Abstract
In this study, a new family of poly(ε-caprolactone) (PCL) copolymers that bear oligo(ethylene glycol) (OEG) moieties is described. The synthesis of three different oligo(ethylene glycol) functionalized epoxide monomers derived from 2-methyl-4-pentenoic acid, and their copolymerization with ε-caprolactone (CL) to poly(CL-co-OEG-MPO) copolymers is presented. The statistical copolymerization initiated with SnOct2/BnOH yielded the copolymers with varying OEG content and composition. The linear relationship between feed ratio and incorporation of the OEG co-monomer enables control over backbone functional group density. The introduction of OEG moieties influenced both the thermal and the hydrophilic characteristics of the copolymers. Both increasing OEG length and backbone content resulted in a decrease in static water contact angle. The introduction of OEG side chains in the PCL copolymers had no adverse influence on MC-3TE3-E1 cell interaction. However, changes to cell form factor (Φ) were observed. While unmodified PCL promoted elongated (anisotropic) morphologies (Φ = 0.094), PCL copolymer with tri-ethylene glycol side chains at or above seven percent backbone incorporation induced more isotropic cell morphologies (Φ = 0.184) similar to those observed on glass controls (Φ = 0.151).
Highlights
Biodegradable polyesters are widely used in various biological and medical applications [1,2,3] such as tissue engineering [4,5], injectable and implantable drug delivery systems [6], medical devices, orthopaedic implants [7], and bioactive coatings [8]
PCL in comparison to PLA or poly(glycolic acid) (PGA) is considerably more hydrophobic [15]. This decreased hydrophilicity derives from the polymer backbone that consists of hydrophobic aliphatic hexane units that are linked with ester moieties which limits water uptake and prolongs the onset of hydrolytic degradation
We recently described the synthesis of functionalized PCL via the copolymerization of e-caprolactone (CL) with a novel a,v-epoxy esters derived from 2-methyl-4-pentenoic acid [27]
Summary
Biodegradable polyesters are widely used in various biological and medical applications [1,2,3] such as tissue engineering [4,5], injectable and implantable drug delivery systems [6], medical devices, orthopaedic implants [7], and bioactive coatings [8]. The high crystallinity of PCL up to 69% [13] in comparison to poly(glycolic acid) (PGA) (46% to 52%), poly(Llactic acid) (L-PLA) (0% to 7%), and poly(D,L-lactic acid) (D,L-PLA) (amorphous) results in the formation of phase separated microstructures composed of large spherulites. This poses some challenges in achieving homogeneous degradation in vivo, but affords considerable life-time of 24 to 36 months under physiological conditions [14]. In spite of eco-credentials of PCL it has seen limited use outside the medical arena and this could change if new strategies are developed to introduce diversity in chemical structure and function
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