Non-specific inhibition of human cytochrome P450-catalyzed reactions by hemin

Toxicology Letters

Volumn 153, Issue 2, 2004, Pages 239-246

  Kim, Eun Young ^a   Kim, Joon Sik ^b   Kim, Min Young ^b   Koh, Woo Suk ^c   Guengerich, F Peter ^d   Yun, Chul Ho ^e  

^a 302 735 ^*  (South Korea)

^b PaiChai University   (South Korea)

^c Korea Research Institute of Chemical Technology   (South Korea)

^d VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e Chonnam National University   (South Korea)

Author keywords

Cytochrome P450; Heme destruction; Hemin; NADPH cytochrome P450 reductase; Non specific inhibition

Indexed keywords

CYTOCHROME P450 1A2; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; CYTOCHROME P450 INHIBITOR; ETHOXYRESORUFIN DEETHYLASE; FERRICYANIDE; HEMIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE;

ARTICLE; CATALYSIS; CATALYST; DEMETHYLATION; LIVER MICROSOME; PRIORITY JOURNAL; PROTEIN PURIFICATION; REDUCTION;

CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; HEMIN; HUMANS; MICROSOMES, LIVER; NADPH-FERRIHEMOPROTEIN REDUCTASE;

EID: 4644329141     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxlet.2004.04.017     Document Type: Article

References (39)

1. Ahn T., Yim S.-K., Choi H.-I., Yun C.-H. Polyacrylamide gel electrophoresis without a stacking gel: use of amino acids as electrolytes. Anal. Biochem. 291:2001;300-303
2. Backes W.L., Kelley R.W. Organization of multiple cytochrome P450s with NADPH-cytochrome P450 reductase in membranes. Pharmacol. Ther. 98:2003;221-233
3. Bissell D.M., Hammaker L., Schmid R. Hemoglobin and erythrocyte catabolism in rat liver: the separate roles of parenchymal and sinusoidal cells. Blood. 40:1972;812-822
4. Burke M.D., Thompson S., Weaver R.J., Wolf C.R., Mayer R.T. Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol. 48:1994;923-936
5. Chauret N., Dobbs B., Lackman R.L., Bateman K., Nicoll-Griffith D.A., Stresser D.M., Ackermann J.M., Turner S.D., Miller V.P., Crespi C.L. The use of 3-[2-(N,N-diethyl-N-methylammonium)ethyl]-7-methoxy-4-methylcoumarin (AMMC) as a specific CYP2D6 probe in human liver microsomes. Drug Metab. Dispos. 29:2001;1196-2200
6. Dennery P.A. Pharmacological interventions for the treatment of neonatal jaundice. Semin. Neonatol. 7:2002;111-119
7. Furman G.M., Silverman D.M., Schatz R.A. The effect of toluene on rat lung benzo[a]pyrene metabolism and microsomal membrane lipids. Toxicology. 68:1991;75-87
8. Guengerich F.P. Destruction of heme and hemoproteins mediated by liver microsomal reduced nicotinamide adenine dinucleotide phosphate-cytochrome P-450 reductase. Biochemistry. 17:1978;3633-3639
9. Guengerich F.P. Reactions and significance of cytochrome P450 enzymes. J. Biol. Chem. 266:1991;10019-10022
10. Guengerich, F.P., 2001. Analysis and characterization of enzymes. In: Hayes, A.W. editor. Principles and Methods of Toxicology. 3rd ed. New York: Raven Press; p. 1625-87.
11. Guengerich F.P. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 14:2001;611-650
12. Hanna I.H., Kim M.S., Guengerich F.P. Heterologous expression of cytochrome P450 2D6 mutants, electron transfer, and catalysis of bufuralol hydroxylation: the role of aspartate 301 in structural integrity. Arch. Biochem. Biophys. 393:2001;255-261
13. Hanna I.H., Teiber T.D., Kokones K.L., Hollenberg P.F. Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities. Arch. Biochem. Biophys. 350:1998;324-332
14. Hosea N.A., Miller G.P., Guengerich F.P. Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochemistry. 39:2000;5929-5939
15. Katoh Y., Nemoto N., Tanaka M., Takayama S. Inhibition of benzo(a)pyrene-induced mutagenesis in Chinese hamster V79 cells by hemin and related compounds. Mutat. Res. 121:1983;153-157
16. Kobayashi Y., Ohshiro N., Suzuki M., Sasaki T., Tokuyama S., Yoshida T., Yamamoto T. Sex-related effect of hemin on cytochrome P450 and drug-metabolizing enzymes in rat liver. J. Toxicol. Sci. 25:2000;213-222
17. Miwa G.T., Lu A.Y. The association of cytochrome P-450 and NADPH-cytochrome P-450 reductase in phospholipid membranes. Arch. Biochem. Biophys. 234:1984;161-166
18. Namkung M.J., Chao S.T., Juchau M.R. Placental monooxygenation: characteristics and partial purification of a hematin-activated human placental mono-oxygenase. Drug Metab. Dispos. 11:1983;10-14
19. Omiecinski C.J., Bond J.A., Juchau M.R. Stimulation by hematin of monoxygenase activity in extra-hepatic tissues from rats, rabbits and chickens. Biochem. Biophys. Res. Commun. 83:1978;1004-1011
20. Omiecinski C.J., Namkung M.J., Juchau M.R. Mechanistic aspects of the hematin-mediated increases in brain monooxygenase activities. Mol. Pharmacol. 17:1980;232-255
21. Omiecinski C.J., Namkung M.J., Juchau M.R. Substrate and position specificity of hematin-activated monooxygenation reactions. Biochem. Pharmacol. 30:1981;2837-2845
22. Omura T., Sato R. The carbon monoxide-binding pigment of the liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239:1964;2370-2378
23. Osawa Y., Yarborough C., Osawa Y. Norethisterone, a major ingredient of contraceptive pills, is a suicide inhibitor of estrogen biosynthesis. Science. 215:1982;1249-1251
24. Salim M., Brown-Kipphut B.A., Maines M.D. Human biliverdin reductase is autophosphorylated, and phosphorylation is required for bilirubin formation. J. Biol. Chem. 276:2001;10929-10934
25. Schaefer W.H., Harris T.M., Guengerich F.P. Characterization of the enzymatic and nonenzymatic peroxidative degradation of iron porphyrins and cytochrome P-450 heme. Biochemistry. 24:1985;3254-3261
26. Sevrioukova I.F., Peterson J.A. NADPH-P-450 reductase: structural and functional comparisons of the eukaryotic and prokaryotic isoforms. Biochimie. 77:1995;562-572
27. Shimada T., Misono K.S., Guengerich F.P. Human liver microsomal cytochrome P-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. Purification and characterization of two similar forms involved in the reaction. J. Biol. Chem. 261:1986;909-921
28. Shimada T., Yamazaki H., Mimura M., Inui Y., Guengerich F.P. Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J. Pharmacol. Exp. Ther. 270:1994;414-423
29. Stickney D.R., Anderson L.D., Slater J.B., Ahlem C.N., Kirk G.A., Schweighardt S.A., Frincke J.M. Bifunctional antibody: a binary radiopharmaceutical delivery system for imaging colorectal carcinoma. Cancer Res. 51:1991;6650-6655
30. Tenhunen R., Mustajoki P. Acute porphyria: treatment with heme. Semin. Liver Dis. 18:1998;53-55
31. Venkatakrishnan K., von Moltke L.L., Court M.H., Harmatz J.S., Crespi C.L., Greenblatt D.J. Comparison between cytochrome P450 (CYP) content and relative activity approaches to scaling from cDNA-expressed CYPs to human liver microsomes: ratios of accessory proteins as sources of discrepancies between the approaches. Drug Metab. Dispos. 28:2000;1493-1504
32. Vermilion J.L., Coon M.J. Identification of the high and low potential flavins of liver microsomal NADPH-cytochrome P-450 reductase. J. Biol. Chem. 253:1978;8812-8819
33. Voznesensky A.I., Schenkman J.B. The cytochrome P450 2B4-NADPH cytochrome P450 reductase electron transfer complex is not formed by charge-pairing. J. Biol. Chem. 267:1992;14669-14676
34. Wang P.P., Beaune P.H., Kaminsky L.S., Dannan G.A., Kadlubar F.F., Larrey D., Guengerich F.P. Purification and characterization of six cytochrome P450 isozymes from human liver microsomes. Biochemistry. 22:1983;5375-5383
35. 5. J. Biol. Chem. 271:1996;27438-27444
36. Yoshida T., Migita C.T. Mechanism of heme degradation by heme oxygenase. J. Inorg. Biochem. 82:2000;33-41
37. Yun C.-H., Miller G.P., Guengerich F.P. Rate-determining steps in phenacetin oxidations by human cytochrome P450 1A2 and selected mutants. Biochemistry. 39:2000;11319-11329
38. Yun C.-H., Song M., Ahn T., Kim H. Conformational change of cytochrome P450 1A2 induced by sodium chloride. J. Biol. Chem. 271:1996;31312-31316
39. Yun C.-H., Shimada T., Guengerich F.P. Roles of human liver cytochrome P4502C and 3A enzymes in the 3-hydroxylation of benzo(a)pyrene. Cancer Res. 52:1992;1868-1874