Interaction of antiaggregant molecule ajoene with membranes

Abstract

The structure of ajoene, a molecule extracted from garlic, has been studied by 1H-NMR and its interaction with model membranes by 1H-, 2H-, 31-P-NMR and ESR experiments. This study clearly shows that the ajoene molecule is located deep in the layer and is close to the interlayer medium. Moreover while NMR experiments show that the membrane structure is only slightly affected by the presence of ajoene, ESR experiments reveal significant modifications in phospholipid dynamics. This interaction, observed before with the phenothiazine derivative, promazine, results in an increase of the membrane fluidity in its hydrophobic part and could be related to clinical properties of ajoene.

Garlic allyl derivatives interact with membrane lipids to modify the membrane fluidity

“…As shown by DPH and TMA-DPH polarization decreases, DATS and DADS fluidized liposomal membranes consisting of 80-100 mol% DPPC, which is the phospholipid most frequently used in drug and membrane interaction studies [14,24,29]. These results are compatible with the effects of ajoene which was previously reported to fluidize 80-90 mol% phosphatidylcholine liposomes [22,23]. However, the membrane effects of DASs were remarkably changed when preparing liposomes with unsaturated phospholipids and cholesterol.…”

“…In comparison of garlic allyl derivatives, lipid-soluble compounds are more active than water-soluble ones [3], suggesting that the hydrophobic interaction with cell membrane lipids is possibly included in their pharmacological background. However, only ajoene was previously reported to act on lipid bilayers and modify membrane properties like fluidity [22,23]. Other allyl derivatives remain to be studied as to whether they interact with membrane lipids and induce the membrane fluidity changes associated with antiproliferative, antiplatelet and antimicrobial effects.…”

Physicochemical properties and membrane interactions of anti-apoptotic derivatives 2-(4-fluorophenyl)-3-(pyridin-4-yl)imidazo[1,2-a]pyridine depending on the hydroxyalkylamino side chain length and conformation: An NMR and ESR study

“…Fig. 8-B is representative of axially symmetric powder phosphorus spectrum of standard bilayer structures of DMPC below phase transition [38]. The temperature dependance of 31 P Chemical Shift Anisotropy (CSA, figured by an horizontal bar) was measured on the phosphorus-NMR spectra of multilayers (MLV) [39] of pure DMPC or in the presence of 3a, 3b or 3c (see legend of Fig.…”

Study of Alkylglycerol Containing Shark Liver Oil: A Physico Chemical Support for Biological Effect?

“…[30] Also, the anti oxidant properties were found similar as those of vitamin E and were related mainly to the general properties of polyinsatured fatty acids. [31] Finally, the presence of non specifi c membrane properties of SLO, associated with its low toxicity is consistent with the great diversity of biological effects evoqued in the past, [32] such as anticancer, antioxidant and anti-infl ammatory properties.…”