2026-04-29T20:47:11Zhttps://repisalud.isciii.es/rest/oai/requestoai:repisalud.isciii.es:20.500.12105/182722024-11-28T14:58:29Zcom_20.500.12105_15322com_20.500.12105_2051col_20.500.12105_16927
Repisalud
author
Mayorga, Cristobalina
author
Montañez, Maria I.
author
Najera, Francisco
author
Bogas, Gador
author
Fernandez, Tahía D.
author
Rodriguez Gil, David
author
Palacios, Ricardo
author
Torres, Maria J.
author
Vida, Yolanda
author
Perez-Inestrosa, Ezequiel
authoraffiliation
[Mayorga,C; Montañez,MI; Bogas,G; Fernandez,TD; Torres,MJ] Allergy Research Group, Instituto de Investigación Biomédica de Málaga-IBIMA, Málaga, Spain. [Mayorga,C; Bogas,G; Torres,MJ] Allergy Unit, Hospital Regional Universitario de Málaga, Málaga, Spain. [Mayorga,C; Montañez,MI; Najera,F; Torres,MJ; Vida,Y; Perez-Inestrosa,E] Centro Andaluz de Nanomedicina y Biotecnología-BIONAND, Parque Tecnológico de Andalucía, Málaga, Spain. [Najera,F; Vida,Y; Perez-Inestrosa,E] Universidad de Málaga-IBIMA Departamento de Química Orgánica, Málaga, Spain. [Fernandez,TD] Universidad de Málaga-IBIMA, Departamento de Biología celular, Genética y Fisiología, Málaga, Spain. [Gil,DR; Palacios,R] Diater Laboratorios S.A., Madrid, Spain. [Torres,MJ] Universidad de Málaga-IBIMA, Departamento de Medicina, Málaga, Spain.
2024-02-19T15:26:13Z
2024-02-19T15:26:13Z
2021-02-26
10.3389/fphar.2021.585890
1663-9812
Frontiers in Pharmacology
http://hdl.handle.net/10668/4065
33716734
http://hdl.handle.net/20.500.12105/18272
The high prevalence of allergy to β-lactam antibiotics is a worldwide issue. Accuracy of diagnostic methods is important to prove tolerance or allergy, with skin test considered the best validated in vivo method for diagnosing immediate reactions to β-lactams. Although drug provocation test is the reference standard, it cannot be performed in highly risk reactions or in those with positive skin tests. For skin tests, the inclusion of major and minor determinants of benzylpenicillin (BP) is recommended. Commercial skin test reagents have changed along time, including as minor determinants benzylpenicillin, benzylpenicilloate (BPO), and benzylpenilloate (PO). Major determinants consists of multivalent conjugates of benzylpenicilloyl coupled through amide bond to a carrier polymer, such as penicilloyl-polylysine (PPL) or benzylpenicilloyl-octalysine (BP-OL). The chemical stability of such reagents has influenced the evolution of the composition of the commercial kits, as this requirement is necessary for improving the quality and standardization of the product. In this work, we provide a detailed study of the chemical stability of BP determinants. We observed that those structures suffer from an epimerization process in C-5 at different rates. Butylamine-Benzylpenicilloyl conjugates (5R,6R)-Bu-BPO and (5S,6R)-Bu-BPO were selected as a simple model for mayor determinant to evaluate the role of the different epimers in the immunoreactivity with sera from penicillin-allergic patients. In vitro immunoassays indicate that any change in the chemical structure of the antigenic determinant of BP significantly affects IgE recognition. The inclusion of stereochemically pure compounds or mixtures may have important implications for both the reproducibility and sensitivity of in vivo and in vitro diagnostic tests.
eng
Antigenic determinant
Diagnostic test
Drug allergy
Penicillin
Specific IgE
Epítopos
Pruebas diagnósticas rutinarias
Hipersensibilidad medicamentosa
Penicilinas
Inmunoglobulina E
The Role of Benzylpenicilloyl Epimers in Specific IgE Recognition
research article