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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


Charlotte A.E. Hauser

Fan Lee

Jaehong Lim

Michael R. Reithofer

Su Seong Lee

Joo Eun Chung

Charlotte A. E. Hauser

Motoichi Kurisawa


(-)-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.

Journal Article Type Article
Publication Date Jun 28, 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
APA6 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 .
Keywords (−)-Epigallocatechin-3-gallate; Green tea catechins; Green tea polyphenols; Hyaluronic acid
Publisher URL!divAbstract


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