Mass spectrometric strategies for the identification and characterization of human serum albumin covalently adducted by amoxicillin: Ex Vivo Studies

Chemical Research in Toxicology

Volumn 27, Issue 9, 2014, Pages 1566-1574

  Garzon, Davide ^a   Ariza, Adriana ^b,c   Regazzoni, Luca ^a   Clerici, Riccardo ^a   Altomare, Alessandra ^a   Sirtori, Federico Riccardi ^a,d   Carini, Marina ^a   Torres, María José ^c   Perez Sala, Dolores ^b   Aldini, Giancarlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^c HOSPITAL REGIONAL UNIVERSITARIO DE MÁLAGA   (Spain)

^d Medical Oncology Unit   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMOXICILLIN; HUMAN SERUM ALBUMIN; PEPTIDE; SERUM ALBUMIN;

ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG PROTEIN BINDING; ELECTROSPRAY MASS SPECTROMETRY; EX VIVO STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN EXPERIMENT; MASS SPECTROMETRY; NORMAL HUMAN; PROTEIN ANALYSIS; PROTEIN DEGRADATION; PROTEIN MODIFICATION; TANDEM MASS SPECTROMETRY; AMINO ACID SEQUENCE; BIOLOGY; CHEMISTRY; METABOLISM;

AMINO ACID SEQUENCE; AMOXICILLIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMPUTATIONAL BIOLOGY; HUMANS; PEPTIDES; SERUM ALBUMIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84918526640     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500210e     Document Type: Article

References (29)

1. Riedl, M. A., and Casillas, A. M. (2003) Adverse drug reactions: types and treatment options. Am. Fam. Physician 68, 1781-1790.
2. Thong, B. Y., and Tan, T. C. (2011) Epidemiology and risk factors for drug allergy. Br. J. Clin. Pharmacol. 71, 684-700.
3. Lopez, S., Blanca-Lopez, N., Cornejo-Garcia, J. A., Canto, G., Torres, M. J., Mayorga, C., and Blanca, M. (2007) Nonimmediate reactions to betalactams. Curr. Opin. Allergy Clin. Immunol. 7, 310-316.
4. Guengerich, F. P. (2011) Mechanisms of drug toxicity and relevance to pharmaceutical development. Drug Metab. Pharmacokinet. 26, 3-14.
5. Ariza, A., and Montanez., M. I., and Perez-Sala, D. (2011) Proteomics in immunological reactions to drugs. Curr. Opin. Allergy Clin. Immunol. 11, 305-312.
6. Cars, O., Molstad, S., and Melander, A. (2001) Variation in antibiotic use in the European Union. Lancet 357, 1851-1853.
7. McCaig, L. F., and Hughes, J. M. (1995) Trends in antimicrobial drug prescribing among office-based physicians in the United States. JAMA 273, 214-219.
8. Adriaenssens, N., Coenen, S., Kroes, A. C., Versporten, A., Vankerckhoven, V., Muller, A., Blix, H. S., Goossens, H., and Group, E. P. (2011) European Surveillance of Antimicrobial Consumption (ESAC): systemic antiviral use in Europe. J. Antimicrob. Chemother. 66, 1897-1905.
9. Versporten, A., Coenen, S., Adriaenssens, N., Muller, A., Minalu, G., Faes, C., Vankerckhoven, V., Aerts, M., Hens, N., Molenberghs, G., Goossens, H., and Group, E. P. (2011) European Surveillance of Antimicrobial Consumption (ESAC): outpatient penicillin use in Europe (1997-2009). J. Antimicrob. Chemother. 66, vi13-23.
10. Blanca, M. (1995) Allergic reactions to penicillins. A changing world? Allergy 50, 777-782.
11. Dona, I., Blanca-Lopez, N., Torres, M. J., García-Campos, J., García-Nunez, I., Gomez, F., Salas, M., Rondon, C., Canto, M. G., and Blanca, M. (2012) Drug hypersensitivity reactions: response patterns, drug involved, and temporal variations in a large series of patients. J. Investig. Allergol. Clin. Immunol. 22, 363-371.
12. Renaudin, J. M., Beaudouin, E., Ponvert, C., Demoly, P., and Moneret-Vautrin, D. A. (2013) Severe drug-induced anaphylaxis: analysis of 333 cases recorded by the Allergy Vigilance Network from 2002 to 2010. Allergy 68, 929-937.
13. Blanca, M., Romano, A., Torres, M. J., Fernandez, J., Mayorga, C., Rodriguez, J., Demoly, P., Bousquet, P. J., Merk, H. F., Sanz, M. L., Ott, H., and Atanaskovic-Markovic, M. (2009) Update on the evaluation of hypersensitivity reactions to betalactams. Allergy 64, 183-193.
14. García-Nunez, I., Barasona Villarejo, M. J., Algaba Marmol, M. A., Moreno Aguilar, C., and Guerra Pasadas, F. (2012) Diagnosis of patients with immediate hypersensitivity to beta-lactams using retest. J. Investig. Allergol. Clin. Immunol. 22, 41-47.
15. Montanez, M. I., Perez-Inestrosa, E., Suau, R., Mayorga, C., Torres, M. J., and Blanca, M. (2008) Dendrimerized cellulose as a scaffold for artificial antigens with applications in drug allergy diagnosis. Biomacromolecules 9, 1461-1466.
16. Ruiz-Sanchez, A. J., Montanez, M. I., Mayorga, C., Torres, M. J., Kehr, N. S., Vida, Y., Collado, D., Najera, F., De Cola, L., and Perez-Inestrosa, E. (2012) Dendrimer-modified solid supports: nano-structured materials with potential drug allergy diagnostic applications. Curr. Med. Chem. 19, 4942-4954.
17. Blanca, M., Mayorga, C., Perez, E., Suau, R., Juarez, C., Vega, J. M., Carmona, M. J., Perez-Estrada, M., and Garcia, J. (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.
18. Blanca, M., Romano, A., Torres, M. J., Demoly, P., and De Weck, A. (2007) Continued need of appropriate betalactam-derived skin test reagents for the management of allergy to betalactams. Clin. Exp. Allergy 37, 166-173.
19. Sanz, M. L., and Gamboa., P. M., Antepara, I., Uasuf, C., Vila, L., Garcia-Aviles, C., Chazot, M., and De Weck, A. L. (2002) Flow cytometric basophil activation test by detection of CD63 expression in patients with immediate-type reactions to betalactam antibiotics. Clin. Exp. Allergy 32, 277-286.
20. Torres, M. J., Padial, A., Mayorga, C., Fernandez, T., Sanchez-Sabate, E., Cornejo-García, J. A., Antunez, C., and Blanca, M. (2004) The diagnostic interpretation of basophil activation test in immediate allergic reactions to betalactams. Clin. Exp. Allergy 34, 1768-1775.
21. Ariza, A., Garzon, D., Abanades, D. R., de los Rios, V., Vistoli, G., and Torres., M. J., Carini, M., Aldini, G., and Perez-Sala, D. (2012) Protein haptenation by amoxicillin: high resolution mass spectrometry analysis and identification of target proteins in serum. J. Proteomics 77, 504-520.
22. Elschenbroich, S., and Kislinger, T. (2011) Targeted proteomics by selected reaction monitoring mass spectrometry: applications to systems biology and biomarker discovery. Mol. BioSyst. 7, 292-303.
23. Jenkins, R. E., Meng, X., Elliott, V. L., Kitteringham, N. R., Pirmohamed, M., and Park, B. K. (2009) Characterisation of flucloxacillin and 5-hydroxymethyl flucloxacillin haptenated HSA in vitro and in vivo. Proteomics Clin. Appl. 3, 720-729.
24. Aldini, G., Regazzoni, L., Orioli, M., Rimoldi, I., and Facino., R. M., and Carini, M. (2008) A tandem MS precursor-ion scan approach to identify variable covalent modification of albumin Cys34: a new tool for studying vascular carbonylation. J. Mass. Spectrom. 43, 1470-1481.
25. Chierakul, W., Wangboonskul, J., Singtoroj, T., Pongtavornpinyo, W., and Short., J. M., Maharjan, B., Wuthiekanun, V., Dance, D. A., Teparrukkul, P., Lindegardh, N., and Peacock., S. J., Day, N. P., Chaowagul, W., and White, N. J. (2006) Pharmacokinetic and pharmacodynamic assessment of co-amoxiclav in the treatment of melioidosis. J. Antimicrob. Chemother. 58, 1215-1220.
26. Yvon, M., Anglade, P., and Wal, J. M. (1990) Identification of the binding sites of benzyl penicilloyl, the allergenic metabolite of penicillin, on the serum albumin molecule. FEBS Lett. 263, 237-240.
27. Whitaker, P., Meng, X., Lavergne, S. N., El-Ghaiesh, S., Monshi, M., Earnshaw, C., Peckham, D., Gooi, J., Conway, S., Pirmohamed, M., Jenkins, R. E., Naisbitt, D. J., and Park, B. K. (2011) Mass spectrometric characterization of circulating and functional antigens derived from piperacillin in patients with cystic fibrosis. J. Immunol. 187, 200-211.
28. Meng, X., and Jenkins., R. E., Berry, N. G., Maggs, J. L., Farrell, J., Lane, C. S., Stachulski, A. V., French, N. S., Naisbitt, D. J., Pirmohamed, M., and Park, B. K. (2011) Direct evidence for the formation of diastereoisomeric benzylpenicilloyl haptens from benzylpenicillin and benzylpenicillenic acid in patients. J. Pharmacol. Exp. Ther. 338, 841-849.
29. Jaffe, J. D., Keshishian, H., Chang, B., Addona, T. A., Gillette, M. A., and Carr, S. A. (2008) Accurate inclusion mass screening: a bridge from unbiased discovery to targeted assay development for biomarker verification. Mol. Cell. Proteomics 7, 1952-1962.