Supramolecular surface functionalization via catechols for the improvement of cell–material interactions

Abstract

Optimization of cell-material interactions is crucial for the success of synthetic biomaterials in guiding tissue regeneration. To do so, catechol chemistry is often used to introduce adhesiveness into biomaterials. Here, a supramolecular approach based on ureido-pyrimidinone (UPy) modified polymers is combined with catechol chemistry in order to achieve improved cellular adhesion onto supramolecular biomaterials. UPy-modified hydrophobic polymers with non-cell adhesive properties are developed that can be bioactivated via a modular approach using UPy-modified catechols. It is shown that successful formulation of the UPy-catechol additive with the UPy-polymer results in surfaces that induce cardiomyocyte progenitor cell adhesion, cell spreading, and preservation of cardiac specific extracellular matrix production. Hence, by functionalizing supramolecular surfaces with catechol functionalities, an adhesive supramolecular biomaterial is developed that allows for the possibility to contribute to biomaterial-based regeneration.

Carbohydrate‐Responsive Surface Adhesion Based on the Dynamic Covalent Chemistry of Phenylboronic Acid‐ and Catechol‐Containing Polymer Brushes

“…For the functionalization of surfaces with specific polymer brushes containing catechol or phenylboronic acids, controlled radical polymerization, such as the reversible addition‐fragmentation chain transfer polymerization (RAFT) or the atom‐transfer radical polymerization (ATRP) are well explored . Catechol‐based initiators are often used for ATRP, because they tend to bind strongly to a wide range of surfaces . Zhang et al.…”

“…[16] Soboczenski and Edwards discovered the reaction of boronic acids with 1,2-and 1,3-diols in the middle of the 20th century. [33,34] Zhang et al polymerized phenylboronic acids via ATRP on iron oxide nanoparticles to enrich glycoproteins selectively. [20] Thestrongest interactions are obtained by combining phenylboronic acids,which have alow pK a ,with catechol, which has ap erfect geometry for binding owing to its rigid aromatic backbone.Inthe literature several examples of boronic acids as receptors or sensors for carbohydrates can be found.…”

“…[30][31][32] Catechol-based initiators are often used for ATRP,b ecause they tend to bind strongly to aw ide range of surfaces. [33,34] Zhang et al polymerized phenylboronic acids via ATRP on iron oxide nanoparticles to enrich glycoproteins selectively. [35] Ye et al functionalized silica particles with boronic acid functionalized polymer brushes by ATRP.Asaresult of the multivalencyof the fluorescent boronic acid, they could identify and separate carbohydrates.…”

Kohlenhydratresponsive Oberflächenhaftung basierend auf dynamisch kovalenter Chemie zwischen Phenylboronsäure‐ und Catecholpolymerbürsten

“…[15] Die DCC nutzt kovalente aber reversible Bindungen, welche in einem thermodynamischen Gleichgewicht stehen und leicht auf ¾nderungen in ihrer Zusammensetzung reagieren. [33,34] Zhang und Mitarbeiter nutzten Eisenoxidnanopartikel, welche sie zuvor über ATRP mit Phenylboronsäuren funktionalisierten, um Glycoproteine selektiv anzureichern. [16] In der Mitte des 20.…”

“…[30][31][32] Catecholbasierte Polymerinitiatoren werden dank ihrer guten Bindung zu verschiedensten Oberflächen häufig in der ATRP eingesetzt. [33,34] Zhang und Mitarbeiter nutzten Eisenoxidnanopartikel, welche sie zuvor über ATRP mit Phenylboronsäuren funktionalisierten, um Glycoproteine selektiv anzureichern. [35] Ye und Mitarbeiter funktionalisierten Silikapartikel mittels ATRP mit fluoreszierenden Boronsäurepolymerbürsten.…”