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A Route to Aliphatic Poly(ester)s with Thiol Pendant Groups: From Monomer Design to Editable Porous Scaffolds
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology. University of Salerno, Italy.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.ORCID iD: 0000-0002-1922-128X
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology. University of Sannio, Italy.ORCID iD: 0000-0001-9699-9151
2016 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 17, no 4, 1383-1394 p.Article in journal (Refereed) Published
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Text
Abstract [en]

Biodegradable aliphatic polyesters such as poly(lactide) and poly(ϵ-caprolactone), largely used in tissue engineering applications, lack suitable functional groups and biological cues to enable interactions with cells. Because of the ubiquity of thiol groups in the biological environment and the pliability of thiol chemistry, we aimed to design and synthesize poly(ester) chains bearing pendant thiol-protected groups. To achieve this, 3-methyl-6-(tritylthiomethyl)-1,4-dioxane-2,5-dione, a lactide-type monomer possessing a pendant thiol-protected group, was synthesized. This molecule, when used as a monomer in controlled ring-opening polymerization in combination with lactide and ϵ-caprolactone, appeared to be a convenient "building block" for the preparation of functionalized aliphatic copolyesters, which were easily modified further. A polymeric sample bearing pyridyl disulfide groups, able to bind a cysteine-containing peptide, was efficiently obtained from a two-step modification reaction. Porous scaffolds were then prepared by blending this latter copolymer sample with poly(l-lactide-co-ϵ-caprolactone) followed by salt leaching. A further disulfide exchange reaction performed in aqueous medium formed porous scaffolds with covalently linked arginine-glycine-aspartic acid sequences. The scaffolds were characterized by thermal and mechanical tests, and scanning electron microscopy surface images revealed a highly porous morphology. Moreover, a cytotoxicity test indicated good cell viability.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 17, no 4, 1383-1394 p.
Keyword [en]
Ring-Opening Polymerization, Functionalized Poly(Lactic Acid), Dimethyl(Salicylaldiminato)Aluminum Compounds, Biomedical Applications, Epsilon-Caprolactone, O-Carboxyanhydrides, Peptide-Synthesis, Mercapto Groups, Amino-Acids, Polyesters
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-187075DOI: 10.1021/acs.biomac.6b00005ISI: 000374076900016PubMedID: 26915640Scopus ID: 2-s2.0-84964661506OAI: oai:DiVA.org:kth-187075DiVA: diva2:929206
Funder
VINNOVA, 201304323EU, FP7, Seventh Framework Programme, GROWTH 291795Swedish Research Council, 621-2013-3764
Note

QC 20160518

Available from: 2016-05-18 Created: 2016-05-17 Last updated: 2016-05-18Bibliographically approved

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