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  3. Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives

Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives

  • Bioorg Med Chem Lett. 2019 Jun 1;29(11):1390-1394. doi: 10.1016/j.bmcl.2019.03.034.
Yasuha Kusakabe 1,  Shoma Mizutani 2,  Shogo Kamo 3,  Tatsuki Yoshimoto 1,  Shusuke Tomoshige 1,  Tsuneomi Kawasaki 4,  Ryoko Takasawa 5,  Kazunori Tsubaki 2,  Kouji Kuramochi 6
Affiliations

Affiliations

  • 1 Department of Applied Biological Science, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
  • 2 Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Sakyo-ku, Kyoto 606-8522, Japan.
  • 3 Department of Applied Biological Science, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan; Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Sakyo-ku, Kyoto 606-8522, Japan.
  • 4 Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
  • 5 Department of Pharmacy, Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
  • 6 Department of Applied Biological Science, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan. Electronic address: kuramoch@rs.tus.ac.jp.
PMID: 30935798 DOI: 10.1016/j.bmcl.2019.03.034
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.

Keywords

Antibacterial activity; Cytotoxicity; Lactam; Natural product.

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