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

Area of Science:

• Supramolecular chemistry
• Biomaterials science
• Polymer chemistry

Background:

• Dynamic binding events are crucial for biological functions, often driven by electrostatic and hydrophobic interactions.
• Synthetic supramolecular polymers offer a route to biomaterials that mimic natural dynamic processes.

Purpose of the Study:

• To design and synthesize functional monomers based on the benzene-1,3,5-tricarboxamide (BTA) motif.
• To create supramolecular polymers capable of competing with bacterial cell walls for binding essential choline-binding proteins (CBPs).

Main Methods:

• Synthesis of four new functional monomers: two atropine-functionalized (BTA-Atr) and two choline-functionalized (BTA-Chol).
• Investigation of monomer assembly properties, including hydrophobicity and charge effects on fiber formation.
• Copolymerization of BTA-Chol with non-functionalized BTA-(OH) to form dynamic fibers.

Main Results:

• Atropine-functionalized monomers were too hydrophobic for homogeneous assembly.
• Choline-functionalized monomers failed to form fibers due to charge repulsion.
• Copolymerization of BTA-Chol with BTA-(OH) successfully yielded dynamic fibers with increased affinity for CBPs due to multivalent effects.

Conclusions:

• Benzene-1,3,5-tricarboxamide-based supramolecular copolymers represent a versatile platform for designing bioactive materials.
• These dynamic supramolecular polymers exhibit novel biotechnological properties.
• The study demonstrates a strategy for creating functional biomaterials by controlling monomer interactions and copolymerization.