with water as the proton acceptor proves a general feature of amino acid oxidation, and provide further experimental support for understanding of the PCET process in detail. © 2011 American Chemical Society

  19. The Role of Amino Acid Permeases and Tryptophan Biosynthesis in Cryptococcus neoformans Survival

    Science.gov (United States)

    Fernandes, João Daniel Santos; Martho, Kevin; Tofik, Veridiana; Vallim, Marcelo A.; Pascon, Renata C.

    2015-01-01

    Metabolic diversity is an important factor during microbial adaptation to different environments. Among metabolic processes, amino acid biosynthesis has been demonstrated to be relevant for survival for many microbial pathogens, whereas the association between pathogenesis and amino acid uptake and recycling are less well-established. Cryptococcus neoformans is an opportunistic fungal pathogen with many habitats. As a result, it faces frequent metabolic shifts and challenges during its life cycle. Here we studied the C. neoformans tryptophan biosynthetic pathway and found that the pathway is essential. RNAi indicated that interruptions in the biosynthetic pathway render strains inviable. However, auxotroph complementation can be partially achieved by tryptophan uptake when a non preferred nitrogen source and lower growth temperature are applied, suggesting that amino acid permeases may be the target of nitrogen catabolism repression (NCR). We used bioinformatics to search for amino acid permeases in the C. neoformans and found eight potential global permeases (AAP1 to AAP8). The transcriptional profile of them revealed that they are subjected to regulatory mechanisms which are known to respond to nutritional status in other fungi, such as (i) quality of nitrogen (Nitrogen Catabolism Repression, NCR) and carbon sources (Carbon Catabolism Repression, CCR), (ii) amino acid availability in the extracellular environment (SPS-sensing) and (iii) nutritional deprivation (Global Amino Acid Control, GAAC). This study shows that C. neoformans has fewer amino acid permeases than other model yeasts, and that these proteins may be subjected to complex regulatory mechanisms. Our data suggest that the C. neoformans tryptophan biosynthetic pathway is an excellent pharmacological target. Furthermore, inhibitors of this pathway cause Cryptococcus growth arrest in vitro. PMID:26162077

  20. Tryptophan catabolism and immune activation in primary and chronic HIV infection.

    Science.gov (United States)

    Gelpi, Marco; Hartling, Hans J; Ueland, Per M; Ullum, Henrik; Trøseid, Marius; Nielsen, Susanne D

    2017-05-16

    Kynurenine/Tryptophan ratio (KTR) is increased in HIV infection, and linked to immune activation. We hypothesized that early cART initiation results in lower KTR compared to late initiation. Furthermore, we hypothesized that KTR prior to cART is a predictor of the magnitude of subsequent reduction in immune activation. Prospective study including 57 HIV-infected individuals (primary HIV infection (N = 14), early presenters (>350 CD4+ T cells/μL, N = 24), late presenters (tryptophan were analysed by liquid chromatography-tandem mass spectrometry. Total CD4+ and CD8+ T cells were determined and proportion of activated CD38 + HLA-DR+ Tcells was measured using flow cytometry at baseline and after 6 and 12 months of cART. At baseline, primary HIV infection had higher KTR than early presenters. However, similar KTR in primary HIV infection and early presenters was found after cART initiation, while late presenters had higher KTR at all time points. In primary HIV infection and early presenters, KTR was positively associated with proportion of activated cells at baseline. Furthermore, in early presenters the KTR at baseline was associated with proportion of activated cells after 6 and 12 months. Interestingly, in primary HIV infection the KTR at baseline was positively associated with reduction in proportion of CD8 + CD38 + HLA-DR T cells after 6 and 12 months. Lower kynurenine/tryptophan ratio during follow-up was found after early initiation of cART. KTR in primary HIV infection and early presenters was positively associated with immune activation. Importantly, KTR in primary HIV infection predicted the magnitude of subsequent reduction in immune activation. Thus, a beneficial effect of early cART on KTR was suggested.

  1. The Role of Amino Acid Permeases and Tryptophan Biosynthesis in Cryptococcus neoformans Survival.

    Directory of Open Access Journals (Sweden)

    João Daniel Santos Fernandes

    Full Text Available Metabolic diversity is an important factor during microbial adaptation to different environments. Among metabolic processes, amino acid biosynthesis has been demonstrated to be relevant for survival for many microbial pathogens, whereas the association between pathogenesis and amino acid uptake and recycling are less well-established. Cryptococcus neoformans is an opportunistic fungal pathogen with many habitats. As a result, it faces frequent metabolic shifts and challenges during its life cycle. Here we studied the C. neoformans tryptophan biosynthetic pathway and found that the pathway is essential. RNAi indicated that interruptions in the biosynthetic pathway render strains inviable. However, auxotroph complementation can be partially achieved by tryptophan uptake when a non preferred nitrogen source and lower growth temperature are applied, suggesting that amino acid permeases may be the target of nitrogen catabolism repression (NCR. We used bioinformatics to search for amino acid permeases in the C. neoformans and found eight potential global permeases (AAP1 to AAP8. The transcriptional profile of them revealed that they are subjected to regulatory mechanisms which are known to respond to nutritional status in other fungi, such as (i quality of nitrogen (Nitrogen Catabolism Repression, NCR and carbon sources (Carbon Catabolism Repression, CCR, (ii amino acid availability in the extracellular environment (SPS-sensing and (iii nutritional deprivation (Global Amino Acid Control, GAAC. This study shows that C. neoformans has fewer amino acid permeases than other model yeasts, and that these proteins may be subjected to complex regulatory mechanisms. Our data suggest that the C. neoformans tryptophan biosynthetic pathway is an excellent pharmacological target. Furthermore, inhibitors of this pathway cause Cryptococcus growth arrest in vitro.

  2. The Kynurenine Pathway of Tryptophan Catabolism and AIDS-Associated Kaposi Sarcoma in Africa.

    Science.gov (United States)

    Byakwaga, Helen; Hunt, Peter W; Laker-Oketta, Miriam; Glidden, David V; Huang, Yong; Bwana, Bosco M; Mocello, A Rain; Bennett, John; Walusansa, Victoria; Dollard, Sheila C; Bangsberg, David R; Mbidde, Edward K; Martin, Jeffrey N

    2015-11-01

    Other than Kaposi sarcoma (KS)-associated herpesvirus and CD4 T-cell lymphopenia, the mechanisms responsible for KS in the context of HIV are poorly understood. One recently explored pathway of HIV pathogenesis involves induction of the enzyme indoleamine 2,3-dioxygenase-1 (IDO), which catabolizes tryptophan into kynurenine and several other immunologically active metabolites that suppress T-cell proliferation. We investigated the role of IDO in the development of KS in HIV disease. In a case-control study among untreated HIV-infected Ugandans, cases were adults with KS and controls were without KS. IDO activity was assessed by the ratio of plasma kynurenine to tryptophan levels (KT ratio), measured by liquid chromatography-tandem mass spectrometry. We studied 631 HIV-infected subjects: 222 KS cases and 409 controls. Non-KS controls had a higher median plasma KT ratio (130, interquartile range: 90 to 190 nM/μM) than KS cases (110, interquartile range: 90 to 150 nM/μM) (P = 0.004). After adjustment for age, sex, CD4 count, and plasma HIV RNA level, subjects with the highest (fourth quartile) plasma KT ratios had a 59% reduction (95% confidence interval: 27% to 77%) in the odds of KS compared with those with the lowest (first quartile) levels. KS was also independently associated with lower CD4 count, higher plasma HIV RNA, and men. Among HIV-infected individuals, greater activity of the kynurenine pathway of tryptophan catabolism, as evidenced by higher levels of plasma KT ratio, was associated with lower occurrence of KS. Some consequences of immune activation in HIV infection might actually suppress certain cancers.

  3. Radiation and photochemiluminescence in solutions of tryptophan-containing peptides and proteins

    International Nuclear Information System (INIS)

    Sapezhinskij, I.I.; Lozovskaya, E.L.

    1995-01-01

    The review dwells on the studies relating to chemiluminescence appearing in tryptophan-containing peptides and proteins under the effect of ionizing and optical radiation. Data on radiation-induced chemiluminescence in various objects are presented. Classification of chemiluminescent phenomena according to life time of radiation defects, types of objects and methods of recording has been made. Initial photo and radiation processes resulting in chemiluminescence are considered. The influence of acceptors on chemiluminescence is analyzed. Possible mechanisms of dioxetan formation under various conditions of initiation are discussed. Methods based on glycyltryptophan photochemiluminescence for testing pharmaceuticals, cosmetic preparations and other substances for antioxidant or photosensiticizing activity are presented. 140 refs., 4 tabs

  4. Low tryptophan diet decreases brain serotonin and alters response to apomorphine

    Science.gov (United States)

    Sahakian, B. J.; Wurtman, R. J.; Barr, J. K.; Millington, W. R.; Chiel, H. J.

    1979-01-01

    The role of the serotoninergic system in the regulation of apomorphine-induced behavior, a behavior primarily controlled by dopaminergic neurotransmission, was investigated in rats fed on a low tryptophan diet since weaning. It was found that reductions in brain seritonin (5-HT) produced by diet result in decreased stereotypy after apomorphine administration. This indicates that although stereotyped behavior is primarily mediated by dopaminergic mechanisms, it can also be modulated by other neurotransmitter including 5-HT. It was also shown that changes in brain seritonin levels can affect psychomotor stimulant-induced hypothermia.

  5. Cysteine and tryptophan anomalies found when scanning all the binding sites in the Protein Data Bank.

    Science.gov (United States)

    Iván, Gábor; Szabadka, Zoltán; Grolmusz, Vince

    2010-01-01

    The Protein Data Bank (PDB) is one of the richest sources of structural biological information in the World. It started to exist as the computer-readable depository of crystallographic data complementing printed papers. The proper interpretation of the content of the individual files in the PDB still needs the detailed information found in the citing publication. An advanced graph theoretical method is presented here for automatically repairing, re-organising and re-structuring PDB data yielding the identification of all the protein-ligand complexes and all the binding sites in the PDB. As an application, we identified strong cysteine and tryptophan irregularities in the data.

  6. Variation in tryptophan hydroxylase-2 gene is not associated to male completed suicide in Estonian population.

    Science.gov (United States)

    Must, Anne; Tasa, Gunnar; Lang, Aavo; Vasar, Eero; Kõks, Sulev; Maron, Eduard; Väli, Marika

    2009-04-03

    Dysfunction of the central serotonergic system has been related to a spectrum of psychiatric disorders, including suicidal behavior. Tryptophan hydroxylase isoform 2 (TPH2) is the rate-limiting enzyme in the biosynthetic pathway of serotonin, being expressed in serotonergic neurons of raphe nuclei. We investigated genetic variation in TPH2 gene in two samples of male subjects: 288 suicide completers and 327 volunteers, in order to reveal any associations between 14 single nucleotide polymorphisms and completed suicide. No associations were revealed neither on allelic nor haplotype level. Our finding does not support the hypothesis of TPH2 being a susceptibility factor for completed suicide in males of Estonian origin.

  7. Synthesis and Characterization of Poly(ethylene glycol)-block-Poly(Nα-Boc-L-tryptophan) copolymers

    Science.gov (United States)

    Voda, Andreea S.; Guo, Qipeng

    2010-06-01

    Amphiphilic diblock and triblock copolymers were synthesized from poly(ethylene glycol) (PEG) and Nα-Boc-L-tryptophan. A number of reaction conditions were investigated in order to achieve optimum yield and maximum chain extension for the newly formed block copolymers. Characterization of the novel copolymers was evaluated by means of 1D and 2D solution state nuclear magnetic resonance (NMR), infrared (IR) spectroscopy and size exclusion chromatography (SEC). The 2D NMR investigation of the block copolymers provided evidence to suggest that protonation of the nitrogen atoms present along the newly formed peptide back bone was occurring when the solvent environment was under acidic conditions.

  8. Simultaneous determination of the UV-filters benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in human placental tissue by LC-MS/MS. Assessment of their in vitro endocrine activity.

    Science.gov (United States)

    Jiménez-Díaz, I; Molina-Molina, J M; Zafra-Gómez, A; Ballesteros, O; Navalón, A; Real, M; Sáenz, J M; Fernández, M F; Olea, N

    2013-10-01

    UV-filters are widely used in many personal care products and cosmetics. Recent studies indicate that some organic UV-filters can accumulate in biota and act as endocrine disruptors, but there are few studies on the occurrence and fate of these compounds in humans. In the present work, a new liquid chromatography-tandem mass spectrometry (LC-MS/MS) method to assess the presence of six UV-filters in current use (benzyl salicylate, phenyl salicylate, octyl salicylate, homosalate, 3-(4-methylbenzylidene) camphor, and 3-benzylidene camphor) in human placental tissue is proposed. The method involves the extraction of the analytes from the samples using ethyl acetate, followed by a clean-up step using centrifugation prior to their quantification by LC-MS/MS using an atmospheric pressure chemical ionization (APCI) interface. Bisphenol A-d16 was used as surrogate for the determination of benzyl salicylate, phenyl salicylate, octyl salicylate and homosalate in negative mode and benzophenone-d10, was used as surrogate for the determination of 3-(4-methylbenzylidene) camphor and 3-benzylidene camphor in positive mode. The found limits of detection ranged from 0.4 to 0.6ngg(-1) and the limits of quantification ranged from 1.3 to 2.0ngg(-1), while variability was under 13.7%. Recovery rates for spiked samples ranged from 97% to 104%. Moreover, the interactions of these compounds with the human estrogen receptor alpha (hERα) and androgen receptor (hAR), using two in vitro bioassays based on reporter gene expression and cell proliferation assessment, were also investigated. All tested compounds, except benzyl salicylate and octyl salicylate, showed estrogenic activity in the E-Screen bioassay whereas only homosalate and 3-(4-methylbenzylidene) camphor were potent hAR antagonists. Although free salicylate derivatives and free camphor derivatives were not detected in the human placenta samples analyzed, the observed estrogenic and anti-androgenic activities of some of these

  9. Neuroendocrine and immune responses undertake different fates following tryptophan or methionine dietary treatment: tales from a teleost model

    DEFF Research Database (Denmark)

    Azeredo, Rita; Machado, M.; Afonso, A.

    2017-01-01

    cells proliferation. Differently, tryptophan effects on inflammatory transcripts suggested an inhibitory mode of action. This, together with a high production of brain monoamine and cortisol levels, suggests that tryptophan might mediate regulatory mechanisms of neuroendocrine and immune systems...... the immunomodulatory effect of these amino acids on the inflammatory and neuroendocrine responses in juveniles of European seabass, Dicentrarchus labrax. To achieve this, goal fish were fed for 14 days methionine and tryptophan-supplemented diets (MET and TRP, respectively, 2x dietary requirement level) or a control......, brain monoamines, plasma cortisol, and immune-related gene expression showed distinct and sometimes opposite patterns regarding the effects of dietary amino acids. While neuroendocrine intermediates were not affected by any dietary treatment at the end of the feeding trial, both supplemented diets led...

  10. Tryptophan 2,3-dioxygenase (TDO)-reactive T cells differ in their functional characteristics in health and cancer

    DEFF Research Database (Denmark)

    Hjortsø, Mads Duus; Larsen, Stine Kiaer; Kongsted, Per

    2015-01-01

    Tryptophan-2,3-dioxygenase (TDO) physiologically regulates systemic tryptophan levels in the liver. However, numerous studies have linked cancer with activation of local and systemic tryptophan metabolism. Indeed, similar to other heme dioxygenases TDO is constitutively expressed in many cancers....... In the present study, we detected the presence of both CD8(+) and CD4(+) T-cell reactivity toward TDO in peripheral blood of patients with malignant melanoma (MM) or breast cancer (BC) as well as healthy subjects. However, TDO-reactive CD4(+) T cells constituted distinct functional phenotypes in health...... and disease. In healthy subjects these cells predominately comprised interferon (IFN)γ and tumor necrosis factor (TNF)-α producing Th1 cells, while in cancer patients TDO-reactive CD4(+) T-cells were more differentiated with release of not only IFNγ and TNFα, but also interleukin (IL)-17 and IL-10 in response...

  11. Synchrotron ultraviolet microspectroscopy on rat cortical bone: involvement of tyrosine and tryptophan in the osteocyte and its environment.

    Directory of Open Access Journals (Sweden)

    Stéphane Pallu

    Full Text Available Alcohol induced osteoporosis is characterized by a bone mass decrease and microarchitecture alterations. Having observed an excess in osteocyte apoptosis, we aimed to assess the bone tissue biochemistry, particularly in the osteocyte and its environment. For this purpose, we used a model of alcohol induced osteoporosis in rats. Bone sections of cortical bone were investigated using synchrotron UV-microspectrofluorescence at subcellular resolution. We show that bone present three fluorescence peaks at 305, 333 and 385 nm, respectively corresponding to tyrosine, tryptophan and collagen. We have determined that tyrosine/collagen and tryptophan/collagen ratios were higher in the strong alcohol consumption group. Tryptophan is related to the serotonin metabolism involved in bone formation, while tyrosine is involved in the activity of tyrosine kinases and phosphatases in osteocytes. Our experiment represents the first combined synchrotron UV microspectroscopy analysis of bone tissue with a quantitative biochemical characterization in the osteocyte and surrounding matrix performed separately.

  12. Intrinsic Tryptophan Fluorescence in the Detection and Analysis of Proteins: A Focus on Förster Resonance Energy Transfer Techniques

    Directory of Open Access Journals (Sweden)

    Amar B. T. Ghisaidoobe

    2014-12-01

    Full Text Available F resonance energy transfer (FRET occurs when the distance between a donor fluorophore and an acceptor is within 10 nm, and its application often necessitates fluorescent labeling of biological targets. However, covalent modification of biomolecules can inadvertently give rise to conformational and/or functional changes. This review describes the application of intrinsic protein fluorescence, predominantly derived from tryptophan (\\(\\uplambda_{\\textsc{ex}}\\sim\\ nm, \\(\\uplambda_{\\textsc{em}}\\sim\\ 350 nm, in protein-related research and mainly focuses on label-free FRET techniques. In terms of wavelength and intensity, tryptophan fluorescence is strongly influenced by its (or the proteinlocal environment, which, in addition to fluorescence quenching, has been applied to study protein conformational changes. Intrinsic F resonance energy transfer (iFRET, a recently developed technique, utilizes the intrinsic fluorescence of tryptophan in conjunction with target-specific fluorescent probes as FRET donors and acceptors, respectively, for real time detection of native proteins.

  13. 1,1'-Binaphthyl-based imidazolium chemosensors for highly selective recognition of tryptophan in aqueous solutions.

    Science.gov (United States)

    Yang, Li; Qin, Song; Su, Xiaoyu; Yang, Fei; You, Jingsong; Hu, Changwei; Xie, Rugang; Lan, Jingbo

    2010-01-21

    A type of 1,1'-binaphthyl-based imidazolium chemosensor module has been synthesized for the highly selective recognition of tryptophan (Trp) among the eleven alpha-amino acids investigated in aqueous solutions via synergistic effects of multiple hydrogen bonding and electrostatic interactions. These results have demonstrated that the C-2 hydrogen atom of the imidazolium ring plays a key role as a hydrogen bond donor. The UV/vis, fluorescence and mass spectral studies have indicated that a 1 : 1 complex is formed between the host and tryptophan. The binding affinity and selectivity of the cleft-like receptor (R)- with l-Trp are superior to those of (R)-. In spite of an inferior selectivity towards various aromatic amino acids, the macrocyclic (R)- displays a remarkable enantiodiscrimination for the two enantiomers of tryptophan with a K(D)/K(L) value as high as 6.2.

  14. Ingestion of branched-chain amino acids and tryptophan during sustained exercise in man: failure to affect performance

    DEFF Research Database (Denmark)

    Van Hall, Gerrit; Raaymakers, J S; Saris, W H

    1995-01-01

    1. An increased uptake of tryptophan in the brain may increase serotoninergic activity and recently has been suggested to be a cause of fatigue during prolonged exercise. The present study, therefore, investigates whether ingestion of tryptophan or the competing branched-chain amino acids (BCAAs......) affect performance. Ten endurance-trained male athletes were studied during cycle exercise at 70-75% maximal power output, while ingesting, ad random and double-blind, drinks that contained 6% sucrose (control) or 6% sucrose supplemented with (1) tryptophan (3 g l-1), (2) a low dose of BCAA (6 g l-1...... or that manipulation of serotoninergic activity functionally does not contribute to mechanisms of fatigue....

  15. Boric ester-type molten salt via dehydrocoupling reaction.

    Science.gov (United States)

    Matsumi, Noriyoshi; Toyota, Yoshiyuki; Joshi, Prerna; Puneet, Puhup; Vedarajan, Raman; Takekawa, Toshihiro

    2014-11-14

    Novel boric ester-type molten salt was prepared using 1-(2-hydroxyethyl)-3-methylimidazolium chloride as a key starting material. After an ion exchange reaction of 1-(2-hydroxyethyl)-3-methylimidazolium chloride with lithium (bis-(trifluoromethanesulfonyl) imide) (LiNTf2), the resulting 1-(2-hydroxyethyl)-3-methylimidazolium NTf2 was reacted with 9-borabicyclo[3.3.1]nonane (9-BBN) to give the desired boric ester-type molten salt in a moderate yield. The structure of the boric ester-type molten salt was supported by 1H-, 13C-, 11B- and 19F-NMR spectra. In the presence of two different kinds of lithium salts, the matrices showed an ionic conductivity in the range of 1.1 × 10⁻⁴-1.6 × 10⁻⁵ S cm⁻¹ at 51 °C. This was higher than other organoboron molten salts ever reported.

  16. Saliva-catalyzed hydrolysis of a ketobemidone ester prodrug

    DEFF Research Database (Denmark)

    Hansen, L.B.; Christrup, Lona Louring; Bundgaard, H.

    1992-01-01

    Saliva enzyme-catalysed hydrolysis of ester prodrugs or drugs containing sensitive ester groups may be a limiting factor for the buccal absorption of such compounds. Using the isopropyl carbonate ester of ketobemidone as a model substance of a hydrolysis-sensitive prodrug the esterase activity...... of human saliva has been characterized as a function of various factors. The esterase activity was found to decrease rapidly upon storage of the saliva at 37°C. The activity increased with increasing pH in the range 4.5-7.4 and with increasing salivation flow rate up to a rate of 0.9 ml min. Under resting...... conditions, the flow rate was about 0.2 ml min which implied a greatly decreased esterase activity. The activity was highest after fasting and decreased after intake of a meal. The intraindividual variation in the saliva esterase activity was small whereas a larger interindividual variation was found....

  17. Long-Acting Diclofenac Ester Prodrugs for Joint Injection

    DEFF Research Database (Denmark)

    Mertz, Nina; Larsen, Susan Weng; Kristensen, Jesper

    2016-01-01

    A prodrug approach for local and sustained diclofenac action after injection into joints based on ester prodrugs having a pH-dependent solubility is presented. Inherent ester prodrug properties influencing the duration of action include their pH-dependent solubility and charge state, as well...... as susceptibility to undergo esterase facilitated hydrolysis. In this study, physicochemical properties and pH rate profiles of 3 diclofenac ester prodrugs differing with respect to the spacer carbon chain length between the drug and the imidazole-based promoiety were determined and a rate equation for prodrug...... degradation in aqueous solution in the pH range 1-10 was derived. In the pH range 6-10, the prodrugs were subject to parallel degradation to yield diclofenac and an indolinone derivative. The prodrug degradation was found to be about 6-fold faster in 80% (vol/vol) human plasma as compared to 80% (vol...

  18. Maximization of fructose esters synthesis by response surface methodology.

    Science.gov (United States)

    Neta, Nair Sampaio; Peres, António M; Teixeira, José A; Rodrigues, Ligia R

    2011-07-01

    Enzymatic synthesis of fructose fatty acid ester was performed in organic solvent media, using a purified lipase from Candida antartica B immobilized in acrylic resin. Response surface methodology with a central composite rotatable design based on five levels was implemented to optimize three experimental operating conditions (temperature, agitation and reaction time). A statistical significant cubic model was established. Temperature and reaction time were found to be the most significant parameters. The optimum operational conditions for maximizing the synthesis of fructose esters were 57.1°C, 100 rpm and 37.8 h. The model was validated in the identified optimal conditions to check its adequacy and accuracy, and an experimental esterification percentage of 88.4% (±0.3%) was obtained. These results showed that an improvement of the enzymatic synthesis of fructose esters was obtained under the optimized conditions. Copyright © 2011 Elsevier B.V. All rights reserved.

  19. Isolation and pharmacological activity of phenylpropanoid esters from Marrubium vulgare.

    Science.gov (United States)

    Sahpaz, Sevser; Garbacki, Nancy; Tits, Monique; Bailleul, Francois

    2002-03-01

    The isolation and identification of major phenylpropanoid esters from Marrubium vulgare: (+) (E)-caffeoyl-L-malic acid 1, acteoside 2, forsythoside B 3, arenarioside 4, ballotetroside 5, as well as their anti-inflammatory activity are reported for the first time. We evaluated the inhibitory effects of these five compounds on cyclooxygenase (Cox) catalysed prostaglandin biosynthesis activity. Only the glycosidic phenylpropanoid esters showed an inhibitory activity towards the Cox-2 enzyme and three of them: acteoside 2, forsythoside B 3, arenarioside 4, exhibited higher inhibitory potencies on Cox-2 than on Cox-1. These results are of interest, as Cox-2 is mainly associated with inflammation and the Cox-1 inhibition with adverse side effects often observed with non-steroidal anti-inflammatory drugs. The occurrence of these phenylpropanoid esters could also explain some other pharmacological properties of M. vulgare.

  20. Boric Ester-Type Molten Salt via Dehydrocoupling Reaction

    Directory of Open Access Journals (Sweden)

    Noriyoshi Matsumi

    2014-11-01

    Full Text Available Novel boric ester-type molten salt was prepared using 1-(2-hydroxyethyl-3-methylimidazolium chloride as a key starting material. After an ion exchange reaction of 1-(2-hydroxyethyl-3-methylimidazolium chloride with lithium (bis-(trifluoromethanesulfonyl imide (LiNTf2, the resulting 1-(2-hydroxyethyl-3-methylimidazolium NTf2 was reacted with 9-borabicyclo[3.3.1]nonane (9-BBN to give the desired boric ester-type molten salt in a moderate yield. The structure of the boric ester-type molten salt was supported by 1H-, 13C-, 11B- and 19F-NMR spectra. In the presence of two different kinds of lithium salts, the matrices showed an ionic conductivity in the range of 1.1 × 10−4–1.6 × 10−5 S cm−1 at 51 °C. This was higher than other organoboron molten salts ever reported.