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J Phys Chem B. 2013 Aug 22;117(33):9699-708. doi: 10.1021/jp4061413. Epub 2013 Aug 9.

Ionic liquid expedites partition of curcumin into solid gel phase but discourages partition into liquid crystalline phase of 1,2-dimyristoyl-sn-glycero-3-phosphocholine liposomes.

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  • 1Department of Chemistry, American University of Beirut, Beirut, Lebanon.

Abstract

The hydrolysis of curcumin in alkaline and neutral buffer conditions is of interest because of the therapeutic applicability of curcumin. We show that hydrolysis of curcumin can be remarkably suppressed in 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) liposomes. The fluorescence of curcumin sensitively detects the phase transition temperature of liposomes. However, at greater concentrations, curcumin affects the phase transition temperature, encouraging fusion of two membrane phases. The interaction of curcumin with DMPC is found to be strong, with a partition coefficient value of Kp = 2.78 × 10(5) in the solid gel phase, which dramatically increases in the liquid crystalline phase to Kp = 1.15 × 10(6). The importance of ionic liquids as green solvents has drawn interest because of their toxicological effect on human health; however, the impact of ionic liquids (ILs) on liposomes is not yet understood. The present study establishes that ILs such as 1-methyl-3-octylimidazolium chloride (moic) affect the permeability and fluidity of liposomes and thus influence parition of curcumin into DMPC liposomes, helping in the solid gel phase but diminishing in the liquid crystalline phase. The Kp value of curcumin does not change appreciably with moic concentration in the solid gel state but decreases with moic concentration in the liquid crystalline phase. Curcumin, a rotor sensitive to detect phase transition temperature, is applied to investigate the influence of ionic liquids such as 1-methyl-3-octylimidazolium chloride, 1-buytl-3-methyl imadazolium tetrafluoroborate, and 1-benzyl-3-methyl imidazolium tetrafluoroborate on DMPC liposome properties. 1-Methyl-3-octylimidazolium chloride lowers the phase transition temperature, but 1-buytl-3-methyl imidazolium tetrafluoroborate and 1-benzyl-3-methyl imidazolium tetrafluoroborate do not perceptibly modify the phase transition temperature; rather, they broaden the phase transition.

PMID:
23895644
[PubMed - indexed for MEDLINE]
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