A protein structure-guided covalent scaffold selectively targets the B1 and B2 subclass metallo-β-lactamases

被引：52

作者：

Chen, Cheng ^{[1
]}

Xiang, Yang ^{[1
]}

Yang, Ke-Wu ^{[1
]}

Zhang, Yuejuan ^{[1
]}

Wang, Wen-Ming ^{[1
]}

Su, Jian-Peng ^{[1
]}

Ge, Ying ^{[1
]}

Liu, Ya ^{[1
]}

机构：

[1] Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Innovat Lab Chem Biol,Minist Educ, Xian 710127, Shaanxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 38期

基金：

中国国家自然科学基金;

关键词：

CRYSTAL-STRUCTURE; INHIBITION; HYDROLYSIS; L1;

D O I：

10.1039/c8cc01067f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the discovery of ebselen-based dual covalent inhibitors of metallo-beta-lactamases. Fluorescence and MALDI-TOF analysis suggested that the scaffold could bind to NDM-1 by forming a S-Se bond with Cys221 and an amide bond with Lys224 of NDM-1, thereby exhibiting selective inhibition and labeling against B1 and B2 subclass enzymes in vitro and in vivo.

引用

收藏

页码：4802 / 4805

页数：4

相关论文

共 22 条

[1] THE STRUCTURE OF BETA-LACTAMASES [J].

AMBLER, RP .

PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY B-BIOLOGICAL SCIENCES, 1980, 289 (1036) :321-331

[2] Structural basis of metallo-β-lactamase, serine-β-lactamase and penicillin-binding protein inhibition by cyclic boronates [J].

Brem, Juergen ;

Cain, Ricky ;

Cahill, Samuel ;

McDonough, Michael A. ;

Clifton, Ian J. ;

Jimenez-Castellanos, Juan-Carlos ;

Avison, Matthew B. ;

Spencer, James ;

Fishwick, Colin W. G. ;

Schofield, Christopher J. .

NATURE COMMUNICATIONS, 2016, 7

[3] Updated Functional Classification of β-Lactamases [J].

Bush, Karen ;

Jacoby, George A. .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2010, 54 (03) :969-976

[4] Proliferation and significance of clinically relevant β-lactamases [J].

Bush, Karen .

ANTIMICROBIAL THERAPEUTICS REVIEWS: THE BACTERIAL CELL WALL AS AN ANTIMICROBIAL TARGET, 2013, 1277 :84-90

[5] Ebselen as a potent covalent inhibitor of New Delhi metallo-β-lactamase (NDM-1) [J].

Chiou, Jiachi ;

Wan, Shengbiao ;

Chan, Kin-Fai ;

So, Pui-Kin ;

He, Dandan ;

Chan, Edward Wai-chi ;

Chan, Tak-hang ;

Wong, Kwok-yin ;

Tao, Jiang ;

Chen, Sheng .

CHEMICAL COMMUNICATIONS, 2015, 51 (46) :9543-9546

[6] Discovery of a novel covalent non-β-lactam inhibitor of the metallo-β-lactamase NDM-1 [J].

Christopeit, Tony ;

Albert, Anastasia ;

Leiros, Hanna-Kirsti S. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (13) :2947-2953

[7]

Cornaglia G., 2011, Lancet Infect Dis, V11, P381, DOI DOI 10.1016/S1473-3099(11)70056-1

[8] Metallo-β-lactamases:: Novel weaponry for antibiotic resistance in bacteria [J].

Crowder, Michael W. ;

Spencer, James ;

Vila, Alejandro J. .

ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (10) :721-728

[9] Three Decades of β-Lactamase Inhibitors [J].

Drawz, Sarah M. ;

Bonomo, Robert A. .

CLINICAL MICROBIOLOGY REVIEWS, 2010, 23 (01) :160-+

[10] AN OVERVIEW OF THE KINETIC-PARAMETERS OF CLASS-B BETA-LACTAMASES [J].

FELICI, A ;

AMICOSANTE, G ;

ORATORE, A ;

STROM, R ;

LEDENT, P ;

JORIS, B ;

FANUEL, L ;

FRERE, JM .

BIOCHEMICAL JOURNAL, 1993, 291 :151-155