Synthesis and bioevaluation of alkyl 2-cyanoacryloyl glycolates as potential soft tissue adhesives

A series of alkyl 2-cyanoacryloyl glycolate tissue adhesives were synthesized and characterized by NMR. Physical properties and bond strengths are presented. Within the series, bond strength decreased with increasing molecular weight. Corresponding polymers were evaluated by in vitro and in vivo techniques for biocompatibility. In general, in vitro biocompatibility increased with molecular weight. Based on in vitro and in vivo results, the isobutyl and isoamyl derivatives gave polymers that were most biocompatible, however, the entire series was found to be less reactive than poly(methyl 2-cyanoacrylate) and only the isopropyl derivative polymers more reactive than poly(isobutyl 2-cyanoacrylate). Approximately one-third of the isobutyl polymer biodegraded in vivo after 6 weeks.