Detail of "64920-31-6"

Reference

High mutagenicity of metabolically activated chrysene 1,2 dihydrodiol: evidence for bay region activation of chrysene

High mutagenicity of metabolically activated chrysene 1,2 dihydrodiol: evidence for bay region activation of chrysene. Wood, A. W.; Levin, W.; Ryan, D.; Thomas, P. E.; Yagi, H.; Mah, H. D.; Thakker, D. R.; Jerina, D. M.; Conney, A. H. (Dep. Biochem. Drug Metab., Hoffmann-La Roche, Inc., Nutley, N. J., USA). Biochem. Biophys. Res. Commun., 78(3), 847-54 (English) 1977. CODEN: BBRCA9. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) Chrysene (I) [218-01-9] and the 3 metabolically possible vicinal trans-dihydrodiols of I were tested for mutagenicity towards S. typhimurium strain TA100 in the presence of hepatic microsomes or a highly purified hepatic microsomal monooxygenase system. The products formed during the metabolic activation of trans-chrysene 1,2-dihydrodiol [64920-31-6], were 20-fold more mutagenic to the bacteria than the metabolites formed from I, trans-chrysene 3,4-dihydrodiol [64920-32-7], or trans-chrysene 5,6-dihydrodiol [56183-24-5]. When the double bond in the 3,4-position of chrysene 1,2-dihydrodiol was satd., the resulting tetrahydrodiol could not be metabolically activated. These results, which strongly suggest that chrysene 1,2-dihydrodiol is activated by metab. to either or both of the diastereomeric chrysene 1,2-diol-3,4-epoxide 1,2,3,4-tetrahydro [64920-33-8], provide addnl. support for the bay region theory of polycyclic hydrocarbon carcinogenicity.

Stereoselective metabolism of chrysene by rat liver microsomes

Stereoselective metabolism of chrysene by rat liver microsomes. Direct separation of diol enantiomers by chiral stationary phase HPLC. Weems, Henri B.; Fu, Peter P.; Yang, Shen K. (F. Edward Hebert Sch. Med., Uniformed Serv. Univ. Health Sci., Bethesda, MD 20814, USA). Carcinogenesis (London), 7(7), 1221-30 (English) 1986. CODEN: CRNGDP. ISSN: 0143-3334. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The direct enantiomeric resoln. of non-K region, trans-1,2-dihydrodiol [64920-31-6], 1,2,3,4-tetrahydro-trans-1,2-diol [73771-79-6], trans-3,4-dihydrodiol [64920-32-7] and 1,2,3,4-tetrahydro-trans-3,4-diol [106138-30-1], K region trans [56183-24-5]- and cis-5,6-dihydrodiol [82041-83-6] and their monomethyl ethers of chrysene (I) was studied by chiral stationary phase (CSP) HPLC. The chiral stationary phase columns were packed with g-aminopropylsilanized silica to which either (R)-N-(3,5-dinitrobenzoyl)phenylglycine or (S)-N-(3,5-dinitrobenzoyl)leucine was bonded either ionically or covalently. Enantiomers of all dihydrodiol derivs. were resolved by 1 or more, but not all, of the chiral stationary phases used. Enantiomeric resolns. were substantially improved when the non-K region dihydrodiols were converted to tetrahydrodiols. The abs. configurations of the K region trans- and cis-5,6-dihydrodiols were established by the exciton chirality CD method. The (R,R):(S,S) enantiomer ratios, detd. by CSP-HPLC, of the 1,2-, 3,4- and 5,6-trans-dihydrodiols formed in the metab. of chrysene by liver microsomes from untreated male rats of the Sprague-Dawley strain were , and , resp.; from phenobarbital-treated rats, , and , resp.; from 3-methylcholanthrene-treated rats, , and , resp. The abs. configurations of chrysene 5,6-epoxide enantiomers, resolved by CSP-HPLC, were elucidated by the detn. of the structures and abs. configurations of their methoxylation products. Both enantiomers of chrysene 5,6-epoxide were hydrated by microsomal epoxide hydrolase [9048-63-9] to chrysene trans-5,6-dihydrodiol enriched (67-92%) in the 5R,6R enantiomer. Chrysene 5R,6S-epoxide [98243-93-7] was hydrated to trans-5,6-dihydrodiol at a rate ~6-fold faster than chrysene 5S,6R-epoxide [98243-92-6].