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Chemical Compound Review

oxanthren     oxanthrene

Synonyms: Oxanthrene, Phenodioxin, Dibenzodioxin, CPD-922, CCRIS 211, ...
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Disease relevance of oxanthrene


High impact information on oxanthrene

  • The dibenzodioxin nucleus, is however, rather resistant to chemical attack and in the absence of a suitable control procedure the use of 2,4,5-T has been restricted in the US by the Environmental Protection Agency. I now report the oxidative degeneration of TCDD and related compounds by ruthenium tetroxide [6].
  • Model studies of polychlorinated dibenzo-p-dioxin formation during municipal refuse incineration [7].
  • The polychlorinated dibenzodioxin [3H]-2,3,7, 8-tetrachlorodibenzo-p-dioxin (TCDD) and the carcinogens [3H]benzo(a)pyrene and [3H]-3-methylcholanthrene bound to saturable binding sites in cytosol from the rat ventral prostate [8].
  • Some polycyclic aromatic hydrocarbons bound to the peptide beads, but nonchlorinated dibenzo-p-dioxin and PCB did not [9].
  • Chlorinated derivatives of dibenzo-p-dioxin and related compounds for use as reference compounds in method development and environmental toxicology [10].

Chemical compound and disease context of oxanthrene


Biological context of oxanthrene


Anatomical context of oxanthrene

  • Dioxins (polychlorinated dibenzo-p-dioxin (PCDD)+polychlorinated dibenzofuran (PCDF)) and polychlorinated biphenyls (PCBs) are potentially hazardous compounds and have structural similarity with thyroid hormones [19].
  • In tests of environmental samples, the results from the assay using primary hepatocyte culture were comparable to those from the assay using the H4IIE cell line and chemical analysis of concentrations of mixtures of polychlorinated dibenzo-p-dioxin and dibenzofuran (PCDD/PCDF) [20].
  • Polychlorinated dibenzo-p-dioxin (PCDD) and polychlorinated dibenzofuran (PCDF) levels were determined in adipose tissue of 15 autopsied subjects who at the time of death had lived in the city of Tarragona (Catalonia, Spain) and surroundings during at least the last 10 years [21].
  • The in vitro metabolism of several chlorinated dibenzo-p-dioxin congeners (PCDDs) was studied using rat liver microsomes as a source of CYP 1 enzymes [22].

Associations of oxanthrene with other chemical compounds


Gene context of oxanthrene

  • Among four CYPs, rat CYP1A1 showed the highest activity toward dibenzo-p-dioxin (DD) and mono-, di-, and trichloroDDs [28].
  • Remarkable metabolism by the multiple CYP forms was observed toward dibenzo-p-dioxin (DD) and mono-, di-, and trichloroDDs [29].
  • Use of monoclonal antibodies against dibenzo-p-dioxin degrading Sphingomonas sp. strain RW1 [30].
  • Results of a more limited investigation of dibenzo-p-dioxin (DD) chlorination by CuCl(2) to form chlorinated DD (CDD) products are also presented [31].
  • The separate and concurrent effects of polychlorinated dibenzo-p-dioxin (PCDD) and dibenzofuran (PCDF) congeners on aryl hydrocarbon hydroxylase (AHH) activity in human lymphoblastoid cells were examined [32].

Analytical, diagnostic and therapeutic context of oxanthrene


  1. Metabolism of dibenzo-p-dioxin by Sphingomonas sp. strain RW1. Wittich, R.M., Wilkes, H., Sinnwell, V., Francke, W., Fortnagel, P. Appl. Environ. Microbiol. (1992) [Pubmed]
  2. Diverse oxygenations catalyzed by carbazole 1,9a-dioxygenase from Pseudomonas sp. Strain CA10. Nojiri, H., Nam, J.W., Kosaka, M., Morii, K.I., Takemura, T., Furihata, K., Yamane, H., Omori, T. J. Bacteriol. (1999) [Pubmed]
  3. Halogenated aromatic hydrocarbons and toxicity equivalency factors (TEFs) from the public health assessment perspective. Pohl, H., Holler, J. Chemosphere (1995) [Pubmed]
  4. Genetic and biochemical characterization of the dioxygenase involved in lateral dioxygenation of dibenzofuran from Rhodococcus opacus strain SAO101. Kimura, N., Kitagawa, W., Mori, T., Nakashima, N., Tamura, T., Kamagata, Y. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  5. Environmental contaminants and biomarker responses in fish from the Columbia River and its tributaries: spatial and temporal trends. Hinck, J.E., Schmitt, C.J., Blazer, V.S., Denslow, N.D., Bartish, T.M., Anderson, P.J., Coyle, J.J., Dethloff, G.M., Tillitt, D.E. Sci. Total Environ. (2006) [Pubmed]
  6. Destruction of polychlorodibenzo-p-dioxins. Ayres, D.C. Nature (1981) [Pubmed]
  7. Model studies of polychlorinated dibenzo-p-dioxin formation during municipal refuse incineration. Karasek, F.W., Dickson, L.C. Science (1987) [Pubmed]
  8. Carcinogen-binding proteins in the rat ventral prostate: specific and nonspecific high-affinity binding sites for benzo(a)pyrene, 3-methylcholanthrene, and 2,3,7,8-tetrachlorodibenzo-p-dioxin. Söderkvist, P., Poellinger, L., Gustafsson, J.A. Cancer Res. (1986) [Pubmed]
  9. Dioxin-binding pentapeptide for use in a high-sensitivity on-bead detection assay. Nakamura, C., Inuyama, Y., Goto, H., Obataya, I., Kaneko, N., Nakamura, N., Santo, N., Miyake, J. Anal. Chem. (2005) [Pubmed]
  10. Chlorinated derivatives of dibenzo-p-dioxin and related compounds for use as reference compounds in method development and environmental toxicology. Barnhart, E.R., Patterson, D.G., Ashley, D.L., Maggio, V., Alley, C.C., Alexander, L.R., MacBride, J.A. Anal. Chem. (1987) [Pubmed]
  11. Characterization of 2,2',3-trihydroxybiphenyl dioxygenase, an extradiol dioxygenase from the dibenzofuran- and dibenzo-p-dioxin-degrading bacterium Sphingomonas sp. strain RW1. Happe, B., Eltis, L.D., Poth, H., Hedderich, R., Timmis, K.N. J. Bacteriol. (1993) [Pubmed]
  12. Genetic analysis of dioxin dioxygenase of Sphingomonas sp. Strain RW1: catabolic genes dispersed on the genome. Armengaud, J., Happe, B., Timmis, K.N. J. Bacteriol. (1998) [Pubmed]
  13. A functional 4-hydroxysalicylate/hydroxyquinol degradative pathway gene cluster is linked to the initial dibenzo-p-dioxin pathway genes in Sphingomonas sp. strain RW1. Armengaud, J., Timmis, K.N., Wittich, R.M. J. Bacteriol. (1999) [Pubmed]
  14. Putative link between transcriptional regulation of IgM expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin and the aryl hydrocarbon receptor/dioxin-responsive enhancer signaling pathway. Sulentic, C.E., Holsapple, M.P., Kaminski, N.E. J. Pharmacol. Exp. Ther. (2000) [Pubmed]
  15. Characterization of Novel Carbazole Catabolism Genes from Gram-Positive Carbazole Degrader Nocardioides aromaticivorans IC177. Inoue, K., Habe, H., Yamane, H., Nojiri, H. Appl. Environ. Microbiol. (2006) [Pubmed]
  16. Kinetics of the association of several tritiated polychlorinated dibenzo-p-dioxin and dibenzofuran congeners with hepatic cytosolic Ah receptor from the Wistar rat. Rosengren, R., Safe, S., Bunce, N.J. Chem. Res. Toxicol. (1992) [Pubmed]
  17. Breast-feeding exposure of infants to environmental contaminants--a public health risk assessment viewpoint: chlorinated dibenzodioxins and chlorinated dibenzofurans. Pohl, H.R., Hibbs, B.F. Toxicology and industrial health. (1996) [Pubmed]
  18. Development of quantitative structure-activity relationship (QSAR) models for predicting risk of exposure from carcinogens in animals. Singh, A.K. Cancer Invest. (2001) [Pubmed]
  19. Effects of dioxins on the quantitative levels of immune components in infants. Kaneko, H., Matsui, E., Shinoda, S., Kawamoto, N., Nakamura, Y., Uehara, R., Matsuura, N., Morita, M., Tada, H., Kondo, N. Toxicology and industrial health. (2006) [Pubmed]
  20. EROD activities in a primary cell culture of grass carp (Ctenopharyngodon idellus) hepatocytes exposed to polychlorinated aromatic hydrocarbonas. Wan, X., Ma, T., Wu, W., Wang, Z. Ecotoxicol. Environ. Saf. (2004) [Pubmed]
  21. Dioxin and dibenzofuran concentrations in adipose tissue of a general population from Tarragona, Spain. Schuhmacher, M., Domingo, J.L., Llobet, J.M., Lindström, G., Wingfors, H. Chemosphere (1999) [Pubmed]
  22. Metabolism of polychlorinated dibenzo-p-dioxins by rat liver microsomes. Hu, K., Bunce, N.J. J. Biochem. Mol. Toxicol. (1999) [Pubmed]
  23. Chlorella accelerates dioxin excretion in rats. Morita, K., Matsueda, T., Iida, T., Hasegawa, T. J. Nutr. (1999) [Pubmed]
  24. Interactions of polychlorinated dibenzo-p-dioxin, dibenzofuran, and biphenyl congeners for producing rainbow trout early life stage mortality. Zabel, E.W., Walker, M.K., Hornung, M.W., Clayton, M.K., Peterson, R.E. Toxicol. Appl. Pharmacol. (1995) [Pubmed]
  25. Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on hepatic and uterine estrogen receptor levels in rats. Romkes, M., Piskorska-Pliszczynska, J., Safe, S. Toxicol. Appl. Pharmacol. (1987) [Pubmed]
  26. Comparison of dibenzodioxin levels in blood and milk in agricultural workers and others following pentachlorophenol exposure in China. Schecter, A., Jiang, K., Päpke, O., Fürst, P., Fürst, C. Chemosphere (1994) [Pubmed]
  27. Oxidation of dibenzo- p-dioxin, dibenzofuran, biphenyl, and diphenyl ether by the white-rot fungus Phlebia lindtneri. Mori, T., Kondo, R. Appl. Microbiol. Biotechnol. (2002) [Pubmed]
  28. Metabolic pathways of dioxin by CYP1A1: species difference between rat and human CYP1A subfamily in the metabolism of dioxins. Shinkyo, R., Sakaki, T., Ohta, M., Inouye, K. Arch. Biochem. Biophys. (2003) [Pubmed]
  29. Metabolism of polychlorinated dibenzo-p-dioxins (PCDDs) by human cytochrome P450-dependent monooxygenase systems. Inouye, K., Shinkyo, R., Takita, T., Ohta, M., Sakaki, T. J. Agric. Food Chem. (2002) [Pubmed]
  30. Use of monoclonal antibodies against dibenzo-p-dioxin degrading Sphingomonas sp. strain RW1. Thakur, I.S. Lett. Appl. Microbiol. (1996) [Pubmed]
  31. Chlorination of dibenzofuran and dibenzo-p-dioxin vapor by copper (II) chloride. Ryu, J.Y., Mulholland, J.A., Chu, B. Chemosphere (2003) [Pubmed]
  32. Effects of polychlorinated dibenzo-p-dioxin and dibenzofuran congeners in human lymphoblastoid cells on aryl hydrocarbon hydroxylase activity. Kiyohara, C., Hirohata, T., Masuda, Y. Chemosphere (1995) [Pubmed]
  33. Dioxin detection based on immunoassay using a polyclonal antibody against octa-chlorinated dibenzo-p-dioxin (OCDD). Shimomura, M., Nomura, Y., Lee, K.H., Ikebukuro, K., Karube, I. The Analyst. (2001) [Pubmed]
  34. Body mass index and serum chlorinated dibenzo-p-dioxin and dibenzofuran levels. Collins, J.J., Bodner, K., Burns, C.J., Budinsky, R.A., Lamparski, L.L., Wilken, M., Martin, G.D., Carson, M.L. Chemosphere (2007) [Pubmed]
  35. Preparation of DNA-loaded polysulfone microspheres by liquid-liquid phase separation and its functional utilization. Zhao, C., Liu, X., Nomizu, M., Nishi, N. Journal of colloid and interface science. (2004) [Pubmed]
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