Inhibition of Protein and Cell Attachment on Materials Generated from N-(2-Hydroxypropyl) Acrylamide

Abstract

Effective control over biointerfacial interactions is essential for a broad range of biomedical applications. At this point in time, only a relatively small range of radically polymerizable monomers have been described that are able to generate low fouling polymer materials and surfaces. The most important examples that have been successfully used in the context of the reduction of nonspecific protein adsorption and subsequent cell attachment include PEG-based monomers such as poly(ethylene glycol) methacrylate (PEGMA), zwitterionic monomers such as 2-methacryloyloxyethyl phosphorylcholine and noncharged monomers such as acrylamide and N-(2-hydroxypropyl) methacrylamide (HPMAm). However, issues such as oxidative degradation and poor polymerization characteristics limit the applicability of most of these candidates. Here we have synthesized the monomer N-(2-hydroxypropyl) acrylamide (HPAm), examined its polymerization kinetics and evaluated its suitability for RAFT mediated polymerization in comparison to HPMAm. We also synthesized hydrogels using HPMAm and HPAm and evaluated the ability of HPAm polymers to occlude protein adsorption and cell attachment. In RAFT-controlled polymerization, much faster (8×) polymerization was observed for HPAm relative to HPMAm and better control was achieved over the molecular weight distribution. The performance of hydrogels prepared from HPAm in the prevention of protein adsorption and cellular attachment was equivalent to or better than that observed for materials made from HPMAm and PEG. These results open the door for HPAm based polymers in applications where effective control over biointerfacial interactions is required.

Promising biocompatible hydrogels of crosslinked polyelectrolytes for biomedical applications

“…Concerning their biocompatibility the HGs of this study can compete with hyaluronic acid or alginate based HGs, which exhibit longstanding clinical use [13,14].…”

“…1-vinyl-3-ethylimidazolium bromide [11,12], 1-vinyl-3-isopropylimidazolium bromide [13] and 2-hydroxypropyl methacrylamide [14] were synthessed according to a literature procedures. All other monomers were purchased from Sigma Aldrich or TCI and used as received.…”

RAFT Polymerization – Then and Now

“…These will not be recounted in detail here. Significant developments have been made in electroactive and optoelectronic polymers (101) (organic semiconductors (202)(203)(204)(205), materials for organic light emitting diodes (204), photochromics (206)), the biomedical field (therapeutic delivery (184,(187)(188)(189)(207)(208)(209), surfaces (210,211) personal care (212)), and industrial applications (rheology control agents (213), surface functionalized membranes (214)) and many other areas.…”

A Novel Approach to Quantitatively Assess the Uniformity of Binary Colloidal Crystal Assemblies

“…To control biointerfacial interactions through surface chemistry many sophisticated surface modification strategies have been developed. These approaches include the fabrication of polymeric coatings to prevent biofouling, such as the grafting of poly(ethylene glycol) [3][4][5], polyacrylamide [6][7][8], poly(N-hydroxy methacrylamide) [9] and poly(N-hydroxy acrylamide) [10] or zwitterionic polymer coatings [11,12], amongst others. Through the simultaneous or subsequent immobilisation of bioactive signals such as peptides onto these non-fouling backgrounds it is possible to generate surfaces capable of directing specific cellular responses such as attachment and proliferation.…”