Mutagenicity and putative carcinogenicity tests of several polycyclic aromatic compounds associated with impurities of the insecticide methoxychlor

Grant, Elizabeth; Mitchell, Reginald H.; West, Paul R.; Mazuch, Ludvik; Ashwood-Smith, M.J.

doi:10.1016/0165-1218(76)90047-1

Cited by 16 publications

(3 citation statements)

References 2 publications

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“…The predominant methylated derivative of benzo(a)pyrene, 6-Methylbenzo(a)pyrene is approximately 10 times more mutagenic than benzo(a) pyrene in the Salmonella typhimurium strain TA98 and twice as mutagenic in strain TA100 (8,67,68). The complete carcinogenic activity of 6-methylbenzo(a)pyrene has been reported to be similar to benzo(a)pyrene.…”

Section: Resultsmentioning

confidence: 94%

Benzo(a)pyrene Metabolism: Role of Bioalkylation

Myers

Ali

Wright

et al. 2007

Polycyclic Aromatic Compounds

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Previous studies of the metabolic activation of chemical carcinogens including benzo(a)pyrene have demonstrated that selected aromatic hydrocarbons can undergo a series of biological substitution reactions in tissue cytosolpreparations when in the presence of the methyl donor S-adenosyl-L-methionine. Although identification of the methylated metabolites of carcinogens had been tentatively established using liquid chromatographic techniques, confirmation of the identity of these methylated derivatives has remained elusive. In the present study, the carcinogen benzo(a)pyrene was found to undergo methylation reactions in the presence of rat liver cytosol preparations to yield products that were identified as methylated, formyl and hydroxyalkyl derivatives of the parent carcinogen. Identification and confirmation of the identity of the 6-methylbenzo(a)pyrene metabolite was confirmed by both UV detection, gas chromatographic and mass spectral identification, and NMR analysis of metabolic fractions obtained from incubations of benzo(a)pyrene. The results conclusively demonstrate that the carcinogen benzo(a)pyrene undergoes biological substitution reactions to yield 6-methylbenzo(a)pyrene in the presence of cytosolic enzymes. The presence of 6-methylbenzo(a)pyrene as a 339 340 S. R. Myers et al. metabolite of benzo(a)pyrene illustrates and confirms the presence of centers of reactivity in unsubstituted aromatichydrocarbons. These centers of reactivity serve as sites for biochemical substitution reactions, yielding methyl substituted hydrocarbons. Furthermore, these methylated metabolites of polycyclic aromatic hydrocarbons are further metabolically activated to hydroxyalkyl and formyl derivatives which can be subsequently activated to electrophilic esters leading to DNA and protein reactive species.

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Section: Resultsmentioning

confidence: 94%

Benzo(a)pyrene Metabolism: Role of Bioalkylation

Myers

Ali

Wright

et al. 2007

Polycyclic Aromatic Compounds

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“…The Salmonella typhimurium strain used was TA 98 (1 538 plus an R factor plasmid), kindly provided by Professor B. N. Ames (Berkeley). The microsomal fractions were obtained from rat liver homogenates as described by us previously (35). Without microsomes neither 1 or 2 produced any revertant colonies with TA 98.…”

Section: Mutagenicity Resultsmentioning

confidence: 99%

“…These were carried out using DMSO solutions of 1 and 2 (0.1 mg/mL) on Salmonella typhimurium TA 98 (with and without microsomes) as described by us previously (35).…”

Section: Mutagenicity Testsmentioning

confidence: 99%

Straining strained molecules. III. The spectral and mutagenic properties and an alternate synthesis of diaceperylene and dicyclopenta[1,2,3-cd:1′,2′,3′-lm]perylene

Mitchell¹,

Chaudhary²,

Williams³

et al. 1992

Can. J. Chem.

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. Can. J. Chem. 70, 1015 (1992). The synthesis of diaceperylene (I) from 5,6-dilithioacenaphthene via nickel or cobalt catalysed couplings proceeded in better yield than a multistep synthesis involving formation of 5,5'-diacenaphthene first. Dehydrogenation of 1 to dicyclopenta[l,2,3-cd: 11,2',3'-lmlperylene (2) proved a better route than coupling of 5,6-disubstituted acenaphthylene derivatives. Ultraviolet, proton, and carbon nuclear magnetic resonance spectra and electrode reduction potential data of 1 and 2 are discussed with respect to molecular mechanics calculations of strain in these and related bridged naphthalenes. Both 1 and 2 were found to be weakly mutagenic in an Ames microsome test, in contrast to cyclopenta[cd]pyrene. [Traduit par la redaction]

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3,6,11,14‐Tetramethoxydibenzo( g , p )‐Chrysene 60223‐52‐1

2004

Sax's Dangerous Properties of Industrial Materials

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Mutagenicity and putative carcinogenicity tests of several polycyclic aromatic compounds associated with impurities of the insecticide methoxychlor

Cited by 16 publications

References 2 publications

Benzo(a)pyrene Metabolism: Role of Bioalkylation

Benzo(a)pyrene Metabolism: Role of Bioalkylation

Straining strained molecules. III. The spectral and mutagenic properties and an alternate synthesis of diaceperylene and dicyclopenta[1,2,3-cd:1′,2′,3′-lm]perylene

3,6,11,14‐Tetramethoxydibenzo( g , p )‐Chrysene 60223‐52‐1

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