Syntheses and cytotoxic properties of the curcumin analogs 2,6-bis(benzylidene)-4-phenylcyclohexanones

Ryan Davis, Umashankar Das, Hilary Mackay, Toni Brown, Susan L. Mooberry, Jonathan R. Dimmock, Moses Lee, Hari Pati

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

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 IC50 = 1.6 μM; L1210 IC50 = 0.35 μM) and 9 (B16 IC50 = 0.51 μM; L1210 IC50 = 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.

Original languageEnglish (US)
Pages (from-to)440-445
Number of pages6
JournalArchiv der Pharmazie
Volume341
Issue number7
DOIs
StatePublished - Jul 2008
Externally publishedYes

Keywords

  • B16
  • Curcumin analogs
  • L1210
  • Microtubules
  • Structure-activity relationships

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery

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