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Chemical Compound Review

AC1L1OEZ     2,2,5,6-tetrachloro-1,7- bis(chloromethyl)...

Synonyms: LS-45095, 101053-41-2, 2,2,5-Endo,6-exo,8,9,9,10-octachlorobornane, 2,2,5-endo,6-exo,8,8,9,10-Octachlorobornane
 
 
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Disease relevance of toxaphene

  • Toxaphene, the most widely used chlorinated insecticide, is mutagenic in the Salmonella test without requiring liver homogenate for activity [1].
  • The results of this study demonstrate that for several estrogen-responsive assays in the mouse uterus, MCF-7 human breast cancer cells, and yeast-based reporter gene assays, the activities of both dieldrin and toxaphene were minimal, and no synergistic interactions were observed with a binary mixture of the two compounds [2].
  • These results show that while technical toxaphene is a weak, direct-acting mutagen in some bacterial tests, a dose-dependent toxicity and genotoxicity of its photoproducts could be conclusively demonstrated by the umuC test [3].
  • A toxaphene-degrading bacterium related to Enterobacter cloacae, strain D1 isolated from aged contaminated soil in Nicaragua [4].
  • Toxaphene genotoxicity was also examined in a mammalian system using Chinese hamster V79 lung fibroblasts with metabolic activation provided by human HepG2 hepatoma cells [5].
 

Psychiatry related information on toxaphene

  • The significance of the selection of parent ions (Ip) and daughter ions (Id) on the detection of these toxaphene congeners was assessed in standard solution and biological samples [6].
 

High impact information on toxaphene

  • Combinations of two weak environmental estrogens, such as dieldrin, endosulfan, or toxaphene, were 1000 times as potent in hER-mediated transactivation as any chemical alone [7].
  • A 24-h incubation of an ERR alpha-1-transfected HepG2 cell line with 10 microM toxaphene reduced its aromatase activity to the level in the untransfected cell line [8].
  • Toxaphene was found to be capable of suppressing the GRIP1 coactivator-induced ERR alpha-1 activity in SK-BR-3 cells [8].
  • Although estrogens are not ligands of ERR alpha-1, our recent results suggest that toxaphene and chlordane, two organochlorine pesticides with estrogen-like activity, behave as antagonists for this orphan nuclear receptor [8].
  • The mammalian cell transfection experiments revealed that the ERRalpha-1 mutant F329A, like wild-type ERalpha, recognized toxaphene (an organochlorine pesticide) as an agonist [9].
 

Chemical compound and disease context of toxaphene

 

Biological context of toxaphene

  • Crystal and molecular structure of 2,2,5-endo,6-exo,8,9,10-heptachlorobornane, c10H11Ci7, a toxic component of toxaphene insecticide [15].
  • The relative competitive binding of the organochlorine pesticides was determined by incubating MCF-7 cells with 10(-9) M [3H]E2 in the presence or absence of 2 x 10(-7) M unlabeled E2 (to determine nonspecific binding), toxaphene (10(-5) M), dieldrin (10(-5) M), and equimolar concentrations of the dieldrin plus toxaphene mixture (10(-5) M) [2].
  • Treatment of MCF-7 cells with dieldrin, toxaphene, or an equimolar mixture of dieldrin plus toxaphene (10(-8)-10(-5) M) did not significantly induce cell proliferation or CAT activity in the transient transfection experiment with both plasmids [2].
  • These reproducible results indicate that toxaphene can disturb hormonal signals mediated by the ER and suggest that these environmental chemicals have potential endocrine disrupting activities which may affect the reproductive health and increase the risk of carcinogenesis [16].
  • Rats were given a single dose of toxaphene (120 mg/kg equilavent to 1/2 LD50) and sacrificed at 1, 5, and 15 days [17].
 

Anatomical context of toxaphene

  • The estrogenic activity of dieldrin, toxaphene, and an equimolar mixture of both compounds (dieldrin/toxaphene) was investigated in the 21-day-old B6C3F1 mouse uterus, MCF-7 human breast cancer cells, and in yeast-based reporter gene assays [2].
  • 2. Dissociation studies showed that dieldrin, ketoendrin, toxaphene, heptachlor epoxide and alpha and beta endosulphan displace bound [3H]-BIDN from rootworm membranes by a competitive mechanism [18].
  • Technical toxaphene and some individual congeners were found to be weakly estrogenic in in vitro test systems; no evidence for endocrine effects in vivo has been reported [19].
  • This is the first study that focuses on toxaphene/human neutrophil interactions [20].
  • When toxaphene mutagenicity was re-evaluated in the Ames Salmonella/microsome assay at 10-10,000 microg/plate, a dose-dependent increase in His revertants occurred in all five strains of S. typhimurium tested (TA97, TA98, TA100, TA102 and TA104) with higher mutation frequencies observed in the absence of S9 metabolic activation [5].
 

Associations of toxaphene with other chemical compounds

  • These results are consistent with the hypothesis that DDT, dieldrin, toxaphene, 2,3,4-HCB, 2,4,5-HCB, and 2,4,5-HBB could have tumor-promoting potential in human breast tissue [21].
  • Toxaphene at 10 microM induced luciferase activity in the absence of DHT but decreased cell viability [22].
  • Atmospheric transport of toxaphene from the southern United States to the Great Lakes Region [23].
  • In general, the levels observed were higher than those reported in children from developed countries, such as Germany and United States. Toxaphene, aldrin, dieldrin, and beta-HCH could not be identified in any sample [24].
  • Future trends are estimated for the measured air and soil concentrations of lindane and six highly persistent pesticides (toxaphene, p,p'-DDE, dieldrin, cis- and trans-chlordane and trans-nonachlor) over a twenty-year period due to volatilization and leaching into the deeper soil [25].
 

Gene context of toxaphene

  • Indications for the involvement of a CYP3A-like iso-enzyme in the metabolism of chlorobornane (Toxaphene) congeners in seals from inhibition studies with liver microsomes [26].
  • Effect of toxaphene on estrogen receptor functions in human breast cancer cells [16].
  • The interference of toxaphene with the ER mediated responses was supported by a significant suppression of endogenously expressed pS2 RNA and decreased levels of secreted pS2 protein [16].
  • The modulation of aromatase expression by endocrine disrupting chemicals is exemplified by two organochlorine pesticides (i.e. toxaphene and chlordane) that have been found to be antagonists of ERRalpha-1 orphan receptor [27].
  • In the umuC assay, a dose-dependent increase in genotoxic activity was observed at toxaphene concentrations from 2.5 to 40.0 mg/l, but these results were found to be not significant [3].
 

Analytical, diagnostic and therapeutic context of toxaphene

  • Attempt to unravel the composition of toxaphene by comprehensive two-dimensional gas chromatography with selective detection [28].
  • If a quantitative dose-response assessment for toxaphene is to be performed, the data from both the NCI and Litton cancer bioassays should be used [29].
  • Production of toxaphene enantiomers by enantioselective HPLC after isolation of the compounds from an anaerobically degraded technical mixture [30].
  • Genotoxic activity of a technical toxaphene mixture and its photodegradation products in SOS genotoxicity tests [3].
  • Hatchery-reared Arctic charr were subjected to one of four treatments: (1) oral administration of corn oil (control); (2) single oral dose of 10 microg/g wet wt toxaphene dissolved in corn oil; (3) exposure to 15 larval D. dendriticum; and (4) exposure to toxaphene and D. dendriticum in combination [31].

References

  1. Toxaphene, a complex mixture of polychloroterpenes and a major insecticide, is mutagenic. Hooper, N.K., Ames, B.N., Saleh, M.A., Casida, J.E. Science (1979) [Pubmed]
  2. Estrogenic activity of a dieldrin/toxaphene mixture in the mouse uterus, MCF-7 human breast cancer cells, and yeast-based estrogen receptor assays: no apparent synergism. Ramamoorthy, K., Wang, F., Chen, I.C., Norris, J.D., McDonnell, D.P., Leonard, L.S., Gaido, K.W., Bocchinfuso, W.P., Korach, K.S., Safe, S. Endocrinology (1997) [Pubmed]
  3. Genotoxic activity of a technical toxaphene mixture and its photodegradation products in SOS genotoxicity tests. Bartos, T., Skarek, M., Cupr, P., Kosubová, P., Holoubek, I. Mutat. Res. (2005) [Pubmed]
  4. A toxaphene-degrading bacterium related to Enterobacter cloacae, strain D1 isolated from aged contaminated soil in Nicaragua. Lacayo-Romero, M., Quillaguamán, J., van Bavel, B., Mattiasson, B. Syst. Appl. Microbiol. (2005) [Pubmed]
  5. In vitro investigation of toxaphene genotoxicity in S. typhimurium and Chinese hamster V79 lung fibroblasts. Schrader, T.J., Boyes, B.G., Matula, T.I., Héroux-Metcalf, C., Langlois, I., Downie, R.H. Mutat. Res. (1998) [Pubmed]
  6. Analysis of six relevant toxaphene congeners in biological samples using ion trap MS/MS. Gouteux, B., Lebeuf, M., Trottier, S., Gagné, J.P. Chemosphere (2002) [Pubmed]
  7. Synergistic activation of estrogen receptor with combinations of environmental chemicals. Arnold, S.F., Klotz, D.M., Collins, B.M., Vonier, P.M., Guillette, L.J., McLachlan, J.A. Science (1996) [Pubmed]
  8. Two organochlorine pesticides, toxaphene and chlordane, are antagonists for estrogen-related receptor alpha-1 orphan receptor. Yang, C., Chen, S. Cancer Res. (1999) [Pubmed]
  9. Molecular basis for the constitutive activity of estrogen-related receptor alpha-1. Chen, S., Zhou, D., Yang, C., Sherman, M. J. Biol. Chem. (2001) [Pubmed]
  10. Toxicity of mixtures of parathion, toxaphene and/or 2,4-D in mice. Kuntz, D.J., Rao, N.G., Berg, I.E., Khattree, R., Chaturvedi, A.K. Journal of applied toxicology : JAT. (1990) [Pubmed]
  11. Toxicity of chlorinated bornane (toxaphene) residues isolated from Great Lakes lake trout (Salvelinus namaycush). Gooch, J.W., Matsumura, F. Arch. Environ. Contam. Toxicol. (1987) [Pubmed]
  12. Regression analysis of pesticide use and breast cancer incidence in California Latinas. Mills, P.K., Yang, R. Journal of environmental health. (2006) [Pubmed]
  13. Field control of bovine parasitic otitis. Msolla, P., Mmbuji, W.E., Kasuku, A.A. Tropical animal health and production. (1987) [Pubmed]
  14. Toxicities and description of some toxaphene fractions: isolation and identification of a highly toxic component. Pollock, G.A., Kilgore, W.W. Journal of toxicology and environmental health. (1980) [Pubmed]
  15. Crystal and molecular structure of 2,2,5-endo,6-exo,8,9,10-heptachlorobornane, c10H11Ci7, a toxic component of toxaphene insecticide. Palmer, K.J., Wong, R.Y., Lundin, R.E., Khalifa, S., Casida, J.E. J. Am. Chem. Soc. (1975) [Pubmed]
  16. Effect of toxaphene on estrogen receptor functions in human breast cancer cells. Bonefeld Jørgensen, E.C., Autrup, H., Hansen, J.C. Carcinogenesis (1997) [Pubmed]
  17. Effect of toxaphene on pyruvic and lactic acid levels in the rat. Peakall, D.B. Environ. Health Perspect. (1979) [Pubmed]
  18. Effects of [3H]-BIDN, a novel bicyclic dinitrile radioligand for GABA-gated chloride channels of insects and vertebrates. Rauh, J.J., Benner, E., Schnee, M.E., Cordova, D., Holyoke, C.W., Howard, M.H., Bai, D., Buckingham, S.D., Hutton, M.L., Hamon, A., Roush, R.T., Sattelle, D.B. Br. J. Pharmacol. (1997) [Pubmed]
  19. Environmental occurrence, analysis, and toxicology of toxaphene compounds. de Geus, H.J., Besselink, H., Brouwer, A., Klungsøyr, J., McHugh, B., Nixon, E., Rimkus, G.G., Wester, P.G., de Boer, J. Environ. Health Perspect. (1999) [Pubmed]
  20. Activation of human neutrophils by technical toxaphene. Gauthier, M., Roberge, C.J., Pelletier, M., Tessier, P.A., Girard, D. Clin. Immunol. (2001) [Pubmed]
  21. Inhibition of gap junctional intercellular communication in normal human breast epithelial cells after treatment with pesticides, PCBs, and PBBs, alone or in mixtures. Kang, K.S., Wilson, M.R., Hayashi, T., Chang, C.C., Trosko, J.E. Environ. Health Perspect. (1996) [Pubmed]
  22. Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro. Schrader, T.J., Cooke, G.M. Toxicol. Sci. (2000) [Pubmed]
  23. Atmospheric transport of toxaphene from the southern United States to the Great Lakes Region. James, R.R., Hites, R.A. Environ. Sci. Technol. (2002) [Pubmed]
  24. Persistent organochlorine pollutants in children working at a waste-disposal site and in young females with high fish consumption in Managua, Nicaragua. Cuadra, S.N., Linderholm, L., Athanasiadou, M., Jakobsson, K. Ambio. (2006) [Pubmed]
  25. Modelling of the long-term fate of pesticide residues in agricultural soils and their surface exchange with the atmosphere: Part II. Projected long-term fate of pesticide residues. Scholtz, M.T., Bidleman, T.F. Sci. Total Environ. (2007) [Pubmed]
  26. Indications for the involvement of a CYP3A-like iso-enzyme in the metabolism of chlorobornane (Toxaphene) congeners in seals from inhibition studies with liver microsomes. van Hezik , C.M., Letcher, R.J., de Geus , H.J., Wester, P.G., Goksøyr, A., Lewis, W.E., Boon, J.P. Aquat. Toxicol. (2001) [Pubmed]
  27. Modulation of aromatase expression in human breast tissue. Chen, S., Zhou, D., Yang, C., Okubo, T., Kinoshita, Y., Yu, B., Kao, Y.C., Itoh, T. J. Steroid Biochem. Mol. Biol. (2001) [Pubmed]
  28. Attempt to unravel the composition of toxaphene by comprehensive two-dimensional gas chromatography with selective detection. Korytár, P., van Stee, L.L., Leonards, P.E., de Boer, J., Brinkman, U.A. Journal of chromatography. A. (2003) [Pubmed]
  29. Reevaluation of the cancer potency factor of toxaphene: recommendations from a peer review panel. Goodman, J.I., Brusick, D.J., Busey, W.M., Cohen, S.M., Lamb, J.C., Starr, T.B. Toxicol. Sci. (2000) [Pubmed]
  30. Production of toxaphene enantiomers by enantioselective HPLC after isolation of the compounds from an anaerobically degraded technical mixture. Vetter, W., Kirchberg, D. Environ. Sci. Technol. (2001) [Pubmed]
  31. Growth, nutritional composition, and hematology of Arctic charr (Salvelinus alpinus) exposed to toxaphene and tapeworm (Diphyllobothrium dendriticum) larvae. Blanar, C.A., Curtis, M.A., Chan, H.M. Arch. Environ. Contam. Toxicol. (2005) [Pubmed]
 
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