N-Phenyl-N’-(2-chloroethyl)ureas (CEUs) as potential antineoplastic agents. part 3 : role of carbonyl group

Authors: Moreau, EmmanuelFortin, SébastienLacroix, Jacques M.Patenaude, AlexandreRousseau, JeanC. Gaudreault, René
Abstract: n the course of the development of N-phenyl-N′-(2-chloroethyl)ureas (CEUs) as potential antineoplastic agents, we investigated the effect of carbonylated substituting chains of the aromatic ring of CEU on their covalent binding to the colchicine-binding site (C-BS). In this study, we found that CEU, 5e, 5f, 8e, and 8f substituted by either a methyl ester or a methyl ketyl group at the ω-position exhibited a significant antiproliferative activity on HT-29, M21, and MCF-7 tumor cells. SDS–PAGE assays and cell cycle analysis confirmed that 5e, 5f, 8e, and 8f covalently bind to the C-BS and arrest the cell division in G2/M phase. Surprisingly, the presence of ω-carboxyl, ω-ethyl esters or ω-amides decreased significantly both the antiproliferative activity and the specificity toward β-tubulin.
Document Type: Article de recherche
Issue Date: 27 October 2007
Open Access Date: 13 May 2019
Document version: AM
Permalink: http://hdl.handle.net/20.500.11794/34833
This document was published in: Bioorganic & Medicinal Chemistry, Vol. 16 (3), 1206-1217 (2008)
Oxford Pergamon
Alternative version: 10.1016/j.bmc.2007.10.078
Collection:Articles publiés dans des revues avec comité de lecture

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