Solubilization as a method for studying self-association: Solubility of naphthalene in the bile salt sodium cholate and the complex pattern of its aggregation

Mukerjee, Pasupati; Cardinal, John R.

doi:10.1002/jps.2600650620

Cited by 116 publications

(42 citation statements)

References 15 publications

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“…5a, only a very slight increase in G and G is found with increasing glycocholic acid concentration with the elastic and viscous moduli remaining at the level reached, even at higher surfactant concentrations. This is analogous to the CP results, again suggesting that this surfactant, with its gradual micellar growth and thus limited capacity for cooperative association, is not able to bind excessively to the polymer (19,20,31). Thus, glycocholic acid only affects CP and G and G to a limited extent.…”

Section: Anionic Surfactantssupporting

confidence: 80%

“…3a by the anionic glycocholic acid surfactant, which shows a less pronounced increase in CP with increasing concentration. This might be caused by the difference in aggregation behavior between bile salts and typical ionic surfactants, which, in the case of bile salts, occurs over a broader concentration range starting with the formation of dimers and oligomers that polymerize into larger aggregates with increasing concentration (19,20,31). Furthermore, initial addition of glycocholic acid is found to result in a significantly more extensive reduction of CP than the corresponding SDS addition.…”

Section: Anionic Surfactantsmentioning

confidence: 89%

“…Benzyldimethyltetradecyl ammonium chloride (benzalkonium chloride) (C 14 ), cmc approximately 3 mM (18), benzyldimethylhexadecyl ammonium chloride (benzalkonium chloride) (C 16 ), cmc 0.026 mM (Sigma), hexadecyltrimethylammonium bromide, CTAB (C 16 ), cmc 0.9 mM (16), glycocholic acid sodium salt, bile salt (99% purified grade), cmc 7.1 mM (Sigma), and sodium chloride were all obtained from Sigma Chemicals, USA. [Note that the cmc value, taken as the midpoint of the concentration range where aggregation occurs, is more gradual for bile salt compared to most typical ionic surfactants and thus less well-defined (19,20).] The active ingredients prilocaine and lidocaine (Fig.…”

Section: Chemicalsmentioning

confidence: 99%

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Nonionic Cellulose Ethers as Potential Drug Delivery Systems for Periodontal Anesthesia

Scherlund

Brodin

Malmsten³

2000

Journal of Colloid and Interface Science

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Section: Anionic Surfactantssupporting

confidence: 80%

Section: Anionic Surfactantsmentioning

confidence: 89%

Section: Chemicalsmentioning

confidence: 99%

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Nonionic Cellulose Ethers as Potential Drug Delivery Systems for Periodontal Anesthesia

Scherlund

Brodin

Malmsten³

2000

Journal of Colloid and Interface Science

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“…SC is an anionic, chiral surfactant used in MEKC, usually for the separation of enantiomers [13-151. There has been considerable discussion about the critical micelle concentration of SC and about the structure of the micelles [16,171. One theory, perhaps the most popular one, suggests that the CMC of SC should be about 12 mM [18] and that SC will then form helicalstructured micelles [19, 201. The next task was to choose the right buffer.…”

Section: Resultsmentioning

confidence: 99%

Optimization of selectivity and resolution in micellar electrokinetic capillary chromatography with a mixed micellar system of sodium dodecyl sulfate and sodium cholate

Wiedmer

Jumppanen²,

Haario

et al. 1996

Electrophoresis

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Selectivity and resolution were studied for the separation of seven corticosteroids by micellar electrokinetic capillary chromatography (MEKC) using a mixed micellar solution of sodium dodecyl sulfate (SDS) and sodium cholate (SC), buffered with 3-(N-morpholino)propanesulfonic acid (MOPS) or 3-[(1,1-dimethyl-2-hydroxyethyl)amino]-2-hydroxypropane sulfonic acid (AMPSO). The changes in selectivity were compared for the AMPSO-SDS-SC system by varying the pH and the concentrations of AMPSO, SDS and SC. The experimental design started with the central composite design and continued in a sequential manner. The optimum selectivity for the separation of the corticosteroids was calculated from the analyte migration times and the analyte velocities, by using empirical quadratic regression models. Satisfactory regression fits and coefficients of determination for prediction were obtained with cross-validated models. To optimize the resolution, the physical parameters of capillary length and analysis time were varied under the conditions optimal for the selectivity. In both the selectivity and the resolution, optimization the overall optimum was determined by using the desirability function technique. Analysis times were controlled by using 1,3-diaminopropane to influence the electroosmotic flow velocity (veo). The voltage was kept constant, which resulted in higher electric field strength in shorter capillaries. No changes in the selectivity were observed when 1,3-diaminopropane was used to control the electroosmotic flow velocity. Such an optimization technique, where the chemical and physical factors affecting the separation are treated independently, seemed to be effective for finding the best possible resolution for the corticosteroids.

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“…Dilute aqueous solutions of detergents (e.g., sodium dodecyl sulfate) consist of monomers located at the air-water interface. When the amount of the surfactant is increased past the critical micelle concentration (CMC), the monomer concentration becomes constant (at the CMC), as large water-soluble micelles (aggregation numbers ~50, low polydispersity) form, accompanied by sharp transitions in many physical properties of the solution (Pramauro andPelezetti, 1996, Ekwall, 1954;Fontell, 1971;Mukerjee and Cardinal, 1976;Chang and Cardinal, 1978).…”

Section: Introductionmentioning

confidence: 99%

Phenothiazines solution complexity – Determination of pKa and solubility-pH profiles exhibiting sub-micellar aggregation at 25 and 37°C

Pobudkowska

Ràfols

Subirats

et al. 2016

European Journal of Pharmaceutical Sciences

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The ionization constants (pK a ) and the pH-dependent solubility (log S-pH) of six phenothiazine derivatives (promazine hydrochloride, chlorpromazine hydrochloride, triflupromazine hydrochloride, fluphenazine dihydrochloride, perphenazine free base, and trifluoperazine dihydrochloride) were determined at 25 and 37 o C. The pK a values of these low-soluble surface active molecules were determined by the cosolvent method (n-propanol/water at 37 o C and methanol/water at 25 o C). The log S-pH profiles were measured at 24 h incubation time in 0.15 M phosphate buffers. The log S-pH "shape-template" method, which critically depends on accurate pK a values (determined independently of solubility data), was used to propose speciation models, which were subsequently refined by rigorous mass-action weighted regression procedure described recently. Differential scanning calorimetry (DSC), UV-visible spectrophotometry, potentiometric, and high performance liquid chromatography (HPLC) measurements were used to characterize the compounds. The intrinsic solubility (S 0 ) values of the three least-soluble drugs (chlorpromazine·HCl, triflupromazine·HCl, and trifluoperazine·2HCl) at 25 o C were 0.5, 1.1, and 2.7 μg/mL (resp.). These values increased to 5.5, 9.2, and 8.7 μg/mL (resp.) at the physiological temperature. The enthalpies of solution for the latter compounds were exceptionally high positive (endothermic) values (99-152 kJ·mol -1 ).Cationic sub-micellar aggregates were evident (from the distortions in the log S-pH profiles) for chlorpromazine, fluphenazine, perphenazine, and trifluoperazine at 25 o C. The effects persisted at 37 o C for chlorpromazine and trifluoperazine. The solids in suspension were apparently amorphous in cases where the drugs were introduced as the chloride salts.3

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Solubilization as a method for studying self-association: Solubility of naphthalene in the bile salt sodium cholate and the complex pattern of its aggregation

Cited by 116 publications

References 15 publications

Nonionic Cellulose Ethers as Potential Drug Delivery Systems for Periodontal Anesthesia

Nonionic Cellulose Ethers as Potential Drug Delivery Systems for Periodontal Anesthesia

Optimization of selectivity and resolution in micellar electrokinetic capillary chromatography with a mixed micellar system of sodium dodecyl sulfate and sodium cholate

Phenothiazines solution complexity – Determination of pKa and solubility-pH profiles exhibiting sub-micellar aggregation at 25 and 37°C

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