Synthesis of Photocrosslinkable Copolymers of Cinnamoyl Group-modified Methacrylate and 2-Hydroxyethyl Methacrylate, and Fibroblast Cell Growth on Their Thin Films

Abstract

Cinnamoyl-modified methacrylate, 2-cinnamoyloxyethyl methacrylate (CEMA), was synthesized from 2-hydroxyethyl methacrylate (HEMA) and cinnamoyl chloride. Copolymers with various cinnamoyl contents were synthesized by random copolymerization of HEMA and CEMA at different feed ratios. Thus three copolymers with different CEMA contents were synthesized, and the monomer composition ([HEMA]:[CEMA]) in the copolymers ranged from 75:25 to 0:100. The coating films of copolymers on glass plates were prepared by the dip-coating method. Photo-induced dimerization of the cinnamoyl groups in the copolymers was confirmed by the ultraviolet-visible (UV-Vis) spectral changes. The cell proliferation on the photocrosslinked copolymers was tested using 3T3 Swiss albino mouse embryo fibroblasts. The results of the cell proliferation assay revealed that the photocrosslinked copolymers carrying more cinnamoyl groups promoted the cell proliferation compared with the photocrosslinked copolymers carrying less cinnamoyl groups. According to the results in the present study and our previous studies on cinnamoyl-modified trehalose and cinnamoyl-modified hydroxypropyl cellulose, it is presumable that the photodimerized cinnamoyl groups existing on the surface of materials at high density have some preferable effect on promoting fibroblast cell adhesion.

Bio-sourced monomers and cationic photopolymerization–The green combination towards eco-friendly and non-toxic materials

“…These photocrosslinkable cinnamoyl-conjugated bio-based polymers are widely prepared by condensing the carboxylic acid of cinnamic acid with hydroxyl or amino groups of bio-based building blocks [451]. Cinnamoyl moieties were therefore associated with biodegradable polyesters such as poly(lactic acid) and poly(-caprolactone) [452], gelatin [453][454][455], hyaluronic acid [456][457][458], alginate [459,460] and hydroxylpropyl cellulose [460], but also benzoxazines, lithocholic acid [461], oil-based ricinoleic acid [462], acrylate monomers [463] and butyl rubber derivatives [464]. Polymers containing cinnamoyl moieties have been used in a wide of applications to produce photo-crosslinked polymer materials [465][466][467][468][469][470], photo-crosslinked hydrogels [471][472][473], materials for photoinduced alignment of liquid crystals [474][475][476][477][478], in advanced microelectronics [479], in photolithography [480], in non-linear-optical materials [481], and for the synthesis of photocurable coatings [482].…”

Photocrosslinkable natural polymers in tissue engineering

“…In most cases, the stimulus of chemical crosslinking is a chemical agent or light source. Remarkably, light-initiated photocrosslinking has attracted attention due to its easily controllable parameters such as light intensity, exposure time, or irradiation distance (Chandrasekharan et al, 2019;Choi and Cha, 2019;Yano et al, 2020). Most of all, the non-invasiveness and capability of in situ photopolymerizations represent the unique and powerful merits of light-initiated photocrosslinking.…”