Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development

The use of agrochemicals for crop protection may result in the presence of toxic residues in soils and aquatic environments, besides in foodstuffs. Most often just the parent compound is included in the definition of pesticide residue, even though chemicals resulting from biotransformation and degra...

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Authors: Parra, Javier, Mercader Badia, Josep Vicent, Agulló, Consuelo, Abad Somovilla, Antonio, Abad Fuentes, Antonio
Format: article
Publication Date:2012
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/112221
Online Access:http://hdl.handle.net/10261/112221
Access Level:Open access
Keyword:Generic antibody
Immunoanalytical methods
Strobilurins
Fungicide
Degradate
Metabolite
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spelling Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay developmentParra, JavierMercader Badia, Josep VicentAgulló, ConsueloAbad Somovilla, AntonioAbad Fuentes, AntonioGeneric antibodyImmunoanalytical methodsStrobilurinsFungicideDegradateMetaboliteThe use of agrochemicals for crop protection may result in the presence of toxic residues in soils and aquatic environments, besides in foodstuffs. Most often just the parent compound is included in the definition of pesticide residue, even though chemicals resulting from biotransformation and degradation routes might also be of toxicological relevance. Azoxystrobin is a broad-spectrum systemic fungicide widely used worldwide to combat pathogenic fungi affecting plants. We herein report the synthesis and detailed chemical characterization of several of the most relevant metabolites and degradates of azoxystrobin. These compounds were further employed as ligands for screening a collection of monoclonal antibodies to azoxystrobin, which had been previously generated from haptens functionalized at different positions of the target chemical. As a result, an antibody was identified capable of binding, with subnanomolar affinity, not only azoxystrobin but also its main transformation products, such as the so-called acid and enol derivatives, as well as the azoxystrobin (Z)-isomer. The selected binder was demonstrated as a useful immunoreagent for the development of immunochemical assays as novel analytical tools for the qualitative determination of azoxystrobin and its metabolites and degradates.This work was supported by Ministerio de Educación y Ciencia (AGL2006-12750-C02-01/02/ALI) and cofinanced by FEDER funds. J.P. and J.V.M. were hired by the CSIC, the former under a predoctoral I3P contract and the latter under a Ramón y Cajal postdoctoral contract, both of them financed by the Spanish Ministerio de Ciencia e Innovación and the European Social Fund.Peer ReviewedElsevier2015201520122015info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501http://hdl.handle.net/10261/112221reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglésinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1122212026-05-22T06:33:51Z
dc.title.none.fl_str_mv Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
title Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
spellingShingle Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
Parra, Javier
Generic antibody
Immunoanalytical methods
Strobilurins
Fungicide
Degradate
Metabolite
title_short Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
title_full Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
title_fullStr Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
title_full_unstemmed Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
title_sort Synthesis of azoxystrobin transformation products and selection of monoclonal antibodies for immunoassay development
dc.creator.none.fl_str_mv Parra, Javier
Mercader Badia, Josep Vicent
Agulló, Consuelo
Abad Somovilla, Antonio
Abad Fuentes, Antonio
author Parra, Javier
author_facet Parra, Javier
Mercader Badia, Josep Vicent
Agulló, Consuelo
Abad Somovilla, Antonio
Abad Fuentes, Antonio
author_role author
author2 Mercader Badia, Josep Vicent
Agulló, Consuelo
Abad Somovilla, Antonio
Abad Fuentes, Antonio
author2_role author
author
author
author
dc.subject.none.fl_str_mv Generic antibody
Immunoanalytical methods
Strobilurins
Fungicide
Degradate
Metabolite
topic Generic antibody
Immunoanalytical methods
Strobilurins
Fungicide
Degradate
Metabolite
description The use of agrochemicals for crop protection may result in the presence of toxic residues in soils and aquatic environments, besides in foodstuffs. Most often just the parent compound is included in the definition of pesticide residue, even though chemicals resulting from biotransformation and degradation routes might also be of toxicological relevance. Azoxystrobin is a broad-spectrum systemic fungicide widely used worldwide to combat pathogenic fungi affecting plants. We herein report the synthesis and detailed chemical characterization of several of the most relevant metabolites and degradates of azoxystrobin. These compounds were further employed as ligands for screening a collection of monoclonal antibodies to azoxystrobin, which had been previously generated from haptens functionalized at different positions of the target chemical. As a result, an antibody was identified capable of binding, with subnanomolar affinity, not only azoxystrobin but also its main transformation products, such as the so-called acid and enol derivatives, as well as the azoxystrobin (Z)-isomer. The selected binder was demonstrated as a useful immunoreagent for the development of immunochemical assays as novel analytical tools for the qualitative determination of azoxystrobin and its metabolites and degradates.
publishDate 2012
dc.date.none.fl_str_mv 2012
2015
2015
2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/112221
url http://hdl.handle.net/10261/112221
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869403045383634944
score 15.811543

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