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Syntheses and Cytotoxic Properties of the Curcumin Analogs 2,6‐Bis(benzylidene)‐4‐phenylcyclohexanones
Author(s) -
Davis Ryan,
Das Umashankar,
Mackay Hilary,
Brown Toni,
Mooberry Susan L.,
Dimmock Jonathan R.,
Lee Moses,
Pati Hari
Publication year - 2008
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200800028
Subject(s) - cytotoxicity , curcumin , stereochemistry , chemistry , l1210 cells , in vitro , mtt assay , tubulin , cell culture , structure–activity relationship , chemical synthesis , microtubule , biochemistry , biology , genetics , microbiology and biotechnology
Fifteen curcumin analogs were synthesized and tested for in‐vitro cytotoxicity towards B16 and L1210 murine cancer cell lines using an MTT assay. Significant activity was discovered for two analogs: 8 (B16 IC 50 = 1.6 μM; L1210 IC 50 = 0.35 μM) and 9 (B16 IC 50 = 0.51 μM; L1210 IC 50 = 1.2 μM). Several other analogs exhibited notable cytotoxicity. The data from quantitative structure‐activity relationships suggest that large electron‐withdrawing substituents placed in the meta ‐position of the arylidene aryl rings enhance potencies. Compounds 8 and 9 were found using a cell‐based assay to have virtually no effects on microtubules at concentrations up to 40 μM. These results suggest that tubulin inhibition is not the principal mechanism by which the curcumin analogs act.