Porphyrinogenic Action of Polyhalogenated Aromatic Compounds, With Special Reference to Porphyria and Environmental Impact

  • J. J. T. W. A. Strik

Abstract

Some compounds which are able to produce porphyria are presently known as environmental contaminants (70).

Keywords

Chlorinate Acne Furan Toxicology Dermatol 

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References

  1. 1.
    Ariyoshi, T., Ideguchi, K., Ishizuka, Y., Iwasaki, K., Arakaki, M.: Relationship between chemical structure and activity. I. Effects of number of chlorine atoms in chlorinated benzenes on the components of drug-metabolizing system and the hepatic constituents. Chem. Pharm. Bull. (Tokyo) 23, 817–823 (1975a)Google Scholar
  2. 2.
    Ariyoshi, T., Ideguchi, K., Iwasaki, K., Arakaki, M.: Relationship between chemical structure and activity. II. Influences of isomers in dichlorobenzene, trichlorobenzene and tetrachlorobenzene on the activities of drug-metabolizing enzymes. Chem. Pharm. Bull. (Tokyo) 23, 824–830 (1975b)Google Scholar
  3. 3.
    Baughman, R., Meselson, M.: An analytical method for detecting TCDD (Dioxin): Levels of TCDD in samples from Vietnam. Environ. Health Perspect. 5, 27–35 (1973)PubMedCrossRefGoogle Scholar
  4. 4.
    Bleiberg, J., Wallen, M., Brodkin, R., Appelbaum, I.L.: Industrially acquired porphyria. Arch. Dermatol. 89, 793–797 (1964)Google Scholar
  5. 5.
    Booth, N.H., McDowell, J.R.: Toxicity of hexachlorobenzene and associated residues in edible animal tissues. J. Am. Vet. Med. Assoc. 166, 591–595 (1975)PubMedGoogle Scholar
  6. 6.
    Brodie, B.: Possible mechanisms of drug-induced tissue lesions. Chem. Biol. Interact. 3, 247 (1971)PubMedCrossRefGoogle Scholar
  7. 7.
    Cam, C., Nigogosyan, G.: Acquired toxic porphyria cutanea tarda due to hexachlorobenzene. J. Am. Med. Assoc. 183, 88–91 (1963)Google Scholar
  8. 8.
    Chalmers, J.N.M., Gillam, A.E., Kench, J.E.: Porphyrinuria. In a case of industrial methylchloride poisoning. Lancet 1940/XXVIII, pp. 806–808CrossRefGoogle Scholar
  9. 9.
    Dean, G.D.: The porphyrias. A Story of Inheritance and Environment, 2nd ed. London: Pitman Medical 1971, pp. 67–71Google Scholar
  10. 10.
    Dejonckheere, W., Steurbaut, W., Kips, R.H.: Residu’s van hexachloorbenzeen (HCB) en organische chloorinsecticiden in pollard-pellets, dierenvoeders en dierlijk vet. Landbouwtijdschrift 27, 32 3–338 (1974)Google Scholar
  11. 11.
    Doss, M., Schermuly, E., Koss, G.: Hexachlorobenzene porphyria in rats as a model for human chronic hepatic porphyrias. Ann. Clin. Res. 8, 171–181 (1976)PubMedGoogle Scholar
  12. 12.
    Dunckel, A.E.: An updating on the polybrominated biphenyl disaster in Michigan. J. Am. Vet. Med. Assoc. 167, 838–841 (1975)Google Scholar
  13. 13.
    Elder, G.H., Evans, J.O., Matlin, S.A.: The effect of the porphyrinogenic compound, hexachlorobenzene, on the activity of hepatic uroporphyrinogen decarboxylase in the rat. Clin. Sci. Mol. Med. 51, 71–80 (1976)PubMedGoogle Scholar
  14. 14.
    Gilbertson, M., Fox, G.A.: Pollutant-associated embryonic mortality of Great Lakes Herring gulls. Environ. Pollut. 12, 211–216 (1977)CrossRefGoogle Scholar
  15. 15.
    Goldstein, J.A., Hickman, P., Bergman, H., Burse, V.: A comparative study of two polychlorinated biphenyl mixtures (aroclors 1242 and 1016) containing 42% chlorine on induction of hepatic porphyria and drug metabolizing enzymes. Toxicol. Appl. Pharmacol. 32, 461–473 (1975)PubMedCrossRefGoogle Scholar
  16. 16.
    Goldstein, J.A., Hickman, P., Bergman, H., Vos, J.G.: Hepatic porphyria induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in the mouse. Res. Commun. Chem. Pathol. Pharmacol. 6, 919–928 (1973)PubMedGoogle Scholar
  17. 17.
    Goldstein, J.A., Hickman, P., Jue, D.L.: Experimental hepatic porphyria induced by polychlorinated biphenyls. Toxicol. Appl. Pharmacol. 27, 437–448 (1974a)PubMedCrossRefGoogle Scholar
  18. 18.
    Goldstein, J.A., Mc Kinney, J.D., Lucier, G.W., Hickman, P., Bergman, H., Moore, J.A.: Toxicological assessment of hexachlorobiphenyl isomers and 2,3,7,8-tetrachloro-dibenzo furan in chicks. II. Effects on drug metabolism and porphyrin accumulation. Toxicol. Appl. Pharmacol. 36, 81–92 (1976a)CrossRefGoogle Scholar
  19. 19.
    Goldstein, J.A., Mc Kinney, J.D., Lucier, G.W., Moore, J.A., Hickman, P., Bergman, H.: Effects of hexachlorobiphenyl isomers and 2,3,7,8-tetrachlorodibenzofuran (TCDF) on hepatic drug metabolism and porphyrin accumulation. Pharmacologist 16, 239 (abstract) (1974b)Google Scholar
  20. 20.
    Goldstein, J.A.,.Linder, R.E., Hickman, P., Bergman, H. : Effects of pentachlorophenol on hepatic drug metabolism and porphyria related to contamination with chlorinated dibenzo-p-dioxins. Toxicol. Appl. Pharmacol. 37, 145 (abstract) (1976b)Google Scholar
  21. 21.
    Granick, S.: The induction in vitro of the synthesis of δ-aminolevulinic acid synthase and foreign compounds. J. Biol. Chem. 241, 1359–1375 (1966)PubMedGoogle Scholar
  22. 22.
    Grant, D.L., Iverson, F.J., Hatina, G.V., Villeneuve, D.C.: Effects of hexachlorobenzene on liver porphyrin levels and microsomal enzymes in the rat. Environ. Physiol. Biochem. 4, 195–165 (1974)Google Scholar
  23. 23.
    Grant, D.L., Shields, J.B., Villeneuve, D.C.: Chemical (HCB) porphyria. Effect of removal of sex organs in the rat. Bull. Environ. Contam. Toxicol. 14, 422–425 (1975)PubMedCrossRefGoogle Scholar
  24. 24.
    Greve, P.A.: Potential hazardous substances in surface waters. Part I. Pesticides in the river Rhine. Sci. Total Environ.1 173–180 (1972)PubMedCrossRefGoogle Scholar
  25. 25.
    Ippen, H., Aust, D., Goerz, G.: Klinisch-experimentelle Untersuchungen zur Entstehung der Porphyrien III. Wirkung einiger Steroid-Hormone auf die ’latente Hexachlorbenzol-Porphyrie’ der Ratte. Arch. Dermatol. Forsch. 245, 305–317 (1972)PubMedCrossRefGoogle Scholar
  26. 26.
    Ivanov, E., Krustev, L., Azharov, D., Chernev, Kh., Apostolov, I., Dimitrov, P., Drinska, E., Stefanova, M., Pramatarova, V.: Mechanism of the changes in serum and liver y-glutamyl-transpeptidase activity. II. Experimental hexachlorobenzene porphyria in rabbits. Enzyme 21, 17–29 (1976)Google Scholar
  27. 27.
    Jackson, T.F., Halbert, F.L.: A toxic syndrome associated with the feeding of polybrominated biphenyls-contaminated concentrate to dairy cattle. J. Am. Vet. Med. Assoc. 165, 437–439 (1974)PubMedGoogle Scholar
  28. 28.
    Jensen, S., Renberg, L.: Contaminants in Pentachlorophenol: chlorinated dioxins and predioxins. Ambio 1, 62–65 (1972)Google Scholar
  29. 29.
    Jirásek, L., Kalenský, J., Kubec, K., Pazderová, J., Lukás, E.: Chloracne, Porphyria cutanea tarda und andere Intoxikationen durch Herbizide. Hautarzt 27, 328–333 (1976)PubMedGoogle Scholar
  30. 30.
    Kan, C.A., Strik, J.J.T.W.A., Rombout, P.J.A., Heide, N.v.d., Koeman, J.H.: Toxicity of hexachlorocyclohexane (g-HCH) and hexachlorobenzene (HCB) in laying hens. In prep. (1977)Google Scholar
  31. 31.
    Kearny, P.C., Woolson, E.A., Isensce, A.R., Helling, C.S.: Tetrachlorodibenzodioxin in the environment: sources, fate, and decontamination. Environ. Health Perspect. 5, 273–277 (1973)CrossRefGoogle Scholar
  32. 32.
    Kimbrough, R.D., Carter, C.D., Liddle, J.A., Cline, R.E., Phillips, P.E.: Epidemiology and pathology of a tetrachlorodibenzodioxin poisoning episode. Arch. Environ. Health 32, 77–86 (1977)PubMedGoogle Scholar
  33. 33.
    Koeman, J.H.: Het voorkomen en de toxicologische betekenis van enkele chloorkoolwaterstoffen aan de Nederlandse kust in de periode van 1965-1970. Thesis, Utrecht, 1971Google Scholar
  34. 34.
    Koeman, J.H., Noever de Brauw, M.C., ten, Vos, R.H., de: Chlorinated biphenyls in fish, mussels, and birds from the river Rhine and the Netherlands coastal area. Nature (Lond.) 221, 1126 (1969)CrossRefGoogle Scholar
  35. 35.
    Koeman, J.H., Velzen-Blad, H.C.W., van, Vries, R., de, Vos, J.G.: Effects of PCB’s and DDE in cormorants and evaluation of PCB residues from an experimental study. J. Reprod. Fertil (Suppl.),19, 353–364 (1973)Google Scholar
  36. 36.
    Koss, G., Koransky, W., Steinback, K.: Studies on the toxicology of hexachlorobenzene. II. Identification and determination of metabolites. Arch. Toxikol. 35, 107–114 (1976)CrossRefGoogle Scholar
  37. 37.
    Koss, G., Manz, D.: Residues of hexachlorobenzene in wild mammals of Germany. Bull. Environ. Contam. Toxicol. 15, 189–191 (1976)CrossRefGoogle Scholar
  38. 38.
    Kószó, F., Siklósi, Cs., Simon, N.: Liposome model experiment for the study of assumed membrane damage in porphyria cutanea tarda. Biochem. Biophys. Acta 363, 182–189 (1974)PubMedCrossRefGoogle Scholar
  39. 39.
    Lange, C.E., Block, H., Veltman, G., Doss, M.: Urinary porphyrins among PVC workers. In: Porphyrins in Human Diseases. Doss, M. (ed.). Basel: Karger 1976, pp. 352–355Google Scholar
  40. 40.
    Leoni, V., D’Arca, S.U. : Experimental data and critical review of the occurrence of hexachlorobenzene in the Italian environment. Sci. Total. Environ. 5, 253–272 (1976)CrossRefGoogle Scholar
  41. 41.
    Lissner, R., Goerz, G., Eichenauer, M.G., Ippen, H.: Hexachlorobenzene-induced porphyria in rats - Relationship between porphyria excretion and induction of drug metabolizing liver enzymes. Biochem. Pharmacol. 24, 1729–1731 (1975)CrossRefGoogle Scholar
  42. 42.
    Lynch, R.E., Lee, G.R., Kushner, J.P.: Porphyria cutanea tarda associated with disinfectant misuse. Arch. Intern. Med. 135, 549–552 (1975)PubMedCrossRefGoogle Scholar
  43. 43.
    Matteis, F., de, Prior, B.E., Rimington, C.: Nervous and biochemical disturbances following hexachlorobenzene intoxication. Nature (Lond.) 291, 363–366 (1961)Google Scholar
  44. 44.
    Mattsson, P.E., Norstrōm, Å., Rappe, C.: Identification of the flame retardant pentabromotoluene in sewage sludge. J. Chromatogr. Ill, 209–213 (1975)CrossRefGoogle Scholar
  45. 45.
    Morita, M., Mimura, S., Ohi, G., Y-agyu, H.: A systematic determination of chlorinated benzenes in human adipose tissue. Environ. Pollut. 9, 175–179 (1975)CrossRefGoogle Scholar
  46. 46.
    Morley, A., Geary, D., Harben, F.: Hexachlorobenzene pesticides and porphyria. Med. J. Aust. 1, 565 (1973)PubMedGoogle Scholar
  47. 47.
    Noever de Brauw, M.C., ten, Koeman, J.H.: Identification of chlorinated styrenes in cormorant tissues by a computerized gas chromatography-mass spectrometry system. Sci. Total Environ. 1, 427–432 (1972/73)Google Scholar
  48. 48.
    Norstrom, Å., Andersson, K., Rappe, C.: Major components of some brominated aromatics used as flame retardants. Chemosphere 4, 255–261 (1976)CrossRefGoogle Scholar
  49. 49.
    Ockner, R.K., Schmid, R.: Acquired porphyria in man and rat due to hexachlorobenzene intoxication. Nature (Lond.) 189, 499 (1961)CrossRefGoogle Scholar
  50. 50.
    Peakall, D.: Polychlorinated biphenyls: Occurrence and biological effects. In: Residue Reviews. Gunther, F.A. (ed.). New York-Heidelberg-Berlin’: Springer-Verlag 1972, Vol. XXXXIV, pp. 1–21Google Scholar
  51. 51.
    Pietschmann, H., Raab, W.: Hepatische Porphyrien: Veranderungen der Serumenzymaktivitaten und hamatologische Befunde beim Menschen und bei der Ratte. Congress Int. Dermatol. 13, 1293–1294 (1967)Google Scholar
  52. 52.
    Poland, A., Kende, A.: 2,3,7,8-tetrachlorodibenzo-p-dioxin: environmental contaminant and molecular probe. Fed. Proc. 35, 2404–2411 (1976)PubMedGoogle Scholar
  53. 53.
    Poland, A., Smith, D., Metter, C., Possick, P.: A health survey of workers in a 2,4-D and 2,4,5-T plant. Arch. Environ. Health 22, 316–327 (1971)PubMedGoogle Scholar
  54. 54.
    Rimington, C., Ziegler, G.: Experimental porphyria in rats induced-by chlorinated benzenes. Biochem. Pharmacol. 12, 1387–1397 (1963)PubMedCrossRefGoogle Scholar
  55. 55.
    Robertson, L.W., Chynoweth, D.P.: Another halogenated hydrocarbon (PBB: Environmental contamination by another halogenated hydrocarbon). Environment 17, 25–27 (1975)CrossRefGoogle Scholar
  56. 56.
    Rombout, P., Strik, J.J.T.W.A., Toxiciteit van hexachloorbenzeen en B-hexachloorcyclohexaan bij legkippen, met speciale aandacht voor de verstoring der porfyrine stofwisseling. Internal report, Department of Toxicology, 1976Google Scholar
  57. 57.
    Schulz, K.H.: Klinische und experimentelle Untersuchungen zur Atiologie der Chloracne. Arch. Klin. Exp. Dermatol. 206, 589–596 (1957)PubMedCrossRefGoogle Scholar
  58. 58.
    Simon, M., Berko, G., Dobozy, A.: Influence of sex hormones on porphyrin metabolism in model experiments. Borgyogy. Venerol. Szemle 49, 49–52 (1973)Google Scholar
  59. 59.
    Simon, N., Siklosi, Cs.: Beeinflussung des Porphyrinstoffwechsels durch Umweltfaktoren. Berufsdermatosen 22, 237–259 (1974)PubMedGoogle Scholar
  60. 60.
    Sinclair, P., Granick, S.: Uroporphyrin formation induced by chlorinated hydrocarbons (Lindane, polychlorinated biphenyls, tetrachlorodibenzo-p-dioxin). Requirements for endogenous iron, protein synthesis and drug-metabolizing activity. Biochem. Biophys. Res. Commun. 61, 124–133 (1974)PubMedCrossRefGoogle Scholar
  61. 61.
    Siyali, D.S., Simson, R.E.: Chlorinated hydrocarbon pesticides in human blood and fat. Med. J. Aust. 1, 212 (1973)PubMedGoogle Scholar
  62. 62.
    Stijve, T.: Determination and occurrence of hexachlorobenzene residues. Mitt. Geb. Lebensmittelunders. Hyg. 62, 406–414 (1971)Google Scholar
  63. 63.
    Stonard, M.D., Greig, J.B. : Diffe’rent patterns of hepatic microsomal enzyme produced by administration of pure hexachlorobiphenyl isomers and hexachlorobenzene. Chem. Biol. Interact. 15., 365–379 (1976)PubMedCrossRefGoogle Scholar
  64. 64.
    Stonard, M.D., Zenov, P.Z.: Effect of hexachlorobenzene on hepatic microsomal enzymes in the rat. Biochem. Pharmacol. 23, 2175–2183 (1974)PubMedCrossRefGoogle Scholar
  65. 65.
    Strik, J.J.T.W.A.: Experimentele leverporfyrie bij vogels. Thesis, Utrecht, 1973, pp. 79–90, 107-118Google Scholar
  66. 66.
    Strik, J.J.T.W.A.: Species differences in experimental porphyria caused by polyhalogenated aromatic compounds. Enzyme 16, 224–230 (1973b)PubMedGoogle Scholar
  67. 67.
    Strik, J.J.T.W.A.: Toxicity of hexachlorobenzene (HCB) and hexabromobiphenyl (HBB). Meded. Rijksfac. Landbouwwet. Gent 38, 709–716 (1973c)Google Scholar
  68. 68.
    Strik, J.J.T.W.A.: Chemical porphyria in Japanese quail (Coturnix c. Japonica). Enzyme 16, 211–223 (1973d)PubMedGoogle Scholar
  69. 69.
    Strik, J.J.T.W.A., Koeman, J.H.: Porphyrinogenic action of hexachlorobenzene and octachlorostyrene. In: Porphyrins in Human Diseases. Doss, M. (ed). Basel: Karger 1976, pp. 418–423Google Scholar
  70. 70.
    Strik, J.J.T.W.A., Wit, J.G.: Hepatic porphyria in birds and mammals. TNO-nieuws 27, 604–610 (1972)Google Scholar
  71. 71.
    Strik, J.J.T.W.A., Forlin, L., Butijn, G.D.: Correlation P-450 spectral binding with in vivo toxicity. Abstract. International conference on in vivo aspects of biotransformation and toxicity of industrial and environmental xenobiotics. Prague, Sept. 1977Google Scholar
  72. 72.
    Strik, J.J.T.W.A., Doss, M., Robertson, L.W., Tiepermann, R. von, Harmsen, E.G.M.: Secondary coproporphyrinuria and chronic hepatic porphyria type A in farm families in Michigan exposed to polybrominated biphenyls (PBB). In prep. (1977)Google Scholar
  73. 73.
    Sweeney, G.D., Janigan, D., Mayman, D., Lai, H.: Experimental porphyria. I. The experimental porphyrias - a group of distinctive metabolic lesions. S. Afr. J. Lab. Clin. Med. 45, 68–72 (1971)Google Scholar
  74. 74.
    Taljaard, J.J.F., Shanley, B.C., Joubert, S.M.: Decreased uroporphyrinogen decarboxylase activity in experimental symptomatic porphyria. Life Sci. 10, 887–893 (1971)CrossRefGoogle Scholar
  75. 75.
    Umeda, G.: PCB poisoning in Japan, Ambio 1, 132–134 (1972)Google Scholar
  76. 76.
    Villanueva, E.C., Jennings, R.W., Burse, V.W., Kimbrough, R.D.: Evidence of chlorodibenzo-p-dioxin and chlorodibenzo furan in hexachlorobenzene. J. Agric. Food Chem. 22, 916–917 (1974)PubMedCrossRefGoogle Scholar
  77. 77.
    Vliet, P.W. van, Strik, J.J.T.W.A.: Porfyrines in de urine als parameter voor de belasting met epichloorhydrine. Internal report, Department of Toxicology, 1977Google Scholar
  78. 78.
    Vos, J.G., Botterweg, P.F., Strik, J.J.T.W.A., Koeman, J.H.: Experimental studies with HCB in birds. TNO-nieuws 27, 599–603 (1972)Google Scholar
  79. 79.
    Vos, J.G., Breeman, H.A., Benschop, H.: The occurrence of the fungicide hexachlorobenzene in wild birds and its toxicological importance - a preliminary communication. Meded. Rijksfac. Landbouwwetensch. Gent 33, 1236–1269 (1968)Google Scholar
  80. 80.
    Vos, J.G., Koeman, J.H.: Comparative toxicologic study with polychlorinated biphenyls in chickens with special reference to porphyria, edema formation, liver necrosis and tissue residues. Toxicol. Appl. Pharmacol. 17, 656–668 (1970)PubMedCrossRefGoogle Scholar
  81. 81.
    Vos, J.G., Maas, H.L., van der, Musch, A., Ram, E.: Toxicity of hexachlorobenzene in Japanese quail with special reference to porphyria, liver damage, reproduction, and tissue residues. Toxicol. Appl. Pharmacol. 18, 944–957 (1971a)PubMedCrossRefGoogle Scholar
  82. 82.
    Vos, J.G., Strik, J.J.T.W.A., Holsteijn, C.W.M., Pennings, J.H.: Polychlorinated biphenyls as inducers of hepatic porphyria in Japanese quail, with special reference to delta-aminolevulinic acid synthetase activity, fluorescence and residues in the liver. Toxicol. Appl. Pharmacol. 20, 232–240 (1971b)PubMedCrossRefGoogle Scholar
  83. 83.
    Wetzels, W.A.M., Strik, J.J.T.W.A.: Porfyrines in urine na blootstelling aan endrin. Internal report, Department of Toxicology, 1977Google Scholar
  84. 84.
    Wit, J.G.: Enzyme induction with special reference to chemical porphyria. A biological-toxicological study on the halogenated biphenyls. Report on third technical meeting on occurrence and significance of chemicals in the environment. O.E.C.D. Berlin 1972, pp. 50-59Google Scholar

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© Springer-Verlag Berlin Heidelberg 1978

Authors and Affiliations

  • J. J. T. W. A. Strik
    • 1
  1. 1.Department of ToxicologyAgricultural UniversityWageningenThe Netherlands

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