Study of the relationship between lipid binding properties of cyclodextrins and their effect on the integrity of liposomes

Piel, Géraldine; Piette, M; Barillaro, Valery; Castagne, Delphine; Évrard, Brigitte; Delattre, Luc

doi:10.1016/j.ijpharm.2007.01.015

Cited by 59 publications

(62 citation statements)

References 25 publications

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“…It is unlikely that MBCD extracted phospholipids from the cells or vesicles in our experiments because our MBCD concentrations never exceeded 0.2 mM for delivery or 0.7 mM in the extraction experiments. CD at a concentration of 10 mM extracted <0.2% of phospholipids present in a lipid membrane, but considerable extraction of phospholipids with perturbation of the membrane structure has been observed at CD concentrations of 30-50 mM ( 35,36 ). However, our study does reveal an important pitfall in the use of MBCD to extract cholesterol and/or phospholipids in cells: MBCD at these higher concentrations also will extract FA, and possibly other cellular constituents, and other single-chain amphiphiles, such as lysophospholipids and acyl-CoA, thus altering the nutriconcentrations of total OA, unbound OA was 2 to 3 times lower in the presence of albumin than in the presence of MBCD because of the multiple binding sites and higher affi nity of albumin.…”

Section: Mbcd Extracts Oa Rapidly From Phospholipid Membranesmentioning

confidence: 96%

Fatty acids are rapidly delivered to and extracted from membranes by methyl-β-cyclodextrin

Brunaldi

Huang

Hamilton

2010

Journal of Lipid Research

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A frequently used approach for adding FA at higher concentration is to complex the FA with albumin, which allows preparation of FA that is solubilized at millimolar concentrations. Although albumin is a physiologically relevant carrier of FA, careful consideration must be given to the facts that albumin can deliver impurities to cells and can extract FA and other nutrients from cells, which could alter their metabolic state ( 3 ). In addition, there is continuing disagreement about the rates of FA dissociation from albumin and whether this affects biophysical measurements of FA transport ( 4, 5 ). Furthermore, the binding properties of albumin are complex: different FA binding sites have different relative affi nities, and the kinetics of desorption are dependent on acyl chain length ( 6 ). The high affi nity of albumin for FA may result in very little delivery to membranes ( 7 ).A promising new vehicle for solubilization of FA is the family of cyclodextrins (CDs), which are cyclic oligosaccharides formed by bacterial degradation of starch. These molecules typically contain six ( ␣ ), seven ( ␤ ), or eight ( ␥ ) glucose residues linked by (1 → 4) glycosidic bonds. They have a polar surface and a hydrophobic cylindrical cavity that can bind and solubilize a wide variety of hydrophobic molecules, such as cholesterol and FA, while remaining soluble in water ( 8 ). The number of CD molecules required to solubilize one FA molecule increases with an increase in the hydrocarbon chain length of FA ( 9 ), although the exact stoichiometry is diffi cult to determine.In pharmaceutical applications, CD is widely used to solubilize hydrophobic drugs and enhance drug absorption in the gastrointestinal tract ( 8 ). It is used as a lipidbinding agent in the culture media of bacteria and animal cells ( 10, 11 ) and as a substitute for albumin for intrave- The very low aqueous solubility of long-chain fatty acids (FAs) is one of the major limitations in studies of FA transport in vitro and in vivo. A common misconception is that FA can form micelles at physiological pH because the pk a values for monomeric FA are typically 4.8. Instead, they form insoluble structures similar to phospholipid bilayers, in which ‫ف‬ 50% of the FA is ionized ( 1 ). The aqueous solubilities of the monomeric forms of the common 16-and 18-carbon dietary FA are <10 µM ( 2 ).

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Section: Mbcd Extracts Oa Rapidly From Phospholipid Membranesmentioning

confidence: 96%

Fatty acids are rapidly delivered to and extracted from membranes by methyl-β-cyclodextrin

Brunaldi

Huang

Hamilton

2010

Journal of Lipid Research

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“…These techniques include chemical, biological, physicochemical and biophysical methodologies. Thus, the relationship between lipid binding properties of cyclodextrins and their effect on the integrity of liposomes was investigated by permeability measurements (Piel et al, 2007). Fluorescence and photometric techniques were employed for the investigation of the release of calcein and griseofulmin from control and liposomal gels.…”

Section: Other Investigation Methodsmentioning

confidence: 99%

Liposomes in chromatography

Cserháti

Szőgyi

2010

Biomedical Chromatography

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The newest achievements in the application of liposomes in different chromatographic technologies such as high-performance liquid chromatography and electrically driven separation methods was compiled and critically evaluated. The employment of chromatographic methodologies for the determination of molecular parameters of biological importance is also discussed in detail. The future trends of the use of liposomes is also shortly discussed.

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“…Several studies showed that cholesterol-containing membranes are more sensitive to methylated CD than to natural CD [16,19,20]. Among the former, the randomly methylated b-CD (RAMEB) passed all toxicological tests [16,[19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

“…Turbidity measurements have been performed to quantify the lipid leakage induced by CD on the liposome bilayer [19]. The structural changes were also assessed using differential scanning calorimetry [48], freeze-fracture electron microscopy [47], binding isotherms [49] or photon-correlation spectroscopy [19,23,49,50]. Despite all these studies, rare are those involving specifically the interaction between b-CD and phospholipids [19,49,51].…”

Section: Introductionmentioning

confidence: 99%

Investigation of the interaction between a β-cyclodextrin and DMPC liposomes: a small angle neutron scattering study

Joset

Grammenos

Hoebeke

et al. 2015

J Incl Phenom Macrocycl Chem

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The small angle neutron scattering technique has been applied to investigate the interaction between a cyclodextrin (CD) and liposomes. From the modelling of the experimental neutron scattering cross sections, the detailed structure of dimyristoylphosphatidylcholine (DMPC) liposomes is assessed upon addition of increasing amounts of randomly methylated b-CD (RAMEB). This study has been performed at two temperatures bracketing the phase transition of the DMPC bilayers. The fraction of DMPC molecules incorporated into the vesicles is inferred. The dose-dependent phospholipidic extraction by RAMEB is quantified as well as the concomitant evolution of the liposome radius and of the thickness of the hydrophobic and hydrophilic parts of the membrane. The possible formation of CD-DMPC inclusion complexes is also assessed. The data suggest the dose-dependent coverage by RAMEB of the outer liposome interface. Our analysis highlights the important role of temperature on the mechanism of action of RAMEB. These results are discussed in the framework of the area-difference-elasticity model.

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Study of the relationship between lipid binding properties of cyclodextrins and their effect on the integrity of liposomes

Cited by 59 publications

References 25 publications

Fatty acids are rapidly delivered to and extracted from membranes by methyl-β-cyclodextrin

Fatty acids are rapidly delivered to and extracted from membranes by methyl-β-cyclodextrin

Liposomes in chromatography

Investigation of the interaction between a β-cyclodextrin and DMPC liposomes: a small angle neutron scattering study

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