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

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

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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
Volume13
Issue number39
DOIs
Publication statusPublished - 2015 Aug 11

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apoptosis
Structure-Activity Relationship
Cytotoxicity
Cells
analogs
Apoptosis
alkaloids
leukemias
Sesquiterpenes
synthesis
activity (biology)
Bioactivity
cultured cells
Alkaloids
cancer
routes
cells
HL-60 Cells
Porifera
Leukemia

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Synthesis and structure-activity relationships for cytotoxicity and apoptosis-inducing activity of (+)-halichonine B. / Hayakawa, Ichiro; Nakamura, Tomomi; Ohno, Osamu; Suenaga, Kiyotake; Kigoshi, Hideo.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 39, 11.08.2015, p. 9969-9976.

Research output: Contribution to journalArticle

Hayakawa, Ichiro ; Nakamura, Tomomi ; Ohno, Osamu ; Suenaga, Kiyotake ; Kigoshi, Hideo. / Synthesis and structure-activity relationships for cytotoxicity and apoptosis-inducing activity of (+)-halichonine B. In: Organic and Biomolecular Chemistry. 2015 ; Vol. 13, No. 39. pp. 9969-9976.
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