Antigenicity of sulfanilamide and its metabolites using fluorescent-labelled compounds

eferences

• Bhargava MM, Listowsky I, Arias IM. Ligandin, bilirubin binding and glutathione-S-transferases activity are independent processes. Journal of Biological Chemistry 1978; 53: 4112–4115
   Google Scholar
• Chai X, Boerman MHEM, Zhai Y, Napoli JL. Cloning of a cDNA for liver microsomal retinol dehydrogenase. A tissue-specific, short-chain alcohol dehydrogenase. Journal of Biological Chemistry 1995; 270: 3900–3904
   Google Scholar
• Chovan LE, Black-Schaefer C, Dandliker PJ, Lau YY. Automatic mass spectrometry methods development for drug discovery: Application in metabolic stability assays. Rapid Communications in Mass Spectrometry 2004; 18: 3105–3112
   PubMed Web of Science ®Google Scholar
• Cirstea M, Cirj M, Suhaciu GH, Petec G, Vacariu A, Mihaileanu M. Spontaneous formaion of immunogenic conjugates by a biotrans-formation product of sulfanilamide. Revue Roumaine de Morphologie, D’Embryologie et de Physiologie Serie Physiologie 1982; 18: 175–180
   Google Scholar
• Clarke B, Golman K, Lerche MH, Looker M, O'Sullivan M, Santos A, Servin R, Thaning M. Hyperpolarization-based methods and compound mixtures for determining protein activity using NMR spectroscopy, and use in determining drug-drug interactions and phenotyping. 2003, International Application Published under the Patent Cooperation Treaty
   Google Scholar
• Cribb AE, Spielberg SP. Hepatic microsomal metabolism of sulfamethoxazole to the hydroxylamine. Drug Metabolism and Disposition 1990; 18: 784–787
   PubMed Web of Science ®Google Scholar
• Cribb AE, Miller M, Leeder JS, Hill J, Spielberg SP. Reactions of the nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione. Implication for idiosyncratic toxicity. Drug Metabolism and Disposition 1991; 19: 900–906
   PubMed Web of Science ®Google Scholar
• Cribb AE, Pohl LR, Spielberg SP, Leeder JS. Patients with delayed–onset sulfonamide hypersensitivity reactions. Have antibodies recognizing endoplasmic reticulum luminal proteins. Journal of Pharmacology and Experimental Therapeutics 1997; 282: 1064–1072
   PubMed Web of Science ®Google Scholar
• Eyanagi R, Hisanari Y, Shigematsu H. Study on the skin allergy induced by sulfanilamide: Antigenicity of 3-hydroxysulfanilamide. Hifu 1992; 34: 37–41
   Google Scholar
• Eyanagi R, Hisanari Y, Shigematsu H, Yoshida K. Metabolism of sulfanilamide by the skin. Hifu 1989; 31: 164–169
   Google Scholar
• Eyanagi R, Hisanari Y, Shigematsu H. Studies of paracetamol/phenacetin toxicity: Isolation and charaterization of p-aminophenol-glutathione conjugate. Xenobiotica 1991; 21: 793–803
   Web of Science ®Google Scholar
• Eyanagi R, Hisanari Y, Shigematsu H, Yoshida K, Yoshimura H. Enhancement of sulfanilamide N-hydroxylase activity in kidney and liver microsomes of rats by pretreatment with 3-methylcholanthrene type polychlorinated biphenyl. Journal of Pharmacobio-Dynamics 1982; 5: 853–858
   PubMedGoogle Scholar
• Eyanagi R, Yoshida K, Yamamoto I. Experimental studies on the antigenicity of some metabolites and related compounds of sulfanilamide. Yakugaku Zasshi 1979; 99: 458–465
   Google Scholar
• Gill HJ, Hough SJ, Naisbitt DJ, Maggs JL, Kitteringham NR, Pirmohamed M, Park BK. The relationship between the disposition and immunogenicity of sulfamethoxazole in the rat. Journal of Pharmcology and Experimental Therapeutics 1997; 282: 795–801
   PubMed Web of Science ®Google Scholar
• Greenberger PA, Pateson R. Management of drug allergy in patients with the acquired–immunodeficiency syndrome. Journal of Allergy and Clinical immunology 1987; 79: 484–488
   PubMed Web of Science ®Google Scholar
• Gruchalla RS, Pesenko RD, Do TT, Skiest DJ. Sulfonamide-induced reactions in desensitized patients with AIDS – The role of covalent protein haptenation by sulfamethoxazole. Journal of Allergy and Clinical Immunology 1998; 101: 371–378
   Google Scholar
• Hershko A. Ubiquitin-mediated protein degradation. Journal of Biological Chemistry 1988; 263: 15237–15240
   PubMed Web of Science ®Google Scholar
• Imaoka S, Wan J, Chow T, Hiroi T, Eyanagi R, Shigematsu H, Funae Y. Cloning and characterization of the CYP2D1-binding protein, retinol dehydrogenase. Archives of Biochemistry and Biophysics 1998; 353: 331–336
   Google Scholar
• Kamei K, Oshino R, Hara S. Amino acid sequence of glutathione S-transferase b from guinea pig liver. Journal of Biochemistry 1990; 107: 111–117
   PubMed Web of Science ®Google Scholar
• Lorwy OH, Rosebrough NJ, Farr AL, Randall RJ. Protein mesurement with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 265–275
   Google Scholar
• Manchanda T, Hess D, Dale L, Ferguson SG, Rieder MJ. Haptenation of sulfonamide reactive metabolites to cellular proteins. Molecular Pharmacology 2002; 62: 1011–1026
   PubMed Web of Science ®Google Scholar
• Mauri-Hellweg D, Bettens F, Mauri D, Brander C, Hunziker T, Pichler WJ. Activation of drug specific CD4+ and CD8+ T cells in individuals allergic to sulfonamides, phenytoin, and carbamazepine. Journal of Immunology 1995; 155: 462–472
   PubMed Web of Science ®Google Scholar
• Meekins CV, Sullivan TJ, Gruchalla RS. Immunochemical analysis of sulfonamide drug allergy: Identification of sulfamethoxazole-substitutied human serum proteins. Journal of allergy and clinical immunology 1994; 94: 1017–1024
   PubMed Web of Science ®Google Scholar
• Naisbitt DJ, Gordon SF, Pirmohamed M, Burkhart C, Cribb AE, Pichler WJ, Park BK. Antigenicity and immunogenicity of sulphamethoxazole: Demonstration of metabolism-dependent haptenation and T-cell proliferation in vivo. British Jounal of Pharmacology 2001; 133: 295–305
   PubMed Web of Science ®Google Scholar
• Naisbitt DJ, Hough SJ, Gill HJ, Pirmohamed M, Kitteringham NR, Park BK. Cellular disposition of sulphamethoxazole and its metabolites: Implications for hypersensitivity. British Jounal of Pharmacology 1999; 126: 1393–1407
   PubMed Web of Science ®Google Scholar
• Nose A, Kudo T. Reduction with sodium borohydride-transition metal salt systems. I. Reduction of aromatic nitro compounds with the sodium borohydride-nickelous chloride system. Chemical and Pharmaceutical Bulletin 1981; 29: 1159–1161
   Web of Science ®Google Scholar
• Oshino R, Kamei K, Nishioka M, rShin M. Purification and characterization of glutathione S-trasferases from guinea pig liver. Journal of Biochemistry 1990; 107: 105–110
   Google Scholar
• Rieder MJ, Krause R, Bird IA. Time-course of toxicity of reactive sulfonamide metabolites. Toxicology 1995; 95: 141–146
   PubMedGoogle Scholar
• Uetrecht JP. Reactivity and possible significance of hydroxylamine and nitroso metabolites of procainamide. Journal of Pharmacology and Experimental Therapeutics 1985; 232: 420–425
   PubMed Web of Science ®Google Scholar
• Varshavsky A. The N-end rule. Cell 1992; 69: 725–735
   PubMed Web of Science ®Google Scholar
• Veerkamp JH, Peeters RA, Maatman RGHJ. Structural and functional features of different types of cytoplasmic fatty acid-binding proteins. Biochimica et Biophysica Acta 1991; 1081: 1–24
   PubMed Web of Science ®Google Scholar
• Yamamoto I, Eyanagi R. Positive skin reaction induced by 4,4′-azoxy-benzene disulfonamide in relationship to the sulfanilamide allergy. International Archives of Allergy and Applied Immunology 1977; 54: 538–541
   Google Scholar
• Zanni MP, Von Greyerz S, Schnyder B, Brander KA, Frutig K, Hari Y, Valitutti S, Pichler WJ. HLA-restricted processing- and metabolism-independent pathway of drug recognition by human alpha beta T lymphocytes. Journal of Clinical Investigation 1998; 102: 1591–1598
   PubMed Web of Science ®Google Scholar