Conformational and topological analysis of the charge density in guanine-a-dicarbonyl adducts at AM1 level.

FIDANZA, N. G.; VALIENSI, P.; NELIDA MARIA PERUCHENA

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM

ELSEVIER SCIENCE BV

Año: 2000 vol. 544 p. 59 - 67

0166-1280

The mutagenic activity molecular mechanism of the á-dicarbonyl compounds was related, by Rodriguez Mellado and coworkers, to the ability to form adducts with the guanine residues of the nucleic acids. In this work, we have made a conformational, structural and topological study, from a theoretical point of view, of the hydrogen bonding interactions in guanine-á-dicarbonyl adducts. The topological properties of the electronic charge density, based on the theory of Atoms in Molecules and the semiempirical AM1 molecular orbital methods, were calculated in the following adducts: G-glyoxal, I, G-methylglyoxal, II, G-phenylglyoxal, G-diacetyl, and G-diphenylglyoxal. The results obtained are compared with the available experimental data over mutagenicity on Salmonella typhimurium strain TA100.