In vivo formation of σ-methyl- and σ-phenyl-ferric complexes of hemoglobin and liver-cytochrome P-450 upon treatment of rats with methyl- and phenylhydrazine

Beaven, 1954, Oxidation of phenylhydrazines in the presence of oxyhemoglobin and the origin of Heinz bodies in erythrocytes, Nature, 173, 389, 10.1038/173389b0 Itano, 1982, Mechanism of initial reaction of phenylhydrazine with oxyhemoglobin and effect of ring substitutions on the bimolecular rate constant of this reaction, Biochemistry, 21, 2421, 10.1021/bi00539a022 Zimmerman, 1978, 491 Hidaka, 1970, Evidence of a hydrazine-reactive group at the active site of the nonheme portion of horseradish peroxidase, Arch. Biochem. Biophys., 140, 174, 10.1016/0003-9861(70)90020-2 Ortiz de Montellano, 1983, Inactivation of catalase by phenylhydrazine: formation of a stable aryl-iron heme complex, J. Biol. Chem., 258, 10558, 10.1016/S0021-9258(17)44492-9 Augusto, 1981, Spin-trapping of free radicals formed during microsomal metabolism of ethylhydrazine and acetylhydrazine, Biochem. Biophys. Res. Commun., 101, 1324, 10.1016/0006-291X(81)91592-8 Jonen, 1982, The reaction of phenylhydrazine with microsomal cytochrome P-450, catalysis of heme modification, J. Biol. Chem., 257, 4404, 10.1016/S0021-9258(18)34737-9 Battioni, 1983, Reaction of monosubstituted hydrazines and diazenes with rat-liver cytochrome P-450: formation of ferrous-diazene and ferric-σ-alkyl complexes, Eur. J. Biochem., 134, 241, 10.1111/j.1432-1033.1983.tb07557.x Augusto, 1982, N-phenylprotoporphyrin IX formation in the hemoglobin-phenylhydrazine reaction, J. Biol. Chem., 257, 6231, 10.1016/S0021-9258(20)65129-8 Mansuy, 1982, Comparison of the hemoglobin reactions with methyl- and phenylhydrazine: intermediate formation of hemoglobin-Fe(II)-methyldiazene complex, Biochem. Biophys. Res. Commun., 106, 30, 10.1016/0006-291X(82)92053-8 Saito, 1981, β-meso-phenylbiliverdin IX and N-phenylprotoporphyrin IX, products of the reaction of phenylhydrazine with oxyhemoproteins, Proc. Natl., Acad. Sci. U.S.A., 78, 5508, 10.1073/pnas.78.9.5508 Ortiz de Montellano, 1981, Formation of N-phenylheme in the hemolytic reaction of phenylhydrazine with hemoglobin, J. Am. Chem. Soc., 103, 6534, 10.1021/ja00411a061 Kunze, 1983, Formation of σ-bonded aryliron complex in the reaction of arylhydrazines with hemoglobin and myoglobin, J. Am. Chem. Soc., 105, 1380, 10.1021/ja00343a057 Hill, 1981, Phenyl radical production during the oxidation of phenylhydrazine in phenylhydrazine-induced haemolysis, FEBS Lett., 125, 235, 10.1016/0014-5793(81)80727-2 Itano, 1961, Evidence for coordination of monophenyldiimide with heme proteins, J. Am. Chem. Soc., 83, 3339, 10.1021/ja01476a041 Ringe, 1984, Reaction of myoglobin with phenylhydrazine: a molecular doorstop, Biochemistry, 23, 2, 10.1021/bi00296a001 Battioni, 1983, Iron porphyrin dependent oxidation of methyl- and phenylhydrazine: isolation of iron(II)-diazene and -alkyliron(III) (or aryliron(III)) complexes. Relevance to the reactions of hemoproteins with hydrazines, J. Am. Chem. Soc., 105, 1399, 10.1021/ja00343a070 Kremers, 1981, Cytochrome P-450 monooxygenase activities in human and rat liver microsomes, Eur. J. Biochem., 118, 599, 10.1111/j.1432-1033.1981.tb05561.x Lowry, 1951, Protein measurement with the Folin phenol reagents, J. Biol. Chem., 193, 265, 10.1016/S0021-9258(19)52451-6 Omura, 1964, The carbon monoxide pigment of rat liver microsomes, I. Evidence for its hemoprotein nature, J. Biol. Chem., 239, 2370, 10.1016/S0021-9258(20)82244-3 Ruf, 1984, Formation of a ferric carbanion complex from halothane and cytochrome P-450: electron spin resonance, electronic spectra, and model complexes, Biochemistry, 231, 5300, 10.1021/bi00317a031 Ahr, 1980, The mechanism of chloroform and carbon monoxide formation from carbon tetrachloride by microsomal cytochrome P-450, Biochem. Pharmacol., 29, 2855, 10.1016/0006-2952(80)90022-2 Buening, 1976, SKF 525-A inhibition, induction and 452 nm complex formation, Drug Metab. Dispos., 4, 244 Pessayre, 1981, Self-induction by triacetyloleandomycin of its own transformation into a metabolite forming a stable 456 nm-absorbing complex with cytochrome P-450, Biochem. Pharmacol., 30, 553, 10.1016/0006-2952(81)90125-8 Mansuy, 1982, Reversible iron-nitrogen migration of alkyl, aryl, or vinyl groups in iron porphyrins: A possible passage between σ-Fe(III) (porphyrin) (R) and Fe(II) (N-R) (porphyrin) complexes, J. Am. Chem. Soc., 104, 6159, 10.1021/ja00386a074 Lux, 1977, Isolation and partial characterization of a high molecular weight red cell membrane protein complex normally removed by the spleen, Blood, 50, 625, 10.1182/blood.V50.4.625.625 Philpot, 1971, The production and modification of cytochrome P-450 difference spectra by in vivo administration of methylenedioxyphenyl compounds, Chem.-Biol. Interact., 4, 181 Mansuy, 1979, Preparation of a porphyrin-iron-carbene model for the cytochrome P-450 complexes obtained upon metabolic oxidation of the insecticide synergists of the 1,3-benzodioxole series, J. Am. Chem. Soc., 101, 3971, 10.1021/ja00508a048