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

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

doi:10.1039/c5ob01488c

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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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 N¹¹-prenyl group is unimportant. Halichonine B and its analogues were also observed to induce apoptosis in HL60 cells.

Original language	English
Pages (from-to)	9969-9976
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	39
DOIs	https://doi.org/10.1039/c5ob01488c
Publication status	Published - 2015 Aug 11

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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 N11-prenyl group is unimportant. Halichonine B and its analogues were also observed to induce apoptosis in HL60 cells.",

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T1 - Synthesis and structure-activity relationships for cytotoxicity and apoptosis-inducing activity of (+)-halichonine B

AU - Hayakawa, Ichiro

AU - Nakamura, Tomomi

AU - Ohno, Osamu

AU - Suenaga, Kiyotake

AU - Kigoshi, Hideo

PY - 2015/8/11

Y1 - 2015/8/11

N2 - 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 N11-prenyl group is unimportant. Halichonine B and its analogues were also observed to induce apoptosis in HL60 cells.

AB - 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 N11-prenyl group is unimportant. Halichonine B and its analogues were also observed to induce apoptosis in HL60 cells.

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

Abstract

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