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2,4-diphenylthiophene induces mainly base pair mutation in Salmonella Typhimurium

Treść / Zawartość
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Heterocyclic aromatic compounds containing sulfur (S-HET), have been detected in air, soil, marine environment and freshwater sediment. Toxicity and mutagenicity data of this class of substances are scarce. The present study focuses on implications of two aryl thiophenes and their mutagenic properties in Salmonella/microsome test. In our experiment only 2,4-diphenylthiophene showed little mutagenic effect in both variants of activaction (+/-S9) in strain TA100. Thiophene ring joined to K-region of phenanthrene did not change the biological activity of 3,6-dimetoxyphenanthro [9,10-c]thiophene and this compound did not show mutagenic potency.
Rocznik
Strony
28--31
Opis fizyczny
Bibliogr. 27 poz., rys.
Twórcy
autor
autor
  • Department of Environmental Biotechnology, University of Warmia and Mazury in Olsztyn, Sloneczna 45G, 10-718 Olsztyn, Poland, kinga.budzikur@uwm.edu.pl
Bibliografia
  • Ashby, J., D. Brusich, B.C. Myhr, N.J. Jones, J.M. Parry, S. Nesnow, D. Paton, H. Tinwell, H.S. Rosenkranz, S. Curti, D. Oilman, R.D. Callander. 1993. Correlation of carcinogenic potency with mouse-skin 32P postlabeling and Muta test-R Mouse lac Z mutation data for DMBA and its K-region sulphur isostere: comparison with activities observed in standard genotoxicity assays. Mutation Research 292: 25-40.
  • Baird, W.M., L.A. Hooven, B. Mahadevan. 2005. Carcinogenic polycyclic aromatic hydrocarbon-DNA adducts and mechanism of action. Environmental and Molecular Mutagenesis 45: 106-114.
  • Binková, B., R.J. Šrám. 2004. The genotoxic effect of carcinogenic PAHs, their artificial and environmental mixtures (EOM) on human diploid lung fibroblasts. Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis 547: 109-121.
  • Brack, W., K. Schirmer. 2003. Effect-directed identification of oxygen and sulfur heterocycles as major polycyclic aromatic cytochrome P4501A-inducers in a contaminated sediment. Environment Science Technology 37: 3062-3070.
  • Broughton, H.B., I.A. Watson. 2004. Selection of heterocycles for drug design. Journal of Molecular Graphics and Modelling 23: 51-58.
  • Budzikur, K.A. M. Góra, A. Chachaj, D. Mielżyńska-Švach, S. Tejs, M.K. Łuczyński. 2011. Mutagenicity induced in Salmonella strains TA98 and TA100 by diphenylthiophenes. Environmental Biotechnology 7: 65-69.
  • Cripps, C., J.A. Bumpus, S.D. Aust. 1990. Biodegradation of azo and heterocyclic dyes by Phanerochaete chrysosporium. Applied and Environmental Microbiology 56: 1114-1148.
  • Devanaboyina, U., A.C. Beach, A. Schouft, M. Castegnaro, H. Bartsch, R.C. Gupta. 1993. DNA adduct-forming potential of thiaarenes. Proceedings of the American Association for Cancer Research 34: 159.
  • Eisentraeger, A., C. Brinkmann, H. Hollert, A. Sagner, A. Tiehm, J. Neuwoehner. 2008. Heterocyclic compounds: Toxic effects using algae, daphnids, and the Salmonella/microsome test taking methodical quantitative aspects into account. Environmental Toxicology and Chemistry 27: 1590-1596.
  • Feldmannová, M., K. Hilscherová, B. Maršálek, L. Bláha. 2006. Effects of N-heterocyclic polyaromatic hydrocarbons on survival, reproduction, and biochemical parameters in Daphnia magna. Environmental Toxicology 21: 425-431.
  • Grant, D.M., P.D. Josephy, H.L. Lord, L.D. Morrison. 1992. Salmonella Typhimurium strains expressing human arylamine N-acetyltransferases: metabolism and mutagenic activation of aromatic amines. Cancer Research 52: 3961-3964.
  • Ioannides, C. 2007. Bioactivation of chemicals by cytochromes P450. Environmental Biotechnology 3: 1-9.
  • Jacob, J. 1990. Sulfur Analogues of Polycyclic Aromatic Hydrocarbons (Thiaarenes). First edition. 295 p. Publishing House Cambridge University Press.
  • King, L.C., M.J. Kohan, L. Brooks, G.B. Nelson, J.A. Ross, J. Allison, L. Adams, D. Desai, S. Amin, W. Padgett, G.R. Lambert, A.M. Richard, S. Nesnow. 2001. An evaluation of the mutagenicity, metabolism, and DNA adduct formation of 5-nitrobenzo[b]naphtho [2,1-d]thiophene. Chemical Research Toxicology 14: 661-671.
  • Lin, M., T.G. Wang, R.T.B. Simoneit, S. Shengbao, L. Zhang, Y. Fulin. 2012. Qualitative and quantitative analysis of dibenzothiophene, its methylated homologues, and benzonaphthothiophenes in crude oils, coal, and sediment extracts. Journal of Chromatography A 1233: 126-136.
  • Lübcke-von Varel, U., M. Bataineh, S. Lohrmann, I. Löffler, T. Schulze, S. Flückiger-Isler, J. Neca, M. Machala, W. Brack. 2012. Identification and quantitative confirmation of dinitropyrenes and 3-nitrobenzanthrone as major mutagens in contaminated sediments. Environment International 44: 31-39.
  • Maron, D.M., B.N. Ames. 1983. Revised methods for the Salmonella mutagenicity test. Mutation Research 113: 173-215.
  • Mortelmans, K., E. Zeiger. 2000. The Ames Salmonella/microsome mutagenicity assay. Mutation Research 455: 29-60.
  • Peddinghaus, S., M. Brinkmann, K. Bluhm, A. Sagner, G. Hinger, T. Braunbeck, A. Eisenträger, A. Tiehm, H. Hollert, S.H. Keiter. 2012. Quantitative assessment of the embryotoxic potential of NSO-heterocyclic compounds using zebrafish (Danio rerio). Reproductive Toxicology 32: 224-232.
  • Schreiner, C.A. 2011. Review of mechanistic studies relevant to the potential carcinogenicity of asphalts. Regulatory Toxicology and Pharmacology 59: 270-284.
  • Shields, J.E., D.E. Remy, J. Bornstein. 1975. Phenanthro[9,10-c]thiophene. Syntheses and Reactions, Journal of Organic Chemistry 40: 477-479.
  • Sivak, A., R. Niemeier, D. Lynch, K. Beltis, S. Simon, R. Salomon, R. Latta, B. Belinsky, K. Menzies, A. Lunsford, C. Cooper, A. Ross, R. Bruner. 1997. Skin carcinogenicity of condensed asphalt roofing fumes and their fractions following dermal application to mice. Cancer Letter 117: 113-123.
  • Swartz, C.D., L.C King, S. Nesnow, D.M. Umbach, S. Kumar, D.M. DeMarini. 2009. Mutagenicity, stable DNA adducts, and abasic sites induced in Salmonella by phenanthro[3,4-b]-and phenanthro[4,3-b]thiophenes, sulfur analogs of benzo[c]phenanthrene. Mutation Research 661: 47-56.
  • Valadon, P., P.M. Dansette, J.P. Girault, C. Amar, D. Mansuy. 1996. Thiophene sulfoxides as reactive metabolites: formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo. Chemical Research in Toxicology 9: 1403-1413.
  • Wassenberg, D.M., A. L. Nerlinger, L.P. Battle, R.T. Di Giulio. 2005. Effects of the polycyclic aromatic hydrocarbon heterocycles, carbazole and dibenzothiophene, on in vivo and in vitro cyp1a activity and polycyclic aromatic hydrocarbon-derived embryonic deformities. Environmental Toxicology and Chemistry 24: 2526-2532.
  • Xu, P., J. Feng, B. Yu, F. Li, M. Cuiging. 2009. Recent developments in biodesulfurization of fossil fuels. Advances in Biochemical Engineering/Biotechnology 113: 255-274.
  • Zamfirescu, D., P. Grathwohl. 2001. Occurrence and attenuation of specific organic compounds in the groundwater plume at a former gasworks site. Journal of Contaminant Hydrology 53: 407-427.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAR0-0067-0023
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