Fan Lee
Synthesis and bioactivity of a conjugate composed of green tea catechins and hyaluronic acid
Lee, Fan; Lim, Jaehong; Reithofer, Michael R.; Lee, Su Seong; Chung, Joo Eun; Hauser, Charlotte A. E.; Kurisawa, Motoichi
Authors
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 |
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 |
Contract Date | Jun 11, 2015 |
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