Structure-activity relationships of the antitumor C5-Curcuminoid GO-Y030

Aki Kohyama, Hiroyuki Yamakoshi, Shoko Hongo, Naoki Kanoh, Hiroyuki Shibata, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (2) was isolated from Curcuma domestica as a curcumin (1)-related compound, which we named C5-curcumin. Intrigued by the potent antitumor activity of C5-curcumin (2)-related 1,5-bisaryl-1,4-pentadiene-3-ones [bis(arylmethylidene)acetones, termed C5-curcuminoids], we previously conducted a structure-activity relationship study of C5-curcuminoids and showed that highly active GO-Y030 [1,5-bis(3,5-bis(methoxymethoxy)phenyl)-1,4-pentadiene-3-one (4)] is the most promising antitumor compound. In this study, a panel of C5-curcuminoids based on GO-Y030, consisting of 30 new and 10 known compounds, was synthesized to elucidate in detail which moiety of GO-Y030 is significant for antitumor activity. The results confirmed that both the cross-conjugated dienone moiety and the 3,5-bis(methoxymethoxy) substituent are important for the antitumor activity.

Original languageEnglish
Pages (from-to)15374-15391
Number of pages18
JournalMolecules
Volume20
Issue number8
DOIs
Publication statusPublished - 2015 Aug 1

Keywords

  • Antitumor
  • Curcumin
  • Michael reaction
  • Structure-activity relationship

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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