TY - JOUR
T1 - Choline-Functionalized Supramolecular Copolymers
T2 - Toward Antimicrobial Activity against Streptococcus pneumoniae
AU - Vleugels, Marle E.J.
AU - Varela-Aramburu, Silvia
AU - de Waal, Bas F.M.
AU - Schoenmakers, Sandra M.C.
AU - Maestro, Beatriz
AU - Palmans, Anja R.A.
AU - Sanz, Jesús M.
AU - Meijer, E.W.
PY - 2021/12/13
Y1 - 2021/12/13
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85120875330&partnerID=8YFLogxK
U2 - 10.1021/acs.biomac.1c01293
DO - 10.1021/acs.biomac.1c01293
M3 - Article
C2 - 34846847
SN - 1525-7797
VL - 22
SP - 5363
EP - 5373
JO - Biomacromolecules
JF - Biomacromolecules
IS - 12
ER -