Role of Free Catecholamine in Thiol-Ene Crosslinking for Hyaluronic Acid Hydrogels with High Loading Efficiency of Anticancer Drugs.

Content Provider	Europe PMC
Author	Kim, Sumin Shin, Mikyung
Abstract	Background: Hyaluronic acid (HA) is a widely used polysaccharide in biomedical field because of its excellent biocompatibility. Its chemical structure can be modified with various functional groups. Recently, dopamine has been tethered onto the polymeric backbone to ensure long-term stability and tissue adhesiveness of HA hydrogel. However, the radical scavenging effect of dopamine on typical photo-induced crosslinking for hydrogels has not been specifically studied. Methods: Photo-crosslinkable norbornene-modified HA (NorHA) was synthesized and crosslinked by dithiothreitol containing dopamine at different concentrations. During in situ ultraviolet light-triggered crosslinking, storage moduli were monitored using an oscillatory rheometer. Additionally, the amount of thiol utilized for HA crosslinking was investigated under the presence and absence of dopamine. Finally, doxorubicin was encapsulated in the hydrogels, and the drug loading efficiency and release kinetics were measured. Results: Adding dopamine into the NorHA pre-gel solution delayed the gelation time, yet the final storage modulus of the hydrogel remained constant. That is, dopamine might partially consume the energy required for thiol-ene reaction to generate semiquinone radicals. Furthermore, the residual thiols which were not involved in the crosslinking decreased when the hydrogel was formed at a high concentration of dopamine, indicating the formation of Michael adducts of semiquinone and thiols. Interestingly, the presence of dopamine in the hydrogel increased the loading efficiency of the hydrophobic drugs due to π-π stacking and hydrogen bonding between dopamine and drugs. Conclusion: The presence of free catecholamines in a photo-crosslinkable polymer can delay the gelation time but improve the drug loading efficiency. Supplementary Information The online version contains supplementary material available at 10.1007/s13770-021-00388-3.
Related Links	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC8971260&blobtype=pdf
ISSN	17382696
Volume Number	19
DOI	10.1007/s13770-021-00388-3
PubMed Central reference number	PMC8971260
Issue Number	2
PubMed reference number	34564837
Journal	Tissue Engineering and Regenerative Medicine [Tissue Eng Regen Med]
e-ISSN	22125469
Language	English
Publisher	Springer Singapore
Publisher Date	2021-09-26
Publisher Place	Singapore
Access Restriction	Open
Rights License	© The Korean Tissue Engineering and Regenerative Medicine Society 2021
Subject Keyword	Hydrogel Dopamine Radical scavenging Thiol-ene crosslinking Drug encapsulation
Content Type	Text
Resource Type	Article
Subject	Medicine Biomedical Engineering