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Chemical Compound Review

dibenzofuran     dibenzofuran

Synonyms: Dibenzofurans, PubChem7058, SureCN8207, CPD-926, AGN-PC-009YJS, ...
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Disease relevance of dibenzofuran

  • Several members of the class, including certain polychlorinated biphenyls (PCBs) and polychlorinated dibenzofurans and dibenzodioxins, produce a characteristic toxicity syndrome, manifestations of which are increased mortality, oedema, hyperkeratosis, thymic involution and hepatotoxicity [1].
  • In this work, we describe the evolved biphenyl dioxygenase (BPDO) RR41 that exhibits a higher turnover rate of metabolism toward dibenzofuran and chlorodibenzofurans than the parental Burkholderia xenovorans LB400 BPDO [2].
  • C. elegans also oxidized dibenzofuran to 2- and 3-hydroxydibenzofuran under conditions that would not lead to the dehydration of the trans-dihydrodiol [3].
  • Cunninghamella elegans and a mutant strain (B8/36) of Beijerinckia both oxidized dibenzofuran to 2,3-dihydroxy-2,3-dihydrodibenzofuran [3].
  • Dibenzofuran 4,4a-dioxygenase from Sphingomonas sp. strain RW1: angular dioxygenation by a three-component enzyme system [4].

High impact information on dibenzofuran

  • During the past decade it has been shown conclusively that the incineration of municipal and industrial wastes gives rise to emissions of chlorinated dibenzodioxins and dibenzofurans [5].
  • Comparative toxicology and mechanism of action of polychlorinated dibenzo-p-dioxins and dibenzofurans [6].
  • We measured the blood serum levels of polychlorinated dibenzo-p-dioxins and dibenzofurans, which were substituted with chlorine at the 2,3,7,8 position, in the nine pesticide applicators and in a matched group of nine control subjects [7].
  • Semen quality after prenatal exposure to polychlorinated biphenyls and dibenzofurans [8].
  • 6DBF7 is composed of a beta-sheet-inducing dibenzofuran (DBF)-turn mimetic and two short key amino acid sequences from anginex [9].

Chemical compound and disease context of dibenzofuran


Biological context of dibenzofuran


Anatomical context of dibenzofuran

  • Methods for the quantitative determination of multiple, specific polychlorinated dibenzo-p-dioxin and dibenzofuran isomers in human adipose tissue in the parts-per-trillion range. An interlaboratory study [20].
  • This article on PBDEs is an extension of our previous studies on concentrations of dioxins, dibenzofurans, polychlorinated biphenyls, and other chlorinated organic compounds in human milk in a number of countries [21].
  • An international workshop reviewed 20 ongoing or recently completed studies of the effects of perinatal exposures to dioxins, dibenzofurans, and PCBs on the reproductive, endocrine, neurodevelopmental, and immune systems [22].
  • We analyzed placentas for 17 polychlorinated dibenzo-p-dioxins and dibenzofurans and 12 dioxin-like PCB congeners with the World Health Organization-defined toxic equivalent factors, and six indicator PCBs by high-resolution gas chromatography and high-resolution mass spectrometry [23].
  • Recent reports have shown that alpha-naphthoflavone (alpha-NF) in vivo enhances the sister chromatid exchange (SCE) frequency in lymphocytes from human populations exposed to cigarette smoke or polychlorinated biphenyls and dibenzofurans [24].

Associations of dibenzofuran with other chemical compounds


Gene context of dibenzofuran

  • Many polycyclic aromatic hydrocarbons (PAH) such as benzo[a]pyrene, and chlorinated PAH such as polychlorinated dibenzodioxins, dibenzofurans and biphenyls induce CYP1A1 expression through activation of an endogenous protein, the Ah receptor [29].
  • The AHR mRNA expression levels exhibited significant positive correlations with total TEQs and most of individual congener TEQs derived from polychorinated dibenzo-p-dioxins, dibenzofurans and non-ortho coplanar polychorinated biphenyls (PCBs), indicating the transcriptional up-regulation of AHR expression by these congeners [30].
  • A number of structural analogs of TCDD, such as the polychlorinated dibenzofurans, also interact with the Ah receptor, and they produce the same spectrum of responses as TCDD in animal and cell models [31].
  • These data suggest that the dibenzofuran-mediated decreases in GRc and EGF receptor binding capacities are similar to those caused by TCDD [32].
  • Since kinetic stabilization of the TTR native state by interallelic trans suppression is known to ameliorate disease, there is reason to be optimistic that the dibenzofuran-based inhibitors will do the same [33].

Analytical, diagnostic and therapeutic context of dibenzofuran


  1. Benoxaprofen suppression of polychlorinated biphenyl toxicity without alteration of mixed function oxidase function. Rifkind, A.B., Muschick, H. Nature (1983) [Pubmed]
  2. Resolving the profile of metabolites generated during oxidation of dibenzofuran and chlorodibenzofurans by the biphenyl catabolic pathway enzymes. Mohammadi, M., Sylvestre, M. Chem. Biol. (2005) [Pubmed]
  3. Bacterial and fungal oxidation of dibenzofuran. Cerniglia, C.E., Morgan, J.C., Gibson, D.T. Biochem. J. (1979) [Pubmed]
  4. Dibenzofuran 4,4a-dioxygenase from Sphingomonas sp. strain RW1: angular dioxygenation by a three-component enzyme system. Bünz, P.V., Cook, A.M. J. Bacteriol. (1993) [Pubmed]
  5. Phenol and HCl at 550 degrees C yield a large variety of chlorinated toxic compounds. Eklund, G., Pedersen, J.R., Strömberg, B. Nature (1986) [Pubmed]
  6. Comparative toxicology and mechanism of action of polychlorinated dibenzo-p-dioxins and dibenzofurans. Safe, S.H. Annu. Rev. Pharmacol. Toxicol. (1986) [Pubmed]
  7. Serum 2,3,7,8-tetrachlorodibenzo-p-dioxin levels of New Zealand pesticide applicators and their implication for cancer hypotheses. Smith, A.H., Patterson, D.G., Warner, M.L., MacKenzie, R., Needham, L.L. J. Natl. Cancer Inst. (1992) [Pubmed]
  8. Semen quality after prenatal exposure to polychlorinated biphenyls and dibenzofurans. Guo, Y.L., Hsu, P.C., Hsu, C.C., Lambert, G.H. Lancet (2000) [Pubmed]
  9. Design of a partial peptide mimetic of anginex with antiangiogenic and anticancer activity. Mayo, K.H., Dings, R.P., Flader, C., Nesmelova, I., Hargittai, B., van der Schaft, D.W., van Eijk, L.I., Walek, D., Haseman, J., Hoye, T.R., Griffioen, A.W. J. Biol. Chem. (2003) [Pubmed]
  10. 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]
  11. A second [2Fe-2S] ferredoxin from Sphingomonas sp. Strain RW1 can function as an electron donor for the dioxin dioxygenase. Armengaud, J., Gaillard, J., Timmis, K.N. J. Bacteriol. (2000) [Pubmed]
  12. Simultaneous biodetoxification of s, N, and o pollutants by engineering of a carbazole-degrading gene cassette in a recombinant biocatalyst. Yu, B., Ma, C., Zhou, W., Zhu, S., Wang, Y., Qu, J., Li, F., Xu, P. Appl. Environ. Microbiol. (2006) [Pubmed]
  13. 3-(2-hydroxyphenyl)catechol as substrate for proximal meta ring cleavage in dibenzofuran degradation by Brevibacterium sp. strain DPO 1361. Strubel, V., Engesser, K.H., Fischer, P., Knackmuss, H.J. J. Bacteriol. (1991) [Pubmed]
  14. Body Burdens of Polychlorinated Dibenzo-p-dioxins, Dibenzofurans, and Biphenyls and Their Relations to Estrogen Metabolism in Pregnant Women. Wang, S.L., Chang, Y.C., Chao, H.R., Li, C.M., Li, L.A., Lin, L.Y., Päpke, O. Environ. Health Perspect. (2006) [Pubmed]
  15. The toxicokinetics and metabolism of polychlorinated dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) and their relevance for toxicity. Van den Berg, M., De Jongh, J., Poiger, H., Olson, J.R. Crit. Rev. Toxicol. (1994) [Pubmed]
  16. Comparative molecular field analysis of polyhalogenated dibenzo-p-dioxins, dibenzofurans, and biphenyls. Waller, C.L., McKinney, J.D. J. Med. Chem. (1992) [Pubmed]
  17. Intake, fecal excretion, and body burden of polychlorinated dibenzo-p-dioxins and dibenzofurans in breast-fed and formula-fed infants. Abraham, K., Knoll, A., Ende, M., Päpke, O., Helge, H. Pediatr. Res. (1996) [Pubmed]
  18. Structure-activity relationships for the toxicity of polychlorinated dibenzofurans: approach through density functional theory-based descriptors. Arulmozhiraja, S., Morita, M. Chem. Res. Toxicol. (2004) [Pubmed]
  19. Biologic and toxic effects of polychlorinated dibenzo-p-dioxin and dibenzofuran congeners in the guinea pig. Quantitative structure-activity relationships. Holcomb, M., Yao, C., Safe, S. Biochem. Pharmacol. (1988) [Pubmed]
  20. Methods for the quantitative determination of multiple, specific polychlorinated dibenzo-p-dioxin and dibenzofuran isomers in human adipose tissue in the parts-per-trillion range. An interlaboratory study. Albro, P.W., Crummett, W.B., Dupuy, A.E., Gross, M.L., Hanson, M., Harless, R.L., Hileman, F.D., Hilker, D., Jason, C., Johnson, J.L. Anal. Chem. (1985) [Pubmed]
  21. Polybrominated diphenyl ethers (PBDEs) in U.S. mothers' milk. Schecter, A., Pavuk, M., Päpke, O., Ryan, J.J., Birnbaum, L., Rosen, R. Environ. Health Perspect. (2003) [Pubmed]
  22. Workshop on perinatal exposure to dioxin-like compounds. I. Summary. Lindström, G., Hooper, K., Petreas, M., Stephens, R., Gilman, A. Environ. Health Perspect. (1995) [Pubmed]
  23. In utero exposure to dioxins and polychlorinated biphenyls and its relations to thyroid function and growth hormone in newborns. Wang, S.L., Su, P.H., Jong, S.B., Guo, Y.L., Chou, W.L., Päpke, O. Environ. Health Perspect. (2005) [Pubmed]
  24. Dioxin treatment of rats results in increased in vitro induction of sister chromatid exchanges by alpha-naphthoflavone: an animal model for human exposure to halogenated aromatics. Lundgren, K., Andries, M., Thompson, C., Lucier, G.W. Toxicol. Appl. Pharmacol. (1986) [Pubmed]
  25. Thyroid-hormone-disrupting chemicals: evidence for dose-dependent additivity or synergism. Crofton, K.M., Craft, E.S., Hedge, J.M., Gennings, C., Simmons, J.E., Carchman, R.A., Carter, W.H., DeVito, M.J. Environ. Health Perspect. (2005) [Pubmed]
  26. Influence of the nonionic surfactant Brij 35 on the bioavailability of solid and sorbed dibenzofuran. Garcia, J.M., Wick, L.Y., Harms, H. Environ. Sci. Technol. (2001) [Pubmed]
  27. PCDD and PCDF emissions from simulated sugarcane field burning. Gullett, B.K., Touati, A., Huwe, J., Hakk, H. Environ. Sci. Technol. (2006) [Pubmed]
  28. Toxic equivalency factors of polybrominated dibenzo-p-dioxin, dibenzofuran, biphenyl, and polyhalogenated diphenyl ether congeners based on rainbow trout early life stage mortality. Hornung, M.W., Zabel, E.W., Peterson, R.E. Toxicol. Appl. Pharmacol. (1996) [Pubmed]
  29. CYP1A1 mRNA levels as a human exposure biomarker: use of quantitative polymerase chain reaction to measure CYP1A1 expression in human peripheral blood lymphocytes. Vanden Heuvel, J.P., Clark, G.C., Thompson, C.L., McCoy, Z., Miller, C.R., Lucier, G.W., Bell, D.A. Carcinogenesis (1993) [Pubmed]
  30. Aryl hydrocarbon receptor (AHR) and AHR nuclear translocator (ARNT) expression in Baikal seal (Pusa sibirica) and association with 2,3,7,8-TCDD toxic equivalents and CYP1 expression levels. Kim, E.Y., Iwata, H., Suda, T., Tanabe, S., Amano, M., Miyazaki, N., Petrov, E.A. Comp. Biochem. Physiol. C Toxicol. Pharmacol. (2005) [Pubmed]
  31. Integrated approach for evaluating species and interindividual differences in responsiveness to dioxins and structural analogs. Clark, G., Tritscher, A., Bell, D., Lucier, G. Environ. Health Perspect. (1992) [Pubmed]
  32. Decreased ligand binding to the hepatic glucocorticoid and epidermal growth factor receptors after 2,3,4,7,8-pentachlorodibenzofuran and 1,2,3,4,7,8-hexachlorodibenzofuran treatment of pregnant mice. Ryan, R.P., Sunahara, G.I., Lucier, G.W., Birnbaum, L.S., Nelson, K.G. Toxicol. Appl. Pharmacol. (1989) [Pubmed]
  33. Potent and selective structure-based dibenzofuran inhibitors of transthyretin amyloidogenesis: kinetic stabilization of the native state. Petrassi, H.M., Johnson, S.M., Purkey, H.E., Chiang, K.P., Walkup, T., Jiang, X., Powers, E.T., Kelly, J.W. J. Am. Chem. Soc. (2005) [Pubmed]
  34. Determination of polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls by gas chromatography/mass spectrometry in the negative chemical ionization mode with different reagent gases. Chernetsova, E.S., Revelsky, A.I., Revelsky, I.A., Mikhasenko, I.A., Sobolevsky, T.G. Mass spectrometry reviews. (2002) [Pubmed]
  35. Isolation and characterization of a dibenzofuran-degrading yeast: identification of oxidation and ring cleavage products. Hammer, E., Krowas, D., Schäfer, A., Specht, M., Francke, W., Schauer, F. Appl. Environ. Microbiol. (1998) [Pubmed]
  36. Plasmid-borne genes code for an angular dioxygenase involved in dibenzofuran degradation by Terrabacter sp. strain YK3. Iida, T., Mukouzaka, Y., Nakamura, K., Kudo, T. Appl. Environ. Microbiol. (2002) [Pubmed]
  37. Workshop on human health impacts of halogenated biphenyls and related compounds. Kamrin, M.A., Fischer, L.J. Environ. Health Perspect. (1991) [Pubmed]
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