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© 1996 Oxford University Press

research-article

32P-Postlabelling of diastereomeric 7-alkylguanine adducts of butadiene monoepoxide

Rajiv Kumar, Pavel Vodicka 1, Pertti Koivista 2, Kimmo Peltonen 2 and Kari Hemminki

Center for Nutrition and Toxicology, Karolinska Institute Novum, 141 57 Huddinge, Sweden
1Department of Developmental Genotoxicology, Institute of Experimental Medicine Czech Academy of Science, Videnska 1083, 14020 Prague 4, Czech Republic
2Finish Institute of Occupational Health, Molecular Dosimetry Group Topeliuksenkatu 41 aA, FIN-00250 Helsinki, Finland

The reaction of 3, 4-epoxy-1-butene (BMO) with deoxygu-anosine-3'-monophosphate (3'-dGMP) resulted in the formation of two pairs of diastereomeric 7-alkyl-3'-dGMP derivatives corresponding to two isomers C''-1 and C''-2. The T4 polynucleotide kinase-mediated phosphorylation with ({gamma}-32P)-ATP showed preferential labelling of diastereo-mers of the C''-1 isomer. The diastereomers 1 and 2 of the C''-1 isomer had labelling efficiencies of 42%.However, the labelling efficiencies of diastereomers 3 and 4 of the C''-2 isomer were 11 and 10%, respectively.The 32P-postlabelling of BMO-modified DNA yielded four isomers in the ratio of 4: 4: 1: 1 with overall recoveries being 14%. The two isomers had a half-life of 270 min (C''-1 isomer) and 300 min (C''-2 isomer) which is in accordance with the stability predicted by other similar adduct experiments. The molecular modelling experiments showed more pronounced restricted rotation of butadiene residue in C''-2 isomers due to steric interaction between butadiene residue at N-7 and O6 atom of guanine than in C''-1 isomer. The butadiene residue also leads to steric overcrowding at 3'-phosphate in C''-2 isomer which probably restricts the access to the active site of T4 polynucleotide kinase.


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