Levine Michael N, Lavis Luke D, Raines Ronald T
Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706-1544, USA.
Molecules. 2008 Jan 31;13(2):204-11. doi: 10.3390/molecules13020204.
p-Nitrophenyl acetate is the most commonly used substrate for detecting the catalytic activity of esterases, including those that activate prodrugs in human cells. This substrate is unstable in aqueous solution, limiting its utility. Here, a stable chromogenic substrate for esterases is produced by the structural isolation of an acetyl ester and p-nitroaniline group using a trimethyl lock moiety. Upon ester hydrolysis, unfavorable steric interactions between the three methyl groups of this o-hydroxycinnamic acid derivative encourage rapid lactonization to form a hydrocoumarin and release p-nitroaniline. This "prochromophore" could find use in a variety of assays.
对硝基苯乙酸酯是检测酯酶催化活性最常用的底物，包括那些在人体细胞中激活前药的酯酶。该底物在水溶液中不稳定，限制了其应用。在此，通过使用三甲基锁部分对乙酰酯和对硝基苯胺基团进行结构隔离，制备了一种稳定的酯酶显色底物。酯水解后，这种邻羟基肉桂酸衍生物的三个甲基之间不利的空间相互作用促使快速内酯化形成氢化香豆素并释放对硝基苯胺。这种“前发色团”可用于多种检测。
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