Issue 11, 2013

Synthesis and in vitro cytotoxicity of deoxyadenosine–bile acid conjugates linked with 1,2,3-triazole

Abstract

We report herein the synthesis and biological evaluation of novel deoxynucleoside–bile acid conjugates linked through a 1,2,3-triazole ring. The conjugates were synthesized via Cu(I) mediated 1,3-dipolar cycloaddition reaction (‘click’ chemistry) of 3-azidobile acid derivatives and terminal alkyne moieties linked to the C-8 position of deoxyadenosine. All novel molecules were evaluated in vitro for their anti-proliferative activity against four human cell lines (i.e., leukemic T Jurkat and K562; colon carcinoma HCT116; and ovarian cancer A2780) and their cytotoxicity toward human fibroblast cells. Several conjugates exhibited strong anti-proliferative activity against human leukemia T cells. The best cytotoxicity was observed for HdA-CDC on both leukemia cell lines with IC50 up to 8.51 μM. The apoptotic activity of several conjugates was also established.

Graphical abstract: Synthesis and in vitro cytotoxicity of deoxyadenosine–bile acid conjugates linked with 1,2,3-triazole

Article information

Article type
Paper
Submitted
14 May 2013
Accepted
23 Aug 2013
First published
23 Aug 2013

New J. Chem., 2013,37, 3559-3567

Synthesis and in vitro cytotoxicity of deoxyadenosine–bile acid conjugates linked with 1,2,3-triazole

D. Perrone, O. Bortolini, M. Fogagnolo, E. Marchesi, L. Mari, C. Massarenti, M. L. Navacchia, F. Sforza, K. Varani and M. L. Capobianco, New J. Chem., 2013, 37, 3559 DOI: 10.1039/C3NJ00513E

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