Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae

Dynamic binding events are key to arrive at functionality in nature, and these events are often governed by electrostatic or hydrophobic interactions. Synthetic supramolecular polymers are promising candidates to obtain biomaterials that mimic this dynamicity. Here, we created four new functional mo...

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Authors: Vleugels, Merle, Varela-Aramburu, Silvia, de Waal, Bas, Schoenmakers, Sandra, Maestro García-Donas, María Beatriz, Palmans, Anja, Sanz, Jesús, Meijer, Bert
Format: article
Publication Date:2021
Country:España
Institution:Universidad Complutense de Madrid (UCM)
Repository:Docta Complutense
Language:English
OAI Identifier:oai:docta.ucm.es:20.500.14352/95503
Online Access:https://hdl.handle.net/20.500.14352/95503
Access Level:Open access
Keyword:577.1
Supramolecular polymers
Multivalent fibers
Self-assembly
Biomaterials
Choline-binding proteins
Atropine
Pneumococcus
Bioquímica (Química)
2403 Bioquímica
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oai_identifier_str oai:docta.ucm.es:20.500.14352/95503
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spelling Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniaeVleugels, MerleVarela-Aramburu, Silviade Waal, BasSchoenmakers, SandraMaestro García-Donas, María BeatrizPalmans, AnjaSanz, JesúsMeijer, Bert577.1Supramolecular polymersMultivalent fibersSelf-assemblyBiomaterialsCholine-binding proteinsAtropinePneumococcusBioquímica (Química)2403 BioquímicaDynamic binding events are key to arrive at functionality in nature, and these events are often governed by electrostatic or hydrophobic interactions. Synthetic supramolecular polymers are promising candidates to obtain biomaterials that mimic this dynamicity. Here, we created four new functional monomers based on the benzene-1,3,5-tricarboxamide (BTA) motif. Choline or atropine groups were introduced to obtain functional monomers capable of competing with the cell wall of Streptococcus pneumoniae for binding of essential choline-binding proteins (CBPs). Atropine-functionalized monomers BTA-Atr and BTA-Atr3 were too hydrophobic to form homogeneous assemblies, while choline-functionalized monomers BTA-Chol and BTA-Chol3 were unable to form fibers due to charge repulsion. However, copolymerization of BTA-Chol3 with non-functionalized BTA-(OH)3 yielded dynamic fibers, similar to BTA-(OH)3. These copolymers showed an increased affinity toward CBPs compared to free choline due to multivalent effects. BTA-based supramolecular copolymers are therefore a versatile platform to design bioactive and dynamic supramolecular polymers with novel biotechnological properties.American Chemical SocietyUniversidad Complutense de Madrid20212021-01-0120212021-01-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://hdl.handle.net/20.500.14352/95503reponame:Docta Complutenseinstname:Universidad Complutense de Madrid (UCM)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:docta.ucm.es:20.500.14352/955032026-06-02T12:44:21Z
dc.title.none.fl_str_mv Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
title Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
spellingShingle Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
Vleugels, Merle
577.1
Supramolecular polymers
Multivalent fibers
Self-assembly
Biomaterials
Choline-binding proteins
Atropine
Pneumococcus
Bioquímica (Química)
2403 Bioquímica
title_short Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
title_full Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
title_fullStr Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
title_full_unstemmed Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
title_sort Choline-functionalized supramolecular copolymers: toward antimicrobial activity against Streptococcus pneumoniae
dc.creator.none.fl_str_mv Vleugels, Merle
Varela-Aramburu, Silvia
de Waal, Bas
Schoenmakers, Sandra
Maestro García-Donas, María Beatriz
Palmans, Anja
Sanz, Jesús
Meijer, Bert
author Vleugels, Merle
author_facet Vleugels, Merle
Varela-Aramburu, Silvia
de Waal, Bas
Schoenmakers, Sandra
Maestro García-Donas, María Beatriz
Palmans, Anja
Sanz, Jesús
Meijer, Bert
author_role author
author2 Varela-Aramburu, Silvia
de Waal, Bas
Schoenmakers, Sandra
Maestro García-Donas, María Beatriz
Palmans, Anja
Sanz, Jesús
Meijer, Bert
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidad Complutense de Madrid
dc.subject.none.fl_str_mv 577.1
Supramolecular polymers
Multivalent fibers
Self-assembly
Biomaterials
Choline-binding proteins
Atropine
Pneumococcus
Bioquímica (Química)
2403 Bioquímica
topic 577.1
Supramolecular polymers
Multivalent fibers
Self-assembly
Biomaterials
Choline-binding proteins
Atropine
Pneumococcus
Bioquímica (Química)
2403 Bioquímica
description Dynamic binding events are key to arrive at functionality in nature, and these events are often governed by electrostatic or hydrophobic interactions. Synthetic supramolecular polymers are promising candidates to obtain biomaterials that mimic this dynamicity. Here, we created four new functional monomers based on the benzene-1,3,5-tricarboxamide (BTA) motif. Choline or atropine groups were introduced to obtain functional monomers capable of competing with the cell wall of Streptococcus pneumoniae for binding of essential choline-binding proteins (CBPs). Atropine-functionalized monomers BTA-Atr and BTA-Atr3 were too hydrophobic to form homogeneous assemblies, while choline-functionalized monomers BTA-Chol and BTA-Chol3 were unable to form fibers due to charge repulsion. However, copolymerization of BTA-Chol3 with non-functionalized BTA-(OH)3 yielded dynamic fibers, similar to BTA-(OH)3. These copolymers showed an increased affinity toward CBPs compared to free choline due to multivalent effects. BTA-based supramolecular copolymers are therefore a versatile platform to design bioactive and dynamic supramolecular polymers with novel biotechnological properties.
publishDate 2021
dc.date.none.fl_str_mv 2021
2021-01-01
2021
2021-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/20.500.14352/95503
url https://hdl.handle.net/20.500.14352/95503
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
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
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
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:Docta Complutense
instname:Universidad Complutense de Madrid (UCM)
instname_str Universidad Complutense de Madrid (UCM)
reponame_str Docta Complutense
collection Docta Complutense
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869416198916014080
score 15,301629

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