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Título

Ready Access to Proquinazid Haptens via Cross-Coupling Chemistry for Antibody Generation and Immunoassay Development

AutorEsteve Turrillas, Francesc A. ; Mercader Badia, Josep Vicent ; Parra, Javier ; Agulló, Consuelo; Abad Somovilla, Antonio; Abad Fuentes, Antonio
Palabras claveHaptens
Antibodies
Immunoassays
Enzyme-linked immunoassays
Immune serum
Antibody production
iodine
Fecha de publicación27-jul-2015
EditorPublic Library of Science
CitaciónPLoS ONE 10(7): e0134042 (2015)
ResumenBioconjugate preparation is a fundamental step for antibody generation and immunoassay development to small chemical compounds. For analytical targets holding in their structure an aryl halogen atom, cross-coupling reactions may be a simple and efficient way to obtain functionalized derivatives; thus offering great potential to elicit robust and selective immune responses after being coupled to immunogenic carrier proteins. However, substitution of the halogen atom by an aliphatic chain might eventually compromise the affinity and specificity of the resulting antibodies. In order to address this issue, proquinazid, a new-generation fungicide with outstanding performance, was chosen as model analyte. Two functionalized derivatives differing in spacer arm rigidity were synthesized by Sonogashira cross-coupling chemistry. These haptens were covalently coupled to bovine serum albumin and the resulting immunoconjugates were employed for rabbit vaccination. Antibodies were tested for proquinazid recognition by direct and indirect competitive immunoassay, and IC50 values in the low nanomolar range were found, thus demonstrating the suitability of this straightforward synthetic strategy for the generation of immunoreagents to compounds bearing an aryl halide. Following antibody characterization, competitive immunoassays were developed and employed to determine proquinazid residues in grape musts, and their analytical performance was satisfactorily validated by comparison with GC–MS. Besides having described the development of the first immunochemical method for proquinazid analysis, an efficient functionalization approach for analytes comprising aryl halides is reported.
Descripción17 pages, 4 tables, 5 figures.-- Publisher's PDF
Versión del editorhttp://dx.doi.org/10.1371/journal.pone.0134042
URIhttp://hdl.handle.net/10261/127775
DOI10.1371/journal.pone.0134042
ISSN1932-6203
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