"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 Citations (Scopus)

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

Fingerprint

Click Chemistry
Curcumin
Polylysine
curcumin
chemistry
azides
Azides
oxygen radical absorbance capacity
triazoles
Biopolymers
Triazoles
biopolymers
Antioxidants
antioxidant activity
Cycloaddition Reaction
Fourier transform infrared spectroscopy
assays
Fourier Analysis
Fourier Transform Infrared Spectroscopy
functional properties

Keywords

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

ASJC Scopus subject areas

  • Food Science

Cite this

"Click chemistry" based conjugation of lipophilic curcumin to hydrophilic ε-polylysine for enhanced functionality. / Tikekar, Rohan V.; Hernandez, Mateo; Land, Donald P.; Nitin, N.

In: Food Research International, Vol. 54, No. 1, 11.2013, p. 44-47.

Research output: Contribution to journalArticle

Tikekar, Rohan V. ; Hernandez, Mateo ; Land, Donald P. ; Nitin, N. / "Click chemistry" based conjugation of lipophilic curcumin to hydrophilic ε-polylysine for enhanced functionality. In: Food Research International. 2013 ; Vol. 54, No. 1. pp. 44-47.
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