Synthesis of a new photoreactive gelatin with BTDA and HEMA derivatives

Abstract

A novel bio-affinitive, photocuring, and membrane-forming gelatin derivative was synthesized in this study. This process was based on the amide formation between carboxylic acid and the amine in methanol-water media using dicycloliexyl-carbodiimide (DCC) as a condenser. Gelatin and glycine were the sources of amine in the model reaction. Since there were two anhydride groups in each 3,3,4,4'-benzophenone tetra-carboxylic dianhydride (BTDA) molecule, two 2-hydroxyethyl methacrylate (HEMA) molecules were used to induce the ring-opening reaction of BTDA and release two carboxylic acid groups. The resulting photoreactive gelatin was called GE-BTHE, of which the photoreactive component was the ketone groups of BTDA and HEMA that played the role of double bond supplier. This photoreactive gelatin could be converted from the transparent liquid phase into swollen membrane by a 6-min irradiation of high pressure mercury lamp. The most efficient irradiation was at 267 nm and the highest degree of swelling of the cured GE-BTHE membrane could reach 5.9. The elongation from the dried gel remained 5-10'%, i.e., relatively elastic. The properties of this gelatin derivative were investigated using amide formation analysis, calculation of the gel content and the swelling ratio, and monitoring of the photocuring process. The GE-BTHE synthesized in this study should be very potential in applications such as protective wound dressings and hemostatic absorbents for minimally invasive surgery. (c) 2008 Wiley Periodicals, Inc

Visible light-induced crosslinkable gelatin

“…Similarly, the Hubbell group's visible light-induced photopolymerizable glue, based on hydrolytically degradable poly(ethylene glycol) diacrylate derivatives and a visible light-induced photoradical generator (eosin Y), is now commercially available [3]. Other types of polymerizable biomacromolecule derivatives have also been reported [4][5][6][7][8][9][10][11][12][13][14][15][16]. However, these systems usually utilize synthetic polymerizable monomers as their major component.…”

Controlled release of bovine serum albumin from stimuli‐sensitive silk sericin based interpenetrating polymer network hydrogels

“…IPN consists of two or more hydrophilic polymers, each forming either physically or chemically crosslinked networks entangled with each other . IPN hydrogels, especially hybrids of synthetic and natural polymers, with altered morphologies, perform better with a synergistic combination of homopolymer properties.…”

Coating of titanium plate by photocurable azidophenyl chitosan derivative for application to implants

“…In this study, we attempted to coat Ti implant surfaces with photocurable natural polymers, especially chitosan derivatives. Photocurable natural polymers have received a considerable amount of attention in the field of tissue engineering, biomaterial coating, and drug delivery mainly due to their mild crosslinking ability compared to other methods 17,18. Photocurable natural polymers can be used as matrices to immobilize various bioactive compounds such as HA, growth factors, drugs, proteins, and DNA 19–21…”

“…Photocurable natural polymers have received a considerable amount of attention in the field of tissue engineering, biomaterial coating, and drug delivery mainly due to their mild crosslinking ability compared to other methods. 17,18 Photocurable natural polymers can be used as matrices to immobilize various bioactive compounds such as HA, growth factors, drugs, proteins, and DNA. [19][20][21] Chitosan was used as a base polymer in this study.…”