Mechanisms of interaction of polycyclic aromatic diol epoxides with DNA and structures of the adducts

Journal Article · Tue Jan 01 00:00:00 EST 1985 · ACS Symp. Ser.; (United States)

DOI:https://doi.org/10.1021/bk-1985-0283.ch006· OSTI ID:6697889

Geacintov, N E

Spectroscopic studies on complexes derived from the binding of benzo(a)pyrene-7,8-diol-9,10-epoxide (BaPDE) to DNA indicate that the conformations of the adducts can be broadly classified into two types: site I which displays most of the properties of intercalative adducts, and site II which is characterized by an orientation of the planar aromatic residues tilted closer to the axis of the helix. Both the syn and the anti diastereomers of BaPDE form unstable type I physical intercalation complexes and undergo specific and general acid catalysis to form tetraols (>90%) and covalent adducts (<10%). The biologically highly active (+) anti-BaPDE enantiomer undergoes a marked reorientation upon covalent binding to form almost exclusively site II adducts, while the less active (-) anti-BaPDE enantiomer, as well as racemic syn-BaPDE, give mixtures of site I and site II adducts. The presence of site II type of adducts appears to be correlated with high tumorigenic and mutagenic activities in this family of stereoisomeric diol epoxides. 54 references, 6 figures.

• Research Organization: New York Univ., NY
• OSTI ID: 6697889
• Journal Information: ACS Symp. Ser.; (United States), Vol. 6:283
• Country of Publication: United States
• Language: English

Related Subjects

63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
59 BASIC BIOLOGICAL SCIENCES
BENZOPYRENE
BIOCHEMICAL REACTION KINETICS
DNA ADDUCTS
MOLECULAR STRUCTURE
CARCINOGENESIS
COVALENCE
EPOXIDES
EXPERIMENTAL DATA
MUTAGENESIS
ADDUCTS
AROMATICS
CONDENSED AROMATICS
DATA
HYDROCARBONS
INFORMATION
KINETICS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PATHOGENESIS
REACTION KINETICS
560300* - Chemicals Metabolism &amp; Toxicology
550200 - Biochemistry