Dapsone impairs the bile salt-independent fraction of bile flow in rats: Possible involvement of its N-hydroxylated metabolite

Toxicology

Volumn 211, Issue 1-2, 2005, Pages 97-106

  Veggi, Luis M ^a   Crocenzi, Fernando A ^a   Roma, Marcelo G ^a   Mottino, Aldo D ^a  

^a UNIVERSIDAD NACIONAL DE ROSARIO   (Argentina)

Author keywords

AE2; Bicarbonate; Bile salt independent fraction of bile flow; Cholestasis; Dapsone; Mrp2

Indexed keywords

ANTIPORTER; BICARBONATE; BILE SALT; CARRIER PROTEIN; DAPSONE; DRUG METABOLITE; GLUTATHIONE; MULTIDRUG RESISTANCE PROTEIN 2;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BILE FLOW; BILE SECRETION; BILIARY EXCRETION; CONTROLLED STUDY; DRUG EFFECT; DRUG METABOLISM; FEMALE; HYDROXYLATION; MALE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT STRAIN; SEX DIFFERENCE; WESTERN BLOTTING;

RATTUS NORVEGICUS;

EID: 18044363258     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2005.03.002     Document Type: Article

References (44)

1. J.D. Adams Jr., B.H. Lauterburg, and J.R. Mitchell Plasma glutathione disulfide as an index of oxidant stress in vivo: effects of carbon tetrachloride, dimethylnitrosamine, nitrofurantoin, metronidazole, doxorubicin and diquat Res. Commun. Chem. Pathol. Pharmacol. 46 1984 401 410
2. N. Ballatori, and J.F. Rebbeor Roles of MRP2 and oatp1 in hepatocellular export of reduced glutathione Semin. Liver Dis. 18 1998 377 387
3. N. Ballatori, and A.T. Truong Glutathione as a primary osmotic driving force in hepatic bile formation Am. J. Physiol. 263 1992 G617 G624
4. A.D. Bass Chemoterapy of bacterial infections. III. Sulfones J.R. Di Plama Drill's Pharmacology in Medicine 1965 McGraw-Hill New York 1312
5. U. Beuers, M. Bilzer, A. Chittattu, G.A. Kullak-Ublick, D. Keppler, G. Paumgartner, and F. Dombrowski Tauroursodeoxycholic acid inserts the apical conjugate export pump, Mrp2, into canalicular membranes and stimulates organic anion secretion by protein kinase C-dependent mechanisms in cholestatic rat liver Hepatology 33 2001 1206 1216
6. M.D. Coleman Dapsone: modes of action, toxicity and possible strategies for increasing patient tolerance Br. J. Dermatol. 129 1993 507 513
7. M.D. Coleman, J. Simpson, and D.P. Jacobus Reduction of dapsone hydroxylamine to dapsone during methaemoglobin formation in human erythrocytes in vitro. IV. Implications for the development of agranulocytosis Biochem. Pharmacol. 48 1994 1349 1354
8. M.D. Coleman, M.D. Tingle, M.J. Winn, and B.K. Park Gonadal influence on the metabolism and haematological toxicity of dapsone in the rat J. Pharm. Pharmacol. 42 1990 698 703
9. M.D. Coleman, M.J. Winn, A.M. Breckenridge, and B.K. Park Sex-dependent sensitivity to dapsone-induced methaemoglobinaemia in the rat Biochem. Pharmacol. 39 1990 805 809
10. M.D. Coleman, P.E. Hoasey, A.M. Breckenridge, and B.K. Park Inhibition of dapsone induced methaemoglobinemia in the rat isolated perfused liver J. Pharm. Pharmacol. 42 1990 302 307
11. A.E. Cribb, M. Miller, J.S. Leeder, J. Hill, and S.P. Spielberg Reactions of the nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione Implications for idiosyncratic toxicity Drug Metab. Dispos. 19 1991 900 906
12. A.E. Cribb, C.E. Nuss, D.W. Alberts, D.B. Lamphere, D.M. Grant, S.J. Grossman, and S.P. Spielberg Covalent binding of sulfamethoxazole reactive metabolites to human and rat liver subcellular fractions assessed by immunochemical detection Chem. Res. Toxicol. 9 1996 500 507
13. S. Erlinger Bile flow I.M. Arias J.L. Boyer N. Fausto W.B. Jakoby D.A. Schachter D.A. Shafritz The Liver: Biology and Pathobiology 1994 Raven Press New York 768 786
14. K. Evelyn, and H. Malloy Microdetermination of oxyhemoglobin, methemoglobin and sulfohemoglobin in a single sample of blood J. Biol. Chem. 126 1938 655 657
15. B.E. Glader, and M.E. Conrad Hemolysis by diphenylsulfones: comparative effects of DDS and hydroxylamine-DDS J. Lab. Clin. Med. 81 1973 267 272
16. O.W. Griffith Determination of glutathione and glutathione disulfide using glutathione reductase and 2-vinylpyridine Anal. Biochem. 106 1980 207 212
17. S.J. Grossman, and D.J. Jollow Role of dapsone hydroxylamine in dapsone-induced hemolytic anemia J. Pharmacol. Exp. Ther. 244 1988 118 125
18. F.P. Guengerich, M.V. Martin, P.H. Beaune, P. Kremers, T. Wolff, and D.J. Waxman Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism J. Biol. Chem. 261 1986 5051 5060
19. W.G. Hardison, D.E. Hatoff, K. Miyai, and R.G. Weiner Nature of bile acid maximum secretory rate in the rat Am. J. Physiol. 241 1981 G337 G343
20. W.G. Hardison, and C.A. Wood Importance of bicarbonate in bile salt independent fraction of bile flow Am. J. Physiol. 235 1978 E158 E164
21. D.A. Johnson, E.L. Cattau Jr., J.N. Kuritsky, and H.J. Zimmerman Liver involvement in the sulfone syndrome Arch. Intern. Med. 146 1986 875 877
22. J. Konig, A.T. Nies, Y. Cui, I. Leier, and D. Keppler Conjugate export pumps of the multidrug resistance protein (MRP) family: localization, substrate specificity, and MRP2-mediated drug resistance Biochim. Biophys. Acta 1461 1999 377 394
23. W.A. Lawrence, H.W. Olsen, and D.J. Nickles Dapsone hepatitis Arch. Intern. Med. 147 1987 175
24. G.S. Leoung, J. Mills, P.C. Hopewell, W. Hughes, and C. Wofsy Dapsone-trimethoprim for Pneumocystis carinii pneumonia in the acquired immunodeficiency syndrome Ann. Intern. Med. 105 1986 45 48
25. O.H. Lowry, N.J. Rosembrough, A.L. Farr, and R.J. Randall Protein measurement with the Folin phenol reagent J. Biol. Chem. 193 1951 265 275
26. J.F. Medina, A. Martinez, J.J. Vazquez, and J. Prieto Decreased anion exchanger 2 immunoreactivity in the liver of patients with primary biliary cirrhosis Hepatology 25 1997 12 17
27. P.J. Meier, R. Knickelbein, R.H. Moseley, J.W. Dobbins, and J.L. Boyer Evidence for carrier-mediated chloride/bicarbonate exchange in canalicular rat liver plasma membrane vesicles J. Clin. Invest. 75 1985 1256 1263
28. P.J. Meier, E.S. Sztul, A. Reuben, and J.L. Boyer Structural and functional polarity of canalicular and basolateral plasma membrane vesicles isolated in high yield from rat liver J. Cell Biol. 98 1984 991 1000
29. A.D. Mottino, J. Cao, L.M. Veggi, F. Crocenzi, M.G. Roma, and M. Vore Altered localization and activity of canalicular Mrp2 in estradiol-17beta-d- glucuronide-induced cholestasis Hepatology 35 2002 1409 1419
30. M.H. Nathanson, and J.L. Boyer Mechanisms and regulation of bile secretion Hepatology 14 1991 551 566
31. B.K. Park, M. Pirmohamed, and N.R. Kitteringham Role of drug disposition in drug hypersensitivity: a chemical, molecular, and clinical perspective Chem. Res. Toxicol. 11 1998 969 988
32. C.C. Paulusma, M.A. van Geer, R. Evers, M. Heijn, R. Ottenhoff, P. Borst, and R.P. Oude Elferink Canalicular multispecific organic anion transporter/multidrug resistance protein 2 mediates low-affinity transport of reduced glutathione Biochem. J. 338 Pt 2 1999 393 401
33. H. Roelofsen, B. Schoemaker, C. Bakker, R. Ottenhoff, P.L. Jansen, and R.P. Elferink Impaired hepatocanalicular organic anion transport in endotoxemic rats Am. J. Physiol. 269 1995 G427 G434
34. M.L. Ruiz, S.S.M. Villanueva, M.G. Luquita, E.J. Sánchez-Pozzi, F.A. Crocenzi, J.M. Pellegrino, J.E. Ochoa, A.D. Mottino, and V.A. Catania Mechanisms involved in spironolactone-induced choleresis in the rat. Role of Multidrug resistance-associated protein 2 Biochem. Pharmacol. 69 2005 531 539
35. M. Schmitt, R. Kubitz, M. Wettstein, D.S. vom, and D. Haussinger Retrieval of the mrp2 gene encoded conjugate export pump from the canalicular membrane contributes to cholestasis induced by tert-butyl hydroperoxide and chloro-dinitrobenzene Biol. Chem. 381 2000 487 495
36. M. Sokolovsky, T. Sadeh, and A. Patchornik Nonenzimatic cleavages of peptide chains at the cysteine and serine residues through their conversion to dehydroalanine (DHAL). II. The specific chemical cleavage of cysteinyl peptides J. Am. Chem. Soc. 86 1964 1210 1217
37. P. Talalay Enzymatic analysis of steroid hormones Meth. Biochem. Anal. 8 1969 119 143
38. M.D. Tingle, R. Mahmud, J.L. Maggs, S. Hawley, M.D. Coleman, S.A. Ward, and B.K. Park The effect of 2,2′-substitución on the metabolism and toxicity of dapsone in vitro and in vivo Environ. Toxicol. Phar. 5 1998 145 153
39. M.D. Tingle, R. Mahmud, J.L. Maggs, M. Pirmohamed, and B.K. Park Comparision of the metabolism and toxicity of dapsone in rat, mouse and man J. Pharmacol. Exp. Ther. 283 1997 817 823
40. J.P. Uetrecht The role of leukocyte-generated reactive metabolites in the pathogenesis of idiosyncratic drug reactions Drug Metab. Rev. 24 1992 299 366
41. L.M. Veggi, F.A. Crocenzi, M.G. Roma, P.A. Dawson, J.M. Pellegrino, E.J. Sanchez Pozzi, and A.D. Mottino Dapsone-induced cholestasis and impairment of bile salt output in the rat Biochem. Pharmacol. 63 2002 1553 1563
42. Y.I. Zhu, and M.J. Stiller Dapsone and sulfones in dermatology: overview and update J. Am. Acad. Dermatol. 45 2001 420 434
43. H.J. Zimmerman Hepatotoxicity H.J. Zimmerman Hepatotoxicity 1999 Lippincott Williams & Wilkins Philadelphia
44. J. Zuidema, E.S. Hilbers-Modderman, and F.W. Merkus Clinical pharmacokinetics of dapsone Clin. Pharmacokinet. 11 1986 299 315