Add time:08/16/2019 Source:sciencedirect.com
Structure-activity relationships for rigid analogues of combretastatin A-4 (CA-4) were investigated, leading to the discovery of a series of 3,4-diaryl-1,2,5-oxadiazole-N-oxides. Among them, 7n′ and 7n′′ showed remarkable antiproliferative activities against three cancer cell lines in nanomolar concentrations. Interestingly, 7n′ inhibited tubulin polymerization much more efficiently than CA-4. Cellular mechanism investigation elucidated 7n′ disrupted the cellular microtubule structure, arrested cell cycle at G2/M phase and induces apoptosis. Molecular modeling study revealed 1,2,5-oxadiazole-N-oxide ring could increase a hydrogen bond interaction with the binding site. These results provide impetus and further guidance for the development of new CA-4 analogues.
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