Synthesis and structure-activity relationships for cytotoxicity and apoptosis-inducing activity of (+)-halichonine B

Ichiro Hayakawa, Tomomi Nakamura, Osamu Ohno, Kiyotake Suenaga, Hideo Kigoshi

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Halichonine B is a sesquiterpene alkaloid isolated from the marine sponge Halichondria okadai Kadota. Halichonine B has exhibited cytotoxicity against mammalian cancer cells and induced apoptosis in the human leukemia cell line HL60. Here we established a practical route for the synthesis of halichonine B and its analogues, and we evaluated their biological activities. It was revealed that the secondary amino groups in the side chain portion are important for the strong cytotoxicity of halichonine B and that the N<sup>11</sup>-prenyl group is unimportant. Halichonine B and its analogues were also observed to induce apoptosis in HL60 cells.

Original languageEnglish
Pages (from-to)9969-9976
Number of pages8
JournalOrganic and Biomolecular Chemistry
Issue number39
Publication statusPublished - 2015 Aug 11


ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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