45
Views
106
CrossRef citations to date
0
Altmetric
Research Article

Exposure to Toxic Agents: The Heme Biosynthetic Pathway and Hemoproteins as Indicator

Pages 151-180 | Published online: 26 Sep 2008

References

  • Walman S. A., Sinacore M. S., Lewicki J. A., Chang L. Y., Murad F. Selective activation of particulate guanylate cyclase by a specific class of porphyrins. J. Biol. Chem. 1984; 259: 4038
  • Graf H., Ruf H. H., Ullrich V. Prostacyclin synthase, a cytochrome P450 enzyme. Angew. Chem. Int. Ed. Engl 1983; 22: 487
  • Kappas A., Sassa S., Anderson K. E. The porphyrias. The Metabolic Basis of Inherited Disease, B.-J. Stanbury, J. B. Wyngaarden, D. S. Fredrickson. McGraw-Hill, New York 1982; 1301
  • Tyrrell D. L. J., Marks G. S. Drug-induced porphyrin biosynthesis. V. Effect of protohemin on the transcriptional and post-transcriptional phases of β-aminolevulinic acid synthetase induction. Biochem. Pharmacol. 1972; 21: 2077
  • Yamamoto M., Hayashi N., Kikuchi G. Evidence for the transcriptional inhibition by heme of the synthesis of β-aminolevulinate synthase in rat liver. Biochem. Biophys. Res. Commun. 1982; 105(3)985
  • Hayashi N., Watanabe N., Kikuchi G. Inhibition by hemin of in vitro translocation of chicken liver β-aminolevulinic synthase into mitochondria. Biochem. Biophys. Res. Commun. 1983; 115(2)155
  • Tait G. H. Heme and hemoproteins. Handbook of Experimental Pharmacology, F. De Matteis, W. N. Aldridge. Springer-Verlag, Berlin 1978; Vol. 44: 1
  • Marks G. S., Follows S. B., Zelt D. T., Cole S. P. C. Patterns of porphyrin accumulation in response to chemicals in chick embryo liver cells. Can. J. Physiol. Pharmacol. 1983; 61(6)546
  • Zelt D. T., Owen J. A., Marks G. S. Second derivative high performance liquid chromatographic fluorometric detection of porphyrins in chick embryo liver cell culture medium. J. Chromatogr. 1980; 189: 209
  • De Verneuil H., Sassa S., Kappas A. Effects of polychlorinated biphenyl compounds, 2,3,7,8-tetrachlorodibenzo-p-dioxin, phenobarbital and iron on hepatic uroporphyrinogen decarboxylase. Biochem. J. 1983; 214: 145
  • Lim C. K., Rideout J. M., Wright D. J. High-performance liquid chromatography of naturally occurring 8-, 7-, 6-, 5- and 4-carboxylic porphyrin isomers. J. Chromatogr. 1983; 282: 629
  • Sassa S. Toxic effects of lead, with particular reference to porphyrin and heme metabolism. Handbook of Experimental Pharmacology, F. De Matteis, W. N. Aldridge. Springer-Verlag, Berlin 1978; Vol. 44: 333
  • Hodson P. V., Blunt B. R., Spry D. J., Austen K. Evaluation of erythrocyte β-amino levu-linic acid dehydratase activity as a short-term indicator in fish of a harmful exposure to lead. J. Fish. Res. Board Can. 1977; 34(4)501
  • Hodson P. V. β-Amino levulinic acid dehydratase activity of fish blood as an indicator of a harmful exposure to lead. J. Fish. Res. Board Can. 1976; 33(2)268
  • Hutton M. The effects of environmental lead exposure and in vitro zinc on tissue β-aminolevulinic acid dehydratase in urban pigeons. Comp. Biochem. Physiol. 1983; 74C(2)441
  • Lamola A. A., Yamane T. Zinc protoporphyrin in the erythrocytes of patients with lead intoxication and iron deficiency anemia. Science 1974; 186: 936
  • Lamola A. A., Piomelli S., Poh-Fitzpatrick M., Yamane T., Harbo L. Erythropoietic protoporphyria and Pb intoxication: the molecular basis for difference in cutaneous photosensitivity. II. Different binding of erythrocyte protoporphyrin to hemoglobin. J. Clin. Invest. 1975; 56: 1528
  • Valciukas J. A., Lilis R., Fischbein A., Selikoff I. J. Central nervous system dysfunction due to lead exposure. Science 1978; 201: 465
  • Silbergeld E. K. Current status of neurotoxicology, basic and applied. Trends Neurosci. 1982; 5(9)291
  • Lamola A. A., Joselow M., Yamane T. Zinc protoporphyrin (ZPP): a simple, sensitive, fluorometric screening test for lead poisoning. Clin. Chem. 1975; 21(1)93
  • Haeger-Aronsen B. Why is the patient with lead intoxication not light sensitive?. Acta Derm. Ve-nereol. Suppl. 1982; 100: 67
  • Piper W. N., Tephly T. R. Differential inhibition of erythrocyte and hepatic uroporphyrinogen I synthetase activity by lead. Life Sci. 1974; 14: 873
  • Fischbein A., Wallace J., Anderson K. E., Sassa S., Kon S., Rohl A. N., Kappas A. Lead poisoning in an art conservator. JAMA 1982; 247: 2007
  • Fowler B. A., Mahaffey K. R. Interactions among lead, cadmium, and arsenic in relation to porphyrin excretion patterns. Environ. Health Perspect. 1978; 25: 87
  • Martinez G., Cebrian M., Chamorro G., Jauge P. Urinary uroporphyrin as an indicator of arsenic exposure in rats. Proc. West. Pharmacol. Soc. 1983; 26: 171
  • Eiseman J. L., Alvares A. P. Alterations induced in heme pathway enzymes and monooxygen-ases by gold. Mol. Pharmacol. 1978; 14: 1176
  • Eiseman J. L., Alvares A. P. Heme metabolism in the fetoplacental unit and neonatal livers during lactation: effect of gold sodium thiomalate. J. Pharmacol. Exp. Ther. 1980; 214: 250
  • Woods J. S., Fowler B. A. Renal porphyrinuria during chronic methyl mercury exposure. J. Lab. Clin. Med. 1977; 90: 266
  • Woods J. S., Kardish R., Fowler B. A. Studies on the action of porphyrinogenic trace metals on the activity of hepatic uroporphyrinogen decarboxylase. Biochem. Biophys. Res. Commun. 1981; 103: 264
  • Maines M. D., Chung A., Kutty R. K. The inhibition of testicular heme oxygenase activity by cadmium. J. Biol. Cnem. 1982; 257: 14116
  • Woods J. S., Carver G. T., Fowler B. A. Altered regulation of hepatic metabolism by indium chloride. Toxicol. Appl. Pharmacol. 1979; 49: 455
  • Woods J. S., Fowler B. A. Selective inhibition of β-aminolevulinic acid dehydratase by indium chloride in rat kidney: biochemical and ultrastructural studies. Exp. Mol. Pathol 1982; 36: 306
  • Kappas A., Maines M. D. Tin: a potent inducer of heme oxygenase in kidney. Science 1976; 192: 60
  • Tephly T. R., Hibbeln P. The effect of cobalt chloride administration on the synthesis of hepatic microsomal cytochrome P-450. Biochem. Biophys. Res. Commun. 1971; 42: 589
  • Yasukochi Y., Nakamura M., Minakami S. Effect of cobalt on the synthesis and degradation of hepatic catalase in vivo. Biochem. J. 1974; 144: 455
  • Tephly T. R., Webb C., Trussler P., Kniffen F., Hasegawa E., Piper W. The regulation of heme synthesis related to drug metabolism. Drug Metab. Dispos. 1973; 1: 259
  • De Matteis F., Unseld A. Increased liver haem degradation caused by foreign chemicals: a comparison of the effects of 2-ally-2-isopropylacetamide and cobaltous chloride. Biochem. Soc. Trans. 1976; 4: 205
  • Maines M. D., Kappas A. Trace metal regulation of heme and hemoprotein oxidation. Hoppe-Seyler's Z. Physiol. Cnem. 1976; 357: 1038
  • Nakamura M., Yasukochi Y., Minakami S. Effect of cobalt on heme biosynthesis in rat liver and spleen. J. Biochem. (Tokyo) 1975; 78: 373
  • De Matteis F., Gibbs A. H. The effect of cobaltous chloride on liver haem metabolism in the rat. Ann. Clin. Res. 1976; 8: 193, Suppl. 17
  • De Matteis F., Gibbs A. H. Inhibition of haem synthesis caused by cobalt in rat liver. Biochem. J. 1977; 162: 213
  • Sinclair P., Gibbs A. H., Sinclair J. F., De Matteis F. Formation of cobalt protoporphyrin in the liver of rats. Biochem. J. 1979; 178: 529
  • Watkins S., Baron J., Tephly T. R. Identification of cobalt protoporphyrin IX formationin vivo following cobalt administration to rats. Biochem. Pharmacol. 1980; 29: 2319
  • Igarashi J., Hayashi N., Kikuchi G. Effects of administration of cobalt protoporphyrin on β-aminolevulinate synthase in rat liver. J. Biochem. (Tokyo) 1978; 84: 997
  • Sinclair P. R., Sinclair J. F., Bonkowsky H. L., Gibbs A. H., De Matteis F. Formation of cobalt protoporphyrin by chicken hepatocytes in culture. Biochem. Pharmacol. 1982; 31: 993
  • Maines M. D., Kappas A. Metals as regulators of heme metabolism. Science 1977; 198: 1215
  • Maines M. D., Kappas A. Regulation of cytochrome P-450-dependent microsomal drug-metabolizing enzymes by nickel, cobalt, and iron. Clin. Pharmacol. Ther. 1977; 22: 780
  • Tephly T. R., Coffman B. L., Abou Zeit-Har M. S., Sedman R., West E., Simon I. Toxic effects of metals on the synthesis and disposition of heme. Advances in Pharmacology and Therapeutics II, H. Yoshida, Y. Hagihara, S. Ebashi. Pergamon Press, Oxford 1982; Vol. 5: 139
  • Tephly T. R., Wagner G., Sedman R., Piper W. Effects of metals on heme biosynthesis and metabolism. Fed. Proc. 1978; 37: 35
  • Tephly T. R. Inhibition of liver hemoprotein synthesis. Handbook of Experimental Pharmacology, F. De Matteis, W. N. Aldridge. Springer-Verlag, Berlin 1978; Vol. 44: 81
  • Tenhunen R., Savolainen H., Jäppinen P. Changes in haem synthesis associated with occupational exposure to organic and inorganic sulphides. Clin. Sci. 1983; 64: 187
  • Dogramaci I., Wray J. D., Ergene T., Sezer V., Muftu Y. Porphyria turcica. Turk. J. Pediatr. 1962; 4: 138
  • Dogramaci I. Porphyrias and porphyrin metabolism, with special reference to porphyria in childhood. Adv. Pediatr. 1964; 13: 11
  • Peters H. A., Johnson S. A. M., Cam S., Oral S., Muftu Y., Ergene T. Hexachlorobenzene-induced porphyria: effect of chelation on the disease, porphyrin and metal metabolism. Am. J. Med. 1966; 251: 314
  • Schmid R. Cutaneous porphyria in Turkey. N. Engl. J. Med. 1960; 263: 397
  • Cam C., Nigogosyan G. Acquired toxic porphyria cutanea tarda due to hexachlorobenzene. JAMA 1963; 183: 88
  • Courtney K. D. Hexachlorobenzene (HCB): a review. Environ. Res. 1979; 20: 225
  • Ockner R. K., Schmid R. Acquired porphyria in man and rat due to hexachlorobenzene intoxication. Nature (London) 1961; 189: 499
  • De Matteis F., Prior B. E., Rimington C. Nervous and biochemical disturbances following hexachlorobenzene intoxication. Nature (London) 1961; 191: 363
  • Elder G. H. Porphyria caused by hexachlorobenzene and other polyhalogenated aromatic hydrocarbons. Handbook of Experimental Pharmacology, F. De Matteis, W. N. Aldridge. Springer-Verlag, Berlin 1978; Vol. 44: 157
  • Jackson A. H., Sancovich H. A., Ferramola A. M., Evans N., Games D. E., Matlin S. A., Elder G. H., Smith S. G. Macrocyclic intermediates in the biosynthesis of porphyrins. Philos. Trans. R. Soc. London 1976; 273: 191
  • San Martin de Viale L. C., Rios C., Del De Molina M., Wainstock De Calmanovici R., Tomio J. M. Experimental porphyria produced in rats by hexachlorobenzene. IV. Studies on the stepwise decarboxylation of uroporphyrinogen and phyriaporphyrinogenin vivo andin vitro in several tissues. Porphyrins in Human Diseases, M. Doss. S. Karger, Basel 1976; 445
  • Cripps D. J., Goeman A., Peters H. A. Porphyria turcica. Twenty years after hexachlorobenzene intoxication. Arch. Dermatol. 1980; 116: 46
  • Koss G., Seubert S., Seubert A., Seidel J., Koransky W., Ippen H. Studies on the toxicology of hexachlorobenzene. Arch. Toxicol. 1983; 52: 13
  • Koss G., Seubert S., Seubert A., Koransky W., Ippen H. Studies on the toxicology of hexachlorobenzene. Arch. Toxicol. 1978; 40: 285
  • Koss G., Koransky W., Steinbach K. Studies on the toxicology of hexachlorobenzene. Arch. Toxicol. 1979; 42: 19
  • Rizzardini M., Smith A. G. Sex differences in the metabolism of hexachlorobenzene by rats and the development of porphyria in females. Biochem. Pharmacol. 1982; 31: 3543
  • Debets F. M. H., Hamers W. J. H. M. B, Strik J. J. T. W. A. Metabolism as a prerequisite for the porphyrinogenic action of polyhalogenated aromatics, with special reference to hexachlorobenzene and polybrominated biphenyls (Firemaster BP-6). Int. J. Biochem. 1980; 12: 1019
  • Debets F. M. H., Reinders J. H., Debets A. J. M., Lössbroek T. G., Strik J. J. T. W. A, Koss G. Biotransformation and porphyrinogenic action of hexachlorobenzene and its metabolites in a primary liver cell culture. Toxicology 1981; 19: 185
  • Smith A. G., Cabral J. R. P., De Matteis F. A difference between two strains of rats in their liver non-haem iron content and in their response to the porphyrogenic effect of hexachlorobenzene. Chem. Biol Interact. 1979; 27: 353
  • Miranda C. L., Wang J.-L., Henderson M. C., Carpenter H. M., Nakaue H. S., Buhler D. R. Studies on the porphyrinogenic action of 1,2,4-trichlorobenzene in birds. Toxicology 1983; 28: 83
  • Rimington C., Ziegler G. Experimental porphyria in rats induced by chlorinated benzenes. Biochem. Pharmacol. 1963; 12: 1387
  • Carlson G. P. Chlorinated benzene induction of hepatic porphyria. Experientia 1977; 33: 1627
  • Carlson G. P. Brominated benzene induction of hepatic porphyria. Experientia 1979; 35(4)513
  • Mendoza C. E., Shields J. B., Laver G. W. Comparison of the porphyrinogenic activity of hexabromobenzene and hexachlorobenzene in primiparous Wistar rats. Bull. Environ. Contam. Toxicol. 1979; 21: 358
  • Smith A. G., Francis J. E. Relative abilities on a molar basis of hexafluoro-, hexachloro-and hexabromobenzenes to decrease liver uroporphyrinogen decarboxylase activity and cause porphyria in female rats. Res. Commun. Chem. Pathol. Pharmacol. 1980; 28: 377
  • Hay A. The chemical scythe. Lesson of 2,4,5-Tand Dioxin. Plenum Press, New York 1982; 1
  • Bleiberg J., Wallen M., Brodkin R., Appelbaum I. L. Industrially-acquired porphyria. Arch. Dermatol. 1964; 89: 793
  • Jirasek L., Kalensky J., Kubec K. Acne chlorina, porphyria cutanea tards pri vyrobe herbicid. Ceska Dermatol. 1973; 48: 306
  • Riedel D. A review of the toxicology of the herbicide 2,4-D (2,4-dichlorophenoxyacetic acid). Chron. Dis. Can. 1983; 4(1)4
  • Poland A., Knutson J. C. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. Annu. Rev. Pharmacol. Toxicol. 1982; 22: 517
  • Crow K. D. Chloracne. Trans. St. John's Hosp. Dermatol. Soc. 1970; 56: 79
  • Poland A., Glover E. 2,3,7,8-Tetrachlorodibenzo-(p)-dioxin: a potent inducer of β-aminolevu-linic acid synthetase. Science 1973; 179: 476
  • Goldstein J. A., Hickman P., Vos J. G. Hepatic porphyria induced by 2,3,7,8-tetrachlorodi-benzo-p-dioxin in the mouse. Res. Commun. Chem. Pathol. Pharmacol. 1973; 6: 919
  • Cantoni L., Salmona M., Rizzardini M. Porphyrogenic effect of chronic treatment with 2,3,7,8-tetrachlorodibenzo-p-dioxin in female rats. Dose-effect relationship following urinary excretion of porphyrins. Toxicol. Appl. Pharmacol. 1981; 57: 156
  • Kociba R. J., Keyes D. G., Beyer J. E., Carreon R. M., Wade C. E., Dittenber D. A., Kalnins R. P., Frauson L. E., Park C. N., Barnard S. D., Hummel R. A., Humiston C. G. Results of a two-year chronic toxicity and oncogenicity study of 2,3,7,8-tetrachlorodibenzo-p-dioxin in rats. Toxicol. Appl. Pharmacol. 1978; 46: 279
  • Jones K. G., Sweeney G. D. Association between induction of aryl hydrocarbon hydroxylase and depression of uroporphyrinogen decarboxylase activity. Res. Commun. Chem. Pathol. Pharmacol. 1977; 17: 631
  • Elder G. H., Sheppard D. M. Immunoreactive uroporphyrinogen decarboxylase is unchanged in porphyria caused by TCDD and hexachlorobenzene. Biochem. Biophys. Res. Commun. 1982; 109: 113
  • Cantoni L., Fiume D. D., Rizzardini M., Ruggieri R. In vitro inhibitory effect on porphyrinogen carboxylase of liver extracts from TCDD treated mice. Toxicol. Lett. 1984; 20: 211
  • Vos J. G., Koeman J. H. Comparative toxicologic study with polychlorinated biphenyls in chicken with special reference to porphyria, edema formation, liver necrosis, and tissue residues. Toxicol. Appl. Pharmacol. 1970; 17: 656
  • Vos J. G., Strik J. J. T. W. A, Van Holsteyn C. W. M., Pennings J. H. Polychlorinated biphenyls as inducers of hepatic porphyria in Japanese quail, with special reference to β-aminolevu-linic acid synthetase activity, fluorescence, and residues in the liver. Toxicol. Appl. Pharmacol. 1971; 20: 232
  • Vos J. G., Notenboom-Ram E. Comparative toxicity study of 2,4,5,2′,4′,5′-hexachlorobi-phenyl and a polychlorinated biphenyl mixture in rabbits. Toxicol. Appl. Pharmacol. 1972; 23: 563
  • Goldstein J. A., Hickman P., Burse V. W., Bergman H. 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. 1975; 32: 461
  • Goldstein J. A., Hickman P., Jue D. L. Experimental hepatic porphyria induced by polychlorinated biphenyls. Toxicol. Appl. Pharmacol. 1974; 27: 437
  • Kimbrough R. D. The toxicity of polychlorinated polycyclic compounds and related chemicals. CRC Crit. Rev. Toxicol. 1974; 2: 445
  • Chang K.-J., Lu F.-J., Tung T.-C. Studies on patients with polychlorinated biphenyl poisoning. Res. Commun. Chem. Pathol. Pharmacol. 1980; 30: 547
  • Kay K. Polybrominated biphenyls (PBB) environmental contamination in Michigan, 1973-1976. Environ. Res. 1977; 13: 74
  • Strik J. J. T. W. A, Doss M., Schraa G., Robertson L. W., Tiepermann R., Harmsen E. G. M. Coproporphyrinuria and chronic hepatic porphyria type A found in farm families from Michigan (USA) exposed to polybrominated biphenyls (PBB). Chemical Porphyria in Man, J. J. T. W. A Strik, J. H. Koeman. Elsevier, Amsterdam 1979; 29
  • Gupta B. N., McConnell E. E., Goldstein J. A., Harris M. W., Moore J. A. Effects of a polybrominated biphenyl mixture in the rat and mouse. Toxicol. Appl. Pharmacol. 1983; 68: 1
  • 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. 1974; 61: 124
  • Kawanishi S., Mizutani T., Sano S. Induction of porphyrin synthesis in chick embryo liver cell culture by synthetic polychlorobiphenyl isomers. Biochim. Biophys. Acta 1978; 540: 83
  • Marks G. S., Zelt D. T., Cole S. P. C. Alterations in the heme biosynthetic pathway as an index of exposure to toxins. Can. J. Physiol. Pharmacol. 1982; 60: 1017
  • Marks G. S. The effects of chemicals on hepatic heme biosynthesis. Handbook of Experimental Pharmacology, F. De Matteis, W. N. Aldridge. Springer-Verlag, Berlin 1978; Vol. 44: 201
  • Swain M. G., Follows S. B., Marks G. S. Inhibition of uroporphyrinogen decarboxylase by 3,3′,4,4′-tetrachlorobiphenyl in chick embryo liver cell culture, Can. J. Physiol. Pharmacol. 1983; 61: 105
  • De Verneuil H., Grandchamp B., Nordmann Y. Some kinetic properties of human red cell uroporphyrinogen decarboxylase. Biochim. Biophys. Acta 1980; 611: 174
  • Smith A. G., Francis J. E. Investigations of rat liver uroporphyrinogen decarboxylase. Biochem. J. 1981; 195: 241
  • Kawanishi S., Seki Y., Sano S. Polychlorobiphenyls that induce β-aminolevulinic acid synthetase inhibit uroporphyrinogen decarboxylase in cultured chick embryo liver cells. FEBS Lett. 1981; 129: 93
  • Kawanishi S., Seki Y., Sano S. Uroporphyrinogen decarboxylase. J. Biol. Chem. 1983; 258: 4285
  • Slotsve M., Owen J., Marks G. S. 1984, unpublished observations
  • Sinclair P. R., Bement W. J., Bonkovsky H. L., Sinclair J. F. Inhibition of uroporphyrinogen decarboxylase by halogenated biphenyls in chick hepatocyte cultures. Biochem. J. 1984; 222: 737
  • Centen A. H., Strik J. J. T. W. A, Colombi A. Coproporphyrinuria and chronic hepatic porphyria type A found in people from Seveso (Italy) exposed to 2,3,7,8-tetrachlorodibenzo-(p)-dioxin (TCDD). Chemical Porphyria in Man, J. J. T. W. A Strik, J. H. Koeman. Elsevier, Amsterdam 1979; 75
  • Strik J. J. T. W. A, Koeman J. H. Chemical Porphyria in Man, J. J. T. W. A Strik, J. H. Koeman. Elsevier, Amsterdam 1979
  • Doss M., Lange C. E., Veltman G. Toxic porphyrinuria and chronic hepatic porphyria after vinyl chloride exposure in humans. Chemical Porphyria in Man, J. J. T. W. A Strik, J. H. Koeman. Elsevier, Amsterdam 1979; 107
  • Bleakely P., Nichol A. W., Collins A. G. Diazinon and porphyria cutanea tarda. Med. J. Aust. 1979; 1: 314
  • Bopp C., Kosminsky B. Toxic hepato-cutaneous porphyria (occupational disease). Med. Cutanae Ibero Lat. Am. 1975; 3: 271
  • Nichol A. W., Elsbury S., Elder G. H., Jackson A. H., Rao K. R. N. Separation of impurities in diazinon preparations and their effects on porphyrin biosynthesis in tissue culture. Biochem. Pharmacol. 1982; 31: 1033
  • Nichol A. W., Elsbury S., Angel L. A., Elder G. H. The site of inhibition of porphyrin biosynthesis by an isomer of diazinon in rats. Biochem. Pharmacol. 1983; 32: 2653
  • De Matteis F., Gibbs A. H., Tephly T. R. Inhibition of protohaem ferro-lyase in experimental porphyria. Biochem. J. 1980; 188: 145
  • Taira M. C., San Martin de Viale L. C. Porphyrinogen carboxylyase from chick embryo liver—in vivo effect of heptachlor and Lindane. Int. J. Biochem. 1980; 12: 1033
  • De Matteis F. Drugs and porphyria. S. Afr. Med. J. 1971; 45: 126
  • Marks G. S., Hunter E. G., Terner U. K., Schneck D. Studies of the relationship between chemical structure and porphyria-inducing activity. Biochem. Pharmacol. 1965; 14: 1077
  • Onisawa J., Labbe R. F. Effects of diethyl-1,4-dihydro-2,4,6-trimethylpyridine-3,5-dicarboxy-late on the metabolism of porphyrins and iron. J. Biol. Chem. 1963; 238: 724
  • Rifkind A. B. Maintenance of microsomal hemoprotein concentration following inhibition of ferrochelatase activity by 3,5-diethoxycarbonyl-l,4-dihydrocollidine in chick embryo liver. J. Biol. Chem. 1979; 254: 4636
  • Tephly T. R., Gibbs A. H., De Matteis F. Studies on the mechanism of experimental porphyria produced by 3,5-diethoxycarbonyl-1,4-dihydrocollidine. Role of a porphyrin-like inhibitor of protohaem ferrolyase. Biochem. J. 1979; 180: 241
  • Ortiz de Montellano P. R., Beilan H. S., Kunze K. L. N-Methylprotoporphyrin IX: chemical synthesis and identification as the green pigment produced by 3,5-diethoxycarbonyl-1,4-dihydrocol-lidine. Proc. Natl. Acad. Sci. U.S.A. 1981; 78: 1490
  • Cole S. P. C., Whitney R. A., Marks G. S. Ferrochelatase inhibitory and porphyrin-inducing properties of 3,5-diethoxycarbonyl-1,4-dihydro-2,4,6-trimethylpyridine (DDC) and its analogues in chick embryo liver cells. Mol. Pharmacol. 1981; 20: 395
  • Ortiz de Montellano P. R., Beilan H. S., Kunze K. L. N-Alkylprotoporphyrin IX formation in 3,5-dicarbethoxy-l,4-dihydrocollidine-treated rats. J. Biol. Chem. 1981; 256: 6708
  • De Matteis F., Gibbs A. H., Farmer P. B., Lamb J. H. Liver production of N-alkylated porphyrins caused in mice by treatment with substituted dihydropyridines. FEBS Lett. 1981; 129: 328
  • Tephly T. R., Coffman B. L., Ingall G., Abon Zeit-Har G. S., Gogg H. M., Tabba H. D., Smith K. M. Identification of N-methylprotoporphyrin IX in livers of untreated mice and mice treated with 3,5-diethoxycarbonyl-1,4-dihydrocollidine: source of the methyl group. Arch. Biochem. Biophys. 1981; 212: 120
  • De Matteis F., Gibbs A. H. Drug-induced conversion of liver haem into modified porphyrins. Evidence for two classes of products. Biochem. J. 1980; 187: 285
  • Ortiz de Montellano P. R., Correia M. A. Suicidal destruction of cytochrome P-450 during oxidative drug metabolism. Annu. Rev. Pharmacol. Toxicol. 1983; 23: 481
  • Ortiz de Montellano P. R., Mathews J. M. Autocatalytic alkylation of the cytochrome P-450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochem. J. 1981; 195: 761
  • Muakkassah S. F., Yang W. C. T. Mechanism of the inhibitory action of phenelzine on microsomal drug metabolism. J. Pharmacol. Exp. Ther. 1981; 219: 147
  • Jonen H. G., Werringloer J., Prough R. A., Estabrook R. W. The reaction of phenylhydra-zine with microsomal cytochrome P-450: catalysis of heme modification. J. Biol. Chem. 1982; 257: 4404
  • Hanzlik R. P., Kishore V., Tullman R. Cyclopropylamines as suicide substrates for cytochrome P-450. J. Med. Chem. 1979; 22: 759
  • Macdonald T. L., Karimullah Z., Burka L. T., Peyman P., Guengerich F. P. Mechanism of cytochrome P-450 inhibition by cyclopropylamines. J. Am. Chem. Soc. 1982; 104: 2050
  • Hanzlik R. P., Tullman R. H. Suicidal inactivation of cytochrome P-450 by cyclopropylamines. Evidence for cation-radical intermediates. J. Am. Chem. Soc. 1982; 104: 2048
  • De Matteis F. Loss of liver cytochrome P-450 caused by chemicals. Damage to the apoprotein and degradation of the heme moiety. Handbook of Experimental Pharmacology, F. De Matteis, W. N. Aldridge. Springer-Verlag, Berlin 1978; Vol. 44: 95
  • Ortiz de Montellano P. R., Mico B. A., Yost G. S. Suicidal inactivation of cytochrome P-450. Formation of a heme-substrate covalent adduct. Biochem. Biophys. Res. Commun. 1978; 83: 132
  • Ortiz de Montellano P. R., Mico B. A. Destruction of cytochrome P-450 by ethylene and other olefins. Mol. Pharmacol. 1980; 18: 128
  • Ortiz de Montellano P. R., Beilan H. S., Kunze K. L., Mico B. A. Destruction of cytochrome P-450 by ethylene. Structure of the resulting prosthetic heme adduct. J. Biol. Chem. 1981; 256: 4395
  • De Matteis F., Gibbs A. H., Jackson A. H., Weerasinghe S. Conversion of liver haem into N-substituted porphyrins or green pigments. Nature of the substituent at the pyrrole nitrogen atom. FEBS Lett. 1980; 119: 109
  • White I. N. H., Muller-Eberhard U. Decreased liver cytochrome P-450 in rats caused by no-rethindrone or ethynyloestradiol. Biochem. J. 1977; 166: 57
  • Ortiz de Montellano P. R., Kunze K. L., Yost G. S., Mico B. A. Self-catalyzed destruction of cytochrome P-450: covalent binding of ethynyl sterols to prosthetic heme. Proc. Natl. Acad. Sci. U.S.A. 1979; 76: 746
  • White I. N. H. Metabolic activation of acetylenic substituents to derivatives in the rat causing the loss of hepatic cytochrome P-450 and haem. Biochem. J. 1978; 174: 853
  • Skrinjaric-Spoljar M., Matthews H. B., Engel J. L., Casida J. E. Response of hepatic microsomal mixed-function oxidases to various types of insecticide chemical synergists administered to mice. Biochem. Pharmacol. 1971; 20: 1607
  • Ortiz de Montellano P. R., Kunze K. L. Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates. J. Biol. Chem. 1980; 255: 5578
  • Ortiz de Montellano P. R., Kunze K. L., Beilan H. S., Wheeler C. Destruction of cytochrome P-450 by vinyl fluoride, fluroxene, and acetylene. Evidence for a radical intermediate in olefin oxidation. Biochemistry 1982; 21: 1331
  • Smith R. P. Toxic responses of the blood. Cassarett and Doull's Toxicology: The Basic Science of Poisons2nd ed., J. Doull, C. D. Klaassen, M. A. Amdur. MacMillan, New York 1980; 311
  • Kiese M. Methemoglobinemia: A Comprehensive Treatise. CRC Press, Boca Raton, Florida 1974
  • Doyle M. P., Pickering R. A., da Conceicao J. Structural effects in alkyl nitrite oxidation of human hemoglobin. J. Biol. Chem. 1984; 259: 80
  • Bennett B. M., Nakatsu K., Brien J. F., Marks G. S. Biotransformation of glyceryl trinitrate to glyceryl dinitrate by human hemoglobin. Can. J. Physiol. Pharmacol. 1984; 62: 704
  • Augusto O., Kunze K. L., Ortiz De Montellano P. R. N-Phenylprotoporphyrin IX formation in the hemoglobin-phenylhydrazine reaction: evidence for a protein-stabilized iron-phenyl intermediate. J. Biol. Chem. 1982; 257: 6231
  • Ortiz de Montellano P. R., Kunze K. L., Augusto O. Hemoprotein destruction. Iron-nitrogen shift of a phenyl group in a porphyrin complex. J. Am. Chem. Soc. 1982; 104: 3545
  • Saito S., Itano H. A. β-Mesophenylbiliverdin IXα and N-phenylprotoporphyrin IX, products of the reaction of phenylhydrazine with oxyhemoproteins. Proc. Natl. Acad. Sci. U.S.A. 1981; 78: 5508
  • Cole S. P. C., Vavasour E. J., Marks G. S. Drug-induced porphyrin biosynthesis. XIX. Potentiation of the porphyrin-inducing effects of SKF 525-A in the chick embryo liver by 3,5-die-thoxycarbonyl-l,4-dihydro-2,4,6-trimethylpyridine, an inhibitor of ferrochelatase. Biochem. Pharmacol. 1979; 28: 3533
  • De Matteis F. Drug interactions in experimental hepatic porphyria. A model for the exacerbation by drugs of human variegate porphyria. Enzyme 1973; 16: 266

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.