Polycyclic aromatic hydrocarbons 3-methylcholanthrene

Methods for the synthesis of the biologically active dihydrodiol and diol epoxide metabolites of both carcinogenic and noncarcinogenic polycyclic aromatic hydrocarbons are reviewed. Four general synthetic routes to the trans-dihydrodiol precursors of the bay region anti and syn diol epoxide derivatives have been developed. Syntheses of the oxidized metabolites of the following hydrocarbons via these methods are described benzo(a)pyrene, benz(a)anthracene, benzo-(e)pyrene, dibenz(a,h)anthracene, triphenylene, phen-anthrene, anthracene, chrysene, benzo(c)phenanthrene, dibenzo(a,i)pyrene, dibenzo(a,h)pyrene, 7-methyl-benz(a)anthracene, 7,12-dimethylbenz(a)anthracene, 3-methylcholanthrene, 5-methylchrysene, fluoranthene, benzo(b)fluoranthene, benzo(j)fluoranthene, benzo(k)-fluoranthene, and dibenzo(a,e)fluoranthene. 

Figuie 19. Absolute configurations and signs of rotation (tetrahydrofuran) for resolved K-region derivatives of polycyclic aromatic hydrocarbons. References are superscripted. Rotation of the free cis-4,5-dihydrodiol of benzo[a]pyrenc was not determined because of facile autoxidation which resulted in colored solutions. With liver microsomal enzymes from 3-methylcholanthrene-treated rats, the frar7s-(R,R)-dihydrodiol greatly predominates (96%) from benzo[a]pyrene, predominates (68%) from benz[a]anthracene, appears to be the minor enantiomer from 12-methylbenz[a]anthracene, and is the minor enantiomer (42%) from phenanthrene. ... 

Hepatic and extrahepatic CarbE activities have been studied after the exposure of rats to polycyclic aromatic hydrocarbons. In dose- and time-dependent studies, benz(a)anthracene, benzo(a)pyrene, and 3-methylcholanthrene moderately induced the hepatic cytosolic and kidney microsomal CarbEs activities, while anthracene, phenanthrene, and chrysene had... 

Polycyclic aromatic hydrocarbons Benzo(a)pyrenes Methylcholanthrene Dimethylbenz(a)anthracene Solvents Benzene Heavy metals Beryllium Manganese Nickel Cadmium Platinum Air pollutants Ozone... 

Polycyclic aromatic hydrocarbons DMBA (dimethylbenzanthracene), BaP (benzo[ ]pyrene), MCA (methylcholanthrene) ... 

Nearly 50 years ago, it was noted that rats exposed to 3-methylcholanthrene (3-MC) displayed a marked increase in metabolic capacity toward that substrate and other polycyclic aromatic hydrocarbons (PAHs) . This enhanced metabolic activity was referred to as aryl hydrocarbon hydroxylase (AHH) based on the ability of these enzymes to efficiently hydroxylate aromatic hydrocarbons ". It is now known that AHH activity is the collective activities of the CYPlAl, CYPl A2, and CYPIBI enzymes. 

Batel R, Bihari N, Kurelec B, Muller WEG, Zahn RK (1983) Presence of mixed function oxygenases in some marine invertebrates. Thalassia Jugoslav 19 23-29 Batel R, Bihari N, Zahn RK (1986) Purification and characterization of a single form of cytochrome P-450 from the spiny crab Maja crispata. Comp Biochem Physiol 83C 165-170 Batel R, Bihari N, Zahn RK (1988) 3-methylcholanthrene does induce mixed function oxidase activity in hepatopancreas of spiny crab Maja crispata. Comp Biochem Physiol 90C 435-438 Bauer JE, Kerr RP, Bautista MF, Decker C J, Capone DG (1988) Stimulation of microbial activities and polycyclic aromatic hydrocarbon degradation in marine sediments inhabited by Capitella capitata. Mar Env Res 25 63-84... 

Ah locus A gene(s) controlling the trait of responsiveness for induction of enzymes by aromatic hydrocarbons. In addition to aromatic hydrocarbons such as the polycyclics, the chlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls, as well as the brominated biphenyls, are involved. This trait, originally defined by studies of induction of hepatic aryl hydrocarbon hydroxylase activity following 3-methylcholanthrene treatment, is inherited by simple autosomal dominance in crosses and backcrosses between C57BL/6 (Ah-responsive) and DBA/2 (Ah-nonresponsive) mice. 

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