Fatty acid-cyclodextrin complexes: Properties and applications

Szente, Lajos; Szejtli, J.; Szemán, Julianna; Kátó, L

doi:10.1007/bf00708714

Cited by 61 publications

(36 citation statements)

References 21 publications

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“…Accordingly, one molecule of stearic acid (C18:0) would require at least three molecules of MBCD, which implies that in our experiments with SA:MBCD of 1:22, either some empty MBCD was present or, possibly, additional MBCD capped the ends of the complex. For the saturated FA with 14 to 18 carbons, we found that higher ratios of MBCD to FA were required to produce a clear solution at room temperature and that the MBCD/FA increased with increasing FA chain length, as noted before ( 26 ). cell studies using CD as a donor have not been able to measure the rate of dissociation of FA from CD because they typically used incubation times of hours ( 15,16 ).…”

Section: Mbcd Maintains a Low Concentration Of Unbound Oa In Buffermentioning

confidence: 59%

“…The pK a of the carboxyl group of the FA is not changed in the presence of CD ( 28 ). The number of CD molecules required to solubilize one FA molecule increases with an increase in the hydrocarbon chain length of FA; one MBCD can accommodate about 5 to 6 CH 2 units of FA ( 26 ). Accordingly, one molecule of stearic acid (C18:0) would require at least three molecules of MBCD, which implies that in our experiments with SA:MBCD of 1:22, either some empty MBCD was present or, possibly, additional MBCD capped the ends of the complex.…”

Section: Mbcd Maintains a Low Concentration Of Unbound Oa In Buffermentioning

confidence: 98%

“…Formation of FA:CD complexes is considered a true molecular dispersion and not micellization as achieved by detergents ( 26 ). Hydrogen bonds between the FA carboxyl to extract FA from lipid vesicles and cells, a refl ection of the lower affi nity of MBCD for FA.…”

Section: Conditions For Preparation Of Mbcd Complexes With Famentioning

confidence: 99%

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

Brunaldi¹,

Huang²,

Hamilton³

2009

The 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 Maintains a Low Concentration Of Unbound Oa In Buffermentioning

confidence: 59%

Section: Mbcd Maintains a Low Concentration Of Unbound Oa In Buffermentioning

confidence: 98%

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

Brunaldi¹,

Huang²,

Hamilton³

2009

The Journal of Lipid Research

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“…Sweet almond and wheat germ oils (499% TGs) formed smaller beads than soybean oil-based ones but within the same time frame and similar fabrication yield (Trichard et al, 2011). The presence of trace amounts of diglycerides (DGs), monoglycerides (MGs) or FAs from degradation of TGs in soybean oil probably competed with TG for a-CD molecules (Szente et al, 1993;Duchêne et al, 2003) resulting in less efficient emulsification step. Certainly, this reduces the number of CD molecules involved in emulsion stabilization.…”

Section: Type and Concentration Of CD And Oilmentioning

confidence: 99%

“…According to Szente et al (1993) the complex stability depends on the acylation degree and decreases in the order: free FA4MG4DG4TG. It is hypothesized that FAs resulting from TGs degradation competes with TGs for CD cavity.…”

Section: X-ray Diffraction Studiesmentioning

confidence: 99%

Insights on novel particulate self-assembled drug delivery beads based on partial inclusion complexes between triglycerides and cyclodextrins

Aburahma

2014

Drug Delivery

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Most of the newly designed drug molecules are lipophilic in nature and often encounter erratic absorption and low bioavailability after oral administration. Finding ways to enhance the absorption and bioavailability of these lipophilic drugs is one of the major challenges that face pharmaceutical industry nowadays. In view of that, the purpose of this review is to shed some light on a novel particulate self-assembling system named ''beads'' than can act as a safe carrier for delivering lipophilic drugs. The beads are prepared simply by mixing oils with cyclodextrin (CD) aqueous solution in mild conditions. A unique interaction between oil components and CD molecules occurs to form in situ surface-active complexes which are prerequisites for beads formation. This review mainly focuses on the fundamentals of beads preparation through reviewing present, yet scarce, literature. The key methods used for beads characterization are discussed in details. Also, the potential mechanisms by which beads increase the bioavailability of lipophilic drugs are illustrated. Finally, the related research areas that needs to be addressed in future for optimizing this promising delivery system are briefly outlined.

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ChemInform Abstract: Fatty Acid‐Cyclodextrin Complexes: Properties and Applications

et al. 1994

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Fatty acid-cyclodextrin complexes: Properties and applications

Cited by 61 publications

References 21 publications

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

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

Insights on novel particulate self-assembled drug delivery beads based on partial inclusion complexes between triglycerides and cyclodextrins

ChemInform Abstract: Fatty Acid‐Cyclodextrin Complexes: Properties and Applications

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