Choline-Functionalized Supramolecular Copolymers: Toward Antimicrobial Activity against Streptococcus pneumoniae

Marle E.J. Vleugels, Silvia Varela-Aramburu, Bas F.M. de Waal, Sandra M.C. Schoenmakers, Beatriz Maestro, Anja R.A. Palmans, Jesús M. Sanz (Corresponding author), E.W. Meijer (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)
50 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)5363-5373
Number of pages11
JournalBiomacromolecules
Volume22
Issue number12
Early online date30 Nov 2021
DOIs
Publication statusPublished - 13 Dec 2021

Funding

FundersFunder number
FEDER-EU-10.13039/501100011033
Horizon 2020 Framework Programme788618
European Research Council
Ministerie van Onderwijs, Cultuur en Wetenschap024.001.035
Nederlandse Organisatie voor Wetenschappelijk Onderzoek024.003.013
Ministerio de Ciencia e InnovaciónPID2019-105126RB-I00
Agencia Estatal de Investigación

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