一种作为人白细胞弹性蛋白酶基于活性的探针的硼二吡咯标记膦酰肽。
A BODIPY-Tagged Phosphono Peptide as Activity-Based Probe for Human Leukocyte Elastase.
作者信息
Schulz-Fincke Anna-Christina, Blaut Michael, Braune Annett, Gütschow Michael
机构信息
Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn, Germany.
Department of Gastrointestinal Microbiology, German Institute of Human Nutrition Potsdam-Rehbruecke, Arthur-Scheunert-Allee 114-116, 14558 Nuthetal, Germany.
出版信息
ACS Med Chem Lett. 2018 Mar 4;9(4):345-350. doi: 10.1021/acsmedchemlett.7b00533. eCollection 2018 Apr 12.
Abstract
Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at position. The probe was assembled by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition. It was characterized as an active site-directed elastase inhibitor exhibiting a second-order rate constant of inactivation of 88400 Ms. The suitability of as a fluorescent probe for human leukocyte elastase was demonstrated by in-gel fluorescence analysis. Labeling experiments and inhibition data toward a panel of related proteases underlined the selectivity of the probe for the targeted leukocyte elastase.
摘要
人白细胞弹性蛋白酶在多种炎症性疾病中起关键作用，是生物医学研究的重要课题。肽基膦酸酯的化学类型被用于设计一种新型的基于活性的人白细胞弹性蛋白酶探针。其结构将膦酸酯弹头与适当的肽部分以及在特定位置带有可点击乙炔基苯基部分的硼二吡咯荧光团相结合。该探针通过铜催化的炔烃-叠氮化物1,3-偶极环加成反应组装而成。它被表征为一种活性位点导向的弹性蛋白酶抑制剂，失活的二级速率常数为88400 M⁻¹s⁻¹。凝胶内荧光分析证明了其作为人白细胞弹性蛋白酶荧光探针的适用性。标记实验以及对一组相关蛋白酶的抑制数据强调了该探针对目标白细胞弹性蛋白酶的选择性。
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