Wierzchowski Jacek, Antosiewicz Jan M, Shugar David
Department of Biophysics, University of Varmia & Masuria, Oczapowskiego 4, 10-719 Olsztyn, Poland.
Mol Biosyst. 2014 Nov;10(11):2756-74. doi: 10.1039/c4mb00233d.
The 8-azapurines, and their 7-deaza and 9-deaza congeners, represent a unique class of isosteric (isomorphic) analogues of the natural purines, frequently capable of substituting for the latter in many biochemical processes. Particularly interesting is their propensity to exhibit pH-dependent room-temperature fluorescence in aqueous medium, and in non-polar media. We herein review the physico-chemical properties of this class of compounds, with particular emphasis on the fluorescence emission properties of their neutral and/or ionic species, which has led to their widespread use as fluorescent probes in enzymology, including enzymes involved in purine metabolism, agonists/antagonists of adenosine receptors, mechanisms of catalytic RNAs, RNA editing, etc. They are also exceptionally useful fluorescent probes for analytical and clinical applications in crude cell homogenates.
8-氮杂嘌呤及其7-脱氮和9-脱氮类似物是天然嘌呤独特的等排体（同构）类似物，在许多生化过程中常常能够替代天然嘌呤。特别有趣的是，它们在水性介质和非极性介质中倾向于表现出pH依赖性的室温荧光。我们在此综述这类化合物的物理化学性质，特别强调其中性和/或离子形式的荧光发射特性，这使得它们在酶学中被广泛用作荧光探针，包括参与嘌呤代谢的酶、腺苷受体的激动剂/拮抗剂、催化RNA的机制、RNA编辑等。它们也是用于粗细胞匀浆分析和临床应用的非常有用的荧光探针。
