Literature DB >> 17608396

New analogues of the potent cytotoxic saponin OSW-1.

Agnieszka Wojtkielewicz1, Maciej Długosz, Jadwiga Maj, Jacek W Morzycki, Michał Nowakowski, Joanna Renkiewicz, Miroslav Strnad, Jana Swaczynová, Agnieszka Z Wilczewska, Jacek Wójcik.   

Abstract

Saponin OSW-1 (5e-G2; 3 beta,16 beta,17 alpha-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-beta-D-xylopyranosyl]-(1-->3)-2-O-acetyl-alpha-arabinopyranoside}) analogues: with modified side chain (5a/d-G2), 22-deoxo-23,24,25,26,27-pentanor- (14), 22-deoxo-23-oxa- (17), glycosylated with various monosaccharides (5e-G4/G6/G8), and OSW-1 structural isomer (10) were obtained. The analogues were synthesized using a previously published method for the synthesis of OSW-1. The structures of analogues were fully confirmed by spectroscopic methods, and the S-chirality at C-22 of the structural isomer was established by conformational analysis combined with the NMR spectrometry. The cytotoxicity of the analogues toward several types of malignant tumor cells was examined and compared with that of OSW-1. The results suggest that modification of the steroidal aglycone may lead to compounds with high cytotoxicity.

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Year:  2007        PMID: 17608396     DOI: 10.1021/jm0613572

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  8 in total

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  8 in total

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