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Volumn 77, Issue , 2012, Pages 504-520

Protein haptenation by amoxicillin: High resolution mass spectrometry analysis and identification of target proteins in serum

Author keywords

Lactam antibiotics; Amoxicillin binding; Amoxicillin targets; Drug allergy; High resolution mass spectrometry; Protein haptenation

Indexed keywords

AMOXICILLIN; BETA LACTAM ANTIBIOTIC; HAPTEN; HUMAN SERUM ALBUMIN; IMMUNOGLOBULIN HEAVY CHAIN; IMMUNOGLOBULIN LIGHT CHAIN; PEPTIDE; TRANSFERRIN;

EID: 84870390940     PISSN: 18743919     EISSN: 18767737     Source Type: Journal    
DOI: 10.1016/j.jprot.2012.09.030     Document Type: Article
Times cited : (70)

References (32)
  • 2
    • 0025366429 scopus 로고
    • Identification of the binding sites of benzyl penicilloyl, the allergenic metabolite of penicillin, on the serum albumin molecule
    • Yvon M., Anglade P., Wal J.M. Identification of the binding sites of benzyl penicilloyl, the allergenic metabolite of penicillin, on the serum albumin molecule. FEBS Lett 1990, 263:237-240.
    • (1990) FEBS Lett , vol.263 , pp. 237-240
    • Yvon, M.1    Anglade, P.2    Wal, J.M.3
  • 3
    • 0023767723 scopus 로고
    • Identification of lysine residue 199 of human serum albumin as a binding site for benzylpenicilloyl groups
    • Yvon M., Wal J.M. Identification of lysine residue 199 of human serum albumin as a binding site for benzylpenicilloyl groups. FEBS Lett 1988, 239:237-240.
    • (1988) FEBS Lett , vol.239 , pp. 237-240
    • Yvon, M.1    Wal, J.M.2
  • 4
    • 80052152347 scopus 로고    scopus 로고
    • Direct evidence for the formation of diastereoisomeric benzylpenicilloyl haptens from benzylpenicillin and benzylpenicillenic acid in patients
    • Meng X., Jenkins R.E., Berry N.G., Maggs J.L., Farrell J., Lane C.S., et al. Direct evidence for the formation of diastereoisomeric benzylpenicilloyl haptens from benzylpenicillin and benzylpenicillenic acid in patients. J Pharmacol Exp Ther 2011, 338:841-849.
    • (2011) J Pharmacol Exp Ther , vol.338 , pp. 841-849
    • Meng, X.1    Jenkins, R.E.2    Berry, N.G.3    Maggs, J.L.4    Farrell, J.5    Lane, C.S.6
  • 6
    • 79960427633 scopus 로고    scopus 로고
    • Mass spectrometric characterization of circulating and functional antigens derived from piperacillin in patients with cystic fibrosis
    • Whitaker P., Meng X., Lavergne S.N., El-Ghaiesh S., Monshi M., Earnshaw C., et al. Mass spectrometric characterization of circulating and functional antigens derived from piperacillin in patients with cystic fibrosis. J Immunol 2011, 187:200-211.
    • (2011) J Immunol , vol.187 , pp. 200-211
    • Whitaker, P.1    Meng, X.2    Lavergne, S.N.3    El-Ghaiesh, S.4    Monshi, M.5    Earnshaw, C.6
  • 8
    • 0034726407 scopus 로고    scopus 로고
    • In vitro reactivity of penicilloyl and penicillanyl albumin and polylysine conjugates with IgE-antibody
    • Zhao Z., Batley M., D'Ambrosio C., Baldo B.A. In vitro reactivity of penicilloyl and penicillanyl albumin and polylysine conjugates with IgE-antibody. J Immunol Methods 2000, 242:43-51.
    • (2000) J Immunol Methods , vol.242 , pp. 43-51
    • Zhao, Z.1    Batley, M.2    D'Ambrosio, C.3    Baldo, B.A.4
  • 9
    • 0028096071 scopus 로고
    • Allergic reactions to betalactams: studies in a group of patients allergic to penicillin and evaluation of cross-reactivity with cephalosporin
    • Audicana M., Bernaola G., Urrutia I., Echechipia S., Gastaminza G., Munoz D., et al. Allergic reactions to betalactams: studies in a group of patients allergic to penicillin and evaluation of cross-reactivity with cephalosporin. Allergy 1994, 49:108-113.
    • (1994) Allergy , vol.49 , pp. 108-113
    • Audicana, M.1    Bernaola, G.2    Urrutia, I.3    Echechipia, S.4    Gastaminza, G.5    Munoz, D.6
  • 11
    • 78650643665 scopus 로고    scopus 로고
    • Immunocytochemistry for amoxicillin and its use for studying uptake of the drug in the intestine, liver, and kidney of rats
    • Fujiwara K., Shin M., Miyazaki T., Maruta Y. Immunocytochemistry for amoxicillin and its use for studying uptake of the drug in the intestine, liver, and kidney of rats. Antimicrob Agents Chemother 2011, 55:62-71.
    • (2011) Antimicrob Agents Chemother , vol.55 , pp. 62-71
    • Fujiwara, K.1    Shin, M.2    Miyazaki, T.3    Maruta, Y.4
  • 12
    • 0037201572 scopus 로고    scopus 로고
    • Simultaneous determination of amoxicillin and clavulanic acid in human plasma by HPLC with UV detection
    • Hoizey G., Lamiable D., Frances C., Trenque T., Kaltenbach M., Denis J., et al. Simultaneous determination of amoxicillin and clavulanic acid in human plasma by HPLC with UV detection. J Pharm Biomed Anal 2002, 30:661-666.
    • (2002) J Pharm Biomed Anal , vol.30 , pp. 661-666
    • Hoizey, G.1    Lamiable, D.2    Frances, C.3    Trenque, T.4    Kaltenbach, M.5    Denis, J.6
  • 13
    • 84871606867 scopus 로고
    • Intravenous pharmacokinetics and binding to plasmatic proteins of amoxycillin and clavulanic acid in sheeps
    • Serrano J.M., Hita J., Ponferrada C.J., López M.C., Cárceles C.M. Intravenous pharmacokinetics and binding to plasmatic proteins of amoxycillin and clavulanic acid in sheeps. An Vet 1989, 5:75-87.
    • (1989) An Vet , vol.5 , pp. 75-87
    • Serrano, J.M.1    Hita, J.2    Ponferrada, C.J.3    López, M.C.4    Cárceles, C.M.5
  • 14
    • 33645654439 scopus 로고    scopus 로고
    • Performance evaluation of a hybrid linear ion trap/orbitrap mass spectrometer
    • Makarov A., Denisov E., Kholomeev A., Balschun W., Lange O., Strupat K., et al. Performance evaluation of a hybrid linear ion trap/orbitrap mass spectrometer. Anal Chem 2006, 78:2113-2120.
    • (2006) Anal Chem , vol.78 , pp. 2113-2120
    • Makarov, A.1    Denisov, E.2    Kholomeev, A.3    Balschun, W.4    Lange, O.5    Strupat, K.6
  • 15
    • 57249091714 scopus 로고    scopus 로고
    • Orbitrap mass spectrometry: instrumentation, ion motion and applications
    • Perry R.H., Cooks R.G., Noll R.J. Orbitrap mass spectrometry: instrumentation, ion motion and applications. Mass Spectrom Rev 2008, 27:661-699.
    • (2008) Mass Spectrom Rev , vol.27 , pp. 661-699
    • Perry, R.H.1    Cooks, R.G.2    Noll, R.J.3
  • 16
    • 33749020292 scopus 로고    scopus 로고
    • Mass spectrometric characterization of covalent modification of human serum albumin by 4-hydroxy-trans-2-nonenal
    • Aldini G., Gamberoni L., Orioli M., Beretta G., Regazzoni L., Maffei Facino R., et al. Mass spectrometric characterization of covalent modification of human serum albumin by 4-hydroxy-trans-2-nonenal. J Mass Spectrom 2006, 41:1149-1161.
    • (2006) J Mass Spectrom , vol.41 , pp. 1149-1161
    • Aldini, G.1    Gamberoni, L.2    Orioli, M.3    Beretta, G.4    Regazzoni, L.5    Maffei Facino, R.6
  • 17
    • 34548178909 scopus 로고    scopus 로고
    • In-gel digestion for mass spectrometric characterization of proteins and proteomes
    • Shevchenko A., Tomas H., Havlis J., Olsen J.V., Mann M. In-gel digestion for mass spectrometric characterization of proteins and proteomes. Nat Protoc 2006, 1:2856-2860.
    • (2006) Nat Protoc , vol.1 , pp. 2856-2860
    • Shevchenko, A.1    Tomas, H.2    Havlis, J.3    Olsen, J.V.4    Mann, M.5
  • 18
    • 0032010153 scopus 로고    scopus 로고
    • A universal algorithm for fast and automated charge state deconvolution of electrospray mass-to-charge ratio spectra
    • Zhang Z., Marshall A.G. A universal algorithm for fast and automated charge state deconvolution of electrospray mass-to-charge ratio spectra. J Am Soc Mass Spectrom 1998, 9:225-233.
    • (1998) J Am Soc Mass Spectrom , vol.9 , pp. 225-233
    • Zhang, Z.1    Marshall, A.G.2
  • 20
    • 0036284090 scopus 로고    scopus 로고
    • VEGA: a versatile program to convert, handle and visualize molecular structure on Windows-based PCs
    • Pedretti A., Villa L., Vistoli G. VEGA: a versatile program to convert, handle and visualize molecular structure on Windows-based PCs. J Mol Graph Model 2002, 21:47-49.
    • (2002) J Mol Graph Model , vol.21 , pp. 47-49
    • Pedretti, A.1    Villa, L.2    Vistoli, G.3
  • 21
    • 79951476387 scopus 로고    scopus 로고
    • PROPKA3: consistent treatment of internal and surface residues in empirical pKa predictions
    • Olsson M.H.M., Sondergard C.R., Rostkowski M., Jensen J.H. PROPKA3: consistent treatment of internal and surface residues in empirical pKa predictions. J Chem Theory Comput 2011, 7:525-537.
    • (2011) J Chem Theory Comput , vol.7 , pp. 525-537
    • Olsson, M.H.M.1    Sondergard, C.R.2    Rostkowski, M.3    Jensen, J.H.4
  • 22
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
    • Morris G., Goodsell D., Halliday R., Huey R., Hart W., Belew R., et al. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998, 19:1639-1662.
    • (1998) J Comput Chem , vol.19 , pp. 1639-1662
    • Morris, G.1    Goodsell, D.2    Halliday, R.3    Huey, R.4    Hart, W.5    Belew, R.6
  • 23
    • 1642410180 scopus 로고    scopus 로고
    • Intramolecular general acid catalysis in the aminolysis of beta-lactam antibiotics
    • Llinas A., Page M. Intramolecular general acid catalysis in the aminolysis of beta-lactam antibiotics. Org Biomol Chem 2004, 2:651-654.
    • (2004) Org Biomol Chem , vol.2 , pp. 651-654
    • Llinas, A.1    Page, M.2
  • 24
    • 2942741233 scopus 로고    scopus 로고
    • Thiol-catalysed hydrolysis of cephalosporins and possible rate-limiting amine anion expulsion
    • Llinas A., Vilanova B., Page M. Thiol-catalysed hydrolysis of cephalosporins and possible rate-limiting amine anion expulsion. J Phys Org Chem 2004, 17:521-528.
    • (2004) J Phys Org Chem , vol.17 , pp. 521-528
    • Llinas, A.1    Vilanova, B.2    Page, M.3
  • 25
    • 27444444430 scopus 로고    scopus 로고
    • Immunochemical detection of flucloxacillin adduct formation in livers of treated rats
    • Carey M.A., van Pelt F.N.A.M. Immunochemical detection of flucloxacillin adduct formation in livers of treated rats. Toxicology 2005, 216:41-48.
    • (2005) Toxicology , vol.216 , pp. 41-48
    • Carey, M.A.1    van Pelt, F.N.A.M.2
  • 26
    • 0029102208 scopus 로고
    • Two-dimensional electrophoresis of human serum proteins modified by ampicillin during therapeutic treatment
    • Magi B., Marzocchi B., Bini L., Cellesi C., Rossolini A., Pallini V. Two-dimensional electrophoresis of human serum proteins modified by ampicillin during therapeutic treatment. Electrophoresis 1995, 16:1190-1192.
    • (1995) Electrophoresis , vol.16 , pp. 1190-1192
    • Magi, B.1    Marzocchi, B.2    Bini, L.3    Cellesi, C.4    Rossolini, A.5    Pallini, V.6
  • 27
    • 83655165225 scopus 로고    scopus 로고
    • NMR studies and molecular dynamic simulation of synthetic dendrimeric-antigens
    • Montáñez M.I., Nájera F., Pérez-Inestrosa E. NMR studies and molecular dynamic simulation of synthetic dendrimeric-antigens. Polymers 2011, 3:1533-1553.
    • (2011) Polymers , vol.3 , pp. 1533-1553
    • Montáñez, M.I.1    Nájera, F.2    Pérez-Inestrosa, E.3
  • 28
    • 70350452589 scopus 로고    scopus 로고
    • "Danger" conditions increase sulfamethoxazole-protein adduct formation in human antigen-presenting cells
    • Lavergne S.N., Wang H., Callan H.E., Park B.K., Naisbitt D.J. "Danger" conditions increase sulfamethoxazole-protein adduct formation in human antigen-presenting cells. J Pharmacol Exp Ther 2009, 331:372-381.
    • (2009) J Pharmacol Exp Ther , vol.331 , pp. 372-381
    • Lavergne, S.N.1    Wang, H.2    Callan, H.E.3    Park, B.K.4    Naisbitt, D.J.5
  • 29
    • 43149094897 scopus 로고    scopus 로고
    • Albumin is the main nucleophilic target of human plasma: a protective role against pro-atherogenic electrophilic reactive carbonyl species?
    • Aldini G., Vistoli G., Regazzoni L., Gamberoni L., Facino R.M., Yamaguchi S., et al. Albumin is the main nucleophilic target of human plasma: a protective role against pro-atherogenic electrophilic reactive carbonyl species?. Chem Res Toxicol 2008, 21:824-835.
    • (2008) Chem Res Toxicol , vol.21 , pp. 824-835
    • Aldini, G.1    Vistoli, G.2    Regazzoni, L.3    Gamberoni, L.4    Facino, R.M.5    Yamaguchi, S.6
  • 30
    • 74949102287 scopus 로고    scopus 로고
    • Delta(12)-prostaglandin J(2) as a product and ligand of human serum albumin: formation of an unusual covalent adduct at His146
    • Yamaguchi S., Aldini G., Ito S., Morishita N., Shibata T., Vistoli G., et al. Delta(12)-prostaglandin J(2) as a product and ligand of human serum albumin: formation of an unusual covalent adduct at His146. J Am Chem Soc 2010, 132:824-832.
    • (2010) J Am Chem Soc , vol.132 , pp. 824-832
    • Yamaguchi, S.1    Aldini, G.2    Ito, S.3    Morishita, N.4    Shibata, T.5    Vistoli, G.6
  • 31
    • 34347324020 scopus 로고    scopus 로고
    • Physiological and pathological changes in the redox state of human serum albumin critically influence its binding properties
    • Oettl K., Stauber R.E. Physiological and pathological changes in the redox state of human serum albumin critically influence its binding properties. Br J Pharmacol 2007, 151:580-590.
    • (2007) Br J Pharmacol , vol.151 , pp. 580-590
    • Oettl, K.1    Stauber, R.E.2


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