A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer

Poly(hydroxymethyl-3,4-ethylendioxythiophene) (PHMeDOT), a very electroactive polythiophene derivative bearing a dioxane ring fused onto the thiophene ring and an exocyclic hydroxymethyl substituent, is able to electrocatalyze the oxidation of glucose in the presence of interferents (e.g. dopamine,...

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Autores: Zanuy Gomara, David|||0000-0001-7704-2178, Fabregat Jové, Georgina|||0000-0001-8967-9950, Ferreira, Carlos Arthur, Alemán Llansó, Carlos|||0000-0003-4462-6075
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universitat Politècnica de Catalunya (UPC)
Repositorio:UPCommons. Portal del coneixement obert de la UPC
Idioma:inglés
OAI Identifier:oai:upcommons.upc.edu:2117/172649
Acceso en línea:https://hdl.handle.net/2117/172649
https://dx.doi.org/10.1039/c9cp00567f
Access Level:acceso abierto
Palabra clave:Molecular dynamics
Glucose
Conducting polymers
Dinàmica molecular
Glucosa
Polímers conductors
Àrees temàtiques de la UPC::Enginyeria química
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spelling A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymerZanuy Gomara, David|||0000-0001-7704-2178Fabregat Jové, Georgina|||0000-0001-8967-9950Ferreira, Carlos ArthurAlemán Llansó, Carlos|||0000-0003-4462-6075Molecular dynamicsGlucoseConducting polymersDinàmica molecularGlucosaPolímers conductorsÀrees temàtiques de la UPC::Enginyeria químicaPoly(hydroxymethyl-3,4-ethylendioxythiophene) (PHMeDOT), a very electroactive polythiophene derivative bearing a dioxane ring fused onto the thiophene ring and an exocyclic hydroxymethyl substituent, is able to electrocatalyze the oxidation of glucose in the presence of interferents (e.g. dopamine, uric acid and ascorbic acid) without the assistance of an enzymatic catalyst. In this work, after demonstrating that the chronoamperometric response of such polythiophene derivatives allows discrimination of glucose from fructose, the PHMeDOT¿sugar recognition mechanism has been investigated using atomistic computer simulations. More specifically, molecular dynamics simulations were conducted on model systems formed by a steel surface covered with a nanometric film of PHMeDOT, which was immersed in an aqueous environment with a few explicit sugar molecules (i.e. glucose or fructose). Analyses of the trajectories indicate that glucose interacts with PHMeDOT forming a well-defined network of specific hydrogen bonds. More specifically, glucose prefers to interact as a hydrogen bonding donor using the hydroxyl group tether to the main sugar ring, while PHMeDOT acts as the hydrogen bonding acceptor. Interestingly, (glucose)O–H¿O(PHMeDOT) interactions involve, as hydrogen bonding acceptors, not only the oxygen atoms of the dioxane ring but also the oxygen atom of the exocyclic hydroxymethyl substituent, which is a differential trend with respect to the other polythiophene derivatives that do not exhibit sensing ability. In contrast, fructose does not present such well-defined patterns of specific interactions, especially those that are distinctive because of the exocyclic hydroxymethyl substituent, making the experimental observations understandable.Royal Society of Chemistry (RSC)20192019-01-0120192019-11-18journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/172649https://dx.doi.org/10.1039/c9cp00567freponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/1726492026-05-27T15:37:01Z
dc.title.none.fl_str_mv A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
title A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
spellingShingle A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
Zanuy Gomara, David|||0000-0001-7704-2178
Molecular dynamics
Glucose
Conducting polymers
Dinàmica molecular
Glucosa
Polímers conductors
Àrees temàtiques de la UPC::Enginyeria química
title_short A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
title_full A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
title_fullStr A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
title_full_unstemmed A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
title_sort A molecular dynamics study on glucose molecular recognition by a non-enzymatic selective sensor based on a conducting polymer
dc.creator.none.fl_str_mv Zanuy Gomara, David|||0000-0001-7704-2178
Fabregat Jové, Georgina|||0000-0001-8967-9950
Ferreira, Carlos Arthur
Alemán Llansó, Carlos|||0000-0003-4462-6075
author Zanuy Gomara, David|||0000-0001-7704-2178
author_facet Zanuy Gomara, David|||0000-0001-7704-2178
Fabregat Jové, Georgina|||0000-0001-8967-9950
Ferreira, Carlos Arthur
Alemán Llansó, Carlos|||0000-0003-4462-6075
author_role author
author2 Fabregat Jové, Georgina|||0000-0001-8967-9950
Ferreira, Carlos Arthur
Alemán Llansó, Carlos|||0000-0003-4462-6075
author2_role author
author
author
dc.subject.none.fl_str_mv Molecular dynamics
Glucose
Conducting polymers
Dinàmica molecular
Glucosa
Polímers conductors
Àrees temàtiques de la UPC::Enginyeria química
topic Molecular dynamics
Glucose
Conducting polymers
Dinàmica molecular
Glucosa
Polímers conductors
Àrees temàtiques de la UPC::Enginyeria química
description Poly(hydroxymethyl-3,4-ethylendioxythiophene) (PHMeDOT), a very electroactive polythiophene derivative bearing a dioxane ring fused onto the thiophene ring and an exocyclic hydroxymethyl substituent, is able to electrocatalyze the oxidation of glucose in the presence of interferents (e.g. dopamine, uric acid and ascorbic acid) without the assistance of an enzymatic catalyst. In this work, after demonstrating that the chronoamperometric response of such polythiophene derivatives allows discrimination of glucose from fructose, the PHMeDOT¿sugar recognition mechanism has been investigated using atomistic computer simulations. More specifically, molecular dynamics simulations were conducted on model systems formed by a steel surface covered with a nanometric film of PHMeDOT, which was immersed in an aqueous environment with a few explicit sugar molecules (i.e. glucose or fructose). Analyses of the trajectories indicate that glucose interacts with PHMeDOT forming a well-defined network of specific hydrogen bonds. More specifically, glucose prefers to interact as a hydrogen bonding donor using the hydroxyl group tether to the main sugar ring, while PHMeDOT acts as the hydrogen bonding acceptor. Interestingly, (glucose)O–H¿O(PHMeDOT) interactions involve, as hydrogen bonding acceptors, not only the oxygen atoms of the dioxane ring but also the oxygen atom of the exocyclic hydroxymethyl substituent, which is a differential trend with respect to the other polythiophene derivatives that do not exhibit sensing ability. In contrast, fructose does not present such well-defined patterns of specific interactions, especially those that are distinctive because of the exocyclic hydroxymethyl substituent, making the experimental observations understandable.
publishDate 2019
dc.date.none.fl_str_mv 2019
2019-01-01
2019
2019-11-18
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/2117/172649
https://dx.doi.org/10.1039/c9cp00567f
url https://hdl.handle.net/2117/172649
https://dx.doi.org/10.1039/c9cp00567f
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
publisher.none.fl_str_mv Royal Society of Chemistry (RSC)
dc.source.none.fl_str_mv reponame:UPCommons. Portal del coneixement obert de la UPC
instname:Universitat Politècnica de Catalunya (UPC)
instname_str Universitat Politècnica de Catalunya (UPC)
reponame_str UPCommons. Portal del coneixement obert de la UPC
collection UPCommons. Portal del coneixement obert de la UPC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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