Transition Metal Ion Complexes of N-alkylguanines

被引：6
作者：
Ferenc, G. [1 ]
Padar, P. [1 ]
Szolomajer, J. [1 ]
Howarth, N. M. [2 ]
Kovacs, L. [1 ]
机构：
[1] Univ Szeged, Dept Med Chem, H-6720 Szeged, Hungary
[2] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland
来源：
CURRENT ORGANIC CHEMISTRY | 2011年 / 15卷 / 16期
关键词：
N-alkylguanines; transition metal complexes; acid-base properties; cisplatin; X-RAY-STRUCTURE; RUTHENIUM(II) ARENE COMPLEXES; ANTICANCER PLATINUM DRUGS; NUCLEIC-ACIDS; DNA-BINDING; CRYSTAL-STRUCTURE; O; O-CHELATING LIGANDS; NUCLEOBASE ADDUCTS; CARRIER-LIGAND; GUANINE;
D O I：
10.2174/138527211796378451
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The family of cisplatin and its analogues contains some of the most powerful anticancer drugs developed to date and, since their discovery, extensive efforts have been devoted to understand their mode of action. 9-Alkylguanines have featured widely in these studies as model nucleobases. This review describes both the synthesis and the chemical, biological and miscellaneous spectroscopic properties of a variety of transition metal ion (Pt, Pd, Ru, Os, Rh, Re, Tc, Zn, Cu, Cd) complexes of N-alkylguanines (mostly 9-alkylguanines) which have been reported in the literature principally within the 2003-2008 period. Special attention has been given to the acid-base properties of these complexes, where coordination to transition metal ions usually leads to significant acidification of the guaninyl N1-H proton, and its consequences
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收藏
页码：2871 / 2892
页数：22
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共 70 条
[1]   1-Methyl-4-(methylamino)piperidine-platinum(II) adducts with DNA bases [J].
Ali, Mohammad S. ;
Fang, Jane J. ;
Burton, Christian ;
Glenn, Brandon ;
Khokhar, Abdul R. .
JOURNAL OF COORDINATION CHEMISTRY, 2007, 60 (06) :691-698
[2]   Homopiperazine Pt(II) adducts with DNA bases and nucleosides:: Crystal structure of [PtII(homopiperazine)(9-ethylguanine)2](NO3)2 [J].
Ali, Mohammad S. ;
Longoria, Edio, Jr. ;
Ould-Ely, Teyeb ;
Whitmire, Kenton H. ;
Khokhar, Abdul R. .
POLYHEDRON, 2006, 25 (10) :2065-2071
[3]   Model platinum nucleobase and nucleoside complexes and antitumor activity:: X-ray crystal structure of [PtIV(trans-1 R,2R-diaminocyclohexane) trans-(acetate)2(9-ethylguanine)Cl]NO3 • H2O [J].
Ali, MS ;
Khan, SRA ;
Ojima, H ;
Guzman, IY ;
Whitmire, KH ;
Siddik, ZH ;
Khokhar, AR .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (03) :795-804
[4]   cis-1,4-diaminocyclohexane-Pt(II) and -(IV) adducts with DNA bases and nucleosides [J].
Ali, MS ;
Khokhar, AR .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2003, 96 (04) :452-456
[5]   Interguanine hydrogen-bonding patterns in adducts with water and Zn-purine complexes (purine is 9-methyladenine and 9-methylguanine). Unexpected preference of Zn(II) for adenine-N7 over guanine-N7 [J].
Amo-Ochoa, Pilar ;
Miguel, Pablo J. Sanz ;
Castillo, Oscar ;
Sabat, Michal ;
Lippert, Bernhard ;
Zamora, Felix .
JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2007, 12 (04) :543-555
[6]   Perturbation of the NH2 pKa value of adenine in platinum(II) complexes:: Distinct stereochemical internucleobase effects [J].
Añorbe, MG ;
Lüth, MS ;
Roitzch, M ;
Cerdà, MM ;
Lax, P ;
Kampf, G ;
Sigel, H ;
Lippert, B .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (04) :1046-1057
[7]   Covalent and noncovalent interactions for [metal(dien)nucleobase]2+ complexes with L-tryptophan derivatives:: Formation of palladium-tryptophan species by nucleobase substitution under biologically relevant conditions [J].
Anzellotti, AI ;
Sabat, M ;
Farrell, N .
INORGANIC CHEMISTRY, 2006, 45 (04) :1638-1645
[8]   Platination of nucleobases to enhance noncovalent recognition in protein-DNA/RNA complexes [J].
Anzellotti, AI ;
Ma, ES ;
Farrell, N .
INORGANIC CHEMISTRY, 2005, 44 (03) :483-485
[9]   Metal ion interactions with nucleic acid bases in the tripodal tris(2-aminoethyl)amine (tren) ligand-system:: Crystal structures of [Ni(tren)(adeninato)(ClO4)] • adenine, [Cu(tren)(9-ethylguanine)] • (ClO4)2, [{Ni(tren)(H2O)}2(hypoxanthinato)] • (ClO4)3 • 1.5H2O, [Ni(tren)(hypoxanthinato)(H2O)] • ClO4 • 2H2O, and [{Ni(tren)(H2O)}2(hypoxanthinato)]2 • (NO3)6 • 4.5H2O [J].
Aoki, Katsuyuki ;
Salam, Md. Abdus ;
Munakata, Chie ;
Fujisawa, Ikuhide .
INORGANICA CHIMICA ACTA, 2007, 360 (12) :3658-3670
[10]   Pyrazolylboratozinc complexes of nucleosides and nucleoside analogues [J].
Badura, D ;
Vahrenkamp, H .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (20) :3723-3730
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