Structure-activity relationship studies on niphimycin, a guanidylpolyol macrolide antibiotic. Part 1: The role of the N-methyl-N''-alkylguanidinium moiety.
Structure-activity relationship studies on niphimycin, a guanidylpolyol macrolide antibiotic. Part 1: The role of the N-methyl-N''-alkylguanidinium moiety.
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DOI：
10.1016/j.bmcl.2005.12.024
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发表时间：
2006-03
影响因子：
2.7
通讯作者：
Y. Usuki;Keiji Matsumoto;Takatsugu Inoue;Koichi Yoshioka;H. Iio;Toshio Tanaka
中科院分区：
文献类型：
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作者：
Y. Usuki;Keiji Matsumoto;Takatsugu Inoue;Koichi Yoshioka;H. Iio;Toshio Tanaka
合成了几种n -甲基- n″-烷基胍衍生物，并将其作为胍基多元醇大环内酯尼菲霉素（NM）的简化类似物进行了构效关系研究。c16烷基化衍生物与尼菲霉素类似，通过直接破坏真菌质膜和诱导氧化应激发挥杀真菌活性。这些结果表明，n -甲基- n″-烷基胍部分是NM抗真菌活性所必需的。
Several N-methyl-N″-alkylguanidinium derivatives were synthesized and used as simplified analogues of niphimycin (NM), a guanidylpolyol macrolide, in structure–activity relationship studies. The C16-alkylated derivative exerted fungicidal activity by directly damaging the fungal plasma membrane and inducing oxidative stress in a manner similar to niphimycin. These results indicate that the N-methyl-N″-alkylguanidinium moiety is required for antifungal activity by NM.