Novel non-labile covalent binding of sulfamethoxazole reactive metabolites to cultured human lymphoid cells

Chemico-Biological Interactions

Volumn 142, Issue 1-2, 2002, Pages 155-173

  Summan, Mukesh ^a   Cribb, Alastair E ^a  

^a UNIVERSITY OF PRINCE EDWARD ISLAND   (Canada)

Author keywords

Covalent binding; Cytotoxicity; Human; Hypersensitivity; Sulfamethoxazole

Indexed keywords

ANTISERUM; CELL PROTEIN; DRUG METABOLITE; GLUCOSE REGULATED PROTEIN; MERCAPTOETHANOL; PROTEIN DISULFIDE ISOMERASE; SULFAMETHOXAZOLE; TETRAZOLIUM;

ARTICLE; CELL CULTURE; CELL DEATH; CELL MEMBRANE; CELL STRAIN U937; CELL SURVIVAL; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; COVALENT BOND; CYTOSOL; DRUG CYTOTOXICITY; HUMAN; HUMAN CELL; HYPERSENSITIVITY; IMMUNOBLOTTING; INCUBATION TIME; LYMPHOID CELL; MICROSOME; MOLECULAR WEIGHT; PROTEIN BINDING; PROTEIN TARGETING; REDUCTION;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTIBODIES; BIOTRANSFORMATION; BLOTTING, WESTERN; CYTOSOL; CYTOTOXICITY TESTS, IMMUNOLOGIC; HUMANS; HYDROXYLATION; MICROSOMES, LIVER; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; SULFAMETHOXAZOLE; TETRAZOLIUM SALTS; THIAZOLES; U937 CELLS;

EID: 0037058248     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(02)00060-1     Document Type: Article

References (34)

1. Cribb A.E., Belle L.L., Trepanier L.A., Spielberg S.P. Adverse reactions to sulfonamide and sulfonamide-trimethoprim antimicrobials: clinical syndromes and pathogenesis. Adverse Drug React. Toxicol. Rev. 15:1996;9-50.
2. Park B.K., Coleman J.W., Kitteringham N.R. Drug disposition and drug hypersensitivity. Biochem. Pharmacol. 36:1987;581-590.
3. Pohl L.R., Satoh H., Christ D.D., Kenna J.G. The immunological and metabolic basis of drug hypersensitivities. Ann. Rev. Pharmacol. 28:1988;367-387.
4. 4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic micorosomes. Drug Metab. Dipos. 23:1995;406-414.
5. Cribb A.E., Nuss C.E., Alberts D.W., Lamphere D.B., Grant D.M., Grossman S.J., Spielberg S.P. Covalent binding of sulfamethoxazole reactive metabolites to human and rat liver subcellular fractions assessed by immunochemical detection. Chem. Res. Tox. 9:1996;500-507.
6. Cribb A.E., Miller M., Leeeder M.J., Hill J., Spielberg S.P. Reactions of nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione. Implications for idiosyncratic toxicity. Drug Metab. Dispos. 19:1991;900-906.
7. Rieder M.J., Krause R., Bird I.A. Time-course of toxicity of reactive sulfonamide metabolites. Toxicology. 95:1995;141-146.
8. Cribb A.E., Pohl L.R., Spielberg S.P., Leeder J.S. Patients with delayed-onset sulfonamide hypersensitivity reactions have antibodies recognizing endoplasmic reticulum luminal proteins. J. Pharmacol. Exp. Ther. 282:1997;1064-1072.
9. Bedard K.J., Smith S., Cribb A.E. Sequential assessment of an antidrug antibody response in a patient with a systemic delayed onset sulfonamide hypersensitivity syndrome reaction. Br. J. Dermatol. 142:2000;253-258.
10. Harle D.G., Baldo B.A., Wells J.V. Drugs as allergens: detection and combining site specificities of IgE antibodies to sulfamethoxazole. Mol. Immunol. 25:1988;1347-1354.
11. Gruchalla R., Sullivan T. Detection of human IgE to sulfamethoxazole by skin testing with sulfamethoxazole poly-L-tyrosine. J. Allergy Clin. Immunol. 88:1991;784-792.
12. Kenna J.G., Satoh H., Christ D.D., Pohl L.R. Metabolic basis for a drug hypersensitivity: antibodies in sera from patients with halothane hepatitis recognize liver neoantigens that contain the trifluoracetyl group derived from halothane. J. Pharmacol. Exp. Ther. 245:1988;1103-1109.
13. Kretz-Rommel A., Boelsterli U.A. Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol. Appl. Pharmacol. 120:1993;155-161.
14. Bourdi M., Larrey D., Nataf J., Bernuau J., Pessayre D., Iwasaki M., Guengerich F.P., Beaune P.H. Anti-liver endoplasmic reticulum autoantibodies are directed against human cytochrome P-450 1A2: a specific marker of dihydralazine-induced hepatitis. J. Clin. Invest. 85:1990;1967-1973.
15. Bourdi M., Tinel M., Beuane P.H., Pessayre D. Interactions of dihydralazine with cytochromes P4501A: a possible explanation for the appearance of anti-cytochrome P4501A2 autoantibodies. Mol. Pharmacol. 45:1994;1287-1295.
16. Pirmohamed M., Kitteringham N.R., Breckenridgge A.M., Park B.K. The effect of enzyme induction on the cytochrome P450-mediated bioactivation of carbamazepine by mouse liver microsomes. Biochem. Pharmacol. 44:1992;2307-2314.
17. Naisbitt D.J., Gordon S.F., Pirmohamed M., Burkhart C., Cribb A.E., Pichler W.J., Park B.K. Antigenicity and immunogenicity of sulfamethoxazole: demonstration of metabolism-dependent haptenation and T-cell proliferation in vivo. Br. J. Pharmacol. 133:2001;295-305.
18. Meekins C., Sullivan T., Gruchalla R. Immunochemical analysis sulfonamide drug allergy: identification of sulfamethoxazole-substituted human serum proteins. J. Allergy Clin. Immunol. 94:1994;1017-1024.
19. Gruchalla R.S., Pesenko R.D., Thinh T., Do B.S., Skiest D.J. Sulfonamide-induced reactions in desensitized patients with AIDS - the role of covalent protein haptenation by sulfamethoxazole. J. Allergy Clin. Immunol. 101:1988;371-378.
20. Shear N.H., Spielberg S.P., Grant D.M., Tang D.K., Kalow W. Differences in metabolism of sulfonamides predisposing to idiosyncratic toxicity. Ann. Intern. Med. 105:1986;179-184.
21. Shear N.H., Spielberg S.P. In vitro evaluation of a toxic metabolite of sulfadiazine. Can. J. Physiol. Pharmacol. 63:1985;1370-1372.
22. Rieder M.J., Uetrecht J., Shear N.H., Cannon M., Miller M., Spielberg S.P. Diagnosis of sulfonamide hypersensitivity reactions by in vitro 'rechallenge' with hydroxylamine metabolites. Ann. Intern. Med. 110:1989;286-289.
23. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods. 65:1983;55-63.
24. Spielberg S.P. Acetaminophen toxicity in human lymphocytes in vitro. J. Pharmacol. Exp. Ther. 213:1980;395-398.
25. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
26. Laemlli U.K. The cleavage of structural proteins during the assembly of the head bacteriophage T4. Nature. 227:1970;680-685.
27. van der Ven A.J.A.M., Mantel M.A., Vree T.B., Koopmans P.P., van der Meer J.W.M. Formation and elimination of sulfamethoxazole hydroxylamine after oral administration of sulfamethoxazole. Br. J. Clin. Pharmacol. 38:1994;147-150.
28. Stevens R.C., Laizure S.C., Sanders P.L., Stein D.S. Multiple-dose pharmacokinetics of 12 milligrams of trimethoprim and 60 milligrams of sulfamethoxazole per kilogram of body weight per day in healthy volunteers. Antimicrob. Agents Chemother. 37:1993;448-452.
29. Lee B.L., Medina I., Benowitz N.L., Jacob P. Daposone, trimethoprim and sulfamethoxazole plasma levels during treatment of Pneumocystis pneumonia in patients with the acquired immunodeficiency syndrome. Evidence of drug interactions. Ann. Intern. Med. 100:1989;606-611.
30. Reilly T.P., Lash L.H., Doll M.A., Hein D.W., Woster P.M., Svensson C.K. A role for bioactivation and covalent binding within epidermal keratinocytes in sulfonamide-induced cutaneous drug reactions. J. Invest. Dermatol. 114:2000;1164-1173.
31. Hwang C., Sinskey A.J., Lodish H.F. Oxidized redox state of glutathione in the endoplasmic reticulum. Science. 257:1992;1496-1502.
32. Bánhegyi G., Lusini L., Puskás F., Rossi R., Fulceri R., Braun L., Mile V., di Simplicio P., Mandl J., Benedetti A. Preferential transport of glutathione versus glutathione disulfide in rat liver microsomal vesicles. J. Biol. Chem. 274:1999;12213-12216.
33. + cells by the hydroxylamine of sulfamethoxazole. FASEB. 13:1999;1688-1698.
34. van de Water B., Wang Y., Asmellash S., Liu H., Zhan Y., Miller E., Stevens J.L. Distinct endoplasmic reticulum signaling pathways regulate apoptotic and necrotic cell death following iodoacetamide treatment. Chem. Res. Tox. 12:1999;943-951.