Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives

Yasuha Kusakabe, Shoma Mizutani, Shogo Kamo, Tatsuki Yoshimoto, Shusuke Tomoshige, Tsuneomi Kawasaki, Ryoko Takasawa, Kazunori Tsubaki, Kouji Kuramochi

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

The antibacterial and cytotoxic activity of seven racemic lactams and both enantiomers of flavipucine were evaluated. Of the compounds tested in this study, flavipucine and phenylflavipucine displayed bactericidal activity against Bacillus subtilis. These results indicate that the pyridione epoxide moiety is a pharmacophore for antibacterial activity against B. subtilis. Flavipucine showed cytotoxic activity against several cancer cells. The cytotoxic activity of flavipucine against human leukemia HL-60 cells is as strong as that of SN-38, the active metabolite of irinotecan. In contrast, the cytotoxic activity of flavipucine against nonneoplastic HEK293 cells and human normal MRC-5 cells is weaker than that of SN-38. No significant differences in the biological activity of the racemates or enantiomers of flavipucine were observed.

Original languageEnglish
Pages (from-to)1390-1394
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume29
Issue number11
DOIs
Publication statusPublished - 2019 Jun 1
Externally publishedYes

Keywords

  • Antibacterial activity
  • Cytotoxicity
  • Lactam
  • Natural product

ASJC Scopus subject areas

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

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