1996 年 1996 巻 1 号 p. 100-103
The reaction of 2'-deoxyguanosine with N-nitroso-N-methyl-N'-phenylurea 1 in methanol gavo hree alkylated products, N1-(15%), N7-(19%), and O6-(24%)methy1-2'-deoxyguanosine, diffe ring rom the result in the reaction with methyl iodide in which only the N7-methyl derivative was obtained The random distribution of the products may be due to the formation of a carbonium ion from 1, being mpable of the occurrence of the, SN1 reaction at the nucleophilic sites in the guanine residue. The rela ive extent of the O6-alkylation (O6/N1, O6/N7) was found to be decreased significantly when the water was added to the reaction medium. This observation suggests that the importance of the O6-alkylation will grow further if the DNA-alkylations by alkylnitrosoureas occur in hydrophobic environment Lnder certain cellular conditions. Thus the evaluation of the carcinogenicity of alkylnitro soureas may veil be achieved with properly defined experimental conditions including a solvent or a dosage method
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