title: Kinetic analysis of genipin degradation in aqueous solution.
abstract: Degradation of genipin (GP), a low toxicity natural protein crosslinking agent, in aqueous solution was monitored by HPLC at various pH levels. Degradation of GP was consistent with a mechanism consisting of a first order reaction with a reversible first step. Formation of the intermediate was slowest at more neutral pHs while formation of the irreversible product was correlated to increasing alkalinity. Degradation at all pHs was enhanced by the presence of phosphate ions. Degradation of GP most likely proceeds via the reversible opening of the dihydropyran ring by water followed by irreversible polymerization of the intermediate. Degraded solutions containing no detectable GP or intermediate, however, are still capable of crosslinking proteins.
authors.affiliation: Orthopedics, L.P., 111 Cooperative Way, Suite 210, Georgetown, Texas 78626, USA. pslusarewicz@orthopeutics.com
authors.forename: Paul
authors.initials: P
authors.lastname: Slusarewicz
authors.forename: Keng
authors.initials: K
authors.lastname: Zhu
authors.forename: Tom
authors.initials: T
authors.lastname: Hedman
mesh_terms: D003432:Cross-Linking Reagents / Q000737:chemistry*; D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D057889:Iridoid Glycosides / Q000737:chemistry*; D039823:Iridoids; D007700:Kinetics; D012996:Solutions
chemical_list: D003432:Cross-Linking Reagents; D057889:Iridoid Glycosides; D039823:Iridoids; D012996:Solutions; C007834:genipin