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https://open.uns.ac.rs/handle/123456789/13146
Title: | Synthesis and cytotoxic activity of a series of bile acid derivatives | Authors: | Kuhajda K. Cvjetićanin, Stanko Djurendić E. Sakač M. Gaši K. Kojić, Vesna Bogdanović G. |
Issue Date: | 1-Dec-2009 | Journal: | Hemijska Industrija | Abstract: | 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. | URI: | https://open.uns.ac.rs/handle/123456789/13146 | ISSN: | 0367598X | DOI: | 10.2298/HEMIND0904313K |
Appears in Collections: | PEF Publikacije/Publications |
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