title: Molecular electrostatic potential energies and methylation of DNA bases: a molecular orbital-generated quantitative structure-activity relationship.
abstract: 1. The results of molecular orbital (MO) calculations, by the MINDO/3 method, on DNA bases, are reported; which point to a radical mechanism of alkylation. 2. Molecular electrostatic potential energy maps indicate propensity for alkylation by N-methyl-N-nitrosourea at key atoms on DNA bases. 3. A correlation between the MO-derived parameters net atomic charges on heteroatoms and superdelocalizability with percentage alkylation by N-methyl-N-nitrosourea is shown.
mesh_terms: D000477:Alkylating Agents / Q000494:pharmacology*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004247:DNA / Q000187:drug effects* / Q000378:metabolism; D008745:Methylation; D008770:Methylnitrosourea / Q000494:pharmacology*; D009690:Nucleic Acid Conformation; D013329:Structure-Activity Relationship
chemical_list: D000477:Alkylating Agents; D008770:Methylnitrosourea; D004247:DNA