Novel Conducting and Biodegradable Copolymers with Noncytotoxic Properties toward Embryonic Stem Cells

Abstract

Electroactive biomaterials that are easily processed as scaffolds with good biocompatibility for tissue regeneration are difficult to design. Herein, the synthesis and characterization of a variety of novel electroactive, biodegradable biomaterials based on poly(3,4-ethylenedioxythiphene) copolymerized with poly(d,l lactic acid) (PEDOT-co-PDLLA) are presented. These copolymers were obtained using (2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methanol (EDOT-OH) as an initiator in a lactide ring-opening polymerization reaction, resulting in EDOT–PDLLA macromonomer. Conducting PEDOT-co-PDLLA copolymers (in three different proportions) were achieved by chemical copolymerization with 3,4-ethylenedioxythiophene (EDOT) monomers and persulfate oxidant. The PEDOT-co-PDLLA copolymers were structurally characterized by 1H NMR and Fourier transform infrared spectroscopy. Cyclic voltammetry confirmed the electroactive character of the materials, and conductivity measurements were performed via electrochemical impedance spectroscopy. In vitro biodegradability was evaluated using proteinase K over 35 days, showing 29–46% (w/w) biodegradation. Noncytotoxicity was assessed by adhesion, migration, and proliferation assays using embryonic stem cells (E14.tg2a); excellent neuronal differentiation was observed. These novel electroactive and biodegradable PEDOT-co-PDLLA copolymers present surface chemistry and charge density properties that make them potentially useful as scaffold materials in different fields of applications, especially for neuronal tissue engineering.

Conducting Polymer Grafting: Recent and Key Developments

“…Then, PPy-g-PCL was achieved by oxidative polymerization of Py-g-PCL monomer. Recently, Sliva et al [73] reported a series of copolymer of PEDOT with poly(d,l-lactic acid) (PEDOT-co-PDLLA) as a scaffold materials for neuronal tissue engineering. The copolymers were synthesized via subsequent EDOT−PDLLA macromonomer production using ROP of lactide in presence of EDOT-OH, followed by chemical copolymerization of EDOT monomers.…”

An amphiphilic, heterografted polythiophene copolymer containing biocompatible/biodegradable side chains for use as an (electro)active surface in biomedical applications

“…The new amphiphilic heterografted copolymer was synthesized by combining the so-called "macromonomer" or "grafting through" technique, 28,29,[33][34][35] via oxidative polycondensation reaction of an equimolecular mixture of two thiophene-ended macromonomers (Scheme 1), a classical method for CPs chemical synthesis. The hydrophilic macromonomer, Th-PEG, was synthesized by chain-end functionalization method, through Steglich esterification of hydroxyl group of PEG2000 (Scheme 1A), being the first time it has been reported.…”

Gold Nanoparticles and [PEDOT-Poly(D,L-Lactic Acid)] Composite: Synthesis, Characterization and Application to H2O2 Sensing

“…The first step of the synthesis was to obtain an electroactive macromonomer of EDOT-PDLLA, which was developed in our previous study 34 (Figure 1a). Briefly, 3,6-dimethyl-1,4-dioxane-2,5-dione (2.76 g, 20 mmol), hydroxymethyl EDOT (100 mg, 0.6 mmol) and tin(II)-2-ethylhexanoate (0.016 mL, 0.05 mmol) were stirred at 110 °C with 7 mL of toluene for 24 h. The solvent was removed by distillation under reduced pressure (2000 Pa, 60 °C).…”

“…The polymerization of this electroactive macromonomer was tried by electrochemical methods, but (i) only oligomers were formed due to the high solubility in organic solvents, and (ii) no electroactive properties were found. Additionally, the chemical synthesis of a new PEDOT-co-PDLLA copolymer 34 with conductivity, biodegradability and noncytotoxicity properties tested for embryonic stem cells (E14.tg2a) was reported by using the electroactive macromonomer.…”