Department of Pharmacy, University of Pisa, Pisa, Italy.
Department of Veterinary Sciences, University of Pisa, Italy.
Sci Rep. 2017 Apr 3;8:45760. doi: 10.1038/srep45760.
Organocatalysis, which is mostly explored for its new potential industrial applications, also represents a chemical event involved in endogenous processes. In the present study, we provide the first evidence that imidazole and imidazole derivatives have cholinesterase-like properties since they can accelerate the hydrolysis of acetylthiocholine and propionylthiocholine in a concentration-dependent manner. The natural imidazole-containing molecules as L-histidine and histamine show a catalytic activity, comparable to that of imidazole itself, whereas synthetic molecules, as cimetidine and clonidine, were less active. In the experimental conditions used, the reaction progress curves were sigmoidal and the rational of such unexpected behavior as well as the mechanism of catalysis is discussed. Although indirectly, findings of the present study suggests that imidazolic compounds may interfere with the homeostasis of the cholinergic system in vivo.
有机催化，主要因其新的潜在工业应用而被探索，也代表了内源性过程中涉及的一种化学事件。在本研究中，我们首次提供了证据，表明咪唑及其衍生物具有类胆碱酯酶特性，因为它们可以浓度依赖性方式加速乙酰硫代胆碱和丙酰硫代胆碱的水解。天然含咪唑的分子，如 L-组氨酸和组氨酸，表现出与咪唑本身相当的催化活性，而合成分子，如西咪替丁和可乐定，则活性较低。在所使用的实验条件下，反应进度曲线呈“S”型，讨论了这种意外行为的合理性以及催化机制。尽管是间接的，但本研究的结果表明，咪唑类化合物可能会干扰体内胆碱能系统的动态平衡。
