Triggering Tautomerization of Curcumin by Confinement into Liposomes

Although solvent polarity, pH and temperature have been reported to affect the keto‐enol equilibrium of curcumin, the synergistic effect of concentration and confinement is demonstrated for the first time herein. To this end, curcumin was encapsulated into vesicles of soy lecithin of about 100 nm in...

Full description

Saved in:
Bibliographic Details
Published in:ChemPhotoChem 2019-10, Vol.3 (10), p.1034-1041
Main Authors: Girardon, Maxime, Parant, Stéphane, Monari, Antonio, Dehez, François, Chipot, Christophe, Rogalska, Ewa, Canilho, Nadia, Pasc, Andreea
Format: Article
Language:English
Subjects:
Chemical Sciences
curcumin
encapsulation
fluorescence
lecithin
liposomes
tautomers
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Although solvent polarity, pH and temperature have been reported to affect the keto‐enol equilibrium of curcumin, the synergistic effect of concentration and confinement is demonstrated for the first time herein. To this end, curcumin was encapsulated into vesicles of soy lecithin of about 100 nm in diameter. The keto form is favoured in the dilute regime (up to 2 μM). Above this concentration, tautomerization is shifted towards the enol form, as shown by fluorescence and compression isotherm studies. Moreover, molecular modeling and free‐energy profiles, together with simulation of the optical properties of the curcumin isomers, allowed us to dissect the interaction of the keto and enol forms with a model membrane and confirm the concentration‐triggered tautomerization of curcumin under confinement. Triggered tautomerisation: Curcumin was encapsulated into vesicles of soy lecithin of about 100 nm in diameter to study the synergistic effect of concentration and confinement to trigger the keto‐enol equilibrium of the molecule. The keto form is rather stabilized near the polar headgroups of the phospholipids whereas tautomerization is shifted towards the enol form in the lipid core.
ISSN:2367-0932
2367-0932
DOI:10.1002/cptc.201900159