Drugs as haptens, antigens, and immunogens

Drug Hypersensitivity

Volumn , Issue , 2007, Pages 55-65

  Park Dr , B Kevin ^a   Sanderson, Joseph P ^a   Naisbitt, Dean J ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77953630663     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1159/000104189     Document Type: Chapter

References (77)

1. Abbas AK, Lichtman AH: Cellular and Molecular Immunology, ed 5. Philadelphia, Saunders, 2003.
2. Park BK, Coleman JW, Kitteringham NR: Drug disposition and drug hypersensitivity. Biochem Pharmacol 1987;36: 581-590
3. Hemmi H, Kaisho T, Takeuchi O, Sato S, Sanjo H, Hoshino K, Horiuchi T, Tomizawa H, Takeda K, Akira S: Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway. Nat Immunol 2002; 3: 196-200.
4. LeBlanc R, Hideshima T, Catley LP, Shringarpure R, Burger R, Mitsiades N, Mitsiades C, Cheema P, Chauhan D, Richardson PG, Anderson KC, Munshi NC: Immunomodulatory drug costimulates T cells via the B7-CD28 pathway. Blood 2004; 103: 1787-1790.
5. Hadley G, Derry S, Moore RA: Imiquimod for actinic keratosis: systematic review and meta-analysis. J Invest Dermatol 2006; 126: 1251-1255.
6. Sharma RA, Steward WP, Daines CA, Knight RD, O'Byrne KJ, Dalgleish AG: Toxicity profile of the immunomodulatory thalidomide analogue, lenalidomide: phase I clinical trial of three dosing schedules in patients with solid malignancies. Eur J Cancer 2006; 42: 2318-2325.
7. Suntharalingam G, Perry MR, Ward S, Brett SJ, Castello-Cortes A, Brunner MD, Panoskaltsis N: Cytokine storm in a phase 1 trial of the anti-CD28 monoclonal antibody TGN1412. N Engl J Med 2006; 355: 1018-1028.
8. van der Merwe PA, Davis SJ: Molecular interactions mediating T cell antigen recognition. Annu Rev Immunol 2003; 21: 659-684.
9. Speir JA, Stevens J, Joly E, Butcher GW, Wilson IA: Two different, highly exposed, bulged structures for an unusually long peptide bound to rat MHC class I RT1-Aa. Immunity 2001; 14: 81-92.
10. Rammensee HG: Chemistry of peptides associated with MHC class I and class II molecules. Curr Opin Immunol 1995;7: 85-96.
11. Rudolph MG, Wilson IA: The specificity of TCR/pMHC interaction. Curr Opin Immunol 2002; 14: 52-65.
12. Braden BC, Poljak RJ: Structural features of the reactions between antibodies and protein antigens. FASEB J 1995;9: 9-16.
13. Habig WH, Pabst MJ, Jakoby WB: Glutathione S-transferases. The first enzymatic step in mercapturic acid formation. J Biol Chem 1974; 249: 7130-7139.
14. Tingle MD, Clarke JB, Kitteringham NR, Park BK: Influence of glutathione conjugation on the immunogenicity of dinitrophenyl derivatives in the rat. Int Arch Allergy Appl Immunol 1990; 91: 160-165.
15. Kitteringham NR, Maggs JL, Newby S, Park BK: Drug-protein conjugates -VIII. The metabolic fate of the initrophenyl hapten conjugated to albumin. Biochem Pharmacol 1985; 34: 1763-1771.
16. Maggs JL, Kitteringham NR, Grabowski PS, Park BK: Drug-protein conjugates -X. The role of protein conjugation in the disposition of dinitrofluorobenzene. Biochem Pharmacol 1986; 35: 505-513.
17. Jackson GE, Young NM: Determination of chemical properties of individual histidine and tyrosine residues of concanavalin A by competitive labeling with 1-fluoro-2,4-dinitrobenzene. Biochemistry 1986; 25: 1657-1662.
18. Liu LF, Hong JL, Tsai SP, Hsieh JC, Tam MF: Reversible modification of rat liver glutathione S-transferase 3-3 with 1-chloro-2,4-dinitrobenzene: specific labelling of Tyr-115. Biochem J 1993;296: 189-197.
19. Gerberick GF, Vassallo JD, Bailey RE, Chaney JG, Morrall SW, Lepoittevin JP: Development of a peptide reactivity assay for screening contact allergens. Toxicol Sci 2004; 81: 332-343.
20. Bello J, Iijima H, Kartha G: A new arylating agent, 2-carboxy-4,6-dinitrochlorobenzene. Reaction with model compounds and bovine pancreatic ribonuclease. Int J Pept Protein Res 1979;14: 199-212.
21. Landsteiner K, Jacobs J: Studies on the sensitisation of animals with simple chemical compounds. J Exp Med 1935;61: 643-656.
22. Landsteiner K, Jacobs J: Studies on the sensitization of animals with simple chemical compounds II. J Exp Med 1936; 64: 625-639.
23. Soeberg B, Sumerska T, Binns RM, Balfour BM: Contact sensitivity in the pig. III. Induction by intralymphatic infusion of DNP-conjugated cell membranes and soluble proteins, free DNFB and some small molecular weight derivatives. Int Arch Allergy Appl Immunol 1978; 57: 481-487.
24. Soeberg B, Sumerska T, Binns RM, Balfour BM: Contact sensitivity in the pig. II. Induction by intralymphatic infusion of DNP conjugated cells. Int Arch Allergy Appl Immunol 1978; 57: 114-125.
25. Bassolino-Klimas D, Bruccoleri RE, Subramaniam S: Modeling the antigen combining site of an anti-dinitrophenyl antibody, ANO2. Protein Sci 1992; 1: 1465-1476.
26. Halsey JF, Cebra JJ, Biltonen RL: Structural and thermodynamic basis of affinity in anti-dinitrophenyl antibody. Biochemistry 1975; 14: 5221-5224.
27. Knight CG, Green NM: Interaction of dinitrophenyl groups bound to bovine serum albumin with univalent fragments of anti-dinitrophenyl antibody. Biochem J 1979; 177: 225-236.
28. Pickard C, Smith AM, Cooper H, Strickland I, Jackson J, Healy E, Friedmann PS: Investigation of mechanisms underlying the T-cell response to the hapten 2,4-dinitrochlorobenzene. J Invest Dermatol 2006, in press.
29. Cavani A, Hackett CJ, Wilson KJ, Rothbard JB, Katz SI: Characterization of epitopes recognized by hapten-specific CD4+ T cells. J Immunol 1995; 154:1232-1238.
30. Martin S, von Bonin A, Fessler C, Pflugfelder U, Weltzien HU: Structural complexity of antigenic determinants for class I MHC-restricted, hapten-specific T cells. Two qualitatively differing types of H-2Kb-restricted TNP epitopes. J Immunol 1993; 151: 678-687.
31. Kohler J, Martin S, Pflugfelder U, Ruh H, Vollmer J, Weltzien HU: Cross-reactive trinitrophenylated peptides as antigens for class II major histocompatibility complex-restricted T cells and inducers of contact sensitivity in mice. Limited T cell receptor repertoire. Eur J Immunol 1995; 25: 92-101.
32. Aiba S, Terunuma A, Manome H, Tagami H: Dendritic cells differently respond to haptens and irritants by their production of cytokines and expression of co-stimulatory molecules. Eur J Immunol 1997; 27: 3031-3038.
33. Coutant KD, de Fraissinette AB, Cordier A, Ulrich P: Modulation of the activity of human monocyte-derived dendritic cells by chemical haptens, a metal allergen, and a staphylococcal superantigen. Toxicol Sci 1999; 52: 189-198.
34. Jugde F, Boissier C, Rougier-Larzat N, Corlu A, Chesne C, Semana G, Heresbach D: Regulation by allergens of chemokine receptor expression on in vitro-generated dendritic cells. Toxicology 2005; 212: 227-238.
35. Manome H, Aiba S, Tagami H: Simple chemicals can induce maturation and apoptosis of dendritic cells. Immunology 1999; 98: 481-490.
36. Kuhn U, Brand P, Willemsen J, Jonuleit H, Enk AH, van Brandwijk-Petershans R, Saloga J, Knop J, Becker D: Induction of tyrosine phosphorylation in human MHC class II-positive antigenpresenting cells by stimulation with contact sensitizers. J Immunol 1998;160: 667-673.
37. Arrighi JF, Rebsamen M, Rousset F, Kindler V, Hauser C: A critical role for p38 mitogen-activated protein kinase in the maturation of human bloodderived dendritic cells induced by lipopolysaccharide, TNF-alpha, and contact sensitizers. J Immunol 2001; 166:3837-3845.
38. Aiba S, Manome H, Nakagawa S, Mollah ZU, Mizuashi M, Ohtani T, Yoshino Y, Tagami H: p38 Mitogen-activated protein kinase and extracellular signalregulated kinases play distinct roles in the activation of dendritic cells by two representative haptens, NiCl2 and 2,4-dinitrochlorobenzene. J Invest Dermatol 2003; 120: 390-399.
39. Bruchhausen S, Zahn S, Valk E, Knop J, Becker D: Thiol antioxidants block the activation of antigen-presenting cells by contact sensitizers. J Invest Dermatol 2003; 121: 1039-1044.
40. Holzer AM, Kaplan LL, Levis WR: Haptens as drugs: contact allergens are powerful topical immunomodulators. J Drugs Dermatol 2006; 5: 410-416.
41. Nielsen NH, Linneberg A, Menne T, Madsen F, Frolund L, Dirksen A, Jorgensen T: Incidence of allergic contact sensitization in Danish adults between 1990 and 1998; the Copenhagen Allergy Study, Denmark. Br J Dermatol 2002; 147: 487-492.
42. Menne T: Prevention of nickel allergy by regulation of specific exposures. Ann Clin Lab Sci 1996; 26: 133-138.
43. Zhang Y, Wilcox DE: Thermodynamic and spectroscopic study of Cu(II) and Ni(II) binding to bovine serum albumin. J Biol Inorg Chem 2002; 7: 327-337.
44. Tabata M, Sarkar B: Specific nickel(II)-transfer process between the native sequence peptide representing the nickel(II)-transport site of human serum albumin and L-histidine. J Inorg Biochem 1992; 45: 93-104.
45. Moulon C, Vollmer J, Weltzien HU: Characterization of processing requirements and metal cross-reactivities in T cell clones from patients with allergic contact dermatitis to nickel. Eur J Immunol 1995; 25: 3308-3315.
46. Pistoor FH, Kapsenberg ML, Bos JD, Meinardi MM, von Blomberg ME, Scheper RJ: Cross-reactivity of human nickel-reactive T-lymphocyte clones with copper and palladium. J Invest Dermatol 1995; 105: 92-95.
47. Sinigaglia F, Scheidegger D, Garotta G, Scheper R, Pletscher M, Lanzavecchia A: Isolation and characterization of Nispecific T cell clones from patients with Ni-contact dermatitis. J Immunol 1985; 135: 3929-3932.
48. Lu L, Vollmer J, Moulon C, Weltzien HU, Marrack P, Kappler J: Components of the ligand for a Ni ++ reactive human T cell clone. J Exp Med 2003; 197: 567-574.
49. Gamerdinger K, Moulon C, Karp DR, Van Bergen J, Koning F, Wild D, Pflugfelder U, Weltzien HU: A new type of metal recognition by human T cells: contact residues for peptide-independent bridging of T cell receptor and major histocompatibility complex by nickel. J Exp Med 2003; 197: 1345-1353.
50. Kanerva L, Kerosuo H, Kullaa A, Kerosuo E: Allergic patch test reactions to palladium chloride in schoolchildren. Contact Dermatitis 1996; 34: 39-42.
51. Wohrl S, Hemmer W, Focke M, Gotz M, Jarisch R: Copper allergy revisited. J Am Acad Dermatol 2001; 45: 863-870.
52. Griem P, Panthel K, Kalbacher H, Gleichmann E: Alteration of a model antigen by Au(III) leads to T cell sensitization to cryptic peptides. Eur J Immunol 1996; 26: 279-287.
53. Griem P, von Vultee C, Panthel K, Best SL, Sadler PJ, Shaw CF 3rd: T cell crossreactivity to heavy metals: identical cryptic peptides may be presented from protein exposed to different metals. Eur J Immunol 1998; 28: 1941-1947.
54. Ahlstedt S, Kristofferson A: Immune mechanisms for induction of penicillin allergy. Prog Allergy 1982; 30: 67-134.
55. Padovan E, Mauri-hellweg D, Pichler WJ, Weltzien HU: T cell recognition of penicillin G: structural features determining antigenic specificity. Eur J Immunol 1996; 26: 42-48.
56. Padovan E, Bauer T, Tongio MM, Kalbacher H, Weltzien HU: Penicilloyl peptides are recognized as T cell antigenic determinants in penicillin allergy. Eur J Immunol 1997; 27: 1303-1307.
57. Rodriguez-Pena R, Lopez S, Mayorga C, Antunez C, Fernandez TD, Torres MJ, Blanca M: Potential involvement of dendritic cells in delayed-type hypersensitivity reactions to beta-lactams. J Allergy Clin Immunol 2006; 118: 949-956.
58. Pirmohamed M, Park BK: HIV and drug allergy. Curr Opin Allergy Clin Immunol 2001; 1: 311-316.
59. Cribb AE, Spielberg SP, Griffin GP: N4-hydroxylation of sulfamethoxazole by cytochrome P450 of the cytochrome P4502C subfamily and reduction of sulfamethoxazole hydroxylamine in human and rat hepatic microsomes. Drug Metab Dispos 1995; 23: 406-414.
60. Gill HJ, Maggs JL, Madden S, Pirmohamed M, Park BK: The effect of fluconazole and ketoconazole on the metabolism of sulphamethoxazole. Br J Clin Pharmacol 1996; 42: 347-353.
61. Mitra AK, Thummel KE, Kalhorn TF, Kharasch ED, Unadkat JD, Slattery JT: Inhibition of sulfamethoxazole hydroxylamine formation by fluconazole in human liver microsomes and healthy volunteers. Clin Pharmacol Ther 1996; 59: 332-340.
62. van der Ven AJ, Mantel MA, Vree TB, Koopmans PP and van der Meer JW: Formation and elimination of sulphamethoxazole hydroxylamine after oral administration of sulphamethoxazole. Br J Clin Pharmacol 1994; 38: 147-150.
63. Cribb AE, Miller M, Leeder JS, Hill J, Spielberg SP: Reactions of the nitroso and hydroxylamine metabolites of sulfamethoxazole with reduced glutathione. Implications for idiosyncratic toxicity. Drug Metab Dispos 1991; 19: 900-906.
64. Naisbitt DJ, O'Neill PM, Pirmohamed M, Park BK: Synthesis and reactions of nitroso sulphamethoxazole with iological nucleophiles: Implications for immune mediated toxicity. Bioorg Med Chem Lett 1996; 6: 1511-1516.
65. Manchanda T, Hess D, Dale L, Ferguson SG, Rieder MJ: Haptenation of sulfonamide reactive metabolites to cellular proteins. Mol Pharmacol 2002; 62: 1011-1026.
66. Naisbitt DJ, Farrell J, Gordon SF, Maggs JL, Burkhart C, Pichler WJ, Pirmohamed M, Park BK: Covalent binding of the nitroso metabolite of sulfamethoxazole leads to toxicity and major histocompatibility complex-restricted antigen presentation. Mol Pharmacol 2002; 62: 628-637.
67. Kurian JR, Bajad SU, Miller JL, Chin NA, Trepanier LA: NADH cytochrome b5 reductase and cytochrome b5 catalyze the microsomal reduction of xenobiotic hydroxylamines and amidoximes in humans. J Pharmacol Exp Ther 2004; 311: 1171-1178.
68. Farrell J, Naisbitt DJ, Drummond NS, Depta JP, Vilar FJ, Pirmohamed M, Park BK: Characterization of sulfamethoxazole and sulfamethoxazole metabolite-specific T-cell responses in animals and humans. J Pharmacol Exp Ther 2003; 306: 229-237.
69. 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. Br J Pharmacol 2001; 133: 295-305.
70. Park BK, Pirmohamed M, Kitteringham NR: Role of drug disposition in drug hypersensitivity: a chemical, molecular, and clinical perspective. Chem Res Toxicol 1998; 11: 969-988.
71. Schnyder B, Burkhart C, Schnyder-Frutig K, von Greyerz S, Naisbitt DJ, Pirmohamed M, Park BK, Pichler WJ: Recognition of sulfamethoxazole and its reactive metabolites by drug-specific CD4+ T cells from allergic individuals. J Immunol 2000; 164: 6647-6654.
72. Schnyder B, Mauri-Hellweg D, Zanni M, Bettens F, Pichler WJ: Direct, MHCdependent presentation of the drug sulfamethoxazole to human alphabeta T cell clones. J Clin Invest 1997; 100:136-141.
73. 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. J Clin Invest 1998; 102: 1591-1598.
74. Depta JP, Altznauer F, Gamerdinger K, Burkhart C, Weltzien HU, Pichler WJ: Drug interaction with T-cell receptors: T-cell receptor density determines degree of cross-reactivity. J Allergy Clin Immunol 2004; 113: 519-527.
75. Burkhart C, Britschgi M, Strasser I, Depta JP, von Greyerz S, Barnaba V, Pichler WJ: Non-covalent presentation of sulfamethoxazole to human CD4+ T cells is independent of distinct human leucocyte antigen-bound peptides. Clin Exp Allergy 2002; 32: 1635-1643.
76. Nassif A, Bensussan A, Boumsell L, Deniaud A, Moslehi H, Wolkenstein P, Bagot M, Roujeau JC: Toxic epidermal necrolysis: effector cells are drug-specific cytotoxic T cells. J Allergy Clin Immunol 2004; 114: 1209-1215.
77. Sanderson JP, Naisbitt DJ, Farrell J, Ashby CA, Tucker MJ, Rieder MJ, Pirmohamed M, Clarke SE, Park BK: Sulphamethoxazole and its metabolite nitroso sulfamethomazole stimulate denditric cell co-stimulatory signalling. J Immunol, in press.