Integrating Sugar and Dopamine into One Polymer: Controlled Synthesis and Robust Surface Modification

Abstract

Glycopolymers attached to a surface possess the ability to bind to certain carbohydrate binding proteins in a highly specific manner, and because of this, the fabrication of glycopolymer-modified surfaces has evolved as an effective route toward bioresponsive systems. Poly(N-3,4-dihydroxybenzenethyl methacrylamide-co-2-(methacrylamido) glucopyranose) copolymers, containing sugar and catechol functionalities, are for the first time successfully prepared in a well-controlled manner via room temperature single-electron transfer initiation and propagation through radical addition fragmentation chain transfer technique. The polymerization behavior is investigated and it presents controlled features with first-order kinetics and linear relationships between molecular weights and monomer conversions. Moreover, the copolymers are used to modify different types of surfaces (silicon, steel, and plastic), the properties of the surfaces and the specific lectin-binding abilities are investigated by a combination of water contact angle, Fourier transform infrared spectroscopy (FT-IR), X-ray photoelectron spectra, scanning electron microscopy with energy dispersive X-ray (SEM/EDX), atomic force microscopy, and confocal microscope measurements.

Nano‐Star‐Shaped Polymers for Drug Delivery Applications

“…RAFT polymerization utilizes chain‐transfer agents. It then proceeds by a degenerative transfer process, with the chain‐transfer agents being compounds that contain thiocarbonylthio moieties . Among all the LRP techniques mentioned, RAFT polymerization is the most versatile, being able to tolerate a myriad of reaction conditions .…”

Thiol-Reactive Polymers for Titanium Interfaces: Fabrication of Antimicrobial Coatings

“…In particular, mimicking the surface attachment of mussel adhesive proteins that are rich in dopamine (DOPA) has attracted significant interest. It has been reported that the catechol subunit is primarily responsible for their strong affinity toward metal and metal oxide surfaces. − To date, the catechol unit has been widely employed as an anchor for strong attachment of variety of polymeric materials onto inorganic surfaces. − Indeed, a few studies have reported coating copolymers bearing pendant dopamine and reactive groups on solid substrates for biomolecular immobilization. − But most of these reports have focused on conjugation of amine bearing bioactive agents using couplings based on activated esters and epoxides. Development of a robust polymeric coating for the modification of metal and metal oxide based materials where conjugation of a bioactive material possessing a naturally occurring thiol group or a synthetically incorporated amino acid would offer an attractive functional interface.…”

Sunlight-Induced RAFT Synthesis of Multifaceted Glycopolymers with Surface Anchoring, In Situ AgNP Formation, and Antibacterial Properties

“…A protected monomer strategy has been used to synthesize a catechol-containing polymer . Using a dopamine-bearing initiator/iniferter or monomer, dopamine-containing polymers were prepared successfully via methods such as single-electron-transfer living-radical polymerization and photoiniferter-mediated polymerization, where the polymerization normally proceeds at room temperature. ,,,, In our previous reports, sugar moieties and catechol groups were successfully integrated into one polymer via single-electron-transfer and reversible addition–fragmentation chain-transfer (SET-RAFT) living-radical polymerization, which could be immobilized onto many surfaces, and to guide cell growth . However, SET-RAFT is not a good choice for preparing the designed polymer in this project because the catalyst copper can complex with carboxylic groups.…”