Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202300 |
Resumo: | A molecularly imprinted polymer (MIP) for the diuretic drug hydrochlorothiazide (HCTZ) based on theoretical predictions was developed. Molecular modeling calculations were performed to study the intermolecular interactions in the pre-polymerization mixture and to select a suitable functional monomer and a porogenic solvent for the synthesis of the MIP. To confirm the results of the theoretical predictions, three MIPs were synthesized and evaluated using the equilibrium batch rebinding method. A water-compatible MIP was prepared using HCTZ as the template and acrylamide as the functional monomer (FM) with ethylene glycol dimethacrylate as the cross-linker and tetrahydrofuran as the porogen. An imprinting factor of 8.24 was obtained. The polymer was characterized by Fourier transform infrared (FTIR), solid-state nuclear magnetic resonance, scanning electron microscopy, thermogravimetric analysis and nitrogen sorption porosimetry. In addition to HCTZ, six structurally related compounds were tested to evaluate the selectivity of the HCTZ-MIP, and cross-selectivity of the MIP was verified. |
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Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energymolecularly imprinted polymermolecular modelingGibbs free energyhydrochlorothiazidepolarizable continuum modelA molecularly imprinted polymer (MIP) for the diuretic drug hydrochlorothiazide (HCTZ) based on theoretical predictions was developed. Molecular modeling calculations were performed to study the intermolecular interactions in the pre-polymerization mixture and to select a suitable functional monomer and a porogenic solvent for the synthesis of the MIP. To confirm the results of the theoretical predictions, three MIPs were synthesized and evaluated using the equilibrium batch rebinding method. A water-compatible MIP was prepared using HCTZ as the template and acrylamide as the functional monomer (FM) with ethylene glycol dimethacrylate as the cross-linker and tetrahydrofuran as the porogen. An imprinting factor of 8.24 was obtained. The polymer was characterized by Fourier transform infrared (FTIR), solid-state nuclear magnetic resonance, scanning electron microscopy, thermogravimetric analysis and nitrogen sorption porosimetry. In addition to HCTZ, six structurally related compounds were tested to evaluate the selectivity of the HCTZ-MIP, and cross-selectivity of the MIP was verified.Sociedade Brasileira de Química2016-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202300Journal of the Brazilian Chemical Society v.27 n.12 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20160126info:eu-repo/semantics/openAccessBarros,Leonardo A.Custodio,RogérioRath,Susanneeng2016-12-01T00:00:00Zoai:scielo:S0103-50532016001202300Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2016-12-01T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy |
title |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy |
spellingShingle |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy Barros,Leonardo A. molecularly imprinted polymer molecular modeling Gibbs free energy hydrochlorothiazide polarizable continuum model |
title_short |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy |
title_full |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy |
title_fullStr |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy |
title_full_unstemmed |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy |
title_sort |
Design of a New Molecularly Imprinted Polymer Selective for Hydrochlorothiazide Based on Theoretical Predictions Using Gibbs Free Energy |
author |
Barros,Leonardo A. |
author_facet |
Barros,Leonardo A. Custodio,Rogério Rath,Susanne |
author_role |
author |
author2 |
Custodio,Rogério Rath,Susanne |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Barros,Leonardo A. Custodio,Rogério Rath,Susanne |
dc.subject.por.fl_str_mv |
molecularly imprinted polymer molecular modeling Gibbs free energy hydrochlorothiazide polarizable continuum model |
topic |
molecularly imprinted polymer molecular modeling Gibbs free energy hydrochlorothiazide polarizable continuum model |
description |
A molecularly imprinted polymer (MIP) for the diuretic drug hydrochlorothiazide (HCTZ) based on theoretical predictions was developed. Molecular modeling calculations were performed to study the intermolecular interactions in the pre-polymerization mixture and to select a suitable functional monomer and a porogenic solvent for the synthesis of the MIP. To confirm the results of the theoretical predictions, three MIPs were synthesized and evaluated using the equilibrium batch rebinding method. A water-compatible MIP was prepared using HCTZ as the template and acrylamide as the functional monomer (FM) with ethylene glycol dimethacrylate as the cross-linker and tetrahydrofuran as the porogen. An imprinting factor of 8.24 was obtained. The polymer was characterized by Fourier transform infrared (FTIR), solid-state nuclear magnetic resonance, scanning electron microscopy, thermogravimetric analysis and nitrogen sorption porosimetry. In addition to HCTZ, six structurally related compounds were tested to evaluate the selectivity of the HCTZ-MIP, and cross-selectivity of the MIP was verified. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-12-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202300 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016001202300 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0103-5053.20160126 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.27 n.12 2016 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318179099344896 |