生物素-5'-AMP的β-酮和β-羟基膦酸酯类似物是全羧化酶合成酶的抑制剂。
β-Keto and β-hydroxyphosphonate analogs of biotin-5'-AMP are inhibitors of holocarboxylase synthetase.
作者信息
Sittiwong Wantanee, Cordonier Elizabeth L, Zempleni Janos, Dussault Patrick H
机构信息
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588-0304, USA.
Department of Nutrition and Health Sciences, University of Nebraska-Lincoln, Lincoln, NE 68583-0806, USA.
出版信息
Bioorg Med Chem Lett. 2014 Dec 15;24(24):5568-5571. doi: 10.1016/j.bmcl.2014.11.010. Epub 2014 Nov 7.
Abstract
Holocarboxylase synthetase (HLCS) catalyzes the covalent attachment of biotin to cytoplasmic and mitochondrial carboxylases, nuclear histones, and over a hundred human proteins. Nonhydrolyzable ketophosphonate (β-ketoP) and hydroxyphosphonate (β-hydroxyP) analogs of biotin-5'-AMP inhibit holocarboxylase synthetase (HLCS) with IC50 values of 39.7 μM and 203.7 μM. By comparison, an IC50 value of 7 μM was observed with the previously reported biotinol-5'-AMP. The Ki values, 3.4 μM and 17.3 μM, respectively, are consistent with the IC50 results, and close to the Ki obtained for biotinol-5'-AMP (7 μM). The β-ketoP and β-hydroxyP molecules are competitive inhibitors of HLCS while biotinol-5'-AMP inhibited HLCS by a mixed mechanism.
摘要
全羧化酶合成酶（HLCS）催化生物素与细胞质和线粒体羧化酶、核组蛋白以及一百多种人类蛋白质的共价连接。生物素-5'-AMP的不可水解酮膦酸盐（β-酮膦酸盐）和羟基膦酸盐（β-羟基膦酸盐）类似物抑制全羧化酶合成酶（HLCS），IC50值分别为39.7μM和203.7μM。相比之下，先前报道的生物醇-5'-AMP的IC50值为7μM。Ki值分别为3.4μM和17.3μM，与IC50结果一致，且接近生物醇-5'-AMP的Ki值（7μM）。β-酮膦酸盐和β-羟基膦酸盐分子是HLCS的竞争性抑制剂，而生物醇-5'-AMP通过混合机制抑制HLCS。
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