Synthesis and cytotoxic activity of a series of bile acid derivatives | Zendy

Ksenija Kuhajda | Zendy; Stanko Cvjetičanin | Zendy; Evgenija A. Djurendić | Zendy; Marija N. Sakač | Zendy; Katarina PenovGasi | Zendy; Vesna Kojić | Zendy; Gordana Bogdanović | Zendy

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Synthesis and cytotoxic activity of a series of bile acid derivatives

Author(s) -

Ksenija Kuhajda,

Stanko Cvjetičanin,

Evgenija A. Djurendić,

Marija N. Sakač,

Katarina PenovGasi,

Vesna Kojić,

Gordana Bogdanović

Publication year - 2009

Publication title -

hemijska industrija

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.147

H-Index - 19

eISSN - 2217-7426

pISSN - 0367-598X

DOI - 10.2298/hemind0904313k

Subject(s) - deoxycholic acid , hela , chemistry , conjugate , cholic acid , cytotoxicity , cytotoxic t cell , ethyl acetate , triethylamine , bile acid , stereochemistry , dichloromethane , biochemistry , organic chemistry , cell , solvent , in vitro , mathematical analysis , mathematics

The new conjugates of selected bile acids (hyocholic (2), deoxycholic (3), hyodeoxycholic (4) and 12-ketocholic (5) acids) with ethyl 11-aminoundecanoate 7, 8, 11, and 13 were synthesized. The conjugation reaction was carried out in ethyl acetate in the presence of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) and triethylamine. Under the same experimental conditions, the conjugation reaction involving ethyl 6-aminohexanoate resulted in formation of a conjugate 9 only in the case of deoxycholic acid (3) in addition to the unexpected ethyl ester 10. In the case of the other bile acids (cholic (1), hyodeoxycholic (4) and 12-ketocholic (5) acids) only an unexpected ester formation took place giving esters 6, 12, and 14. Cytotoxic activity against four tumor cell lines (human breast adenocarcinoma ER-, MDA-MB-231; breast adenocarcinoma ER+, MCF-7; cervix epiteloid carcinoma, HeLa S-3; and prostate cancer, PC-3) was evaluated. Conjugate 8 showed strong activity against HeLa S-3 and conjugate 11 for PC-3. Ethyl ester of 12-ketocholic acid 14 showed very strong antiproliferative activity against MCF-7 and HeLa S-3

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