Identification of N2-substituted 2'-deoxyguanosine-3'-phosphate adducts detected by 32P-postlabeling of styrene-oxide-treated DNA.
Pongracz-K; Kaur-S; Burlingame-AL; Bodell-WJ
Carcinogenesis 1992 Mar; 13(3):315-319
32P-Postlabeling was used to analyze lymphocytes of workers exposed at the workplace to styrene (100425) in an effort to determine the presence of DNA adducts. An aqueous reaction mixture of 2'- deoxyguanosine-3'-phosphate and styrene-7,8-oxide was prepared. Using liquid secondary ion and four sector tandem mass spectrometry, ultraviolet, circular dichroism, and fluorescence spectrophotometry and 32P-postlabeling, two diastereomers of N2-(2-hydroxy-1- phenylethyl)-2'-deoxyguanosine-3'-phosphate and the corresponding N- 1 substituted compounds were isolated and characterized. Mass spectrometry analysis indicated that the N2-derivatives were formed through ring opening at the alpha position. Both the R-enantiomer and the S-enantiomer of the N2-derivatives were identified through circular dichroic analysis. Adducts 1 and 2 were identified as bis(2- hydroxy-2(1)-phenylethyl)-2'-deoxyguanosine-3',5'-bisphosphate derivatives. Adduct 6 arose as a result of aralkylation at the N2- exocyclic site of the guanine base. The N2-adducts were the principal adducts detected. The chromatographic retention of the N2- derivatives on octadecylsilyl plates was highly dependent on the concentration of the buffer; as ionic strength increased, the N2- derivative was more strongly retained.
NIOSH-Publication; NIOSH-Grant; Grants-other; Plastics-industry; DNA-adducts; DNA-damage; Genotoxic-effects; Blood-cells; Chemical-analysis
Biomedical & Environ Hlth Scis University of California School of Public Health Berkeley, CA 94720
Other Occupational Concerns; Grants-other
University of California Berkeley, Berkeley, California