From Sensors to Silencers: Quinoline-and Benzimidazole-Sulfonamides as Inhibitors for Zinc Proteases

被引：120

作者：

Rouffet, Matthieu ^{[1
]}

de Oliveira, Cesar Augusto F. ^{[2
,3
]}

Udi, Yael ^{[4
]}

Agrawal, Arpita ^{[1
]}

Sagi, Irit ^{[4
]}

McCammon, J. Andrew ^{[2
,3
]}

Cohen, Seth M. ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

[2] Univ Calif San Diego, Howard Hughes Med Inst, Dept Pharmacol, La Jolla, CA 92093 USA

[3] Univ Calif San Diego, Ctr Theoret Biol Phys, La Jolla, CA 92093 USA

[4] Weizmann Inst Sci, Dept Biol Struct, IL-76100 Rehovot, Israel

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 24期

基金：

美国国家科学基金会;

关键词：

MATRIX-METALLOPROTEINASE INHIBITORS; INTRAMOLECULAR PROTON-TRANSFER; FLUORESCENCE; COORDINATION;

D O I：

10.1021/ja101088j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Derived from the extensive work in the area of small molecule zinc(II) ion sensors chelating fragment libraries of quinoline- and benzimidazole-sulfonamides have been prepared and screened against several different zinc(II)-dependent matrix metalloproteinases (MMPs). The fragments show impressive inhibition of these metalloenzymes and preferences for different MMPs based on the nature of the chelating group. The findings show that focussed chelator libraries are a powerful strategy for the discovery of lead fragments for metalloprotein inhibition.

引用

页码：8232 / +

页数：4

共 11 条

[1] Zinc-binding groups modulate selective inhibition of MMPs [J].

Agrawal, Arpita ;

Romero-Perez, Diego ;

Jacobsen, Jennifer A. ;

Villarreal, Francisco J. ;

Cohen, Seth M. .

CHEMMEDCHEM, 2008, 3 (05) :812-820

[2] Metal-mediated inhibition is a viable approach for inhibiting cellular methionine aminopeptidase [J].

Chai, Sergio C. ;

Ye, Qi-Zhuang .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (24) :6862-6864

[3] Recent developments in fragment-based drug discovery [J].

Congreve, Miles ;

Chessari, Gianni ;

Tisi, Dominic ;

Woodhead, Andrew J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (13) :3661-3680

[4] Cancer therapy - Matrix metalloproteinase inhibitors and cancer: Trials and tribulations [J].

Coussens, LM ;

Fingleton, B ;

Matrisian, LM .

SCIENCE, 2002, 295 (5564) :2387-2392

[5] Aqueous coordination chemistry of quinoline-based fluorescence probes for the biological chemistry of zinc [J].

Fahrni, CJ ;

O'Halloran, TV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11448-11458

[6] Excited-state intramolecular proton transfer in 2-(2′-tosylaminophenyl)benzimidazole [J].

Fahrni, CJ ;

Henary, MM ;

VanDerveer, DG .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (34) :7655-7663

[7] Zinc(II)-selective ratiometric fluorescent sensors based on inhibition of excited-state intramolecular proton transfer [J].

Henary, MM ;

Wu, YG ;

Fahrni, CJ .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :3015-3025

[8] Coordination and fluorescence of the intracellular Zn2+ probe [2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxy]acetic acid (Zinquin a) in ternary Zn2+ complexes [J].

Hendrickson, KM ;

Geue, JP ;

Wyness, O ;

Lincoln, SF ;

Ward, AD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3889-3895

[9] The design of inhibitors for medicinally relevant metalloproteins [J].

Jacobsen, Faith E. ;

Lewis, Jana A. ;

Cohen, Seth M. .

CHEMMEDCHEM, 2007, 2 (02) :152-171

[10] In Situ Imaging of Metals in Cells and Tissues [J].

McRae, Reagan ;

Bagchi, Pritha ;

Sumalekshmy, S. ;

Fahrni, Christoph J. .

CHEMICAL REVIEWS, 2009, 109 (10) :4780-4827

← 1 2 →