Synthesis and antiproliferative activity of 1-methoxy-, 1-(α-D-ribofuranosyl)- and 1-(β-D-ribofuranosyl)brassenin B

Čurillová, Zuzana; Kutschy, Peter; Solčániová, Eva; Pilátová, Martina; Mojzis, J; Kováčik, and Vladimír

doi:10.3998/ark.5550190.0009.809

Arkivoc

2008

DOI: 10.3998/ark.5550190.0009.809

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Synthesis and antiproliferative activity of 1-methoxy-, 1-(α-D-ribofuranosyl)- and 1-(β-D-ribofuranosyl)brassenin B

Zuzana Čurillová¹,

Peter Kutschy²,

Eva Solčániová³

et al.

Abstract: Syntheses of indole phytoalexin 1-methoxybrassenin B and a linear synthesis of its nucleoside analogs 1-(α-D-ribofuranosyl)brassenin B and 1-(β-D-ribofuranosyl)brassenin B are reported from the corresponding 1-substituted indole-3-carboxaldehydes and carboxylic acids as key intermediates. Examination of the antiproliferative activity of synthesized compounds on human tumor cell lines Jurkat, CEM, CEM-VCR, MCF-7 and HeLa revealed the highest activity for 1-methoxybrassenin B, whereas activity of the nucleoside … Show more

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Cited by 5 publications

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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Substitution at the indole 3 position yields highly potent indolecombretastatins against human tumor cells

Álvarez

Gajate

Puebla

et al. 2018

European Journal of Medicinal Chemistry

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Resistance to combretastatin A-4 is mediated by metabolic modification of the phenolic hydroxyl and ether groups of the 3-hydroxy-4-methoxyphenyl (B ring). Replacement of the B ring of combretastatin A-4 by a N-methyl-5-indolyl reduces tubulin polymerization inhibition (TPI) and cytotoxicity against human cancer cell lines but cyano, methoxycarbonyl, formyl, and hydroxyiminomethyl substitutions at the indole 3-position restores potent TPI and cytotoxicity against sensitive human cancer cell lines. These highly potent substituted derivatives displayed low nanomolar cytotoxicity against several human cancer cell lines due to tubulin inhibition, as shown by cell cycle analysis, confocal microscopy, and tubulin polymerization inhibitory activity studies, and promoted cell killing mediated by caspase-3 activation. Binding at the colchicine site was suggested by molecular modeling studies. Substituted combretastatins displayed higher potencies than the isomeric isocombretastatins and the highest potencies were achieved for the hydroxyiminomethyl (21) and cyano (23) groups, with TPI values in the submicromolar range and cytotoxicities in the nanomolar and subnanomolar range. Dose-response and time-course studies showed that drug concentrations as low as 1 nM (23) or 10 nM (21) led to a complete G/M cell cycle arrest after 15 h treatment followed by a high apoptosis-like cell response after 48-72 h treatment. The P-glycoprotein antagonist verapamil increased 21 and 23 cytotoxicity to IC values of 10 M, and highly potentiated the cytotoxic activity in 100-fold of the CHO derivative (17), in A-549 human non-small cell lung cancer cells. The cyano substituted indolecombretastatin 23 is by itself highly potent against rather resistant HT-29 and A-549 cell lines. A 3,4,5-trimethoxyphenyl ring always afforded more potent derivatives than a 2,3,4-trimethoxyphenyl ring.

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Glyoxyl analogs of indole phytoalexins: Synthesis and anticancer activity

Kutschy

Sykora

Čurillová

et al. 2010

Collect. Czech. Chem. Commun.

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Glyoxyl analogs of indole phytoalexins brassinin, 1-methoxybrassinin, brassitin, 1-methoxybrassitin and 1-methoxybrassenin B were prepared, using (1H-indol-3-yl)-, (1-methoxyindol-3-yl)- and [1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl]glyoxyl chlorides as starting compounds. Synthesized products were examined for their antiproliferative activity against human cancer cell lines Jurkat (T-cell acute lymphoblastic leukemia), MCF-7 (breast adenocarcinoma, estrogen receptor-positive), MDA-MB-231 (breast adenocarcinoma, estrogen receptor-negative), HeLa (cervical adenocarcinoma), CCRF-CEM cell line (T-cell acute lymphoblastic leukemia) and A-549 cell line (lung adenocarcinoma), and their activity compared with natural phytoalexins and corresponding (1H-indol-3-yl)acetic acid derivatives. The highest potency with IC50 3.3–66.1 μmol l–1 was found for glyoxyl analogs of 1-methoxybrassenin B.

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Synthesis and antiproliferative activity of 1-methoxy-, 1-(α-D-ribofuranosyl)- and 1-(β-D-ribofuranosyl)brassenin B

Cited by 5 publications

References 10 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Substitution at the indole 3 position yields highly potent indolecombretastatins against human tumor cells

Glyoxyl analogs of indole phytoalexins: Synthesis and anticancer activity

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