Sodium taurodeoxycholate

Morimoto et al. [33] demonstrated that the ocular absorption of hydrophilic compounds over a wide range of molecular weights could be increased by 2 and 10 mM sodium taurocholate and sodium taurodeoxycholate in a dose-dependent manner. The compounds were glutathione (307 Da), 6-carboxyfluorescein (376 Da), FTTC-dextran (4 kDa), and insulin (5.7 kDa). Of the two bile salts, sodium taurodeoxycholate was more effective. At 10 mM, this bile salt increased the permeability of 6-carboxyfluorescein from 0.02% to 11%, glutathione from 0.08% to 6%, FITC-dextran from 0% to 0.07%, and insulin from 0.06% to 3.8%. Sodium taurocholate, on the other hand, increased the permeability to 0.13%, 0.38%, 0.0011%, and 0.14%, respectively. Taurodeoxycholate was more effective than taurocholate in the nasal epithelium as well [202], This difference in activities can possibly be attributed to their micelle-forming capability, which is higher for taurodeoxycholate, a dihydroxy bile salt [190],... 

A further group of AT-[(acyloxy)methyl] pro-moieties contains acidic and/or lipid-like substituents. Here again, most published results concern phenytoin. Thus, some phenytoin-lipid conjugates such as 8.183 and 8.186 (with R = various fatty acyl moieties) were reported [233]. Such prodrugs are, of course, insoluble in water but formed dispersions when briefly sonicated in EtOH/water mixtures containing sodium taurodeoxycholate. No significant hydrolysis was seen in buffer or plasma. In contrast, incubation with pancreatic lipase yielded the bis-deacyl derivatives (i.e., 8.182 and 8.185, respectively), with subsequent liberation of phenytoin the time for 50% liberation of phenytoin varied from 20 to 200 min under the conditions of the studies [233][234], The intermediates 8.182, 8.184, and 8.185 were also substrates for human and rat plasma hydrolases. 

Sodium taurocholate Sodium taurochenodeoxycholate A Sodium taurodeoxycholate... 

For phase equilibria experiments, either sodium taurodeoxycholate or an equimolar mixture of sodium taurocholate and sodium taurodeoxycholate was used, unless noted, as previous studies (8) had shown that the behavior of monoolein was similar in all of the bile salt conjugates. Previous studies (7) had also shown that the 1-monoolein and 2-monoolein behaved identically in bile salt solution. Therefore, 1-monoolein was used in all experiments because of its greater availability and stability (7). Lipids, dissolved in an appropriate solvent, were added to... 

For bile salt mixtures, total concentration of bile salts is given. TDC = sodium taurodeoxycholate. TC = sodium taurocholate. OA oleic acid. MO = monoolein. 

Bile salts used in permeation enhancement studies include the trihydroxy salts sodium cholate, sodium glycocholate, and sodium taurocholate (Figure 10.2) and the dihydroxy salts sodium deoxycholate, sodium glycodeoxycholate, and sodium taurodeoxycholate. Several in vitro permeation studies carried out in isolated animal buccal mucosa and in vivo bioavailability studies conducted in animals and human subjects have proven their potential as effective buccal permeation enhancers. 

The reaction mixture contained 50 /xg to 1 mg of protein, 1 m M GMj in 200 ftL of 50 mM citric acid-100 mM sodium phosphate buffer (pH 4.4) containing 100 mM NaCl, and 0.5% sodium taurodeoxycholate. The mixture was incubated at 37°C for 1 hour, and the reaction was terminated by heating at 100°C for 2 minutes. Cooling in an ice bath was followed by addition of 200 /xL of the mobile phase solvent. The supemate obtained by centrifugation was filtered before analysis of an aliquot by HPLC. The reaction was linear for up to 1 hour with up to 0.7 mg protein added. 

Feldman, S. Gibaldi, M. Physiological surface-active agent and drug absorption 1. Effect of sodium taurodeoxycholate on salicylate transfer across the everted rat intestine. J. Pharm. Sci. 1969, 58, 425-428. 

A micellar electrokinetic chromatographic method allows the separation of optically isomeric diltiazem hydrochloride using bile salts as chiral surfactants. The chiral separation of diltiazem hydrochloride from several analogs is achieved at ambient temperature using 0.05M sodium taurodeoxycholate in a 0.02M aqueous phosphate-borate buffer solution of pH 7.0. Separation is performed using a fused-silica capillary tube (650 mm x 50 mm I.D.) and a voltage up to +25 kV. Detection is achieved on-column using UV adsorption at 210 nm (31). 

R. Scow. Effect of sodium taurodeoxycholate, CaCh and albumin on the action of pancreatic lipase on droplets of trioleoylglycerol and the release of lipolytic products into aqueous media. Biochimie 70.1251 (1988). 

Li G, MeGown L. A new approach to polydispersity studies of sodium taurocholate and sodium taurodeoxycholate aggregates using dynamic fluorescence anisotropy. J Phys Chem 1993 97 6745-52. 

Chen, R, Zhang, S., Qi, L., and Chen, Y., Chiral capillary electrophoretic separation of amino acids derivatized with 9-fluorenylmethylchloroformate using mixed chiral selectors of P-cyclodexIrin and sodium taurodeoxycholate. Electrophoresis, 27, 2896, 2006. 

ASE, accelerated solvent extraction HPGPC, high-performance gel permeation chromatography OSUA, oligomers of sodium undecylenic acid SEE, supercritical fluid extraction SDpCD, sulfobutyl ether p-cyclodextrin MpCD, methyl p-cyclodextrin PFOS , perfluorooctanic sulfate DMSO, dimethyl sulfoxide THA+, tetrahexylammonium SPME, solid-phase microextraction STDC, sodium taurodeoxycholate LIE, laser-induced fluorescence LLE, liquid-liquid extraction. 

E. Dabek-Zlotorzynska and E.P.C. Lai, Separation of polynuclear aromatic hydrocarbons by micellar electrokinetic capillary chromatography using sodium taurodeoxycholate modified with organic solvents, J. Cap. Elec., 3, 31-35,1996. 

Fatty acids have a lower solubility in typical ionic detergent solutions than in bile acid solutions, for a given micellar concentration. To paraphrase, the micellar zone in the ternary phase diagram of this system (ionic detergent-fatty acid-water) is smaller than that in the system bile acid-fatty acid-water. Small has constructed the sodium oleate-oleic acid-water phase diagram (32) the micellar zone is extremely small because of the formation of liquid crystalline phases of oleic-sodium oleate at very low oleic acid/ sodium oleate ratios. In unpublished experiments carried out several years ago, we compared the solubility of lauric acid in 40 mM solutions of sodium taurodeoxycholate and sodium glycodeoxycholate with that in sodium octyl benzene sulfonate. Lauric acid at concentrations of 1, 5, and 10 mM was completely soluble in these bile acid solutions at pH 6.3. By contrast, a 5 mM concentration of lauric acid in sodium octyl benzene sulfonate solution was completely turbid. 

For bile salt mixtures, total concentration of bile salts is given. CTAB, cetyl trimethylam-monium bromide HDPC, hexadecyl pyridinium chloride lauryl taurate, sodium lauryl taurate TC-TDC, sodium taurocholate-sodium taurodeoxycholate ABS, sodium p-(H-octyl) benzene sulfonate SIC, a mixture of sodium taurocholate, sodium taurodeoxycholate, sodium taurochenodeoxycholate, sodium glycocholate, sodium glycodeoxycholate, and sodium glycochenodeoxycholate composed to resemble human small intestinal content during fat digestion and absorption (19). 

These mixtures at 5, 10, and 15 mM total concentration were incubated in a 20 mM solution of sodium taurocholate-sodium taurodeoxycholate. The critical micellar concentration of this system should be 2-4 mM. All mixtures at 5 mM were clear micellar solutions. At 10 and 15 mM, samples containing oleic acid were turbid, with oil droplets of oleic acid present. Those containing chiefiy oleic acid, but some mono-olein, were faintly opalescent, indicating large aggregates, possibly very large micelles, or liquid crystalline aggregates. 

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