Affinity capillary electrophoresis and isothermal titration calorimetry for the determination of fatty acid binding with beta-cyclodextrin

Parker, Kevin M.; Stalcup, Apryll M.

doi:10.1016/j.chroma.2008.02.050

Cited by 25 publications

(14 citation statements)

References 39 publications

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“…For linear regression models a nonlinear deviation of the plots was observed at this concentration. This can be explained by a saturation of the complexing ligand at low concentrations . To simplify the calculation of binding constants the total concentration of CD added to the buffer is taken for the free equilibrium concentration of CD [see Eq.…”

Section: Resultsmentioning

confidence: 99%

Characterization of complexes between phenethylamine enantiomers and β‐cyclodextrin derivatives by capillary electrophoresis—Determination of binding constants and complex mobilities

et al. 2017

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To optimize chiral separation conditions and to improve the knowledge of enantioseparation, it is important to know the binding constants K between analytes and cyclodextrins and the electrophoretic mobilities of the temporarily formed analyte-cyclodextrin-complexes. K values for complexes between eight phenethylamine enantiomers, namely ephedrine, pseudoephedrine, methylephedrine and norephedrine, and four different β-cyclodextrin derivatives were determined by affinity capillary electrophoresis. The binding constants were calculated from the electrophoretic mobility values of the phenethylamine enantiomers at increasing concentrations of cyclodextrins in running buffer. Three different linear plotting methods (x-reciprocal, y-reciprocal, double reciprocal) and nonlinear regression were used for the determination of binding constants with β-cyclodextrin, (2-hydroxypropyl)-β-cyclodextrin, methyl-β-cyclodextrin and 6-O-α-maltosyl-β-cyclodextrin. The cyclodextrin concentration in a 50 mM phosphate buffer pH 3.0 was varied from 0 to 12 mM. To investigate the influence of the binding constant values on the enantioseparation the observed electrophoretic selectivities were compared with the obtained K values and the calculated enantiomer-cyclodextrin-complex mobilities. The different electrophoretic mobilities of the temporarily formed complexes were crucial factors for the migration order and enantioseparation of ephedrine derivatives. To verify the apparent binding constants determined by capillary electrophoresis, a titration process using ephedrine enantiomers and β-cyclodextrin was carried out. Furthermore, the isothermal titration calorimetry measurements gave information about the thermal properties of the complexes.

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Section: Resultsmentioning

confidence: 99%

Characterization of complexes between phenethylamine enantiomers and β‐cyclodextrin derivatives by capillary electrophoresis—Determination of binding constants and complex mobilities

et al. 2017

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“…This difference was probably due to the various capacity of fatty acids binding to β‐CD in competition with cholesterol since binding to β‐CD was dependent on compatibility of the whole fatty acid molecules within the hydrophobic cavity of β‐CD . Unsaturated acid (C18:1 and C18:2) had a strong effect for cholesterol removal since fatty acid/β‐CD complex formation was preferred unsaturation of fatty acids well over saturated fatty acids for their compact geometry conformation . For instance, oleic acid (C18:1) had a more compact conformation than stearic acid (C18:0) and was a significant one in interference for cholesterol removal from lard.…”

Section: Resultsmentioning

confidence: 99%

“…removal since fatty acid/b-CD complex formation was preferred unsaturation of fatty acids well over saturated fatty acids for their compact geometry conformation [47][48][49]. For instance, oleic acid (C18:1) had a more compact conformation than stearic acid (C18:0) and was a significant one in interference for cholesterol removal from lard.…”

Section: Effect Of Components In Oil On Cholesterol Removalmentioning

confidence: 99%

High quality lard with low cholesterol content produced by aqueous enzymatic extraction and β‐cyclodextrin treatment

Wang

Jiang

et al. 2015

Euro J Lipid Sci & Tech

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New food processing technology is required for food production with high quality and healthfulness. In this study, a novel application was developed to extract lard from pig fatback, a by‐product of the slaughter plant, by an aqueous enzymatic extraction method (AEE). Various proteases with different properties including Alcalase 2.4 L, Neutrase 1.5 MG, Flavourzyme 1000 L, and Protamex were evaluated for their efficiency in oil release and lard qualities. Alcalase 2.4 L was more effective for oil extraction with a yield of 95.19%. A high quality of lard was produced by AEE in comparison with lards produced by conventional extraction methods in aspects of color, acid value, peroxide value, phospholipids, cholesterol, and oxidation stability. A further refinement to reduce cholesterol from lard by β‐cyclodextrin (β‐CD) was developed and the optimal conditions were established. The optimal conditions were 7% β‐CD addition (w/w) to a mixture of equal amount of lard and distilled water at reaction temperature 50°C for about 60 min. The cholesterol content of lard from this refinement process was about 3.2 mg/100 g which was about 93.7% reduction from 51.2 mg/100 g. This simple process by AEE and cholesterol reduction did not affect the composition of fatty acids and construction of triglyceride. Factors that were components of lard or produced during the lard extraction processes were evaluated for their influence on the cholesterol removal. Phospholipids could slightly enhance cholesterol removal, while free fatty acids with saturated or unsaturated aliphatic chains would have inhibitory effects because of their competition with cholesterol for β‐CD. Practical applications: An excellent quality of lard was produced by a novel application of an aqueous enzymatic extraction method (AEE). This lard could be further refined by β‐cyclodextrin for cholesterol reduction. This procedure would be a promising technology to obtain healthy lard and explore animal by‐products for the food industry. This lard with high nutrients could have very broad applications such as in baking, cooking, deep fat frying in food industry. Lard obtained by combination of aqueous enzymatic extraction and β‐cyclodextrin treatment presented high quality and very low cholesterol.

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“…where For the decanoate ion inclusion in bCD, the following binding constants have been reported: 3.7 Â 10 3 , by affinity capillary electrophoresis [34], 2.6(AE0.2) Â 10 3 , by spectral displacement method [35], and 7.5(AE0.9) Â 10 3 , by potenciometry [36]. …”

Section: Equilibrium Concentrationsmentioning

confidence: 99%

Raman spectroscopic evidence for the inclusion of decanoate ion in trimethyl-β-cyclodextrin

Seica

Carvalho

Marques

et al. 2016

Vibrational Spectroscopy

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Trimethyl-b-cyclodextrin Micelles A B S T R A C TA method for calibrating Raman intensities of diluted aqueous solutions, based on the integrated intensity of the OH stretching bands of liquid water as an external intensity standard, is described and used to obtain a difference spectrum that reveals intensity changes mainly due to the intermolecular interaction between two solutes. The method is applied to trimethyl-b-cyclodextrin in sodium decanoate aqueous solutions. The difference between the interaction spectra above and below the critical micellar concentration of sodium decanoate, in the CH stretching region between 2700 and 3100 cm À1 , shows an intensity increase of the CH stretching bands for trimethyl-b-cyclodextrin above the critical micellar concentration of sodium decanoate, whereas b-cyclodextrin is relatively insensitive to the presence of decanoate ion micelles in aqueous solution.

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Affinity capillary electrophoresis and isothermal titration calorimetry for the determination of fatty acid binding with beta-cyclodextrin

Cited by 25 publications

References 39 publications

Characterization of complexes between phenethylamine enantiomers and β‐cyclodextrin derivatives by capillary electrophoresis—Determination of binding constants and complex mobilities

Characterization of complexes between phenethylamine enantiomers and β‐cyclodextrin derivatives by capillary electrophoresis—Determination of binding constants and complex mobilities

High quality lard with low cholesterol content produced by aqueous enzymatic extraction and β‐cyclodextrin treatment

Raman spectroscopic evidence for the inclusion of decanoate ion in trimethyl-β-cyclodextrin

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