TY - JOUR
T1 - Total Synthesis and Structure-Activity Relationship Study of Vineomycin A1
AU - Matsumoto, Yuka
AU - Kuriki, Hajime
AU - Kitamura, Takashi
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019
Y1 - 2019
N2 - 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.
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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U2 - 10.1021/acs.joc.9b02304
DO - 10.1021/acs.joc.9b02304
M3 - Article
C2 - 31642324
AN - SCOPUS:85074853561
SN - 0022-3263
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
ER -