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

Department of Applied Chemistry

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

3 Citations (Scopus)

Abstract

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.

Original language	English
Journal	Journal of Organic Chemistry
DOIs	https://doi.org/10.1021/acs.joc.9b02304
Publication status	Published - 2019 Jan 1

ASJC Scopus subject areas

Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.joc.9b02304

Cite this

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title = "Total Synthesis and Structure-Activity Relationship Study of Vineomycin A1",

abstract = "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.",

author = "Yuka Matsumoto and Hajime Kuriki and Takashi Kitamura and Daisuke Takahashi and Kazunobu Toshima",

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AU - Kuriki, Hajime

AU - Kitamura, Takashi

AU - Takahashi, Daisuke

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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