Total Synthesis and Structure-Activity Relationship Study of Vineomycin A1

Yuka Matsumoto; Hajime Kuriki; Takashi Kitamura; Daisuke Takahashi; Kazunobu Toshima

doi:10.1021/acs.joc.9b02304

Total Synthesis and Structure-Activity Relationship Study of Vineomycin A₁

Yuka Matsumoto, Hajime Kuriki, Takashi Kitamura, Daisuke Takahashi, Kazunobu Toshima

応用化学科

研究成果: Article › 査読

2 被引用数 (Scopus)

抄録

The first total synthesis of vineomycin A₁ (1) has been accomplished. Structure-activity relationship studies for cytotoxicity against human breast cancer MCF-7 cells using several synthetic vineomycin A₁ analogues differing in the number and position of glycon moieties revealed that the cytotoxicity increased as the number of glycon moieties increased. The position of the glycon moiety was one of the key factors for the cytotoxicity of 1. Moreover, in vitro analysis of the cytotoxicity of 1 against MCF-7 cells indicated for the first time that 1 effectively induced cancer cell death by apoptosis, not by acting as a DNA intercalating agent.

本文言語	English
ジャーナル	Journal of Organic Chemistry
DOI	https://doi.org/10.1021/acs.joc.9b02304
出版ステータス	Published - 2019 1月 1

ASJC Scopus subject areas

有機化学

UN SDG

この成果は、次の持続可能な開発目標に貢献しています

文献へのアクセス

10.1021/acs.joc.9b02304

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引用スタイル

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AU - Toshima, Kazunobu

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AB - The first total synthesis of vineomycin A1 (1) has been accomplished. Structure-activity relationship studies for cytotoxicity against human breast cancer MCF-7 cells using several synthetic vineomycin A1 analogues differing in the number and position of glycon moieties revealed that the cytotoxicity increased as the number of glycon moieties increased. The position of the glycon moiety was one of the key factors for the cytotoxicity of 1. Moreover, in vitro analysis of the cytotoxicity of 1 against MCF-7 cells indicated for the first time that 1 effectively induced cancer cell death by apoptosis, not by acting as a DNA intercalating agent.

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