Reduction of sulfamethoxazole and dapsone hydroxylamines by a microsomal enzyme system purified from pig liver and pig and human liver microsomes

Life Sciences

Volumn 77, Issue 2, 2005, Pages 205-219

  Clement, Bernd ^a   Behrens, Detlef ^a   Amschler, Juliane ^a   Matschke, Katrin ^a   Wolf, Stephanie ^a   Havemeyer, Antje ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

Cytochrome b5; Cytochrome P450; N reduction; NADH cytochrome b5 reductase; Sulfonamide hydroxylamine

Indexed keywords

CYTOCHROME B5; CYTOCHROME B5 REDUCTASE; CYTOCHROME P450 2D; CYTOCHROME P450 ISOENZYME; FUNCTIONAL GROUP; HYDROXYLAMINE; LIVER ENZYME; N HYDROXYDAPSONE HYDROXYLAMINE; NITROGEN; SULFAMETHOXAZOLE; SULFAMETHOXAZOLE HYDROXYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DEGRADATION; DRUG DETOXIFICATION; DRUG HYDROXYLATION; DRUG STRUCTURE; DRUG TRANSFORMATION; ENZYME ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIVER MICROSOME; LIVER MICROSOME METABOLISM; PROTEIN FAMILY; REDUCTION; STRUCTURE ANALYSIS; SWINE;

SUS SCROFA;

EID: 18044392369     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2004.12.028     Document Type: Article

References (48)

1. B. Clement Reduction of N-hydroxylated compounds: Amidoximes (N-hydroxyamidines) as pro-drugs of amidines Drug Metabolism and Disposition 34 3 2002 565 579
2. B. Clement, D. Behrens, W. Möller, and J.R. Cashman Reduction of amphetamine hydroxylamine and other aliphatic hydroxylamines by benzamidoxime reductase and human liver microsomes Chemical Research in Toxicology 13 10 2000 1037 1045
3. B. Clement, M. Demesmaeker, and S. Linne Microsomal catalyzed N-hydroxylation of guanabenz and reductin of the N-hydroxylated metabolite: characterization of the two reactions and genotoxic potential of guanoxabenz Chemical Research in Toxicology 9 1996 682 688
4. B. Clement, S. Immel, S. Schmitt, and U. Steinmann Biotransformation of benzamidine and benzamidoxime in vivo Archiv der Pharmazie 326 1993 807 812
5. 2-insensitive NADH-benzamidoxime-reductase Journal of Biological Chemistry 272 1997 19615 19620
6. B. Clement, S. Schmitt, and M. Zimmermann Enzymatic reduction of benzamidoxime to benzamidine Archiv der Pharmazie 321 1988 955 956
7. B. Clement, M.H. Schultze-Mosgau, and H. Wohlers Cytochrome P450 dependent N-hydroxylation of guanidine (debrisoquine), microsomal catalysed reduction and further oxidation of arginine to citrulline and NO Biochemical Pharmacology 46 1993 2249 2267
8. M.D. Coleman, A.M. Breckenridge, and B.K. Park Bioactivation of dapsone to a cytotoxic metabolite by human hepatic microsomal enzymes British Journal of Clinical Pharmacology 28 1989 389 395
9. R.T. Coutts, and A.H. Beckett Metabolic N-oxidation of primary and secondary aliphatic medicinal amines Drug Metabolism Revue 6 1977 51 104
10. A.E. Cribb, and S.P. Spielberg Hepatic microsomal metabolism of sulfamethoxazole to hydroxylamine Drug Metabolism and Disposition 18 1990 784 787
11. A.E. Cribb, and S.P. Spielberg An in vitro investigation of predisposition to sulfonamide idiosyncratic reactions in dogs Veterinary Research Communication 14 1990 241 252
12. 4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic microsomes Drug Metabolism and Disposition 23 1995 406 414
13. EMBL, 2003. EMBL Nucleotide Sequence Database. http://www.ebi.ac.uk/embl.
14. R.W. Estabrook, and J. Werringloer The measurement of difference spectra: Application to the cytochromes of microsomes Methods in Enzymology 52 1978 212 220
15. C.F. Fleming, R.A. Branch, G.R. Wilkinson, and F.P. Guengerich Human liver microsomal N-hydroxylation of dapsone by cytochrome P450 3A4 Molecular Pharmacology 41 1992 975 980
16. F.J. Gonzalez, R.C. Skoda, S. Kimura, M. Umeno, U.M. Zanger, D.W. Nebert, H.V. Gelboin, J.P. Hardwick, and U.A. Meyer Characterization of the common genetic defect in humans deficient in debrisoquine metabolism Nature 331 6155 1988 442 446
17. F.M. Gordin, G.L. Simon, C.B. Wofsy, and J. Mills Adverse reactions to trimethoprim-sulfamethoxazole in patients with the acquired immunodeficiency syndrome Annals of Internal Medicine 100 1984 495 499
18. J.W. Gorrod, and D. Manson The metabolism of aromatic amines Xenobiotica 16 10-11 1986 933 995
19. K.A. Grindulis, and B. McConkey Rheumatoid arthritis: The effect of treatment with dapsone on hemoglobin The Journal of Rheumatology 11 1984 776 778
20. F.P. Guengerich Common and uncommon cytochrome P450 reactions related to metabolism and chemical Toxicity Chemical Research in Toxicology 14 2001 612 651
21. F. Hosseinpour, M. Hidestrand, M. Ingelman-Sundberg, and K. Wikvall The importance of residues in substrate recognition site 3 for the catalytic function of CYP2D25 (vitamin D 25-hydroxylase) Biochemical and Biophysical Research Communications 288 2001 1059 1063
22. W.T. Hughes, W. Kennedy, and M. Dugdale Prevention of Pneumocystis carinii pneumonitis in AIDS patients with weekly dapsone [Letter] The Lancet 336 1990 1066
23. F.F. Kadlubar, E.M. McKee, and D.M. Ziegler Reduced pyridine nucleotide-dependent N-hydroxy-amine oxidase and reductase activities of hepatic microsomes Archives of Biochemistry and Biphysics 156 1973 46 57
24. F.F. Kadlubar, and D.M. Ziegler Properties of a NADH-dependent N-hydroxylamine reductase isolated from pig liver microsomes Archives of Biochemistry and Biophysics 162 1974 83 99
25. T. Kamataki, K. Fujita, K. Nakayama, Y. Yamazaki, M. Miyamoto, and N. Ariyoshi Role of human cytochrome P450 (CYP) in the metabolic activation of nitrosamine derivatives: application of genetically engineered Salmonella expressing human CYP Drug Metabolism Review 34 3 2002 667 676
26. M. Kiese The biochemical production of ferrihemoglobin-forming derivates from aromatic amines and mechanisms of ferrihemoglobin formation Pharmacological Reviews 18 1966 1091 1161
27. J.A. Kovacs, J.W. Hiementz, and A.M. Macher Pneumocystis carinii pneumonia: a comparison between patients with the acquired immunodeficiency syndrome and patients with other immunodeficiences Annals of Internal Medicine 100 1984 66 71
28. K. Kumano, M. Tani, and Y. Murata Dapsone in the treatment of miliary lupus of the face The British Journal of Dermatology 109 1983 57 62
29. U.K. Laemmli Cleavage of structure proteins during the assembly of the head of bacteriophage T4 Nature 227 1970 680 685
30. B.L. Lee, L. Medina, N.L. Benowitz, P. Jacob, C.B. Wofsy, and J. Mills Dapsone, trimethoprim and sulfamethoxazole plasma levels during treatment of Pneumocystis pneumonia in patients with acquired immunodeficiency syndrome: Evidence of drug interactions Annals Internal Medicine 110 1989 606 611
31. H. Masur Prevention and treatment of Pneumocystis pneumonia The New England Journal of Medicine 26 1992 1853 1860
32. 3 25-hydroxylase European Journal of Pharmaceutical Sciences 17 S1 2002 S35
33. I. Medina, J. Mills, and G. Leoung Oral therapy for Pneumocystis carinii in the acquired immunodeficiency syndrome: A controlled trial of trimethoprim-sulfamethoxazole versus dapsone-trimethoprim The New England Journal of Medicine 323 1990 776 782
34. 5 reductase Methods in Enzymology 52 1978 102 108
35. R.F. Miller, J. Le Noury, E.L. Corbett, J.M. Felton, and K.M. De Cock Pneumocystis carinii infection: Current treatment and prevention The Journal of Antimicrobial Chemotherapy 37 1996 33 53
36. T. Omura, and R. Sato The carbon monoxide-binding pigment of liver microsomes Journal of Biological Chemistry 239 1964 2370 2378
37. 3 25-hydroxylase Biochemical and Biophysical Research Communications 241 1997 491 497
38. A. Poulsen, B. Hultberg, K. Thomsen, and G.L. Wantzin Regression of Kaposi's sarcoma in AIDS after treatment with dapsone The Lancet 1 1984 560
39. M.J. Rieder, J. Uetrecht, M. Cannon, M. Miller, and S.P. Spielberg Diagnosis of sulfonamide hypersensitivity reactions by in vitro "rechallenge" with hydroxylamine metabolites Annals Internal Medicine 110 1989 286 289
40. R.J. Riley, P. Roberts, M.D. Coleman, and N.R. Kitteringham Bioactivation of dapsone to a cytotoxic metabolite: In vitro use of a novel two compartment system which contains human tissues British Journal of Clinical Pharmacology 30 1990 417 426
41. 5 is modulated by its exposed heme edge Biochemistry 37 1998 1485 1494
42. N.H. Shear, S.P. Spielberg, D.M. Grant, B.K. Tang, and W. Kalow Differences in the metabolism of sulfonamides predisposing to idiosyncratic toxicity Annals Internal Medicine 105 1986 179 185
43. P.K. Smith, R.I. Krohn, G.T. Hermanson, A.K. Mallia, F.H. Gartner, M.D. Provenzano, E.K. Fujimoto, N.M. Goeke, B.J. Olson, and D.C. Klenk Measurment of protein using bicinchoninic acid Analytical Biochemistry 150 1985 76 85
44. M.D. Tingle, R. Mahmud, J.L. Maggs, M. Pirmohamed, and B.K. Park Comparison of the metabolism and toxicity of dapsone in rat, mouse and man Phramcology 283 2 1997 817 823
45. L.A. Trepanier, and J.L. Miller NADH-dependent reduction of sulfamethoxazole hydroxylamine in dog and human liver microsomes Xenobiotica 30 2000 1111 1121
46. 5 Journal of American Chemistry Society 110 1988 6234 6240
47. M.F.R. Waters New approaches to chemotherapy for leprosy Drugs 26 1983 465 467
48. Y. Yasukochi, and B.S.S. Masters Some properties of a detergent-solubilized NADPH-cytochrome c (cytochrome P450) reductase purified by biospecific affinity chromatography Journal of Biological Chemistry 251 1976 5337 5344