Microsomal activation of fluoranthene to mutagenic metabolites

Babson, John R.; Russo-Rodriguez, Sandra; Wattley, R. V.; Bergstein, Paul L.; Rastetter, William H.; Liber, Howard L.; Andon, Barbara M.; Thilly, William G.; Wogan, Gerald N.

doi:10.1016/0041-008x(86)90343-1

Cited by 53 publications

(59 citation statements)

References 26 publications

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“…The major metabolic activation pathway of fluoranthene resulting in the production of mutagenic species involves the formation of the 2,3-diol [47] and the subsequent oxidation to the 2,3-diol-1,10b-epoxide [48]. Another minor activation pathway with mutagenic endpoints may involve the formation of 7,8-dihydroxyfluoranthene [48]. Shimada et al [32] showed that human CYP1A1 is able to activate fluoranthene-2,3-diol.…”

Section: Toxicity and Cyp35 Gene Expressionmentioning

confidence: 99%

“…In case of the very related 2,5,2',5'-tetrachlorbiphenyl congener, Koga et al [46] suggested that in hamster liver different P450 isoforms are involved in the 3-and 4-hydroxylation. The major metabolic activation pathway of fluoranthene resulting in the production of mutagenic species involves the formation of the 2,3-diol [47] and the subsequent oxidation to the 2,3-diol-1,10b-epoxide [48]. Another minor activation pathway with mutagenic endpoints may involve the formation of 7,8-dihydroxyfluoranthene [48].…”

Section: Toxicity and Cyp35 Gene Expressionmentioning

confidence: 99%

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CYP35: Xenobiotically induced gene expression in the nematode Caenorhabditis elegans

Menzel

Rödel

Kulas

et al. 2005

Archives of Biochemistry and Biophysics

102

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Abstract:Although over 80 cytochrome P450 (CYP) encoding genes have been identified in the genome of the nematode Caenorhabditis elegans very little is known about their involvement in biotransformation. This paper demonstrates a concentration dependent relationship of C. elegans CYP35A1, A2, A5, and C1 gene expression in response to four organic xenobiotics, namely atrazine, PCB52, fluoranthene, and lansoprazole. The toxicity of these xenobiotics was determined using a reproduction assay. CYP-specific messenger RNA expression was analyzed by semi-quantitative RT-PCR resulting in a strongly increasing, concentration-dependent induction well below the EC 50 for reproduction. For PCB52, approximately 0.5 % of the EC 50 induces a two-fold increase of CYP35 gene expression. Using a double mutant and multiple RNAi of CYP35A/C it was possible to diminish the reproduction decline caused by PCB52 and fluoranthene.

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Section: Toxicity and Cyp35 Gene Expressionmentioning

confidence: 99%

Section: Toxicity and Cyp35 Gene Expressionmentioning

confidence: 99%

CYP35: Xenobiotically induced gene expression in the nematode Caenorhabditis elegans

Menzel

Rödel

Kulas

et al. 2005

Archives of Biochemistry and Biophysics

102

View full text Add to dashboard Cite

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“…Flu has been found to be highly toxic to benthic invertebrates at concentrations down to 10 μg/g dry weight of sediment (Swartz et al, 1990). It may also possess genotoxic (mutagenic and carcinogenic) properties, though these effects are not associated directly with the parent compound, but arise largely as a result of biotransformation processes that lead to the formation of reactive intermediates (Rastetter et al, 1982;Babson et al, 1986).…”

Section: Introductionmentioning

confidence: 99%

Differences in PAH tolerance between Capitella species: Underlying biochemical mechanisms

et al. 2005

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“…The mutagenicity of fluoranthene, however, is equivocal, with both positive (Kaden et al 1979;Kinae et al 1981;LaVoie et al 1982;Babson et al 1986;Bos et al 1988) and negative (Tokiwa et al 1977;Kinae et al 1981;Bos et al 1987) results reported. In this study, fluoranthene or pyrene was detected only from the samples collected in December 2004.…”

Section: Discussionmentioning

confidence: 99%

Contamination of the Shinano River Water with Mutagenic Substances after the Niigata Chuetsu Earthquake

Fujimoto

Tsuchiya

Shibuya

et al. 2007

Tohoku J. Exp. Med.

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While normally monitoring the Shinano River water quality, including examinations for mutagenicity, the Niigata Chuetsu Earthquake suddenly occurred on October 23, 2004. However, the influence of this earthquake on the mutagenicity of river water has not yet been well studied. To clarify the regional and seasonal changes in mutagenicity of the Shinano River water, blue rayon was suspended for 24 hrs at 4 sampling sites, once a month from September 2004 through August 2005. Mutagenicity was evaluated by the Ames test using Salmonella typhimurium TA98 (TA98) and TA100 with or without metabolic activation by S9 mixture. To detect and identify poly-aromatic hydrocarbons that may be responsible for the mutagenicity of the river water, we analyzed benzo[a]pyrene, benzophenone, 4-nitrotoluene, or other compounds using gas chromatography-mass spectrometry and total ion chromatogram spectra. Positive manifestations of TA98 with S9 mixture were observed at the 4 sampling sites throughout the 12-month test, showing a tendency to be higher at the downstream site and in winter. However, the highest mutagenicity was observed in the sample collected at the most upstream sampling site in December 2004, and fluoranthene or pyrene consisting mainly in coal tar was detected only in the samples collected in December 2004. Although benzo[a]pyrene, benzophenone, and 4-nitrotoluene were below the detection limits, non-mutagens such as aliphatic hydrocarbons or esters were frequently detected. Our findings indicate that either fluoranthene or pyrene was mainly responsible for the mutagenicity of the river water in December 2004, suggesting the possibility of oil contamination caused by the Niigata Chuetsu Earthquake.the Shinano River water; mutagenicity; the Ames test; gas chromatography-mass spectrometry; total ion chromatogram spectra

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Microsomal activation of fluoranthene to mutagenic metabolites

Cited by 53 publications

References 26 publications

CYP35: Xenobiotically induced gene expression in the nematode Caenorhabditis elegans

CYP35: Xenobiotically induced gene expression in the nematode Caenorhabditis elegans

Differences in PAH tolerance between Capitella species: Underlying biochemical mechanisms

Contamination of the Shinano River Water with Mutagenic Substances after the Niigata Chuetsu Earthquake

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