A poly(glycerol sebacate) based photo/thermo dual curable biodegradable and biocompatible polymer for biomedical applications

Abstract

Due to its biomimetic mechanical properties to soft tissues, excellent biocompatibility and biodegradability, poly (glycerol sebacate) (PGS) has emerged as a representative bioelastomer and been widely used in biomedical engineering. However, the typical curing of PGS needs high temperature (>120 °C), high vacuum (>1 Torr), and long duration (>12 h), which limit its further applications. Accordingly, we designed, synthesized and characterized a photo/thermo dual curable polymer based on PGS. Treatment of PGS with 2-isocyanatoethyl methacrylate without additional reagents readily produced a methacrylated PGS (PGS-IM). Photo-curing of PGS-IM for 10 min at room temperature using salt leaching method efficiently produced porous scaffolds with a thickness up to 1 mm. PGS-IM was adapt to thermo-curing as well. The combination of photo and thermo curing provided a further way to modulate the properties of resultant porous scaffolds. Interestingly, photo-cured scaffolds exhibited hierarchical porous structures carrying extensive micropores with a diameter from several to hundreds micrometers. All the scaffolds showed good elasticity and biodegradability. In addition, PGS-IM exhibited good compatibility with L929 fibroblast cells. We expect this new PGS based biomaterial will have a wide range of biomedical applications.

Review on the Impact of Polyols on the Properties of Bio-Based Polyesters

“…By increasing the curing temperature (110,120, and 130 • C) the corresponding values of Young's modulus were 0.056, 0.22, 1.2 MPa, respectively [59]. Based on these and other studies, variation in the degree of cross-linking achieved during the curing process has resulted in differences in cross-linked PGS Young's modulus of 0.05-1.5 MPa, ultimate tensile strength values of 0.4−0.7 MPa, and a failure strain of 120−300% [60].…”

“…One alternative to thermal cross-linking is photo-induced cross-linking [113]. Incorporation of ultraviolet (UV) sensitive units along chains or as end chain groups by direct polymerization of unsaturated building blocks (e.g., itaconic acid) as well as UV-sensitive moieties such as acrylates and methacrylates through modification of the terminal and pendant hydroxyl groups of polyol polyester prepolymers, enables a more fine-grained level of control of cross-linking, and consequently of the mechanical properties [110,[114][115][116][117][118][119][120][121]. By this approach, it is possible to prepare cross-linked polyester 3D networks under mild conditions and with significantly faster curing times (minutes versus days) upon exposure to UV light.…”

Hybrid manufacturing strategies for tissue engineering scaffolds using methacrylate functionalised poly(glycerol sebacate)

“…Previously, an alternative form of photocurable PGS, PGS-isocyanatoethyl methacrylate (PGS-IM), was combined with porogen leaching to generate porous scaffold structures. 22 NaCl porogens of 150-300 mm were used to generate the pores. The resulting structures showed some similarities to those described herein, although the ratio of NaCl to PGS-IM was not reported, and solvents were required to combine the polymer and porogens together.…”

“…In combination with a free radical generating photoinitiator and an appropriate wavelength of light, the functionalised PGS prepolymer rapidly crosslinks into an insoluble matrix at room temperature and pressure. [22][23][24][25] We recently reported on the synthesis of a methacrylate functionalised PGS (PGS-M) and demonstrated its excellent biocompatibility and tunable properties. 26 By altering the degree of methacrylation (DM) of PGS-M, it was possible to modulate the material's mechanical properties and degradation rate; a valuable attribute, given the effects these properties have on cell behaviour and ECM deposition in tissue engineering scaffolds.…”

Biobased poly(glycerol citrate) synthesis optimization via design of experiments

“…Poly(glycerol sebacate), a material with properties similar to elastomers, 30 is successfully used in the tissue engineering of soft tissues, 31 incl. of the heart muscle, 32 blood vessels, nerves, 33 the retina of the eye, and eardrum, 34 but its medical applications also include time‐release drug systems 35 and tissue adhesives to fix surgical incisions 36 . Cross‐linked PGS may be challenging to further process due to its poor solubility in organic solvents, which makes it impossible, for example, to use the electrospinning technique 37 …”