Base sequence effects on interactions of aromatic mutagens with DNA (deoxyribonucleic acid)
The base-sequence dependence of the adduct conformations-derived from the covalent binding of trans-7,8-diol-anti-9,10--epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BPDE) (+) and (-) enantiomers to synthetic DNAs of defined base composition and sequence is described. The diol epoxide BPDE is the ultimate mutagenic and tumorigenic metabolite of benzo(a)pyrene, a common air pollutant, which is a byproduct of fossil fuel combustion processes. The covalent addition products of BPDE can be classified according to two types: (1) site I, involving carcinogen-DNA base stacking interactions, and (2) site II, in which the BPDE residue appears to be located at a partially external DNA binding site. The presence of site II adducts, rather than site I adducts, is correlated with high mutagenicities and tumorigenicities of polycyclic aromatic diol epoxides. It is shown here that the formation of site II adducts derived from the binding of the more tumorigenic (+)- BPDE enantiomer to DNA is particularly favored in deoxyguanine-rich sequences. 12 refs., 6 figs., 3 tabs.
- Research Organization:
- New York Univ., NY (USA). Dept. of Chemistry
- Sponsoring Organization:
- DOE/ER
- DOE Contract Number:
- FG02-88ER60674
- OSTI ID:
- 5643342
- Report Number(s):
- DOE/ER/60674-2; ON: DE90002037
- Country of Publication:
- United States
- Language:
- English
Similar Records
Base sequence effects on interactions of aromatic mutagens with DNA
Mechanisms of interaction of polycyclic aromatic diol epoxides with DNA and structures of the adducts
Regio- and stereoselectivity of various forms of purified cytochrome P-450 in the metabolism of benzo(a)pyrene and (-)trans-7-8-dihydroxy-7-8-dihydrobenzo(a)pyrene as shown by product formation and binding to DNA
Technical Report
·
Fri Aug 31 00:00:00 EDT 1990
·
OSTI ID:6368272
Mechanisms of interaction of polycyclic aromatic diol epoxides with DNA and structures of the adducts
Journal Article
·
Mon Dec 31 23:00:00 EST 1984
· ACS Symp. Ser.; (United States)
·
OSTI ID:6697889
Regio- and stereoselectivity of various forms of purified cytochrome P-450 in the metabolism of benzo(a)pyrene and (-)trans-7-8-dihydroxy-7-8-dihydrobenzo(a)pyrene as shown by product formation and binding to DNA
Journal Article
·
Sat Jul 01 00:00:00 EDT 1978
· Proc. Natl. Acad. Sci. U.S.A.; (United States)
·
OSTI ID:6470950
Related Subjects
550200* -- Biochemistry
59 BASIC BIOLOGICAL SCIENCES
AROMATICS
AZOLES
BENZOPYRENE
BIOCHEMICAL REACTION KINETICS
CARCINOGENESIS
CONDENSED AROMATICS
DNA REPLICATION
DNA SEQUENCING
DOCUMENT TYPES
EVALUATION
GENE REGULATION
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
KINETICS
MODIFICATIONS
NUCLEIC ACID REPLICATION
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PATHOGENESIS
POLYCYCLIC AROMATIC HYDROCARBONS
PROGRESS REPORT
REACTION KINETICS
STRUCTURAL CHEMICAL ANALYSIS
STRUCTURE-ACTIVITY RELATIONSHIPS
TETRAZOLES
59 BASIC BIOLOGICAL SCIENCES
AROMATICS
AZOLES
BENZOPYRENE
BIOCHEMICAL REACTION KINETICS
CARCINOGENESIS
CONDENSED AROMATICS
DNA REPLICATION
DNA SEQUENCING
DOCUMENT TYPES
EVALUATION
GENE REGULATION
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
KINETICS
MODIFICATIONS
NUCLEIC ACID REPLICATION
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PATHOGENESIS
POLYCYCLIC AROMATIC HYDROCARBONS
PROGRESS REPORT
REACTION KINETICS
STRUCTURAL CHEMICAL ANALYSIS
STRUCTURE-ACTIVITY RELATIONSHIPS
TETRAZOLES