Synthesis and bioactivity of a conjugate composed of green tea catechins and hyaluronic acid
- Author(s)
- 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.
- Organisation(s)
- External organisation(s)
- Agency for Science, Technology and Research A*STAR
- Journal
- Polymer chemistry
- Volume
- 6
- Pages
- 4462-4472
- No. of pages
- 11
- ISSN
- 1759-9954
- DOI
- https://doi.org/10.1039/c5py00495k
- Publication date
- 06-2015
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 104018 Polymer chemistry
- ASJC Scopus subject areas
- Bioengineering, Biochemistry, Polymers and Plastics, Organic Chemistry
- Sustainable Development Goals
- SDG 3 - Good Health and Well-being
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/bf43c9c8-68fd-41c8-b9e5-e8da331e1903