Comparative analysis of the electrostatic potentials of some structural analogues of 2,3,7,8-tetrachlorodibenzo-p-dioxin and of related aromatic systems

Technical Report · Sun Dec 31 23:00:00 EST 1989

OSTI ID:6315247

Murray, J S; Evans, P; Politzer, P

An ab initio STO-5G computational analysis of the electrostatic potentials of four structural analogs of the highly toxic 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and four related aromatic systems (benzo(a)pyrene, benz(a)anthracene and two isomeric benzoflavones) was carried out. The systems, to varying degrees, induce aryl hydrocarbon hydroxylase activity and are believed to interact with the same cytosolic receptor in initiating their biochemical responses. It was found that a high degree of activity appears to require negative potentials that are non-overlapping above all or most of the lateral regions, with an observed optimum range of magnitudes. In systems with central oxygens, it is required that the negative oxygen potentials be small and weak; however, oxygen negative regions in the molecule are not necessary for high activity. The observed differences between the potential patterns of the four aromatic systems and those of TCDD and its active analogs may reflect an inherent dissimilarity in the nature of their interactions with the cytosolic receptor.

• Research Organization: New Orleans Univ., LA (USA). Dept. of Chemistry
• OSTI ID: 6315247
• Report Number(s): PB-91-109793/XAB
• Country of Publication: United States
• Language: English

Related Subjects

560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
BENZANTHRACENE
BENZOPYRENE
CONDENSED AROMATICS
DIOXIN
ENZYME ACTIVITY
ENZYMES
FLAVENOIDS
FLAVONES
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXYLASES
MEMBRANE PROTEINS
METABOLISM
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDOREDUCTASES
PROTEINS
RECEPTORS