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DNA bindings of a novel anticancer drug, trans-[PtCl2(isopropylamine)(3-picoline)], and kinetic competition of purine bases with protein residues in the bifunctional substitutions: a theoretical DFT study

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Abstract

The coordination of an activated novel anticancer drug, trans-[PtCl2(ipa)(3-pico)] (ipa = isopropylamine, 3-pico = 3-methylpyridine), to DNA in a two-step process has been studied using a combination of DFT theory and IEF–PCM approach. The computed free energy barrier for the first substitution is 16.9/16.9 kcal/mol for trans-Pt-chloroaqua → trans-/cis-Pt–guanine monoadduct, 18.7/18.7 kcal/mol for trans-Pt-chloroaqua → trans-/cis-Pt–adenine monoadduct. Barriers of 20.2/20.2 kcal/mol are evaluated for trans-Pt-diaqua → trans-/cis-Pt–guanine monoadduct, 26.0/26.0 kcal/mol for trans-Pt-diaqua → trans-/cis-Pt–adenine monoadduct. In the second substitution starting from trans-Pt–guanine monoadduct to trans-diadducts, the reaction barrier for (G–Pt–G) head-to-head formation is 22.2 kcal/mol, while 22.0 kcal/mol is evaluated for the head-to-tail configuration. Barriers for (A–Pt–G) head-to-head and head-to-tail formation are 25.7/28.9 kcal/mol, respectively. The observed preference for guanine is explained in terms of remarkable larger complexation energy for the initial reactant complex as well as the lower barrier height for the substitutions. In the competition reactions, cysteine residue stabilizes the transition state (ΔG aq/ZPE = 13.1 kcal/mol) for platination more efficiently than purine bases and other protein residues.

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  1. Department of Chemistry, Jinan University, 510632, Guangzhou, Guangdong, People’s Republic of China

    Yan Gao & Lixin Zhou

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  1. Yan Gao
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Correspondence to Lixin Zhou.

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Gao, Y., Zhou, L. DNA bindings of a novel anticancer drug, trans-[PtCl2(isopropylamine)(3-picoline)], and kinetic competition of purine bases with protein residues in the bifunctional substitutions: a theoretical DFT study. Theor Chem Acc 123, 455–468 (2009). https://doi.org/10.1007/s00214-009-0557-5

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