Abstract
Main chain polyesters have been extensively used in the biomedical field. Despite their many advantages, including biocompatibility, biodegradability, and others, these materials are rather inert and lack specific functionalities which will endow them with additional biological and responsive properties. In this work, novel pH-responsive main chain polyesters have been prepared by a conventional condensation polymerization of a vinyl functionalized diol with a diacid chloride, followed by a photo-induced thiol-ene click reaction to attach functional carboxylic acid side-groups along the polymer chains. Two different mercaptocarboxylic acids were employed, allowing to vary the alkyl chain length of the polymer pendant groups. Moreover, the degree of modification, and as a result, the carboxylic acid content of the polymers, was easily tuned by varying the irradiation time during the click reaction. Both these parameters, were shown to strongly influence the responsive behavior of the polyesters, which presented adjustable pKα values and water solubilities. Finally, the difunctional polyesters bearing the alkene and carboxylic acid functionalities enabled the preparation of cross-linked polyester films by chemically linking the pendant vinyl bonds on the polymer side groups. The biocompatibility of the cross-linked polymers films was assessed in L929 fibroblast cultures and showed that the cell viability, proliferation, and attachment were greatly promoted on the polyester surface, bearing the shorter alkyl chain length side groups and the higher fraction of carboxylic acid functionalities.
Highlights
Aliphatic polyesters such as polylactide (PLA), polycaprolactone (PCL), and polyglycolide have been extensively investigated as promising biodegradable biomaterials in drug delivery and tissue engineering applications due to their biocompatibility with a variety of cells and tissues [1,2,3]
Motivated by the great interest in polyesters as biodegradable biomaterials for use in tissue engineering applications and the recent advances in the development of novel functional polyesters, we report in this study the synthesis of “smart”, pH-responsive biodegradable polyesters bearing alkene/carboxylic acid side groups and their potential for use in tissue engineering applications
The functional polyesters P(TPAE-alt-AD) containing pendant alkene groups were prepared by a polycondensation reaction of trimethylolpropane allyl ether (TPAE), an alkenefunctionalized diol, and adipoyl chloride (ADC), a diacyl chloride with six carbon atoms
Summary
Aliphatic polyesters such as polylactide (PLA), polycaprolactone (PCL), and polyglycolide have been extensively investigated as promising biodegradable biomaterials in drug delivery and tissue engineering applications due to their biocompatibility with a variety of cells and tissues [1,2,3]. Besides these notable properties, polyesters present several drawbacks, among which, the most important are their hydrophobicity and the absence of functional pendant groups along the polymer backbone. It is evident from the above that the presence of functional pendant groups along the polyester backbone is highly desirable and can lead to novel materials with diverse, multi-functional properties that can have great potential
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