Rational Design of an Organometallic Glutathione Transferase Inhibitor

被引:166
作者
Ang, Wee Han [1 ]
Parker, Lorien J. [2 ]
De Luca, Anastasia [3 ]
Juillerat-Jeanneret, Lucienne [4 ]
Morton, Craig J. [2 ]
Lo Bello, Mario [3 ]
Parker, Michael W. [2 ]
Dyson, Paul J. [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland
[2] St Vincents Inst Med Res, Biota Struct Biol Lab, Fitzroy, Vic 3065, Australia
[3] Univ Roma Tor Vergata, Dept Biol, I-00133 Rome, Italy
[4] CHU Vaudois, Univ Inst Pathol, CH-1011 Lausanne, Switzerland
基金
澳大利亚研究理事会; 瑞士国家科学基金会; 英国医学研究理事会;
关键词
bioorganometallic chemistry; chemical biology; inhibitors; transferases; HALF-SANDWICH COMPLEXES; S-TRANSFERASES; IN-VITRO; P1-1; DRUGS; SITE; RAT;
D O I
10.1002/anie.200900185
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Double trouble: A hybrid organic-inorganic (organometallic) inhibitor was designed to target glutathione transferases. The metal center is used to direct protein binding, while the organic moiety acts as the active-site inhibitor (see picture). The mechanism of inhibition was studied using a range of biophysical and biochemical methods. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3854 / 3857
页数:4
相关论文
共 31 条
[1]   Development of organometallic (organo-transition metal) pharmaceuticals [J].
Allardyce, CS ;
Dorcier, A ;
Scolaro, C ;
Dyson, PJ .
APPLIED ORGANOMETALLIC CHEMISTRY, 2005, 19 (01) :1-10
[2]   Organometallic ruthenium inhibitors of glutathione-S-transferase P1-1 as anticancer drugs [J].
Ang, Wee Han ;
De Luca, Anastasia ;
Chapuis-Bernasconi, Catherine ;
Juillerat-Jeanneret, Lucienne ;
Lo Bello, Mario ;
Dyson, Paul J. .
CHEMMEDCHEM, 2007, 2 (12) :1799-1806
[3]   Strategy to tether organometallic ruthenium-arene anticancer compounds to recombinant human serum albumin [J].
Ang, Wee Han ;
Daldini, Elisa ;
Juillerat-Jeanneret, Lucienne ;
Dyson, Paul J. .
INORGANIC CHEMISTRY, 2007, 46 (22) :9048-9050
[4]   Development of organometallic ruthenium-arene anticancer drugs that resist hydrolysis [J].
Ang, Wee Han ;
Daldini, Elisa ;
Scolaro, Claudine ;
Scopelliti, Rosario ;
Juillerat-Jeannerat, Lucienne ;
Dyson, Paul J. .
INORGANIC CHEMISTRY, 2006, 45 (22) :9006-9013
[5]   CYTOPLASMIC AND PERIPLASMIC PRODUCTION OF HUMAN PLACENTAL GLUTATHIONE TRANSFERASE IN ESCHERICHIA-COLI [J].
BATTISTONI, A ;
MAZZETTI, AP ;
PETRUZZELLI, R ;
MURAMATSU, M ;
FEDERICI, G ;
RICCI, G ;
LOBELLO, M .
PROTEIN EXPRESSION AND PURIFICATION, 1995, 6 (05) :579-587
[6]  
BUETLER TM, 1992, J ENVIRON SCI HEAL C, V10, P181
[7]   Nitrosylation of human glutathione transferase P1-1 with dinitrosyl diglutathionyl iron complex in vitro and in vivo [J].
Cesareo, E ;
Parker, LJ ;
Pedersen, JZ ;
Nuccetelli, M ;
Mazzetti, AP ;
Pastore, A ;
Federici, G ;
Caccuri, AM ;
Ricci, G ;
Adams, JJ ;
Parker, MW ;
Lo Bello, M .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (51) :42172-42180
[8]   1,3,5-TRIAZA-7-PHOSPHATRICYCLO[3.3.1.13,7]DECANE AND DERIVATIVES [J].
Daigle, DJ ;
Decuir, TJ ;
Robertson, JB ;
Darensbourg, DJ .
INORGANIC SYNTHESES, VOL 32, 1998, 32 :40-45
[9]   Ruthenium half-sandwich complexes bound to protein kinase Pim-1 [J].
Debreczeni, JÉ ;
Bullock, AN ;
Atilla, GE ;
Williams, DS ;
Bregman, H ;
Knapp, S ;
Meggers, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1580-1585
[10]   X-RAY CRYSTAL-STRUCTURES OF CYTOSOLIC GLUTATHIONE S-TRANSFERASES - IMPLICATIONS FOR PROTEIN ARCHITECTURE, SUBSTRATE RECOGNITION AND CATALYTIC FUNCTION [J].
DIRR, H ;
REINEMER, P ;
HUBER, R .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1994, 220 (03) :645-661