Reaction with DNA and mutagenic specificity of syn-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide
Journal Article
·
· Chemical Research in Toxicology
- ABL-Basic Research Program, Frederick, MD (United States)
- Ben May Institute, Chicago, IL (United States)
- DynCorp., Inc., Frederick, MD (United States)
The spectroscopic characterization of purine deoxyribonucleoside adducts derived from the fjord-region syn-benzo[g]chrysene 11,12-dihydrodiol 13,14-epoxide and the mutagenic specificity of the latter compound for the supF gene in the pSP189 shuttle vector are described. This dihydrodiol epoxide preferentially forms adducts with deoxyadenosine residues in DNA and is preferentially opened trans in reactions with DNA or with deoxyribonucleotides. In common with other fjord-region syn-dihydrodiol epoxides, the most frequently observed mutational changes were A {yields} T and G {yields} T changes. This hydrocarbon dihydrodiol epoxide is structurally similar to syn-benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide but has an additional benzene ring annelated distant from the reaction center. As anticipated, there were some common features in the chemistry and mutagenicities of these two compounds, but there were also substantive differences which indicate factors of importance in controlling reactions of these kinds of compounds with DNA. 38 refs., 11 figs., 2 tabs.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 50622
- Journal Information:
- Chemical Research in Toxicology, Journal Name: Chemical Research in Toxicology Journal Issue: 3 Vol. 7; ISSN 0893-228X; ISSN CRTOEC
- Country of Publication:
- United States
- Language:
- English
Similar Records
Synthesis of optically active Fjord-region 11,12-diol 13,14-epoxides and the K-region 9,10-oxide of the carcinogen benzo(g)chrysene
Mutagenic activity of the 4,5- and 9,10-dihydrodiols of benzo[i]fluoranthene and their syn- and anti-dihydrodiol epoxides in Salmonella typhimurium
Evidence that binding of 7,12-dimethylbenz(a)anthracene to DNA in mouse embryo cell cultures results in extensive substitution of both adenine and guanine residues
Journal Article
·
Fri Jul 21 00:00:00 EDT 1989
· Journal of Organic Chemistry; (USA)
·
OSTI ID:7196625
Mutagenic activity of the 4,5- and 9,10-dihydrodiols of benzo[i]fluoranthene and their syn- and anti-dihydrodiol epoxides in Salmonella typhimurium
Journal Article
·
Thu Dec 31 23:00:00 EST 1992
· Environmental and Molecular Mutagenesis; (United States)
·
OSTI ID:7074811
Evidence that binding of 7,12-dimethylbenz(a)anthracene to DNA in mouse embryo cell cultures results in extensive substitution of both adenine and guanine residues
Journal Article
·
Thu Sep 01 00:00:00 EDT 1983
· Cancer Res.; (United States)
·
OSTI ID:5743999