Synthesis and Evaluation of Novel 7- and 8-Aminophenoxazinones for the Detection of β-Alanine Aminopeptidase Activity and the Reliable Identification of <i>Pseudomonas aeruginosa</i> in Clinical Samples
作者:Alexandre F. Bedernjak、Andrey V. Zaytsev、Michèle Babolat、Marie Cellier、Arthur L. James、Sylvain Orenga、John D. Perry、Paul W. Groundwater、Rosaleen J. Anderson
DOI:10.1021/acs.jmedchem.5b01591
日期:2016.5.26
phenoxazinon-3-ones. 8-Aminophenoxazin-3-one substrates 23c, 23d, and 23e were prepared in good to high overall yield and were selective for β-alanyl aminopeptidase activity in bacteria, producing a lighter agar background coloration facilitating visualization of colored colonies, with variable localization to the colonies, but had lower sensitivities for the detection of Pseudomonas aeruginosa in comparison
合成了一系列新颖的8-aminophenoxazin-3-one和7-aminophenoxazin-3-one色原及其相应的β-丙氨酸衍生物,并评估了它们在已知水解β-丙氨酸衍生化的细菌中检测β-丙氨酸氨基肽酶活性的能力。基材。结果为有效可视化酶活性的结构要求和苯恶嗪酮-3-酮的形成机理提供了见识。8-氨基苯恶嗪-3-酮底物23c,23d和23e制备的产品具有良好的总收率,并且对细菌中的β-丙氨酰氨肽酶活性具有选择性,可产生较浅的琼脂背景色,从而便于对有色菌落进行可视化,并可以对菌落进行局部定位,但对铜绿假单胞菌的检测灵敏度较低。与类似的7-aminophenoxazin-3-one底物进行比较。这里采用的合成方法可以制备各种底物用于评估和建立结构-活性关系。例如,对相应的1-戊基-7-氨基吩恶嗪-3-one底物1具有相似的敏感性,进行了2-戊基取代的氨基苯恶嗪-3-one 22b的反应。