Transition States of Cisplatin Binding to Guanine and Adenine: ab initio Reactivity Study

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Title:Transition States of Cisplatin Binding to Guanine and Adenine: ab initio Reactivity Study
Creators:
Chval, Zdenek
Šíp, Miroslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 6, pp. 1105-1118
Uncontrolled Keywords:Purines, <i>Ab initio</i> calculations, Antitumor drugs, DFT, DNA, Chelates, Nucleobases, Reaction mechanisms, Platinum, Recognition, Hydrogen bonds

Abstract

Fully optimised HF and DFT transition states of cisplatin binding to adenine and guanine are presented for the first time. They have similar structure as the recently published transition states for cisplatin hydrolysis with the angle of about 70° between entering and leaving ligands and corresponding bonds prolonged up to 0.5 Å. Calculated activation energies are in the range of 10.5-18 kcal/mol. The lowest activation energies were found for the binding of <i>cis</i>-Pt[(NH<sub>3</sub>)<sub>2</sub>(H<sub>2</sub>O)(OH)]<sup>+</sup> to guanine. The role of hydrogen bonds in recognition of binding sites, stabilisation of reactants and final yields of individual cisplatin-DNA adducts is discussed. <p>

Title:Transition States of Cisplatin Binding to Guanine and Adenine: ab initio Reactivity Study
Creators:
Chval, Zdenek
Šíp, Miroslav
Uncontrolled Keywords:Purines, <i>Ab initio</i> calculations, Antitumor drugs, DFT, DNA, Chelates, Nucleobases, Reaction mechanisms, Platinum, Recognition, Hydrogen bonds
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:6
Page Range:pp. 1105-1118
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20031105UNSPECIFIED
ID Code:2107
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Chval, Zdenek; Šíp, Miroslav (2003) Transition States of Cisplatin Binding to Guanine and Adenine: ab initio Reactivity Study. Collection of Czechoslovak Chemical Communications, 68 (6). pp. 1105-1118. ISSN 0010-0765

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