"Click chemistry" based conjugation of lipophilic curcumin to hydrophilic ε-polylysine for enhanced functionality

Rohan V. Tikekar, Mateo Hernandez, Donald P. Land, N. Nitin

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

This short communication demonstrates an application of "click chemistry" to conjugate small hydrophobic bioactive molecule such as curcumin with water soluble biopolymer such as ε-polylysine to improve the functionality of the biopolymer. ε-Polylysine and curcumin were modified to ε-polylysine azide and monoalkyne curcumin, respectively. The Huisgen cycloaddition ("click chemistry") between the azide group and monoalkyne group led to formation of a triazole linkage between ε-polylysine and curcumin. The conjugation process was characterized using Fourier transform infrared (FT-IR) spectroscopy. Retention of functional activity of conjugated curcumin was evaluated by comparing the antioxidant activity of conjugates with native ε-polylysine using the oxygen radical absorbance capacity (ORAC) assay. FT-IR spectra showed a significant decrease in the peak intensity of azide group of ε-polylysine (2102cm-1) and a concomitant presence of triazole peak (1459cm-1) after reaction with monoalkyne curcumin, validating that conjugation was successful. ORAC assay showed that the antioxidant activity of ε-polylysine-curcumin conjugate was 3.6 fold higher than control ε-polylysine indicating that conjugated curcumin retained its functional properties. These results highlight the success of "click chemistry" to achieve conjugation of small molecules to polymers.

Original languageEnglish (US)
Pages (from-to)44-47
Number of pages4
JournalFood Research International
Volume54
Issue number1
DOIs
StatePublished - Nov 2013

Keywords

  • Bio-compatible polymer
  • Click chemistry
  • Curcumin
  • Polymer conjugates

ASJC Scopus subject areas

  • Food Science

Fingerprint Dive into the research topics of '"Click chemistry" based conjugation of lipophilic curcumin to hydrophilic ε-polylysine for enhanced functionality'. Together they form a unique fingerprint.

Cite this