Determination of critical micellar concentrations of two monoketo derivatives of cholic acid

Poša, Mihalj; Csanádi, János

doi:10.1016/j.colsurfb.2009.06.029

Cited by 20 publications

(13 citation statements)

References 33 publications

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“…Table 1 shows [18,19]. This is also supported by the literature data for oxo derivatives of bile acid salts [1,19]. Based on Table 1, it can be concluded that the replacement of OH groups with oxo groups leads to an increase in the values c The aggregation number n and the fraction of bound counterion at a concentration c is calculated according to equation (Figure 2.…”

Section: Resultssupporting

confidence: 74%

“…In the experiment, changes in the freezing point depression of the solution, the T k is followed as a function of the total molal concentration of the bile acid can be assumed to be constant [12,14]. Table 1 shows [18,19]. This is also supported by the literature data for oxo derivatives of bile acid salts [1,19].…”

Section: Resultssupporting

confidence: 52%

“…If cholic acid is excluded from the liner regresion, correlation coefficient n = f (CMC) reaches a new value 0.9203. It is researched that hydrogen bonding is also possible in 7-oxo-deoxycholic acid [19], but it is not visible in Figure 4, which means that 7-oxo-deoxycholic acid sodium salt is not an infuential observation. All this shows that freezing point depression determination method is less sensitive or insensitive as far as aggregates such as Small's secondary micelles are concerned.…”

Section: Resultsmentioning

confidence: 98%

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Determination of Aggregation Numbers of Bile Salt Micelles with the Depression of the Solution Freezing Point

Poša¹

2013

J. Appl. Sol. Chem. Model.

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The special geometry of the steroid skeleton causes formation of bile acid anion micelles with small aggregation numbers, in contrast to aliphatic amphiphiles. Relative to the tendency to reduce membrane toxicity, pharmacological investigations of bile acids are mainly concerned with their oxo derivatives. Since micelles of these bile acids have been insufficiently studied, the objective of this work is the determination of aggregation numbers of corresponding micelle monomers. The aggregation numbers were determined using the freezing point depression of the solutions by applying the appropriate equations of Debye-Hückel, Guggenheim and Gibbs-Duhems, and using pNa data measured with a Na-selective electrode. Depending on the structure of the bile acid anion, the values obtained for the aggregation numbers were in the range from 2.09 to 3.44. The increase in number of oxo groups in the molecule is accompanied by a decrease in hydrophobicity of the convex side of the steroid skeleton of the bile acid anion, resulting in a lower aggregation number.

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Section: Resultssupporting

confidence: 74%

Section: Resultssupporting

confidence: 52%

Section: Resultsmentioning

confidence: 98%

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Determination of Aggregation Numbers of Bile Salt Micelles with the Depression of the Solution Freezing Point

Poša¹

2013

J. Appl. Sol. Chem. Model.

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“…Based on critical micellar concentration (CMC) values one might expect that more hydrophobic SDS (CMC = 8.00 mM) [5] has better resveratrol solubilization capacity than S7-OD (CMC = 43 mM) [22]. However, experiments indicated the contrary.…”

Section: Resultsmentioning

confidence: 99%

Comparison of Solubilization Capacity of Resveratrol in Sodium 3α,12α-Dihydroxy-7-oxo-5β-cholanoate and Sodium Dodecyl Sulfate

Cvejić

Poša

Sebenji

et al. 2014

The Scientific World Journal

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In this study we investigated resveratrol (trans-3,5,4′-trihydroxystilbene) solubilization with sodium 3α,12α-dihydroxy-7-oxo-5β-cholanoate (S7-OD) and sodium dodecyl sulfate (SDS). The investigation was aimed at determining whether large spherical micelles (SDS) or small longitudinal micelles (S7-OD) are more convenient for incorporation of resveratrol. Also, we studied resveratrol behavior in mixed micelles with mentioned surfactants using spectroflourimetric method as well as the effects of sodium chloride and urea on resveratrol solubilization capacity in the applied surfactants. Resveratrol solubilization curve was different in the investigated surfactants. Resveratrol solubilization curve for sodium 3α,12α-dihydroxy-7-oxo-5β-cholanoate at concentration 0.9 CMC reached saturation level of 60% dissolved resveratrol. The curve for sodium dodecyl sulfate was linear within the whole range of the investigated concentration; resveratrol solubilization rate reached 13% at 2 CMC. In S7-OD, NaCl increased capacity of resveratrol solubilization up to 1.4 CMC surfactant concentration, whilst maximum level of dissolved resveratrol (90%) was observed at 0.9 CMC. In SDS, NaCl decreased resveratrol solubilization capacity. Urea reduced resveratrol solubilization rate in sodium 3α,12α-dihydroxy-7-oxo-5β-cholanoate, whereas it had inverse effect in sodium dodecyl sulfate. The obtained results strongly suggest that structure, that is, shape, of the surfactant micelles significantly affects their capacity of resveratrol solubilization. Also, presence of NaCl and urea influences solubilization capacities of investigated surfactants.

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“…The spin-lattice relaxation time was determined by fast inversion-recovery experiments (180°-τ-90°-AQC). [13][14][15] The area of the bile acid signal was measured at nine different times τ.…”

Section: H-nmr Relaxation Experimentsmentioning

confidence: 99%

Effect of sodium salts of 3α,12α-dihydroxy-7-oxo-5β-cholanoic and 3,7,12-trioxo-5β-cholanoic acids on verapamil hydrochloride in biophysical-chemical model experiments

Poša

Guzsvány

Mikov

et al. 2011

JSCS

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It is known that certain bile acids have a promotive effect on the action of some drugs. Special attention is paid to bile acids having oxo groups instead of OH groups in the steroid skeleton of their molecule, since these derivatives have a lower hemolytic potential (membrane toxicity). This study examined the effects of sodium salts of 3α,12α-dihydroxy-7-oxo-5β-cholanoic acid (7-oC) and 3,7,12-trioxo-5β-cholanoic acid (3,7,12-toC) on the adsorption of verapamil hydrochloride on activated carbon (model of the cell membrane). The interaction was followed by measuring the effect of verapamil on the functional dependence between the spin-lattice relaxation time T 1 (protons of the C18 angular group of the bile acid molecule) and the bile acid concentration in deuterated chloroform (model of the cell membrane lipid phase). Whether a depot effect of verapamil exists when 7-oC and 3,7,12-toC (in the form of methyl esters) are present in chloroform was also investigated. It was found that 7-oC exhibited a significant effect in the experiments with verapamil, whereas 3,7,12-toC showed no difference of the measured parameters with respect to the control. This indicates that bile acid molecules should have OH groups bound to the steroid nucleus, in order to exhibit an effect on the monitored physico-chemical parameters of verapamil.

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Determination of critical micellar concentrations of two monoketo derivatives of cholic acid

Cited by 20 publications

References 33 publications

Determination of Aggregation Numbers of Bile Salt Micelles with the Depression of the Solution Freezing Point

Determination of Aggregation Numbers of Bile Salt Micelles with the Depression of the Solution Freezing Point

Comparison of Solubilization Capacity of Resveratrol in Sodium 3α,12α-Dihydroxy-7-oxo-5β-cholanoate and Sodium Dodecyl Sulfate

Effect of sodium salts of 3α,12α-dihydroxy-7-oxo-5β-cholanoic and 3,7,12-trioxo-5β-cholanoic acids on verapamil hydrochloride in biophysical-chemical model experiments

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