Identification of alkylation products of styrene oxide in single- and double-stranded DNA.
Radioactive styrene oxide was reacted with double- and single-stranded DNA and the binding products were characterized by HPLC after neutral hydrolysis and enzyme digestion of DNA. More products were formed in single-stranded DNA as compared with double-stranded DNA. In single-stranded DNA at least 95% of the adducts were guanine N-7-,N2- and O6-alkylation products; they were formed in proportions 54:33:12. In double-stranded DNA the respective proportion was 74:23:3.7, indicating a selective suppression of alkylation at atoms N2 and, particularly, O6 that take part in hydrogen bonding in double-stranded DNA. The alpha- and beta-isomers of 7-alkylguanine were formed in a similar proportion in single- and double-stranded DNA, indicating no steric hindrance.
Vodicka
P
P
Institute of Occupational Health, Helsinki, Finland.
Hemminki
K
K
D000478:Alkylation; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000187:drug effects*; D004249:DNA Damage; D004277:DNA, Single-Stranded / Q000187:drug effects; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D006147:Guanine / Q000031:analogs & derivatives; D066298:In Vitro Techniques; D013329:Structure-Activity Relationship
D004277:DNA, Single-Stranded; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D006147:Guanine; D004247:DNA; C013690:styrene oxide