二氢香豆素的卤甲基化衍生物对蛋白酶和酯酶的失活作用。

Inactivation of proteases and esterases by halomethylated derivatives of dihydrocoumarins.

作者信息

Béchet J J, Dupaix A, Roucous C, Bonamy A M

出版信息

Biochimie. 1977;59(3):241-6. doi: 10.1016/s0300-9084(77)80140-5.

Abstract

A series of halomethylated derivatives of dihydrocoumarins has been found to inhibit irreversibly proteases and esterases. alpha-Chymotrypsin, subtilish, elastase are rapidly inactivated in the presence of these compounds, while trypsin, kallicrein, papain are inhibited more slowly. Esterases like acetylcholinesterase and butyrylcholinesterase also lose activity in their presence. Two structural features of these inactivators are essential for inhibition: a reactive cis-ester function and an alkylating function. Analogues of these derivatives having only one of these characteristics are inefficient. Therefore it is suggested that the efficiency of these bifunctional reagents is due to their character of potential "suicide substrates".

摘要

已发现一系列二氢香豆素的卤甲基化衍生物可不可逆地抑制蛋白酶和酯酶。在这些化合物存在的情况下，α-胰凝乳蛋白酶、枯草杆菌蛋白酶、弹性蛋白酶会迅速失活，而胰蛋白酶、激肽释放酶、木瓜蛋白酶的抑制则较为缓慢。像乙酰胆碱酯酶和丁酰胆碱酯酶这样的酯酶在它们存在时也会失去活性。这些灭活剂的两个结构特征对抑制作用至关重要：一个反应性顺式酯功能和一个烷基化功能。仅具有这些特征之一的这些衍生物的类似物效率低下。因此，有人提出这些双功能试剂的效率归因于它们潜在的“自杀底物”特性。