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Sample records for acridones

  1. Bioactive acridone alkaloids from Swinglea glutinosa.

    Weniger, B; Um, B H; Valentin, A; Estrada, A; Lobstein, A; Anton, R; Maillé, M; Sauvain, M

    2001-09-01

    A new prenylated acridone alkaloid, 1,3,5-trihydroxy-2,8-bis(3-methylbut-2-enyl)-10-methyl-9-acridone (1), was isolated from the stembark of Swinglea glutinosa, along with three known acridone alkaloids, 5-hydroxynoracronycine (2), 1,3,5-trihydroxy-4-methoxy-2-(3-methylbut-2-enyl)-10-methyl-9-acridone (3), and 1,3,5-trihydroxy-4-methoxy-10-methylacridone (4). The isolated alkaloids were assessed in vitro against chloroquine-sensitive and -resistant Plasmodium falciparum strains and for cytotoxicity using HeLa cells. PMID:11575960

  2. Reactivity of allenylphosphonates and allenylphosphine oxides toward 9-chloroacridines and acridone- A facile route to new -substituted acridones

    A Leela Siva Kumari; Venu Srinivas; K C Kumara Swamy

    2013-11-01

    Base-mediated addition of acridones to allenylphosphonates/allenylphosphine oxides (OCH2CMe2CH2O)P(O)CH=C=CR1R2 {R1 = R2 = Me (1), R1 = R2 = [−CH2−]5 (2)}, Ph2P(O)C(H)=C=CR1R2 {R1 = R2 = Me (3), R1 = R2 = [−CH2−]5 (4)} and (EtO)2P(O)C(H)=C=CMe2 (5) in DMF results in the regiospecific formation of phosphono-acridones and acridonylphosphine oxides. The acridone addition products were also obtained in the reaction of allenes 1 and 2 with 9-chloroacridine under [Pd]-catalysed conditions, along with (unexpected) -acridinyl substituted allenes. In contrast, 9-benzyl-6-chloro-purine reacted with 1 affording a -substituted purinone phosphonate. Allenes 1-2 did not react with acridones in the absence of base (CsF), but in the presence of Pd(OAc)2/DMF (or DMA)/pivalic acid rearranged to give 1,3-butadienes probably via [Pd]-allyl complexes. The phosphono-acridones were amenable to Horner-Wadsworth-Emmons (HWE) reaction and led to -substituted acridones. Key products have been characterized by single-crystal X-ray crystallography.

  3. Antileishmanial and antifungal acridone derivatives from the roots of Thamnosma rhodesica.

    Ahua, Kouassi Maximin; Ioset, Jean-Robert; Ransijn, Adriana; Mauël, Jacques; Mavi, Steven; Hostettmann, Kurt

    2004-04-01

    Eight furanocoumarins, one coumarin and four acridone derivatives have been identified in the roots of Thamnosma rhodesica (Rutaceae). Rhodesiacridone, one of these acridone derivatives, is reported here for the first time. Its structure was elucidated by spectrometric methods including ESI-HR, EI, DCI mass spectrometry, 1H, 13C and 2D NMR experiments. This novel compound showed activities against the intracellular form of a human pathogen, the protozoan parasite Leishmania major. Two known acridone related compounds, gravacridonediol and 1-hydroxy-10-methylacridone, exhibited activities against the intracellular form of the same parasite and the fungus Cladosporium cucumerinum, respectively. PMID:15081302

  4. Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr

    Eleven acridone alkaloids isolated from Swinglea glutinosa (Bl.) Merr. were examined for in vitro activity against chloroquine-sensitive Plasmodium falciparum 3D7, Trypanosoma brucei rhodesiense STIB900 and Leishmania donovani L82. An assay with KB cells was developed in order to compare in vitro toxicity of alkaloids with the selective action on the parasites. Nine of the compounds had IC50 values ranging from 0.3 to 11.6 μM against P. falciparum. In contrast, a small number of compounds showed significant activity against T. brucei rhodesiense and none had activity against L. donovani. Among the alkaloids three had IC50 50 < 10 μM. The characterization of the acridone alkaloids, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9 (10H)-one (1), 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methylfuro [3,2-b] acridin-5(10H)-one (2) and 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[ 2,3-a]acridin-12(7H)-one (3), is discussed, as well as the structure-activity relationship of all compounds assayed. Isolation and spectral data of alkaloids 1-3 are described for the first time although their cytotoxicities to cancer cells have been described before. (author)

  5. Acridone alkaloids as potent inhibitors of cathepsin V.

    Severino, Richele P; Guido, Rafael V C; Marques, Emerson F; Brömme, Dieter; da Silva, M Fátima das G F; Fernandes, João B; Andricopulo, Adriano D; Vieira, Paulo C

    2011-02-15

    Cathepsin V is a lysosomal cysteine peptidase highly expressed in thymus, testis and corneal epithelium. Eleven acridone alkaloids were isolated from Swinglea glutinosa (Bl.) Merr. (Rutaceae), with eight of them being identified as potent and reversible inhibitors of cathepsin V (IC(50) values ranging from 1.2 to 3.9 μM). Detailed mechanistic characterization of the effects of these compounds on the cathepsin V-catalyzed reaction showed clear competitive inhibition with respect to substrate, with dissociation constants (K(i)) in the low micromolar range (2, K(i)=1.2 μM; 6, K(i)=1.0 μM; 7, K(i)=0.2 μM; and 11, K(i)=1.7 μM). Molecular modeling studies provided important insight into the structural basis for binding affinity and enzyme inhibition. Experimental and computational approaches, including biological evaluation, mode of action assessment and modeling studies were successfully employed in the discovery of a small series of acridone alkaloid derivatives as competitive inhibitors of catV. The most potent inhibitor (7) has a K(i) value of 200 nM. PMID:21277783

  6. Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylum species

    Wouatsa, Vyry NA; Misra, Laxminarain; Kumar, Shiv; Prakash, Om; Khan, Feroz; Tchoumbougnang, Francois; Venkatesh, R Kumar

    2013-01-01

    Background Zanthoxylum zanthoxyloides and Z. leprieurii fruits are commonly used in traditional system of medicine for diarrhea, pain, wound healing, etc. in Cameroon, Africa. Z. leprieurii fruits have been chemically studied for its bioactive compounds whereas the investigation on Z. zanthoxyloides fruits is lacking. Results After a detailed chemical analysis of the fruits of Z. leprieurii and Z. zanthoxyloides, a series of new acridone alkaloids, namely, 3-hydroxy-1,5,6-trimethoxy-9-acridon...

  7. Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr

    Santos, Djalma A.P. dos; Vieira, Paulo C.; Silva, M. Fatima das G.F. da; Fernandes, Joao B. [Universidade Federal de Sao Carlos, SP (Brazil). Dept. de Quimica; Rattray, Lauren; Croft, Simon L. [London School of Hygiene and Tropical Medicine, London (United Kingdom). Dept. of Infectious and Tropical Diseases

    2009-07-01

    Eleven acridone alkaloids isolated from Swinglea glutinosa (Bl.) Merr. were examined for in vitro activity against chloroquine-sensitive Plasmodium falciparum 3D7, Trypanosoma brucei rhodesiense STIB900 and Leishmania donovani L82. An assay with KB cells was developed in order to compare in vitro toxicity of alkaloids with the selective action on the parasites. Nine of the compounds had IC{sub 50} values ranging from 0.3 to 11.6 {mu}M against P. falciparum. In contrast, a small number of compounds showed significant activity against T. brucei rhodesiense and none had activity against L. donovani. Among the alkaloids three had IC{sub 50} < 1.0 {mu}M against P. falciparum, whereas against T. b. rhodesiense five had IC{sub 50} < 10 {mu}M. The characterization of the acridone alkaloids, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9 (10H)-one (1), 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methylfuro [3,2-b] acridin-5(10H)-one (2) and 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[ 2,3-a]acridin-12(7H)-one (3), is discussed, as well as the structure-activity relationship of all compounds assayed. Isolation and spectral data of alkaloids 1-3 are described for the first time although their cytotoxicities to cancer cells have been described before. (author)

  8. Synthesis of a Fluorescent Acridone Using a Grignard Addition, Oxidation, and Nucleophilic Aromatic Substitution Reaction Sequence

    Goodrich, Samuel; Patel, Miloni; Woydziak, Zachary R.

    2015-01-01

    A three-pot synthesis oriented for an undergraduate organic chemistry laboratory was developed to construct a fluorescent acridone molecule. This laboratory experiment utilizes Grignard addition to an aldehyde, alcohol oxidation, and iterative nucleophilic aromatic substitution steps to produce the final product. Each of the intermediates and the…

  9. In vitro cytotoxic activity of isolated acridones alkaloids from Zanthoxylum leprieurii Guill. et Perr.

    Ngoumfo, Rostand M; Jouda, Jean-Bosco; Mouafo, Ferdinand T; Komguem, Justin; Mbazoa, Céline D; Shiao, Tze Chieh; Choudhary, Mohammed I; Laatsch, Hartmut; Legault, Jean; Pichette, André; Roy, René

    2010-05-15

    Chemical investigation of the roots and fruits of Zanthoxylumleprieurii Guill. et Perr. led to the isolation of three new alkaloids including two acridone derivatives, 3-hydroxy-1,4-dimethoxy-10-methyl-9-acridone (2) and 3-hydroxy-1,2-dimethoxy-10-methyl-9-acridone (3) named helebelicine A and B, respectively, and one secobenzo[c]phenantridine, 10-O-demethyl-12-O-methylarnottianamide (10), together with thirteen other compounds. The structures of compounds 2, 3 and 10 as well as those of the known compounds were elucidated by using spectroscopic methods and by comparison with reported data. The brine-shrimp (artemia salina) lethality bioassay of the chloroform extract of the fruits showed modest cytotoxicity with LD(50) at 13.1microg/mL. Isolated compounds 1, 4-6 were found to be moderately active against lung carcinoma cells (A549), colorectal adenocarcinoma cells (DLD-1) and normal cells (WS1) with IC(50) values ranging from 27 to 77microM. In contrast to the positive control etoposide used, the cytotoxicity of the most active compound 4 was found to be selective against cancer cells in comparison to normal cells WS1 with IC(50) of 51+/-8microM and 4.3+/-0.4microM, respectively. PMID:20413315

  10. Crystallization and preliminary crystallographic analysis of an acridone-producing novel multifunctional type III polyketide synthase from Huperzia serrata

    An acridone-producing novel type III polyketide synthase from H. serrata has been overexpressed in E. coli, purified and crystallized. Diffraction data have been collected to 2.0 Å. Polyketide synthase 1 (PKS1) from Huperzia serrata is a plant-specific type III polyketide synthase that shows an unusually versatile catalytic potential, producing various aromatic tetraketides, including chalcones, benzophenones, phlorogulucinols and acridones. Recombinant H. serrata PKS1 expressed in Escherichia coli was crystallized using the hanging-drop vapour-diffusion method. The crystals belonged to space group I222 or I212121, with unit-cell parameters a = 73.3, b = 85.0, c = 137.7 Å, α = β = γ = 90.0°. Diffraction data were collected to 2.0 Å resolution using synchrotron radiation at BL24XU of SPring-8

  11. Acridone Alkaloids from Swinglea glutinosa (Rutaceae) and Their Effects on Photosynthesis.

    Arato Ferreira, Pedro H; Dos Santos, Djalma A P; da Silva, Maria Fátima das G F; Vieira, Paulo C; King-Diaz, Beatriz; Lotina-Hennsen, Blas; Veiga, Thiago A M

    2016-01-01

    Continuing our search for herbicide models based on natural products, we investigated the action mechanisms of five alkaloids isolated from Swinglea glutinosa (Rutaceae): Citrusinine-I (1), glycocitrine-IV (2), 1,3,5-trihydroxy-10-methyl- 2,8-bis(3-methylbut-2-en-1-yl)-9(10H)-acridinone (3), (2R)-2-tert-butyl-3,10-dihydro-4,9-dihydroxy-11-methoxy-10-methylfuro[3,2-b]acridin-5(2H)-one (4), and (3R)-2,3,4,7-tetrahydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-12H-pyrano[2,3-a]acridin-12-one (5) on several photosynthetic activities in an attempt to find new compounds that affect photosynthesis. Through polarographic techniques, the compounds inhibited the non-cyclic electron transport in the basal, phosphorylating, and uncoupled conditions from H2 O to methylviologen (=MV). Therefore, they act as Hill reaction inhibitors. This approach still suggested that the compounds 4 and 5 had their interaction site located at photosystem I. Studies on fluorescence of chlorophyll a suggested that acridones (1-3) have different modes of interaction and inhibition sites on the photosystem II electron transport chain. PMID:26765357

  12. In vitro cytotoxicity activity on several cancer cell lines of acridone alkaloids and N-phenylethyl-benzamide derivatives from Swinglea glutinosa (Bl.) Merr.

    Braga, P A C; Dos Santos, D A P; Da Silva, M F D G F; Vieira, P C; Fernandes, J B; Houghton, P J; Fang, R

    2007-01-01

    The methanol extract from the stems and fruits of Swinglea glutinosa (Rutaceae) afforded 11 known acridone alkaloids and three N-phenylethyl-benzamide derivatives, glycocitrine-IV, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9(10H)-one, 1,3,5- trihydroxy-2,8-bis(3-methylbut-2-enyl)-10-methyl-9-acridone, citbrasine, citrusinine-II, citrusinine-I, 5-dihydroxyacronycine, pyranofoline, 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2H-pyrano[2,3-a]acridin-12(7H)-one, 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxy-propan-2-yl)-11-methoxy-10-methylfuro[3,2-b]acridin-5(10H)-one, bis-5-hydroxyacronycine, N-(2-{4-[(3,7-dimethylocta-2,6-dien-1-yl)oxy]phenyl}ethyl)benzamide, N-(2-{4-[(3,7-dimethyl-4-acethyl-octa-2,6-dien-1-yl)oxy]phenyl}ethyl)benzamide, and severine acetate. All compounds isolated were examined for their activity against three cancer cell lines: human lung carcinoma (COR-L23), human breast adenocarcinoma (MCF7), human melanoma (C32), and normal human fetal lung cell line, MRC-5. The acridones tested exhibited weak cytotoxicity but the amides showed moderate nonselective cytotoxic activity. PMID:17365689

  13. Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1,2,4-oxadiazoles as potential anticonvulsant agents.

    Mohammadi-Khanaposhtani, Maryam; Shabani, Mohammad; Faizi, Mehrdad; Aghaei, Iraj; Jahani, Reza; Sharafi, Zainab; Shamsaei Zafarghandi, Narges; Mahdavi, Mohammad; Akbarzadeh, Tahmineh; Emami, Saeed; Shafiee, Abbas; Foroumadi, Alireza

    2016-04-13

    A number of acridone-based oxadiazoles 11a-n have been synthesized and evaluated for their anticonvulsant activity against pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. Also, their neurotoxicity was evaluated by the rotarod test. Most of the compounds exhibited better anticonvulsant activity and higher safety respect to the standard drug, phenobarbital. Among the tested derivatives, compounds 11l with ED50 value of 2.08 mg/kg was the most potent compound in the PTZ test. The anticonvulsant effect of compound 11l was blocked by flumazenil, suggesting the involvement of benzodiazepine (BZD) receptors in the anticonvulsant activity of prototype compound 11l. Also, docking study of compound 11l in the BZD-binding site of GABAA receptor confirms possible binding of compound 11l with BZD receptors. PMID:26890115

  14. Novel acridone-modified MCM-41 type silica: Synthesis, characterization and fluorescence tuning

    Maximilian Hemgesberg

    2011-06-01

    Full Text Available A Mobil Composition of Matter (MCM-41 type mesoporous silica material containing N-propylacridone groups has been successfully prepared by co-condensation of an appropriate organic precursor with tetraethyl orthosilicate (TEOS under alkaline sol–gel conditions. The resulting material was fully characterized by means of X-ray diffraction (XRD, N2-adsorption–desorption, transmission electron microscopy (TEM, IR and UV–vis spectroscopy, as well as 29Si and 13C CP-MAS NMR techniques. The material features a high inner surface area and a highly ordered two-dimensional hexagonal pore structure. The fluorescence properties of the organic chromophore can be tuned via complexation of its carbonyl group with scandium triflate, which makes the material a good candidate for solid state sensors and optics. The successful synthesis of highly ordered MCM materials through co-condensation was found to be dependent on the chemical interaction of the different precursors.

  15. CHEMISTRY OF BIOACTIVE TRICYCLIC FUSED HETEROCYCLIC RING HAVING ONE HETEROATOM

    Palak K. Parikh

    2011-06-01

    Full Text Available Acridones are well known and important heterocyclic compounds with a tricyclic ring having nitrogen at 10th position and keto group at 9th position. Numerous acridone derivatives have been found to possess considerable biological activities, which stimulated the research activity in this field. They have several prominent effects, such as antimicrobial, antimalarial, antifungal, antileishmanial, antiviral and anticancer activities. The planar structure of these acridones facilitates to act on nucleotides by intercalating DNA and RNA strands, there by emerging as potent anticancer agents. The present review provides an insight view to acridone synthesis and its biological activities along with the compilation of recent patents on pyrazolines.

  16. Phytochemical and chemosystematic studies of Conchocarpus marginatus and C. inopinatus (Rutaceae); Fitoquimica e quimiossistematica de Conchocarpus marginatus e C. inopinatus (Rutaceae)

    Bellete, Barbara Sayuri; Sa, Israel Civico Gil de; Mafezoli, Jair; Cerqueira, Cristovam do Nascimento; Silva, Maria Fatima das Gracas Fernandes da; Fernandes, Joao Batista; Vieira, Paulo Cezar; Zukerman-Schpector, Julio [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Pirani, Jose Rubens, E-mail: dmfs@ufscar.br [Universidade de Sao Paulo (USP), Sao Paulo, SP (Brazil). Inst. de Biociencias

    2012-07-01

    Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methylarborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H)-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H)-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus. (author)

  17. Scintillator material

    A scintillator material for detection and quantitative determination of ionizing radiation is discussed consisting of an acridone dissolved in a fluid or solid medium. Solvent mixtures with at least one protogenic component or polymers and copolymers are used. The scintillator material is distinguished by an excellent stability at high energy doses

  18. ALCALOIDES ACRIDÔNICOS INIBEM CATEPSINA L E V

    Emerson F. Marques

    2016-01-01

    Full Text Available Cathepsins represent a class of enzymes that has the primary function of randomly degrading proteins in the lysosomes, although are also involved in different pathologies. The aim of this paper was to evaluate the capacity of acridone alkaloids isolated from Swinglea glutinosa (Rutaceae to inhibit cathepsin L in vitro . The IC50 values found were in the 0.8-57 µM range and the most promising compounds were alkaloids 1 and 2, with IC50 of 0.9 and 0.8 µM, respectively. Enzyme kinetics revealed that they are reversible competitive inhibitors with respect to the substrate Z-FR-MCA. This small series of acridone alkaloids showed low selectivity for both cathepsins, but represent promising lead candidates for the further development of competitive cathepsin L and V inhibitors.

  19. A comparison of chemiluminescent acridinium dimethylphenyl ester labels with different conjugation sites.

    Natrajan, Anand; Wen, David

    2015-03-01

    Chemiluminescent acridinium dimethylphenyl esters are highly sensitive labels that are used in automated assays for clinical diagnosis. Light emission from these labels and their conjugates is triggered by treatment with alkaline peroxide. Conjugation of acridinium ester labels is normally done at the phenol. During the chemiluminescent reaction of these acridinium esters, the phenolic ester is cleaved and the light emitting acridone moiety is liberated from its conjugate partner. In the current study, we report the synthesis of three new acridinium esters with conjugation sites at the acridinium nitrogen and compare their properties with that of a conventional acridinium ester with a conjugation site at the phenol. Our study is the first that provides a direct comparison of the emissive properties of acridinium dimethylphenyl esters (free labels and protein conjugates) with different conjugation sites, one where the light emitting acridone remains attached to its conjugate partner versus conventional labeling which results in cleavage of the acridone from the conjugate. Our results indicate that the conjugation at the acridinium nitrogen, which also alters how the acridinium ring and phenol are oriented with respect to the protein surface, has a minimal impact on emission kinetics and emission spectra. However, this mode of conjugation to three different proteins led to a significant increase in light yield which should be useful for improving the assay sensitivity. PMID:25581208

  20. Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides.

    Dembitsky, Valery M

    2005-11-01

    This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided into several groups, including: acridone; aporphine; benzoxazinoid; ergot; indole; enediyne alkaloidal antibiotics; glycosidic lupine alkaloids; piperidine, pyridine, pyrrolidine, and pyrrolizidine alkaloid glycosides; glycosidic quinoline and isoquinoline alkaloids; steroidal glycoalkaloids; and miscellaneous alkaloid glycosides. PMID:16459921

  1. ALCALOIDES ACRIDÔNICOS INIBEM CATEPSINA L E V

    Emerson F. Marques; Vieira, Paulo C.; Richele P. Severino

    2016-01-01

    Cathepsins represent a class of enzymes that has the primary function of randomly degrading proteins in the lysosomes, although are also involved in different pathologies. The aim of this paper was to evaluate the capacity of acridone alkaloids isolated from Swinglea glutinosa (Rutaceae) to inhibit cathepsin L in vitro . The IC50 values found were in the 0.8-57 µM range and the most promising compounds were alkaloids 1 and 2, with IC50 of 0.9 and 0.8 µM, respectively. Enzyme kinetics revealed...

  2. Role of quinacrine in prion diseases

    Šafařík, Martin; Moško, T.; Zawada, Zbigniew; Dvořáková, E.; Holada, K.; Šebestík, Jaroslav

    Sofia : Bulgarian Peptide Society, 2015 - (Naydenova, E.; Pajpanova, T.; Danalev, D.), s. 18-20 ISBN 978-619-90427-2-4. [Peptides 2014. European Peptide Symposium /33./. Sofia (BG), 31.08.2014-05.09.2014] R&D Projects: GA ČR(CZ) GA14-00431S Grant ostatní: GA ČR(CZ) GAP303/12/1791 Institutional support: RVO:61388963 Keywords : prions * quinacrine * glutathione * acridones * stability Subject RIV: CC - Organic Chemistry http://bulpepsoc.info/wp-content/uploads/2015/06/PEPTIDES-2014-electronic-version.pdf

  3. Rapid analysis of biogenic amines from rice wine with isotope-coded derivatization followed by high performance liquid chromatography-tandem mass spectrometry.

    Cai, Yiping; Sun, Zhiwei; Chen, Guang; Liu, Xiaomei; You, Jinmao; Zhang, Caiqing

    2016-02-01

    A pair of isotope-coded derivatization reagents, d0-10-methyl-acridone-2-sulfonyl chloride (d0-MASC, light form) and d3-10-methyl-acridone-2-sulfonyl chloride (d3-MASC, heavy form), were used for labeling biogenic amines (BAs). On basis of the isotope-coded derivatization, a global isotope internal standard quantitative method for determining seven BAs by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) was developed. The d0-MASC and d3-MASC can easily label BAs under mild conditions within 15 min at 50 °C. The obtained light and heavy labeled BAs were monitored by the transitions of [M+H](+) → 208 and [M+H](+) → 211, respectively. Relative quantification of BAs was achieved by calculation of the peak area ratios of d0-MASC/d3-MASC labeled derivatives. Excellent linear responses for relative quantification were observed in the range of 1/10-10/1. The developed method has been successfully applied to the quantification of BAs in Chinese rice wine with recoveries ranging from 94.9% to 104.5%. PMID:26304364

  4. Chemiluminescence accompanied by the reaction of acridinium ester and manganese (II).

    Ren, Lingling; Cui, Hua

    2014-11-01

    An acridinium ester (AE) alkaline solution can react with Mn(II) to generate a strong chemiluminescence (CL) centered at 435 nm. The effects of reaction conditions such as pH and Mn(II) concentration on CL intensity were examined. In order to explore the CL mechanism, the effect of oxygen on the CL reaction was examined and an X-ray photoelectron spectroscopy study of the reaction precipitate was carried out. The results indicated that oxygen participated in the CL reaction and Mn(IV) was the primary product in the system. A possible mechanism was proposed that involved two pathways: (1) dissolved oxygen was reduced to reactive oxygen radicals by Mn(II), these reactive intermediates then reacted with AE to produce excited state acridone; (2) Mn(II) could reduce AE to partly reduced AE, which then reacted with oxygen to form excited state acridone. The reactions of other metal ions with AE were also tested, and only Mn(II) was shown to trigger strong CL emission of AE, which indicated that the system had good selectivity for Mn(II). PMID:24677387

  5. Evaluation of new iodinated acridine derivatives for targeted radionuclide therapy of melanoma using 125I, an Auger electron emitter.

    Gardette, Maryline; Papon, Janine; Bonnet, Mathilde; Desbois, Nicolas; Labarre, Pierre; Wu, Ting-Dee; Miot-Noirault, Elisabeth; Madelmont, Jean-Claude; Guerquin-Kern, Jean-Luc; Chezal, Jean-Michel; Moins, Nicole

    2011-12-01

    The increasing incidence of melanoma and the lack of effective therapy on the disseminated form have led to an urgent need for new specific therapies. Several iodobenzamides or analogs are known to possess specific affinity for melanoma tissue. New heteroaromatic derivatives have been designed with a cytotoxic moiety and termed DNA intercalating agents. These compounds could be applied in targeted radionuclide therapy using (125)I, which emits Auger electrons and gives high-energy, localized irradiation. Two iodinated acridine derivatives have been reported to present an in vivo kinetic profile conducive to application in targeted radionuclide therapy. The aim of the present study was to perform a preclinical evaluation of these compounds. The DNA intercalating property was confirmed for both compounds. After radiolabeling with (125)I, the two compounds induced in vitro a significant radiotoxicity to B16F0 melanoma cells. Nevertheless, the acridine compound appeared more radiotoxic than the acridone compound. While cellular uptake was similar for both compounds, SIMS analysis and in vitro protocol showed a stronger affinity for melanin with acridone derivative, which was able to induce a predominant scavenging process in the melanosome and restrict access to the nucleus. In conclusion, the acridine derivative with a higher nuclear localization appeared a better candidate for application in targeted radionuclide therapy using (125)I. PMID:20567996

  6. Fate of Carbamazepine during Water Treatment

    Kosjek, T.; Andersen, Henrik Rasmus; Kompare, Boris; Ledin, Anna; Heath, E.

    2009-01-01

    Seven transformation products of carbamazepine generated by at least one of three common water treatment technologies (W-radiation, oxidation with chlorine dioxide (ClO2), and biological treatment with activated Sludge) were identified by complementary use of ion trap, single quadrupole, and...... quadrupole-time-of-flight mass spectrometers. Acridine was formed during all of the three treatment processes, while acridine 9-carbaldehyde was identified as an intermediate during ClO2 oxidation. Further treatment of acridine with ClO2 produced 9-hydroxy-acridine, UV-treatment resulted in the formation of...... compared the treatment technologies according to the removal of carbamazepine and the production and decay of its transformation products. The most successful method for the removal of carbamazepine was UV treatment, while acridine and acridone were more susceptible to biological treatment. Therefore...

  7. Ecotoxicity of carbamazepine and its UV photolysis transformation products

    Donner, E.; Kosjek, T.; Qualmann, Signe;

    2013-01-01

    considerably more toxic than carbamazepine itself may be produced during UV-treatment of wastewater effluents and/or photo-induced degradation of carbamazepine in natural waters. This study highlights the need to consider mixture toxicity and the formation and persistence of toxicologically relevant......Carbamazepine, an anti-epileptic pharmaceutical agent commonly found in wastewater, is highly recalcitrant to standard wastewater treatment practices. This study investigated the mixture toxicity of carbamazepine transformation products formed during ultraviolet (UV) photolysis using three standard...... treatment period, together with concurrent increases in acridine and acridone concentrations. Ecotoxicity was shown to increase in parallel with carbamazepine degradation indicating that the mixture of degradation products formed was more toxic than the parent compound, and all three ecotoxicity endpoints...

  8. Algicide constituents from Swinglea glutinosa.

    Purcaro, Raffaella; Schrader, Kevin K; Burandt, Charles; DellaGreca, Marina; Meepagala, Kumudini M

    2009-11-25

    Oscillatoria perornata, a cyanobacterium (blue-green alga), common in catfish production ponds in the southeastern United States, produces the monoterpene 2-methylisoborneol (MIB), which is absorbed into catfish flesh and imparts a "musty" taste, rendering them unpalatable and unmarketable. Algicides that are currently in the commercial market to control O. perornata have broad-spectrum toxicity toward other beneficial phytoplankton, such as the green alga Selenastrum capricornutum, as well as low biodegradability. As part of our continuing efforts to search for natural-product-based algicides, the ethyl acetate extract of the roots of Swinglea glutinosa was investigated. This report describes isolation and structure elucidation of one novel coumarin, two known coumarins, and nine acridone alkaloids from S. glutinosa root extracts and the evaluation of these compounds for algicidal activity against O. perornata. PMID:19877680

  9. Synthesis, cytotoxic study and docking based multidrug resistance modulator potential analysis of 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamides.

    Kumar, Rajesh; Kaur, Maninder; Bahia, Malkeet Singh; Silakari, Om

    2014-06-10

    The present study describes the synthesis of fifteen 2-(9-oxoacridin-10(9H)-yl)-N-phenyl acetamide derivatives (13a-o) through condensation of 2-chloro-N-phenyl acetamides (12a-o) with acridone molecule (10). All the synthesized compounds were screened for their anti-cancer activity against three diverse cell lines including breast (MCF-7), cervical (HeLa) and lung adenocarcinoma (A-549) employing standard MTT assay. Among synthesized molecules, 13k and 13l showed good cytotoxicity activity against considered three cancer cell lines. Additionally, in silico studies of multidrug resistance modulator (MDR) effects of these compounds was performed by docking simulation in the ATP binding site of P-gp. The results of docking simulation displayed important interactions of these molecules in the active site of this protein and predicted their MDR modulator behavior. PMID:24769346

  10. De Novo transcriptome assembly (NGS of Curcuma longa L. rhizome reveals novel transcripts related to anticancer and antimalarial terpenoids.

    Ramasamy S Annadurai

    Full Text Available Herbal remedies are increasingly being recognised in recent years as alternative medicine for a number of diseases including cancer. Curcuma longa L., commonly known as turmeric is used as a culinary spice in India and in many Asian countries has been attributed to lower incidences of gastrointestinal cancers. Curcumin, a secondary metabolite isolated from the rhizomes of this plant has been shown to have significant anticancer properties, in addition to antimalarial and antioxidant effects. We sequenced the transcriptome of the rhizome of the 3 varieties of Curcuma longa L. using Illumina reversible dye terminator sequencing followed by de novo transcriptome assembly. Multiple databases were used to obtain a comprehensive annotation and the transcripts were functionally classified using GO, KOG and PlantCyc. Special emphasis was given for annotating the secondary metabolite pathways and terpenoid biosynthesis pathways. We report for the first time, the presence of transcripts related to biosynthetic pathways of several anti-cancer compounds like taxol, curcumin, and vinblastine in addition to anti-malarial compounds like artemisinin and acridone alkaloids, emphasizing turmeric's importance as a highly potent phytochemical. Our data not only provides molecular signatures for several terpenoids but also a comprehensive molecular resource for facilitating deeper insights into the transcriptome of C. longa.

  11. Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

    Louis P. Sandjo

    2015-09-01

    Full Text Available This review focuses on pyridoacridine-related metabolites as one biologically interesting group of alkaloids identified from marine sources. They are produced by marine sponges, ascidians and tunicates, and they are structurally comprised of four to eight fused rings including heterocycles. Acridine, acridone, dihydroacridine, and quinolone cores are features regularly found in these alkaloid skeletons. The lack of hydrogen atoms next to quaternary carbon atoms for two or three rings makes the chemical shift assignment a difficult task. In this regard, one of the aims of this review is the compilation of previously reported, pyridoacridine 13C NMR data. Observations have been made on the delocalization of electrons and the presence of some functional groups that lead to changes in the chemical shift of some carbon resonances. The lack of mass spectra information for these alkaloids due to the compactness of their structures is further discussed. Moreover, the biosynthetic pathways of some of these metabolites have been shown since they could inspire biomimetic synthesis. The synthesis routes used to prepare members of these marine alkaloids (as well as their analogues, which are synthesized for biological purposes are also discussed. Pyridoacridines were found to have a large spectrum of bioactivity and this review highlights and compares the pharmacophores that are responsible for the observed bioactivity.

  12. Synthesis and Evaluation of a Library of Fluorescent Dipeptidomimetic Analogues as Substrates for Modified Bacterial Ribosomes.

    Chowdhury, Sandipan Roy; Chauhan, Pradeep S; Dedkova, Larisa M; Bai, Xiaoguang; Chen, Shengxi; Talukder, Poulami; Hecht, Sidney M

    2016-05-01

    Described herein are the synthesis and photophysical characterization of a library of aryl-substituted oxazole- and thiazole-based dipeptidomimetic analogues, and their incorporation into position 66 of green fluorescent protein (GFP) in lieu of the natural fluorophore. These fluorescent analogues resemble the fluorophore formed naturally by GFP. As anticipated, the photophysical properties of the analogues varied as a function of the substituents at the para position of the phenyl ring. The fluorescence emission wavelength maxima of compounds in the library varied from ∼365 nm (near-UV region) to ∼490 nm (visible region). The compounds also exhibited a large range of quantum yields (0.01-0.92). The analogues were used to activate a suppressor tRNACUA and were incorporated into position 66 of GFP using an in vitro protein biosynthesizing system that employed engineered ribosomes selected for their ability to incorporate dipeptides. Four analogues with interesting photophysical properties and reasonable suppression yields were chosen, and the fluorescent proteins (FPs) containing these fluorophores were prepared on a larger scale for more detailed study. When the FPs were compared with the respective aminoacyl-tRNAs and the actual dipeptide analogues, the FPs exhibited significantly enhanced fluorescence intensities at the same concentrations. Part of this was shown to be due to the presence of the fluorophores as an intrinsic element of the protein backbone. There were also characteristic shifts in the emission maxima, indicating the environmental sensitivity of these probes. Acridon-2-ylalanine and oxazole 1a were incorporated into positions 39 and 66 of GFP, respectively, and were shown to form an efficient Förster resonance energy transfer (FRET) pair, demonstrating that the analogues can be used as FRET probes. PMID:27050631

  13. Evaluation of new iodinated acridine derivatives for targeted radionuclide therapy of melanoma using 125I, an Auger electron emitter

    The full text of the publication follows. The increasing incidence of melanoma and the lack of effective therapy on the disseminated form have led to an urgent need for new specific therapies. Several iodo-benzamides or analogs are known to possess specific affinity for melanoma tissue. New hetero-aromatic derivatives have been designed with a cytotoxic moiety and termed DNA intercalating agents. These compounds could be applied in targeted radionuclide therapy using 125I, Auger electrons emitter which gives high-energetic localized irradiation. Two iodinated acridine derivatives have been reported to present an in vivo kinetic profile conducive to application in targeted radionuclide therapy. The aim of the present study was to perform a preclinical evaluation of these compounds. The DNA intercalating property was confirmed for both compounds. After radiolabeling with 125I, the two compounds induced in vitro a significant radiotoxicity on B16F0 melanoma cells. The acridine compound, ICF01040, appeared more radio toxic than the acridone compound, ICF01035. While cellular uptake was similar for both compounds, SIMS analysis and in vitro protocol showed a stronger affinity for melanin with ICF01035, which was able to induce a predominant scavenging process in the melanosome and restrict access to the nucleus. Nevertheless, an important radiotoxicity was measured for the two compounds while the nuclear accumulation was low. Indeed, even if nuclear localization remains the main target sensitive to Auger electrons, the cell membrane remains sensitive to 125I decays. So, these compounds may induce secondary toxic effects of irradiation, such as membrane lipid damage. Conducted to current experiments are evaluate such hypothesis. Taken together, these results suggest that ICF01040 is a better candidate for application in targeted radionuclide therapy using 125I. The next step will be in vivo evaluation, where high tumoral vectorization gives promising perspectives