3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: A novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity

Umashankar Das, Masami Kawase, Hiroshi Sakagami, Atsushi Ideo, Jun Shimada, J. Molnár, Zoltán Baráth, Z. Bata-Csörgő, Jonathan R. Dimmock

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

This study revealed that various alicyclic and acyclic compounds containing the 3-(3,4,5-trimethoxyphenyl)-2-propenoyl group displayed potent MDR reversal properties. In particular, a concentration of 4 μg/ml of 2,5-bis(3,4,5-trimethoxyphenylmethylene)cyclopentanone was 31 times more potent than verapamil as a MDR revertant. In general, they were selectively toxic to malignant rather than normal cells. Two representative compounds induced apoptosis in human HL-60 cells and markedly activated caspase-3.

Original languageEnglish
Pages (from-to)3373-3380
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume15
Issue number10
DOIs
Publication statusPublished - May 15 2007

Fingerprint

Poisons
HL-60 Cells
Multiple Drug Resistance
Cytotoxicity
Verapamil
Caspase 3
Apoptosis
cyclopentanone
3-(3,4,5-trimethoxyphenyl)-1-oxo-2-propene

Keywords

  • 3-(3,4,5-Trimethoxyphenyl)-2-propenoyl pharmacophore
  • Cytotoxicity
  • Multidrug resistance
  • Unsaturated ketones

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene : A novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity. / Das, Umashankar; Kawase, Masami; Sakagami, Hiroshi; Ideo, Atsushi; Shimada, Jun; Molnár, J.; Baráth, Zoltán; Bata-Csörgő, Z.; Dimmock, Jonathan R.

In: Bioorganic and Medicinal Chemistry, Vol. 15, No. 10, 15.05.2007, p. 3373-3380.

Research output: Contribution to journalArticle

Das, Umashankar ; Kawase, Masami ; Sakagami, Hiroshi ; Ideo, Atsushi ; Shimada, Jun ; Molnár, J. ; Baráth, Zoltán ; Bata-Csörgő, Z. ; Dimmock, Jonathan R. / 3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene : A novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity. In: Bioorganic and Medicinal Chemistry. 2007 ; Vol. 15, No. 10. pp. 3373-3380.
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