Abstract
Elastomeric poly-ester materials have extraordinary potential for soft tissue engineering applications. In connection, in the last 10 years, cross-linkable oligo-(polyethylene glycol fumarate)s emerged as promising materials for obtaining hydrogels for bone tissue engineering applications. In this work we prepared a new family of photo-curable poly-(ethylene glycol)–fumarate elastomers with controlled structural composition. These novel elastomers were obtained by photo-curing of fumarate pre-polymers based on diethylene glycol and oligo-ethylene glycols (PEGs 200 and 400), under extremely mild experimental conditions using a low power UV source. The synthesis of fumarate pre-polymers, which were obtained by thermal poly-condensation, and the photo-curing process, were both here discussed on the basis of their structural differences and proposed operating mechanisms. Finally, the photo-radical cross-linking reactions were performed in the presence of anti-cancer drugs (doxorubicin and paclitaxel), in order to evaluate the potential application of the elastomers as new eluting systems. Thus, different release profiles were obtained for hydrophilic (doxorubicin) and hydrophobic (paclitaxel) anticancer drugs, and these differences are discussed on the basis of the structure of the elastomers.
Highlights
The preparation of new synthetic polyester materials, with tailored mechanical properties and degradation pro les, has been crucial for the development of tissue engineering approaches for regenerative medicine and for the constructions of new drug release systems for cancer treatment.The radical mediated cross-linking reactions ofacrylic acid esters and related compounds are well known processes, traditionally used for the preparation of thermosets and various resins.[1]
Poly-(ethylene glycol) (PEG)-based fumarate pre-polymers can be prepared by the reaction of fumaryl chloride and PEG in the presence of triethylamine as HCl scavenger, or by Steglich esteri cation of fumaric acid and PEG, using DCC for the activation of the carboxyl group and DMAP as catalyst
Given that the poly-condensation reactions were not performed in the presence of a radical polymerization inhibitor, thermally-induced, radical cross-linking at the level of the double bond of fumaric acid could occur
Summary
The preparation of new synthetic polyester materials, with tailored mechanical properties and degradation pro les, has been crucial for the development of tissue engineering approaches for regenerative medicine and for the constructions of new drug release systems for cancer treatment.The radical mediated cross-linking reactions of (met)acrylic acid esters and related compounds are well known processes, traditionally used for the preparation of thermosets and various resins.[1]. The preparation of new synthetic polyester materials, with tailored mechanical properties and degradation pro les, has been crucial for the development of tissue engineering approaches for regenerative medicine and for the constructions of new drug release systems for cancer treatment. Poly-(ethylene glycol) (PEG) is an important hydrophilic polymer of intense application for the improvement of the therapeutic properties of labile peptide and protein biopharmaceuticals (PEGylation technology). Among the various PEG-based materials that have been published, most of the attention has been focused PEG–fumarate hydrogels,[3,4,5] and other cross-linked PEG–fumarates, such as PEG–fumarate cross-linked with PEG-diacrylate;[6] all of which appear as extremely promising candidates for bone tissue engineering
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