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Computational Investigation of Selective DNA Methylation
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Many alkylating agents covalently bind to nucleophilicpositions in cellular DNA, causing DNA damage. This has beendirectly linked to mutagenic and carcinogenic activity. Methanediazonium ions, which are the reactive intermediates formed fromseveral potent carcinogenic methylating agents including methylnitrosourea, can simultaneously react with different DNA sites. Abinitio quantum mechanical SCF and density functional methods havebeen employed to examine diazonium ion-DNA base transition statesand diazonium ion-oligonucleotide model transition states in thegas phase and in an aqueous environment. This characterization oftransition states was used to provide descriptions of site andsequence specific reaction patterns of methane diazonium ions atdifferent DNA bases and at different guanine sites in sequencescontaining multiply stacked guanines. This work provides acomputational methodology that, in principle, can describe the DNAreaction specificity of a large number of mutagens andcarcinogens.
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