Interactions between DNA purinic bases and amodiaquine: A theoretical approach

• Main Authors: Valdemar Lacerda Júnior, José Maria Pires, Adilson Beatriz, Maria Lara Palmeira de Macedo Arguelho
• Format: Article
• Language: English
• Published: Universidade Federal de Mato Grosso do Sul 2010-06-01
• Series: Orbital: The Electronic Journal of Chemistry
• Subjects: amodiaquine; adduct formation; fukui index; softness; density functional theory; dft
• Online Access: http://orbital.ufms.br/index.php/Chemistry/article/view/115

<div align="justify"><span style="font-family: Verdana; font-size: 10pt"><span style="font-family: 'Verdana','sans-serif'; font-size: 10pt">We study theoretically the amodiaquine-adenine and amodiaquine-guanine adducts formation using Density Functional Theory (B3LYP) and the 6-31G(d) basis set for the geometry optimizations and 6-31+G(d,p) for the analysis of the global indexes: electrophilicity (</span><span style="font-family: Symbol"><font face="Symbol">w</font></span><span style="font-family: 'Verdana','sans-serif'; font-size: 10pt">), electronic chemical potential (</span><span style="font-family: Symbol; font-size: 10pt">m</span><span style="font-family: 'Verdana','sans-serif'; font-size: 10pt">), hardness (</span><span style="font-family: Symbol; font-size: 10pt"><font face="Symbol">h</font></span><span style="font-family: 'Arial','sans-serif'; font-size: 10pt">)</span><span style="font-family: 'Verdana','sans-serif'; font-size: 10pt"> and softness (S), based in the Frontier Molecular Orbital Theory &ndash; FMO. Local softness for nucleophilic reaction (s_k</span>^{<span style="font-family: Symbol; font-size: 10pt">+</span>}<span style="font-family: 'Verdana','sans-serif'; font-size: 10pt">) sites over guanine was evaluated using Fukui function (</span><span style="font-family: 'Monotype Corsiva'; font-size: 14pt">f</span><span style="font-family: 'Times New Roman','serif'; font-size: 14pt"> </span>_{<span style="font-family: 'Times New Roman','serif'; font-size: 12pt">k</span>}<span style="font-family: 'Verdana','sans-serif'; font-size: 10pt">). We also evaluated the guanine Electrostatic Potential (EP) values using the (MSK) charge scheme. The theoretical calculations had demonstrated that the amodiaquine has greater electronic affinity for the guanine, with irreversible formation of the amodiaquine-guanine adduct, as reported before on a previous experimental work.</span></span></div>