Studies on the reactivity of organometallic Ru-, Rh- and Os-pta complexes with DNA model compounds

被引：98

作者：

Dorcier, Antoine ^{[1
]}

Hartinger, Christian G. ^{[1
,2
]}

Scopelliti, Rosario ^{[1
]}

Fish, Richard H. ^{[3
]}

Keppler, Bernhard K. ^{[2
]}

Dyson, Paul J. ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland

[2] Univ Vienna, Inst Inorgan Chem, A-1090 Vienna, Austria

[3] Univ Calif Berkeley, Lawrence Berkeley Lab, Berkeley, CA 94720 USA

来源：

JOURNAL OF INORGANIC BIOCHEMISTRY | 2008年 / 102卷 / 5-6期

基金：

奥地利科学基金会;

关键词：

anticancer drugs; DNA binding; electrospray ionization mass spectrometry; pta; arene-ruthenium complexes; bioorganometallic chemistry;

D O I：

10.1016/j.jinorgbio.2007.10.016

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The reactions of arene-metal complexes (arene = p-cymene, benzene or pentamethylcyclopentadienyl, metal = Ru, Rh or Os), including 1,3,5-triaza-7-phosphatricyclo-[3.3.1.1]decanephosphine (pta) and chloro co-ligands, with 9-methylguanine, adenine, and a series of nucleosides were studied in water to ascertain the binding modes. The products were characterized by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Tandem mass spectrometry was found to provide excellent information on preferential binding sites. In general, the N7 position on guanine (the most basic site) was found to be the preferred donor atom for coordination to the metal complexes. The X-ray structures of the precursor complexes, [(eta(5)-C(10)H(15))RhCl(pta-Me)(2)]Cl(2), [(eta(6)-Cl(10)H(14))OsCl(pta)(2)]Cl, and [(eta(6)-C(6)H(6))OsCl(2)(CH(3)CN)], are also reported. (C) 2007 Elsevier Inc. All rights reserved.

引用

页码：1066 / 1076

页数：11

共 46 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] [Ru(η6-p-cymene)Cl2(pta)] (pta=1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane):: a water soluble compound that exhibits pH dependent DNA binding providing selectivity for diseased cells [J].

Allardyce, CS ;

Dyson, PJ ;

Ellis, DJ ;

Heath, SL .

CHEMICAL COMMUNICATIONS, 2001, (15) :1396-1397

[3] 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

[4] ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].

BENNETT, MA ;

SMITH, AK .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02) :233-241

[5] AN EMPIRICAL CORRECTION FOR ABSORPTION ANISOTROPY [J].

BLESSING, RH .

ACTA CRYSTALLOGRAPHICA SECTION A, 1995, 51 :33-38

[6] MONONUCLEAR ETA-6-PARA CYMENEOSMIUM(II) COMPLEXES AND THEIR REACTIONS WITH AL2ME6 AND OTHER METHYLATING REAGENTS [J].

CABEZA, JA ;

MAITLIS, PM .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (03) :573-578

[7] ESI-MS characterisation of protein adducts of anticancer ruthenium(II)-arene PTA (RAPTA) complexes [J].

Casini, Angela ;

Mastrobuoni, Guido ;

Ang, Wee Han ;

Gabbiani, Chiara ;

Pieraccini, Giuseppe ;

Moneti, Gloriano ;

Dyson, Paul J. ;

Messori, Luigi .

CHEMMEDCHEM, 2007, 2 (05) :631-+

[8] Highly selective binding of organometallic ruthenium ethylenediamine complexes to nucleic acids: Novel recognition mechanisms [J].

Chen, HM ;

Parkinson, JA ;

Morris, RE ;

Sadler, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :173-186

[9] Organometallic ruthenium(II) diamine anticancer complexes: Arene-nucleobase stacking and stereospecific hydrogen-bonding in guanine adducts [J].

Chen, HM ;

Parkinson, JA ;

Parsons, S ;

Coxall, RA ;

Gould, RO ;

Sadler, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :3064-3082

[10] CHEMICAL PROOF FOR PREFERRED NITROGEN QUARTERNIZATION IN 1,3,5-TRIAZA-7-PHOSPHAADAMANTANE [J].

DAIGLE, DJ ;

PEPPERMAN, AB .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (03) :579-580

← 1 2 3 4 5 →