Study of protein haptenation by amoxicillin through the use of a biotinylated antibiotic

PLoS ONE

Volumn 9, Issue 3, 2014, Pages

  Ariza, Adriana ^a,b   Collado, Daniel ^c,d   Vida, Yolanda ^c,d   Montañez, María I ^b,d   Pérez Inestrosa, Ezequiel ^c,d   Blanca, Miguel ^b   Torres, María José ^b   Cañada, F Javier ^a   Pérez Sala, Dolores ^a  

^a CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^b HOSPITAL REGIONAL UNIVERSITARIO DE MÁLAGA   (Spain)

^c UNIVERSITY OF MÁLAGA   (Spain)

^d Institute of Biomedical Research in Malaga and BIONAND Nanomedicine Platform   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMOXICILLIN; BETA LACTAM ANTIBIOTIC; BIOTIN; CELL PROTEIN; CLAVULANIC ACID; HUMAN SERUM ALBUMIN; PENICILLIN G;

ADULT; ALLERGIC REACTION; ALLERGY; ANAPHYLACTIC SHOCK; ANAPHYLAXIS; ANGIONEUROTIC EDEMA; ANIMAL CELL; ARTICLE; BIOTINYLATION; CHEMOREACTIVITY; CLINICAL ARTICLE; CONTROLLED STUDY; DRUG BINDING; FEMALE; HUMAN; IMMUNE RESPONSE; MALE; MIDDLE AGED; NONHUMAN; PROTEIN HAPTENATION; PROTEIN MODIFICATION; RADIOALLERGOSORBENT TEST; URTICARIA; YOUNG ADULT;

AMOXICILLIN; ANIMALS; ANTI-BACTERIAL AGENTS; BETA-LACTAMS; BINDING, COMPETITIVE; BIOTINYLATION; BUTYLAMINES; HAPTENS; HUMANS; HYPERSENSITIVITY; IMMUNOGLOBULIN E; MACROPHAGES; MICE; MICROSCOPY, CONFOCAL; MOLECULAR STRUCTURE; SERUM ALBUMIN;

EID: 84896935052     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0090891     Document Type: Article

References (43)

1. Brander C, Mauri-Hellweg D, Bettens F, Rolli H, Goldman M, et al. (1995) Heterogeneous T cell responses to beta-lactam-modified self-structures are observed in penicillin-allergic individuals. J Immunol 155: 2670-2678.
2. Pichler WJ, Beeler A, Keller M, Lerch M, Posadas S, et al. (2006) Pharmacological interaction of drugs with immune receptors: the p-i concept. Allergol Int 55: 17-25.
3. Ariza A, Montañez MI, Pérez-Sala D (2011) Proteomics in immunological reactions to drugs. Curr Opin Allergy Clin Immunol 11: 305-312.
4. Blanca M (1995) Allergic reactions to penicillins. A changing world? Allergy 50: 777-782.
5. Torres MJ, Blanca M (2010) The complex clinical picture of beta-lactam hypersensitivity: penicillins, cephalosporins, monobactams, carbapenems, and clavams. Med Clin North Am 94: 805-820, xii.
6. Torres MJ, Ariza A, Mayorga C, Dona I, Blanca-Lopez N, et al. (2010) Clavulanic acid can be the component in amoxicillin-clavulanic acid responsible for immediate hypersensitivity reactions. J Allergy Clin Immunol 125: 502-505 e2.
7. Blanca M, Mayorga C, Perez E, Suau R, Juarez C, et al. (1992) Determination of IgE antibodies to the benzyl penicilloyl determinant. A comparison between poly-L-lysine and human serum albumin as carriers. J Immunol Methods 153: 99-105.
8. Blanca M, Fernandez M, Moreno F, Pérez E, Mayorga C, et al. (1994) The nature of the carrier in the RAST assay influences the capacity for detecting IgE antibodies to penicillins. J Clin Immunoassay 17: 160-170.
9. Garcia JJ, Blanca M, Moreno F, Vega JM, Mayorga C, et al. (1997) Determination of IgE antibodies to the benzylpenicilloyl determinant: a comparison of the sensitivity and specificity of three radio allergo sorbent test methods. J Clin Lab Anal 11: 251-257. (Pubitemid 27371784)
10. Fujiwara K, Shin M, Miyazaki T, Maruta Y (2011) Immunocytochemistry for amoxicillin and its use for studying uptake of the drug in the intestine, liver, and kidney of rats. Antimicrob Agents Chemother 55: 62-71.
11. Gomez MB, Torres MJ, Mayorga C, Perez-Inestrosa E, Suau R, et al. (2004) Immediate allergic reactions to betalactams: facts and controversies. Curr Opin Allergy Clin Immunol 4: 261-266. (Pubitemid 39006839)
12. Ariza A, Garzon D, Abánades DR, Ríos Vdl, Vistoli G, et al. (2012) Protein haptenation by amoxicillin: high resolution mass spectrometry analysis and identification of target proteins in serum. J Proteomics 77: 504-520.
13. Blanca M, Perez E, Garcia J, Miranda A, Fernandez J, et al. (1988) Anaphylaxis to amoxycillin but good tolerance for benzyl penicillin. In vivo and in vitro studies of specific IgE antibodies. Allergy 43: 508-510.
14. Blanca M, Mayorga C, Sanchez F, Vega JM, Fernandez J, et al. (1991) Differences in serum IgE antibody activity to benzylpenicillin and amoxicillin measured by RAST in a group of penicillin allergic patients. Allergy 46: 632-638.
15. Yvon M, Anglade P, Wal JM (1990) Identification of the binding sites of benzyl penicilloyl, the allergenic metabolite of penicillin, on the serum albumin molecule. FEBS Lett 263: 237-240. (Pubitemid 20142996)
16. Magi B, Marzocchi B, Bini L, Cellesi C, Rossolini A, et al. (1995) Two-dimensional electrophoresis of human serum proteins modified by ampicillin during therapeutic treatment. Electrophoresis 16: 1190-1192.
17. Carey MA, van Pelt FNAM (2005) Immunochemical detection of flucloxacillin adduct formation in livers of treated rats. Toxicology 216: 41-48. (Pubitemid 41531257)
18. Jenkins RE, Meng X, Elliott VL, Kitteringham NR, Pirmohamed M, et al. (2009) Characterisation of flucloxacillin and 5-hydroxymethyl flucloxacillin haptenated HSA in vitro and in vivo. Proteomics Clin Appl 3: 720-729.
19. 1 allows assessment of PPAR-independent effects and identification of novel cellular targets for covalent modification. Chem Biol Interact 183: 212-221.
20. Garzón B, Oeste CL, Díez-Dacal B, Pérez-Sala D (2011) Proteomic studies on protein modification by cyclopentenone prostaglandins: expanding our view on electrophile actions. J Proteomics 74: 2243-2263.
21. Mayorga C, Obispo T, Jimeno L, Blanca M, Moscoso del Prado J, et al. (1995) Epitope mapping of beta-lactam antibiotics with the use of monoclonal antibodies. Toxicology 97: 225-234.
22. Wessel D, Flugge UI (1984) A method for the quantitative recovery of protein in dilute solution in the presence of detergents and lipids. Anal Biochem 138: 141-143. (Pubitemid 14146660)
23. Cernuda-Morollón E, Rodríguez-Pascual F, Klatt P, Lamas S, Pérez-Sala D (2002) PPAR agonists amplify iNOS expression while inhibiting NF-κB: implications for mesangial cell activation by cytokines. J Am Soc Nephrol 13: 2223-2231.
24. Erle DJ, Briskin MJ, Butcher EC, Garcia-Pardo A, Lazarovits AI, et al. (1994) Expression and function of the MAdCAM-1 receptor, integrin alpha 4 beta 7, on human leukocytes. J Immunol 153: 517-528. (Pubitemid 24206281)
25. Torres MJ, Blanca M, Fernandez J, Romano A, Weck A, et al. (2003) Diagnosis of immediate allergic reactions to beta-lactam antibiotics. Allergy 58: 961-972. (Pubitemid 37260337)
26. Brockow K, Romano A, Blanca M, Ring J, Pichler W, et al. (2002) General considerations for skin test procedures in the diagnosis of drug hypersensitivity. Allergy 57: 45-51. (Pubitemid 34146185)
27. Blanca M, Romano A, Torres MJ, Fernandez J, Mayorga C, et al. (2009) Update on the evaluation of hypersensitivity reactions to betalactams. Allergy 64: 183-193.
28. Moreno F, Blanca M, Mayorga C, Terrados S, Moya M, et al. (1995) Studies of the specificities of IgE antibodies found in sera from subjects with allergic reactions to penicillins. Int Arch Allergy Immunol 108: 74-81.
29. Edwards RG, Spackman DA, Dewdney JM (1982) Development and use of three new radioallergosorbent tests in the diagnosis of penicillin allergy. Int Arch Allergy Appl Immunol 68: 352-357. (Pubitemid 12045069)
30. Wide L (1969) Radioimmunoassays employing immunosorbents. Acta Endocrinol Suppl (Copenh) 142: 207-221.
31. Batchelor FR, Dewdney JM, Weston RD, Wheeler AW (1966) The immunogenicity of cephalosporin derivatives and their cross-reaction with penicillin. Immunology 10: 21-33.
32. Praul CA, Brubaker KD, Leach RM, Gay CV (1998) Detection of endogenous biotin-containing proteins in bone and cartilage cells with streptavidin systems. Biochem Biophys Res Commun 247: 312-314. (Pubitemid 28420819)
33. 2 inhibition of NF-κB DNA binding through covalent modification of the p50 subunit. J Biol Chem 276: 35530-35536.
34. Stamatakis K, Pérez-Sala D (2006) Prostanoids with cyclopentenone structure as tools for the characterization of electrophilic eicosanoid-protein interactomes. Ann N Y Acad Sci 1091: 548-570. (Pubitemid 47092266)
35. Diamandis EP, Christopoulos TK (1991) The biotin-(strept)avidin system: principles and applications in biotechnology. Clin Chem 37: 625-636. (Pubitemid 21892699)
36. Zorrilla S, Garzón B, Pérez-Sala D (2010) Selective binding of the fluorescent dye 8-anilinonaphthalene-1-sulfonic acid to PPARγ allows ligand identification and characterization. Anal Biochem 399: 84-92.
37. Whitaker P, Meng X, Lavergne SN, El-Ghaiesh S, Monshi M, et al. (2011) Mass spectrometric characterization of circulating and functional antigens derived from piperacillin in patients with cystic fibrosis. J Immunol 187: 200-211.
38. Jenkins RE, Yaseen FS, Monshi MM, Whitaker P, Meng X, et al. (2013) beta-Lactam antibiotics form distinct haptenic structures on albumin and activate drug-specific T-lymphocyte responses in multiallergic patients with cystic fibrosis. Chem Res Toxicol 26: 963-975.
39. Brooks BM, Thomas AL, Coleman JW (2003) Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity. Clin Exp Immunol 131: 268-274. (Pubitemid 36205138)
40. El-Ghaiesh S, Monshi MM, Whitaker P, Jenkins R, Meng X, et al. (2012) Characterization of the antigen specificity of T-cell clones from piperacillin-hypersensitive patients with cystic fibrosis. J Pharmacol Exp Ther 341: 597-610.
41. Morel E, Bellon T (2007) Amoxicillin conjugates to HLA class I molecules and interferes with signalling through the ILT2/LIR-1/CD85j inhibitory receptor. Allergy 62: 190-196. (Pubitemid 46090302)
42. Tamai I, Terasaki T, Tsuji A (1985) Evidence for the existence of a common transport system of beta-lactam antibiotics in isolated rat hepatocytes. J Antibiot (Tokyo) 38: 1774-1780. (Pubitemid 16194410)
43. Sala-Rabanal M, Loo DD, Hirayama BA, Wright EM (2008) Molecular mechanism of dipeptide and drug transport by the human renal H+/ oligopeptide cotransporter hPEPT2. Am J Physiol Renal Physiol 294: F1422-1432.