Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies

Detalhes bibliográficos
Autor(a) principal: Marestoni, Luiz D. [UNESP]
Data de Publicação: 2016
Outros Autores: Wong, Ademar [UNESP], Feliciano, Gustavo T. [UNESP], Marchi, Mary R. R. [UNESP], Tarley, Cesar R. T., Sotomayor, Maria D. P. T. [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.5935/0103-5053.20150256
http://hdl.handle.net/11449/158685
Resumo: It is well known that selectivity of molecularly imprinted polymers (MIPs) depends on adequate choice of functional monomer before the experimental synthesis. Computational simulation seems to be an ideal way to produce selective MIPs. In this work, we have proposed the use of semi-empirical simulation to obtain the best monomer able to strongly interact with ciprofloxacin. Twenty functional monomers were evaluated through semi-empirical quantum chemistry method and three MIPs were synthesized using the monomers acrylamide (M5), acrylic acid (M4) and 1-vinylimidazole (M16), yielding the maximum adsorption capacities of 282.0, 223.8 and 202.5 mu mol g(-1), respectively, as predicted by the computational simulation. From competitive adsorption studies in the presence of structurally similar compounds, the MIP synthesized with acrylamide was found to possess higher specific selectivity factors (S) if compared to non-imprinted polymer (NIP), thus indicating good recognition selectivity for the ciprofloxacin.
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spelling Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studiesmolecularly imprinted polymersantibioticadsorption isothermIt is well known that selectivity of molecularly imprinted polymers (MIPs) depends on adequate choice of functional monomer before the experimental synthesis. Computational simulation seems to be an ideal way to produce selective MIPs. In this work, we have proposed the use of semi-empirical simulation to obtain the best monomer able to strongly interact with ciprofloxacin. Twenty functional monomers were evaluated through semi-empirical quantum chemistry method and three MIPs were synthesized using the monomers acrylamide (M5), acrylic acid (M4) and 1-vinylimidazole (M16), yielding the maximum adsorption capacities of 282.0, 223.8 and 202.5 mu mol g(-1), respectively, as predicted by the computational simulation. From competitive adsorption studies in the presence of structurally similar compounds, the MIP synthesized with acrylamide was found to possess higher specific selectivity factors (S) if compared to non-imprinted polymer (NIP), thus indicating good recognition selectivity for the ciprofloxacin.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Instituto Nacional de Ciencia e Tecnologia de Bioanalitica (INCTBio)Fundacao Araucaria - ParanaCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Univ Estadual Paulista, Inst Quim, BR-14800900 Araraquara, SP, BrazilInst Fed Parana, BR-84269090 Telemaco Borba, PR, BrazilUniv Estadual Londrina, Dept Quim, BR-86050482 Londrina, PR, BrazilUniv Estadual Paulista, Inst Quim, BR-14800900 Araraquara, SP, BrazilSoc Brasileira QuimicaUniversidade Estadual Paulista (Unesp)Inst Fed ParanaUniversidade Estadual de Londrina (UEL)Marestoni, Luiz D. [UNESP]Wong, Ademar [UNESP]Feliciano, Gustavo T. [UNESP]Marchi, Mary R. R. [UNESP]Tarley, Cesar R. T.Sotomayor, Maria D. P. T. [UNESP]2018-11-26T15:28:38Z2018-11-26T15:28:38Z2016-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article109-118application/pdfhttp://dx.doi.org/10.5935/0103-5053.20150256Journal Of The Brazilian Chemical Society. Sao Paulo: Soc Brasileira Quimica, v. 27, n. 1, p. 109-118, 2016.0103-5053http://hdl.handle.net/11449/15868510.5935/0103-5053.20150256S0103-50532016000100109WOS:000369153700014S0103-50532016000100109.pdfWeb of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal Of The Brazilian Chemical Society0,357info:eu-repo/semantics/openAccess2023-11-13T06:09:41Zoai:repositorio.unesp.br:11449/158685Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T17:33:15.671037Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
title Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
spellingShingle Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
Marestoni, Luiz D. [UNESP]
molecularly imprinted polymers
antibiotic
adsorption isotherm
title_short Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
title_full Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
title_fullStr Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
title_full_unstemmed Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
title_sort Semi-Empirical Quantum Chemistry Method for Pre-Polymerization Rational Design of Ciprofloxacin Imprinted Polymer and Adsorption Studies
author Marestoni, Luiz D. [UNESP]
author_facet Marestoni, Luiz D. [UNESP]
Wong, Ademar [UNESP]
Feliciano, Gustavo T. [UNESP]
Marchi, Mary R. R. [UNESP]
Tarley, Cesar R. T.
Sotomayor, Maria D. P. T. [UNESP]
author_role author
author2 Wong, Ademar [UNESP]
Feliciano, Gustavo T. [UNESP]
Marchi, Mary R. R. [UNESP]
Tarley, Cesar R. T.
Sotomayor, Maria D. P. T. [UNESP]
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (Unesp)
Inst Fed Parana
Universidade Estadual de Londrina (UEL)
dc.contributor.author.fl_str_mv Marestoni, Luiz D. [UNESP]
Wong, Ademar [UNESP]
Feliciano, Gustavo T. [UNESP]
Marchi, Mary R. R. [UNESP]
Tarley, Cesar R. T.
Sotomayor, Maria D. P. T. [UNESP]
dc.subject.por.fl_str_mv molecularly imprinted polymers
antibiotic
adsorption isotherm
topic molecularly imprinted polymers
antibiotic
adsorption isotherm
description It is well known that selectivity of molecularly imprinted polymers (MIPs) depends on adequate choice of functional monomer before the experimental synthesis. Computational simulation seems to be an ideal way to produce selective MIPs. In this work, we have proposed the use of semi-empirical simulation to obtain the best monomer able to strongly interact with ciprofloxacin. Twenty functional monomers were evaluated through semi-empirical quantum chemistry method and three MIPs were synthesized using the monomers acrylamide (M5), acrylic acid (M4) and 1-vinylimidazole (M16), yielding the maximum adsorption capacities of 282.0, 223.8 and 202.5 mu mol g(-1), respectively, as predicted by the computational simulation. From competitive adsorption studies in the presence of structurally similar compounds, the MIP synthesized with acrylamide was found to possess higher specific selectivity factors (S) if compared to non-imprinted polymer (NIP), thus indicating good recognition selectivity for the ciprofloxacin.
publishDate 2016
dc.date.none.fl_str_mv 2016-01-01
2018-11-26T15:28:38Z
2018-11-26T15:28:38Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.5935/0103-5053.20150256
Journal Of The Brazilian Chemical Society. Sao Paulo: Soc Brasileira Quimica, v. 27, n. 1, p. 109-118, 2016.
0103-5053
http://hdl.handle.net/11449/158685
10.5935/0103-5053.20150256
S0103-50532016000100109
WOS:000369153700014
S0103-50532016000100109.pdf
url http://dx.doi.org/10.5935/0103-5053.20150256
http://hdl.handle.net/11449/158685
identifier_str_mv Journal Of The Brazilian Chemical Society. Sao Paulo: Soc Brasileira Quimica, v. 27, n. 1, p. 109-118, 2016.
0103-5053
10.5935/0103-5053.20150256
S0103-50532016000100109
WOS:000369153700014
S0103-50532016000100109.pdf
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Journal Of The Brazilian Chemical Society
0,357
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 109-118
application/pdf
dc.publisher.none.fl_str_mv Soc Brasileira Quimica
publisher.none.fl_str_mv Soc Brasileira Quimica
dc.source.none.fl_str_mv Web of Science
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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