Different stabilities of liposomes containing saturated and unsaturated lipids toward the addition of cyclodextrins

Org Biomol Chem. 2016 Jun 14;14(22):5065-72. doi: 10.1039/c6ob00535g. Epub 2016 May 16.

Abstract

Liposomes composed of unsaturated lipids were more stable than those containing saturated lipids toward DMe-β-CDx, DMe-α-CDx and DMe-β-CDx. The Hill coefficient values (n) indicated that the saturated lipid·DMe-CDx complexes had stoichiometric ratios in the range of 1 : 3-1 : 4, while the unsaturated lipid·DMe-CDx complexes had ratios in the range of 1 : 1.5-1 : 3. That is, a cis alkene group in the unsaturated lipids prevented complexation with a second DMe-CDx in the direction toward each acyl chain. Furthermore, the liposomes composed of the unsaturated lipids were much slower to form precipitates upon the addition of α-CDx than those of the saturated lipids. To the best of our knowledge, this is the first example showing that CDxs interact with unsaturated lipids.

MeSH terms

  • Cyclodextrins / chemistry*
  • Drug Stability
  • Hydrophobic and Hydrophilic Interactions
  • Lipids / chemistry*
  • Liposomes / chemistry*

Substances

  • Cyclodextrins
  • Lipids
  • Liposomes