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Electrostatic effect of the macromolecular structure on the biochemical reactivity of the nucleic acids. Significance for chemical carcinogenesis
Author(s) -
Pullman Alberte,
Pullman Bernard
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560180724
Subject(s) - nucleic acid , chemistry , electrophile , reactivity (psychology) , nucleophile , macromolecule , pyrimidine , nucleotide , purine , stereochemistry , computational chemistry , organic chemistry , biochemistry , enzyme , medicine , alternative medicine , pathology , gene , catalysis
The computation of the electrostatic molecular potentials associated with the reactive sites of the purine and pyrimidine bases of the nucleic acids indicates that the absolute values (depths) of the potential minima increase steadily in the series: free bases (or nucleosides), nucleotides, single‐stranded helices, double helices. It is shown that this evolution parallels the reactivity of the principal types of carcinogenic substances (which act as electrophiles) toward these substrates. It parallels also the reactivity of the anticancer platinum derivatives. Electrophilic reactions occurring at the phosphate oxygens follow the same pattern, which correlates with the parallel increase of the potential minimum associated with these groups. On the other hand, nucleophilic reactions at the bases follow, as predictable from our results, a reverse evolution.