Skip to main content

Research Repository

Advanced Search

Synthesis and bioactivity of a conjugate composed of green tea catechins and hyaluronic acid

Hauser, Charlotte A.E.; Lee, Fan; Lim, Jaehong; Reithofer, Michael R.; Lee, Su Seong; Chung, Joo Eun; Hauser, Charlotte A. E.; Kurisawa, Motoichi

Authors

Charlotte A.E. Hauser

Fan Lee

Jaehong Lim

Michael R. Reithofer

Su Seong Lee

Joo Eun Chung

Charlotte A. E. Hauser

Motoichi Kurisawa



Abstract

(-)-Epigallocatechin-3-gallate (EGCG) is a green tea polyphenol that has several biological activities, including anti-cancer activity and anti-inflammation. Hyaluronic acid (HA) is a naturally-occurring polysaccharide that is widely used as a biomaterial for drug delivery and tissue engineering due to its viscoelastic, biocompatible and biodegradable properties. By conjugating HA with EGCG, the resulting HA-EGCG conjugate is expected to exhibit not only the inherent properties of HA but also the bioactivities of EGCG. Toward this end, we report the synthesis of an amine-functionalized EGCG as an intermediate compound for conjugation to HA. EGCG was reacted with 2,2-diethoxyethylamine (DA) under acidic conditions, forming ethylamine-bridged EGCG dimers. The EGCG dimers were composed of four isomers, which were characterized by HPLC, high-resolution mass spectrometry and NMR spectroscopy. The amine-functionalized EGCG dimers were conjugated to hyaluronic acid (HA) through the formation of amide bonds. HA-EGCG conjugates demonstrated several bioactivities which were not present in unmodified HA, including resistance to hyaluronidase-mediated degradation, inhibition of cell growth and scavenging of radicals. The potential applications of HA-EGCG conjugates are discussed.

Citation

Lee, F., Lim, J., Reithofer, M. R., Lee, S. S., Chung, J. E., Hauser, C. A. E., & Kurisawa, M. (2015). Synthesis and bioactivity of a conjugate composed of green tea catechins and hyaluronic acid. Polymer chemistry, 6(24), 4462-4472 . https://doi.org/10.1039/c5py00495k

Journal Article Type Article
Acceptance Date May 8, 2015
Online Publication Date May 11, 2015
Publication Date Jun 28, 2015
Deposit Date Jun 11, 2015
Publicly Available Date Jun 11, 2015
Journal Journal of polymer science. Part A, Polymer chemistry
Print ISSN 1759-9954
Electronic ISSN 1759-9962
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 6
Issue 24
Pages 4462-4472
DOI https://doi.org/10.1039/c5py00495k
Keywords (−)-Epigallocatechin-3-gallate; Green tea catechins; Green tea polyphenols; Hyaluronic acid
Public URL https://hull-repository.worktribe.com/output/375121
Publisher URL http://pubs.rsc.org/en/content/articlelanding/2015/py/c5py00495k#!divAbstract

Files



You might also like



Downloadable Citations