Structural features required for inhibition of cyanide-insensitive electron transfer by propyl gallate.
Structural features required for inhibition of cyanide-insensitive electron transfer by propyl gallate.
复制标题
没食子酸丙酯抑制氰化物不敏感电子转移所需的结构特征。
DOI：
10.1016/0003-9861(81)90004-7
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发表时间：
1981
影响因子：
3.9
通讯作者：
Bickett,DM
中科院分区：
文献类型：
--
作者：
Siedow,JN;Bickett,DM
对没食子酸丙酯（3，4，5-三羟基苯甲酸丙酯）的一系列19种结构类似物在分离的绿豆线粒体中抑制氰化物不敏感的电子传递途径的能力进行了测试。结果表明，没食子酸丙酯的三羟基取代基，而不是酯，是产生抑制所需的分子的结构特征。此外，只有一个OH基团，如果它位于酯部分的对位，将带来特异性抑制。在含有适当羟基的化合物中，羟基的pKα越低，观察到的阻断旁路途径的抑制常数（Ki′）越低。尽管供试化合物的抑制Ki ′值变化超过两个数量级，但所有抑制化合物的计算的pH无关的内在抑制常数（Ki）均显著相似。结果表明，一个简单的酚阴离子是观察特异性抑制旁路途径所需的最低结构特征，阴离子越容易形成，观察到的抑制作用越好。还注意到上述化合物之间的相似性和与异羟肟酸相关的结构特征。
A series of 19 structural analogs of propyl gallate (3,4,5-trihydroxybenzoic acid propyl ester) were tested for their ability to inhibit the cyanide-insensitive, electron transfer pathway in isolated mung bean mitochondria. The results indicate that the trihydroxy substituent, not the ester, of propyl gallate is the structural feature of the molecule required to produce inhibition. Further, only one OH group, if it is locatedparato the ester moiety, will bring about specific inhibition. Of the compounds which contained the appropriate hydroxyl group, the lower the pKαof the hydroxyl group, the lower the observed inhibition constant (Ki′) for blocking the alternative pathway. Even though the observedKi′ values varied over two orders of magnitude for the compounds tested, the calculated pH-independent, intrinsic inhibition constants (Ki) were markedly similar for all inhibitory compounds. The results indicate that a simple phenolate anion is the minimum structural feature required to observe specific inhibition of the alternative pathway and the more easily the anion can be formed, the better the observed inhibition. Similarities between the above compounds and the structural features associated with hydroxamic acids were also noted.