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Chemical Compound Review

Idryl     fluoranthene

Synonyms: FLUORANTHENE, Fluroanthene, k)fluorene, Benzo(j, F807_ALDRICH, ...
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Disease relevance of fluoranthene


Psychiatry related information on fluoranthene

  • For this reason, the criteria derived for pollutants with reported promotion/cocarcinogenic activities were based on approaches for carcinogenic (e.g., TCDD), toxic (e.g., fluoranthene) or organoleptic effects (e.g., 2,4-dichlorophenol) [6].

High impact information on fluoranthene

  • The diffusive motion of the conducting electrons in the one-dimensional organic conductor FA2PF6 (FA, Fluoranthene) is studied with the ESR pulse-gradient spin-echo (PGSE) signal combined with spatial density ESR imaging [7].
  • In this work, stir bar sorptive extraction and liquid desorption was combined with MEKC and diode-array detection (SBSE-LD-MEKC-DAD) for the determination of polynuclear aromatic hydrocarbons (PAHs) in aqueous medium, using biphenyl, fluorene, anthracene, phenanthrene, fluoranthene and pyrene as model compounds [8].
  • Aldehydic DNA lesions in calf thymus DNA and HeLa S3 cells produced by bacterial quinone metabolites of fluoranthene and pyrene [9].
  • The urine from hamsters treated with pyrene or fluoranthene and NO2 was also highly mutagenic, but that from rats or guinea pigs was not very mutagenic [10].
  • We have established conditions for the in vitro biological preparation of microgram quantities of DNA adducts derived from benzo[a]pyrene (BaP), fluoranthene and 7,12-dimethylbenzanthracene, using isolated rat hepatocytes [11].

Chemical compound and disease context of fluoranthene


Biological context of fluoranthene

  • The enzyme induction response to these compounds occurred in the following order: NFs greater than 3-NF greater than FL [16].
  • Five metabolites produced by Cunninghamella elegans from fluoranthene (FA) in biotransformation studies were investigated for mutagenic activity towards Salmonella typhimurium TA100 and TA104 [17].
  • Thus, our results demonstrate that the toxic effects of BaA and BbF on Sertoli cells are exerted through apoptosis, whereas FL and BaA do not elicit the apoptotic response [18].
  • Utilization of fluoranthene by strain EPA 505 was demonstrated by increase in bacterial biomass, decrease in aqueous fluoranthene concentration, and transient formation of transformation products in liquid cultures where fluoranthene was supplied as the sole carbon source [19].
  • Growth of mixed cultures with phenanthrene and fluoranthene solubilized by a nonionic surfactant prior to inoculation was exponential, indicating a high bioavailability of the solubilized hydrocarbons [20].

Anatomical context of fluoranthene

  • Low levels of fluoranthene derivatives (1 times 10(-5) M) also strongly inhibited polymerase with polyinosinate-oligodeoxycytidylate [poly(I)-(dC)12-18], activated calf thymus DNA, and viral 70S RNA as templates, but not with polycytidylate-oligodeoxyguanylate as template [1].
  • These inhibitory effects were not observed with microsomes prepared from FL-treated rats [16].
  • These results demonstrate the applicability of the HPLC-32P-postlabelling procedure to detect and quantify fluoranthene-DNA adducts formed in vivo, and suggest that analysis of these adducts in accessible tissues such as lymphocytes may be a means of assessing chronic, high level exposure to fluoranthene [21].
  • Chronic administration of fluoranthene in the diet, however, resulted in DNA adduct formation in most tissues examined, including liver, kidney, lung, small intestine, heart, spleen and lymphocytes; adducts were not detectable in testes DNA [21].
  • Sertoli cells cultured in the presence of 10(-6) M and 10(-8) M FL showed morphologic changes [18].

Associations of fluoranthene with other chemical compounds

  • These results suggest that fluoranthene switches from cAMP-dependent HCO(3)(-) secretion to Cl(-) secretion through the hIK-1 channel, whose sensitivity to protein kinase A may be up-regulated by the sustained [Ca(2+)](i) elevation produced by this chemical [22].
  • In the present study, fluorescein diacetate uptake and the Comet assay were used to assess the cytotoxicity and genotoxicity of fluoranthene in HaCaT (human adult low calcium high temperature) cells in the presence or absence of ultraviolet A (UVA) irradiation [23].
  • In in vitro studies, the PAH fluoranthene (FL) failed to increase or enhance CYP1A1-dependent ethoxyresorufin-O-deethylase (EROD) activity in cells, but rather inhibited activities induced by AhR agonists such as 2,3,7,8-tetrachlorodibenzo-p-dioxin and benzo(k)fluoranthene [24].
  • Benz[a]anthracene (B[a]A), benzo[a]pyrene (B[a]P), fluoranthene, chrysene and 7,12-dimethylbenz[a]anthracene (DMBA) were acting as antiandrogens in vitro, resulting in IC(50) values of 3.2, 3.9, 4.6, 10.3 and 10.4 microM, respectively [25].
  • Similarly, growth (biomass and shell size) was not affected by pyrene, fluoranthene, fluorene, carbazole, phenanthrene, or acridine, whereas dibenzothiophene gave a 10% effect concentration of 1600 mg/kg [26].

Gene context of fluoranthene

  • Results indicated individuals that were heterozygous (MF) for the Gpi allozyme survived longer and had less overall mortality than the homozygous MM genotype when exposed to chromium(VI) and to fluoranthene [27].
  • Simultaneous treatment with fluoranthene and NUV was incapable of inducing the uvrA gene product as evidenced by the absence of the induction of beta-galactosidase in an E coli operon fusion strain [uvrA215::Mud(Ap,lac)] [28].
  • The yield of F23Q from fluoranthene ranged from 2% for Sphingomonas yanoikuyae R1 to greater than 20% for Pseudomonas stutzeri P16 and Bacillus cereus P21 [29].
  • Of these, only the fluoranthene derivatives were strong inhibitors of the viral DNA polymerase directed by polyadenylate-oligodeoxythymidylate [poly(A)-(dT)12-18] [1].
  • The results indicate the presence of the nitro group on fluoranthene directs the metabolism away from the C1-C5 positions, and more towards the C6-C10 positions [30].

Analytical, diagnostic and therapeutic context of fluoranthene


  1. Inhibition of purified DNA polymerase of RNA tumor viruses by fluoranthene derivatives and analogues of tilorone hydrochloride. Green, M., Rankin, A., Gerard, G.F., Grandgenett, D.P., Green, M.R. J. Natl. Cancer Inst. (1975) [Pubmed]
  2. Identification of the mutagenic metabolites of fluoranthene, 2-methylfluoranthene, and 3-methylfluoranthene. LaVoie, E.J., Hecht, S.S., Bedenko, V., Hoffmann, D. Carcinogenesis (1982) [Pubmed]
  3. Mammary carcinogenicity in female CD rats of a diol epoxide metabolite of fluoranthene, a commonly occurring environmental pollutant. Hecht, S.S., Amin, S., Lin, J.M., Rivenson, A., Kurtzke, C., el-Bayoumy, K. Carcinogenesis (1995) [Pubmed]
  4. Tumorigenicity of fluoranthene in a newborn mouse lung adenoma bioassay. Busby, W.F., Goldman, M.E., Newberne, P.M., Wogan, G.N. Carcinogenesis (1984) [Pubmed]
  5. Identification of metabolites from the degradation of fluoranthene by Mycobacterium sp. strain PYR-1. Kelley, I., Freeman, J.P., Evans, F.E., Cerniglia, C.E. Appl. Environ. Microbiol. (1993) [Pubmed]
  6. The current use of studies on promoters and cocarcinogens in quantitative risk assessment. Stara, J.F., Mukerjee, D., McGaughy, R., Durkin, P., Dourson, M.L. Environ. Health Perspect. (1983) [Pubmed]
  7. Diffusive diffraction of the local ESR pulse-gradient spin-echo signal in a restricted one-dimensional conductor. Feintuch, A., Grayevsky, A., Kaplan, N., Dormann, E. Phys. Rev. Lett. (2004) [Pubmed]
  8. Combining stir bar sorptive extraction and MEKC for the determination of polynuclear aromatic hydrocarbons in environmental and biological matrices. do Ros??rio, P.M., Nogueira, J.M. Electrophoresis (2006) [Pubmed]
  9. Aldehydic DNA lesions in calf thymus DNA and HeLa S3 cells produced by bacterial quinone metabolites of fluoranthene and pyrene. Zielinska-Park, J., Nakamura, J., Swenberg, J.A., Aitken, M.D. Carcinogenesis (2004) [Pubmed]
  10. In vivo formation of mutagens by intraperitoneal administration of polycyclic aromatic hydrocarbons in animals during exposure to nitrogen dioxide. Miyanishi, K., Kinouchi, T., Kataoka, K., Kanoh, T., Ohnishi, Y. Carcinogenesis (1996) [Pubmed]
  11. Preparation of microgram quantities of BaP-DNA adducts using isolated rat hepatocytes in vitro. Dankovic, D.A., Springer, D.L., Mann, D.B., Smith, L.G., Thomas, B.L., Bean, R.M. Carcinogenesis (1989) [Pubmed]
  12. Comment on "Effect of methyl tert-butyl ether on the bioconcentration and photoinduced toxicity of fluoranthene in fathead minnow larvae (Pimephales promelas)". Mancini, E.R., Stubblefield, W.A. Environ. Sci. Technol. (2003) [Pubmed]
  13. Metabolism of fluoranthene by Mycobacterium sp. strain AP1. López, Z., Vila, J., Minguillón, C., Grifoll, M. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  14. Use of reporter transposons for tagging and detection of Mycobacterium sp. strain 1B in PAH-contaminated soil. Dandie, C.E., Bentham, R.H., Thomas, S.M. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  15. Isolation and characterization of genes encoding polycyclic aromatic hydrocarbon dioxygenase from acenaphthene and acenaphthylene degrading Sphingomonas sp. strain A4. Pinyakong, O., Habe, H., Kouzuma, A., Nojiri, H., Yamane, H., Omori, T. FEMS Microbiol. Lett. (2004) [Pubmed]
  16. Use of monoclonal antibodies to characterize the induction response of the cytochrome P-450-dependent mixed function oxidase system to nitrofluoranthenes. Khan, W.A., Asokan, P., Park, S.S., Gelboin, H.V., Bickers, D.R., Mukhtar, H. Carcinogenesis (1987) [Pubmed]
  17. Fungal metabolism and detoxification of fluoranthene. Pothuluri, J.V., Heflich, R.H., Fu, P.P., Cerniglia, C.E. Appl. Environ. Microbiol. (1992) [Pubmed]
  18. Polycyclic aromatic hydrocarbon-induced cytotoxicity in cultured rat Sertoli cells involves differential apoptotic response. Raychoudhury, S.S., Kubinski, D. Environ. Health Perspect. (2003) [Pubmed]
  19. Isolation and characterization of a fluoranthene-utilizing strain of Pseudomonas paucimobilis. Mueller, J.G., Chapman, P.J., Blattmann, B.O., Pritchard, P.H. Appl. Environ. Microbiol. (1990) [Pubmed]
  20. Degradation of polycyclic aromatic hydrocarbons in the presence of synthetic surfactants. Tiehm, A. Appl. Environ. Microbiol. (1994) [Pubmed]
  21. Formation of DNA and hemoglobin adducts of fluoranthene after single and multiple exposures. Gorelick, N.J., Hutchins, D.A., Tannenbaum, S.R., Wogan, G.N. Carcinogenesis (1989) [Pubmed]
  22. Effects of fluoranthene, a polycyclic aromatic hydrocarbon, on cAMP-dependent anion secretion in human airway epithelia. Ito, Y., Son, M., Sato, S., Ohashi, T., Kondo, M., Shimokata, K., Kume, H. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
  23. DNA damage produced in HaCaT cells by combined fluoranthene exposure and ultraviolet A irradiation. Zheng, B., Hwang, H.M., Yu, H., Ekunwe, S. Environ. Mol. Mutagen. (2004) [Pubmed]
  24. In vivo and in vitro inhibition of CYP1A-dependent activity in Fundulus heteroclitus by the polynuclear aromatic hydrocarbon fluoranthene. Willett, K.L., Wassenberg, D., Lienesch, L., Reichert, W., Di Giulio, R.T. Toxicol. Appl. Pharmacol. (2001) [Pubmed]
  25. Environmental polycyclic aromatic hydrocarbons affect androgen receptor activation in vitro. Vinggaard, A.M., Hnida, C., Larsen, J.C. Toxicology (2000) [Pubmed]
  26. Effects and uptake of polycyclic aromatic compounds in snails (Helix aspersa). Sverdrup, L.E., De Vaufleury, A., Hartnik, T., Hagen, S.B., Loibner, A.P., Jensen, J. Environ. Toxicol. Chem. (2006) [Pubmed]
  27. Protective effects of allozyme genotype during chemical exposure in the grass shrimp, Palaemonetes pugio. Harper-Arabie, R.M., Wirth, E.F., Fulton, M.H., Scott, G.I., Ross, P.E. Aquat. Toxicol. (2004) [Pubmed]
  28. Phototoxic effects of fluoranthene, a polycyclic aromatic hydrocarbon, on bacterial species. Tuveson, R.W., Kagan, J., Shaw, M.A., Moresco, G.M., von Behne, E.M., Pu, H., Bazin, M., Santus, R. Environ. Mol. Mutagen. (1987) [Pubmed]
  29. Fluoranthene-2,3- and -1,5-diones are novel products from the bacterial transformation of fluoranthene. Kazunga, C., Aitken, M.D., Gold, A., Sangaiah, R. Environ. Sci. Technol. (2001) [Pubmed]
  30. Liver microsomal metabolism of the environmental carcinogen 3-nitrofluoranthene. I. Phenolic metabolites. Howard, P.C., Mateescu, G.D., Consolo, M.C. Carcinogenesis (1988) [Pubmed]
  31. Induction of lung and liver tumors by fluoranthene in a preweanling CD-1 mouse bioassay. Wang, J.S., Busby, W.F. Carcinogenesis (1993) [Pubmed]
  32. Fungal transformation of fluoranthene. Pothuluri, J.V., Freeman, J.P., Evans, F.E., Cerniglia, C.E. Appl. Environ. Microbiol. (1990) [Pubmed]
  33. An in vitro and in vivo study on mutagenic activity of fluoranthene: comparison between cytogenetic studies and HPLC analysis. Palitti, F., Cozzi, R., Fiore, M., Palombo, F., Polcaro, C., Perez, G., Possagno, E. Mutat. Res. (1986) [Pubmed]
  34. Chromatographic and cytogenetic analysis of in vivo metabolites of fluoranthene. Polcaro, C., Nicoletti, I., Ossicini, L., Caponecchi, G., Cozzi, R., Fiore, M., Palitti, F. J. Chromatogr. (1988) [Pubmed]
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