Is quercetin an alternative natural crosslinking agent to genipin for long‐term dermal scaffolds implantation?

Abstract

As biocompatible matrices, porcine dermal scaffolds have limited application in tissue engineering due to rapid degradation following implantation. This study compared the physical, chemical and biomechanical changes that occurred when genipin and quercetin were used to crosslink dermal scaffolds and to determine whether quercetin could be used as an alternative to genipin. Physicochemical changes in the collagen were assessed using spectroscopic methods [X-ray diffraction analysis (XRD) and nuclear magnetic resonance (NMR) analysis]. The crosslinking reaction was evaluated by quantification of amino acids and the degree of this reaction by ninhydrin assay. Because the mechanical behaviour of the collagen matrices is highly influenced by crosslinking, the tensile strength of both sets of scaffolds was evaluated. The highest mechanical strength, stiffness, degree of crosslinking and changes in the packing features of collagen (measured by XRD) were achieved using genipin. Some of the results found in the quercetin-crosslinked scaffolds were possibly due to hydration and dehydration effects elicited by the solvents (phosphate-buffered saline or ethanol), as seen in the NMR results. In the quercetin-ethanol-crosslinked scaffolds, possible reorientation of the amino groups of the collagen molecule may have taken place. Therefore, depending on their proximity to the crosslinking reagent, different types and numbers of interactions may have occurred, inducing a higher crosslinking degree (as evidenced by the ninhydrin assay) and reduction in the free amino acids after reaction. Both crosslinking agents and solvents interfere in the physicochemical properties of collagen thereby inducing variations in the matrix structure. Quercetin-crosslinked scaffolds may have broader clinical application where a lower degree of crosslinking and stiffness is required. Copyright © 2016 John Wiley & Sons, Ltd.

Effects of Dentine Pretreatment Solutions Containing Flavonoids on the Resin Polymer-Dentine Interface Created Using a Modern Universal Adhesive

“…However, it should be considered that there was a drop in µTBS after thermocycling in most of the experimental groups, that ranged from 5.3% to approximately 9.8%, while the µTBS value drop in the PLA group was about 17.6%. Such a decrease in µTBS values in the experimental groups in comparison to those observed in the specimens of the PLA group may be attributed to the crosslinking properties of the flavonoids discussed above; their effects in collagen have been widely demonstrated in many biomedical areas [ 47 , 48 , 49 , 50 , 51 ]. Indeed, such “therapeutic” effects may have prevented the µTBS values from dropping as much as the drop observed in the specimens of the PLA and CON groups.…”

Bonding performance of self adhesive flowable composite to dentin pretreated with four different natural matrix metalloproteinases inhibitors

“…Reorientation of the amino groups of collagen can occur depending on their proximity to the structure of the cross-linking agent. (31) Chlorogenic acid; is a polyphenolic antioxidant; was also included in the study. Structurally, 5-caffeoylquinic acid is most predominant form of chlorogenic acid in plants.…”

Membranous Extracellular Matrix-Based Scaffolds for Skin Wound Healing

“…For traditional ECM membranes, the applications of some natural crosslinking agents, such as genipin, quercetin, and proanthocyanins, have been investigated in recent years (Table 1) [65,72,73]. Gobinathan et al reported that genipin-crosslinked AAM possessed a slower degradation rate and a lower swelling percentage than those of the AAM alone [73].…”

“…Gobinathan et al reported that genipin-crosslinked AAM possessed a slower degradation rate and a lower swelling percentage than those of the AAM alone [73]. In addition, the genipin-crosslinked ADM showed significant reductions of amino acids, resulting in 37.75% in lysine, 22.89% in arginine, 21.88% in asparagine, 28.81% in glycine, and 19.48% in alanine [72]. Comparing with genipin-crosslinked ADM, quercetin-crosslinked ADM was more suitable for the applications where a lower crosslinking degree and a lower scaffold stiffness were required [72].…”

“…In addition, the genipin-crosslinked ADM showed significant reductions of amino acids, resulting in 37.75% in lysine, 22.89% in arginine, 21.88% in asparagine, 28.81% in glycine, and 19.48% in alanine [72]. Comparing with genipin-crosslinked ADM, quercetin-crosslinked ADM was more suitable for the applications where a lower crosslinking degree and a lower scaffold stiffness were required [72]. In vitro assays of proanthocyanins-crosslinked SIS showed that the crosslinking procedure resulted in an improved mechanical property and better anti-calcification potential [65].…”