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Syntheses and biological evaluation of ring-C modified colchicine analogs.

ABSTRACT: Ring-C modified alkaloids were synthesized from colchicine using iminonitroso Diels-Alder reactions in a highly regio- and stereoselective fashion. Several analogs exhibited cytotoxic activity similar to that of colchicine itself against PC-3 and MCF-7 cancer cell lines, by serving as prodrugs of colchicine through retro Diels-Alder reactions under the assayed conditions. In vitro microtubule polymerization assays indicated that these modifications affected their interaction with tubulin.

SUBMITTER: Yang B 

PROVIDER: S-EPMC2883562 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Syntheses and biological evaluation of ring-C modified colchicine analogs.

Yang Baiyuan B   Zhu Zhiqing C ZC   Goodson Holly V HV   Miller Marvin J MJ  

Bioorganic & medicinal chemistry letters 20100315 12

Ring-C modified alkaloids were synthesized from colchicine using iminonitroso Diels-Alder reactions in a highly regio- and stereoselective fashion. Several analogs exhibited cytotoxic activity similar to that of colchicine itself against PC-3 and MCF-7 cancer cell lines, by serving as prodrugs of colchicine through retro Diels-Alder reactions under the assayed conditions. In vitro microtubule polymerization assays indicated that these modifications affected their interaction with tubulin. ...[more]

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