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PubMed1976

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

Solubilization of uncharged, slightly soluble solutes is shown to be a useful approach for investigating patterns of self-association. The solubility of naphthalene in aqueous solutions of sodium cholate was determined over the concentration range of 0-0.20 mole/liter at 25 degrees. Bile salts such as sodium cholate have many detergent-like properties and exhibit hydrophobic self-association in aqueous solutions. It has become cutomary to describe this aggregation using the model of micelle formation. The naphthalene solubility data show that the CMC for sodium cholate is not well defined. Comparison with solubilization in a typical micelle-forming system, sodium decanesulfonate, shows clearly that sodium cholate does not resemble a micelle-forming system. Further examination of the solubility data in terms of mutual association of naphthalene with aggregate species shows that the self-association of sodium cholate is not consistent with the formation of (a) only large micelles containing 10 or more monomers, (b) only dimers, (c) dimers and large micelles, and (d) any unique oligomer or multimer. A complex pattern of association, including the formation of dimers and one or more higher oligomers, is indicated.

Chemical Phenomena↗

PubMed1983

Kinetic aspects and mechanism of liposome disintegration in polyoxyethylene lauryl ether and sodium cholate solutions.

The disintegration behaviour of liposomes in polyoxyethylene lauryl ether (PLE) and sodium cholate solutions was studied by the turbidity disappearance method. In maximally solubilized systems of liposomes, the molar ratios (phosphatidylcholine/surfactant) were 0.43 and 1.8 for PLE and sodium cholate, respectively. The disintegration process of either unilamellar or multilamellar liposomes followed first-order kinetics. Based on a physical model in which liposomes heterogeneous in size were assumed to disintegrate from the outermost shell one by one, a mathematical expression of the turbidity disappearance rate was introduced and applied to explain the data thus obtained. Model calculations suggested that the number of disintegrated shells would not be so large, even if up to 50% reduction of the initial turbidity was observed. From the dependence of the pseudo-first-order rate constant (kobs) on the surfactant concentration for unilamellar liposomes, it was assumed in general that kobs consists of the contributions of the monomer and micellar fractions: for PLE, both fractions shared in the disintegration, but only the micellar fraction with sodium cholate. Furthermore, in the latter case, kobs depended on the initial liposome concentration. These results are likely to be consistent with the proposed modes of surfactant action classified as type A and type B (Helenius, A. and Simons, K. (1975) Biochim. Biophys. Acta 415, 29-79).

Cholic Acid↗

PubMed2001

The optical interconversion of the P-450 and P-420 forms of neuronal nitric oxide synthase: effects of sodium cholate, mercury chloride and urea.

We investigated whether or not neuronal nitric oxide synthase (nNOS) (EC 1.14.13.39) was converted to the P-420 form on exposure to sodium cholate, mercury chloride or urea, and the reconversion of the P-420 to the P-450 form. Sodium cholate and mercury chloride induced the conversion of nNOS from the P-450 to the P-420 form in concentration- and incubation time-dependent manners, and the nNOS activity decreased. In the presence of glycerol, L-arginine and/or tetrahydrobiopterin, the sodium cholate-treated P-420 form could be reconverted to the P-450 form under constant experimental conditions, and the nNOS activity could also be restored. The mercury chloride-treated P-420 form of nNOS could be reconverted to the P-450 form on incubation with reduced glutathione (GSH) or L-cysteine, and the nNOS activity was recovered. However, no reconversion of the mercury chloride-treated P-420 form to the P-450 form was observed in the presence of glycerol, L-arginine, or tetrahydrobiopterin. Urea (4.0 M) dissociated nNOS into its subunits, but nNOS remained in the P-450 form. The nNOS monomer was more susceptible to sodium cholate. After removing the urea by dialysis, and supplementation of the nNOS solution with glycerol, L-arginine or BH(4), the P-420 was reconverted to the P-450 form, and the reassociation of nNOS monomers was also observed. These results suggested that nNOS was more stable as to exposure to sodium cholate, mercury chloride or urea in comparison to microsomal cytochrome P-450, which may be due to the different heme environment and protein structure.

Animals↗

PubMed1979

Sodium cholate dissolution of retained biliary stones: mortality rate following intrahepatic infusion.

The reported complication rate from T-tube infusion of sodium cholate for dissolution of retained biliary stones is low. Among 84 patients reported in the English-language literature, and 10 additional cases of our own, there have been no deaths, an incidence of liver enzyme elevation in 7%, fever in 5%, cholangitis in 2%, and pancreatitis in 2%. Recently, we have infused 100mM sodium cholate at 30 cc/hr into patients through transhepatic biliary stents in an effort to rid the intrahepatic biliary tree of retained stones and biliary sludge. Appropriate precautions were taken to prevent increased biliary pressures by the insetion of a 30 cm manometer into the perfusion system. During four transhepatic infusions in three patients, all experienced nausea and vomiting, and two of the three patients developed diarrhea and abdominal pain. Liver enzymes became elevated during all four infusions, and two of the three patients became septic and died shortly after their infusions. Experimental work in animals suggests that intrahepatic sodium cholate infusion results in injury to the ductal epithelium and predisposes patients to bactermia and sepsis. Even though T-tube infusion of sodium cholate into the common bile duct is well tolerated, direct infusion into the intrahepatic biliary tree through a transhepatic tube is not and carries a high risk of sepsis and death.

Abdomen↗

PubMed1988

Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (prepared by reverse-phase evaporation) by triton X-100, octyl glucoside, and sodium cholate.

The mechanisms governing the solubilization by Triton X-100, octyl glucoside, and sodium cholate of large unilamellar liposomes prepared by reverse-phase evaporation were investigated. The solubilization process is described by the three-stage model previously proposed for these detergents [Lichtenberg, D., Robson, R.J., & Dennis, E.A.(1983) Biochim. Biophys. Acta 737, 285-304]. In stage I, detergent monomers are incorporated into the phospholipid bilayers until they saturate the liposomes. At that point, i.e., stage II, mixed phospholipid-detergent micelles begin to form. By stage III, the lamellar to micellar transition is complete and all the phospholipids are present as mixed micelles. The turbidity of liposome preparations was systematically measured as a function of the amount of detergent added for a wide range of phospholipid concentrations (from 0.25 to 20 mM phospholipid). The results allowed a quantitative determination of RSat, the effective detergent to lipid molar ratios in the saturated liposomes, which were 0.64, 1.3, and 0.30 for Triton X-100, octyl glucoside, and sodium cholate, respectively. The corresponding ratios in the mixed micelles, RSol, were 2.5, 3.8, and 0.9 mol of detergent/mol of phospholipid. The monomer concentrations of the three detergents in the aqueous phase were also determined at the lamellar to micellar transitions (0.18, 17, and 2.8 mM, respectively). These transitions were also investigated by 31P NMR spectroscopy, and complete agreement was found with turbidity measurements. Freeze-fracture electron microscopy and permeability studies in the sublytic range of detergent concentrations indicated that during stage I of solubilization detergent partitioning between the aqueous phase and the lipid bilayer greatly affects the basic permeability of the liposomes without significantly changing the morphology of the preparations. A rough approximation of the partition coefficients was derived from the turbidity and permeability data (K = 3.5, 0.09, and 0.11 mM-1 for Triton X-100, octyl glucoside, and sodium cholate, respectively). It is concluded that when performed systematically, turbidity measurements constitute a very convenient and powerful technique for the quantitative study of the liposome solubilization process by detergents.

Bacteriorhodopsins↗

PubMed1998

Chiral separation of polychlorinated biphenyls by micellar electrokinetic chromatography with sodium cholate.

Micellar electrokinetic chromatography (MEKC) with one kind of bile salt (sodium cholate) was used to separate three chiral polychlorinated biphenyls (PCBs; 84, 95, and 176), each one in its two enantiomers. Sodium cholate was used as chiral surfactant in a 2-(N-cyclohexylamino) ethanesulfonic acid (CHES) buffer under alkaline (pH 10) conditions containing urea (2 M). The influence of bile salt concentration on the efficiency and the resolution between the two enantiomers of PCBs 84 and 95 was established. The chiral separation of three PCBs was successfully achieved in less than 30 min (approximately 23 min for PCB 176 and approximately 29 min for PCBs 84 and 95).

1-Propanol↗

PubMed1982

High resolution nuclear magnetic resonance spectroscopy of bile salts: individual proton assignments for sodium cholate in aqueous solution at 400 MHz.

The 400 MHz 1H-nuclear magnetic resonance spectrum of sodium cholate in dilute aqueous solution has been successfully resolved using a combination of decoupling, partial relaxation, and decoupled partial relaxation techniques. The individual carbon resonances in the 13C-NMR spectrum of sodium cholate have also have assigned. Assignments of individual methylene protons were made by consideration of the molecular structure of sodium cholate and the expected couplings and 1H-nuclear Overhauser enhancement experiments. Verification of the assignments of the methine protons was made by application of single frequency 1H-decoupled 13C-NMR. Variation of pH* from 6.0 to 11.0 did not alter the individual chemical shifts except for those between 2.12 delta and 2.30 delta, originating from the protons on the C23 position adjacent to the ionizable carboxyl group. The chemical shifts of the proton resonances were independent of concentration below 5 mM. Above 10 mM (micellar region), the proton chemical shifts were altered slightly and some band broadening occurred. These data are consistent with the formation of small micellar aggregates (up to N = 4) of cholate molecules.

Bile Acids and Salts↗

PubMed1988

Effects of ammonium acetate and sodium cholate on N-methyl-N'-nitro-N-nitrosoguanidine-induced colon carcinogenesis of rats.

This study was conducted to determine the effects of ammonium acetate alone or in combination with sodium cholate upon N-methyl-N'-nitro-N-nitrosoguanidine (MNNG)-induced colon carcinogenesis in rats. Ammonia, acetate, and deconjugated bile acids are produced by microbial enzymes in the gastrointestinal lumen. One hundred twenty male Sprague-Dawley rats, weighing 196 +/- 2 g at 8 wk of age, were given four intrarectal doses of MNNG (2 mg/dose) over 2 wk. They were then randomly assigned among four treatment groups, each containing 30 rats. The groups were arranged in a 2 x 2 factorial design and given intrarectal infusions of the agents under study in 0.3 ml of double-distilled water 3 times weekly for 52 wk beginning 4 wk after the initial MNNG treatment. The experimental treatments were: double-distilled water as control; ammonium acetate (24.8 mg of ammonia); sodium cholate (2 mg of cholic acid); and a combination of ammonium acetate and sodium cholate. Ammonium acetate treatment increased the number of rats with fecal blood 4-fold after 56 wk, and this was associated with a higher incidence of adenocarcinomas with a polypoid morphology. The incidence and total number of carcinomas in situ (high grade dysplasia) increased with ammonium acetate treatment. Ammonium acetate increased the total number of adenocarcinomas. Sodium cholate had no significant main effects on the incidence or morphology of colon lesions. The data support the conclusion that ammonium acetate treatment acted as a promoting agent in MNNG-induced colon carcinogenesis.

Acetates↗

PubMed1996

Fractal analysis of sodium cholate particles.

A fractal analysis was carried out on the powder particles of two samples of sodium cholate. A commercial sample had very irregular particles agglomerated, and accordingly the fractal dimension of the surface was 2.98, suggesting a noteworthy roughness of the particle surface; scanning electron microscopy showed that this was due to irregularities caused by a disordered agglomeration of very small particles, resulting in larger particles showing polygonal and smooth but limited facets. A second sample was obtained by recrystallization from ethanol of the commercial sodium cholate and contained large and regular particles, with very smooth surfaces. The fractal dimension therefore was accordingly low. Despite these differences, the two samples had similar, high reactive dimension values to dissolution (2.96 and 2.76, respectively), suggesting that the surfactant behavior of sodium cholate is an important parameter in driving the dissolution of the solid particles and leveling the surface defects.

Cholic Acid↗

PubMedDate not supplied

Composition of sodium cholate micellar solutions.

To study the composition of sodium cholate solutions, an investigation was carried out at 25 degrees C and in N(CH3)4Cl, as a constant ionic medium, at three different concentrations (W = 0.100; 0.500 and 0.800 mol dm(-3)). Electromotive force measurements of three different galvanic cells, the first involving a glass electrode for hydrogen ions, the second an electrode for sodium ions and the third a lead amalgam electrode, were performed. Independently, lead (II) cholate solubility measurements in the presence of sodium ions were performed, as well. The experimental results obtained from both approaches were explained by assuming the formation of aggregates in cholate and sodium of different composition depending on W and on the cholate concentration. The maximum aggregation found number for cholate was 24 and even aggregation numbers were markedly predominant. Only two species with odd aggregation number were found, but at a low percentage. The assumed species and the relative constants were compared with those found for the other sodium salt of cholanic acids.

Cholic Acids↗

PubMed1998

Hypoglycemic effect of oral insulin in diabetic rabbits using pH-dependent coated capsules containing sodium salicylate without and with sodium cholate.

The hypoglycemic effect of oral insulin (20 U and 40 U) capsules coated with a pH-dependent soluble polymer (Eudragit S100) and containing sodium salicylate (50 mg) without and with sodium cholate (50 mg) was studied in alloxan-hyperglycemic rabbits and compared with that of s.c. insulin injection (20 U). The capsules containing 20 U insulin + sodium salicylate (50 mg) produced a significant reduction in plasma glucose level to 82 and 73% of initial values at 2 and 3 hr after administration, respectively. The blood glucose level slowly returned to normal values at 5 hr. The AUC0-5 hr was 73.7 +/- 43.5 mg.hr/dl compared to 242 +/- 70.5 mg.hr/dl for insulin (20 U, s.c.) with a relative hypoglycemia of 30.4%. A higher dose of oral insulin (40 U) + sodium salicylate (50 mg) was more effective in reducing plasma glucose level which steadily decreased and reached 56% of the initial value by 5 hr (AUC0-5 hr = 132 +/- 41.5 mg.hr/dl and relative hypoglycemia = 27.3%). Sodium cholate (50 mg), however, slightly improved sodium salicylate effect producing an AUC0-5 hr of 139 +/- 37.3 mg.hr/dl with relative hypoglycemia of 28.7%. The relative hypoglycemia of pH-dependent coated capsules reached in the present experiment is the highest found so far.

Animals↗

PubMed1979

Cholate sodium infusion for retained common bile duct stones.

Eight patients with stones retained in the extrahepatic biliary tract underwent cholate sodium infusion for dissolution of the stones. In six patients, the stones disappeared. However, in two of the patients, the stones did not disappear, and they were removed with the ureteral basket. Infusion of cholate sodium was well tolerated by six patients, but was accompanied by nausea, vomiting, and abdominal pain in two patients. In one case, mucosal deformity of the common bile duct was noticed during the infusion, but it was not apparent on a subsequent cholangiogram. As a result of our experience, we conclude that cholate sodium infusion is a safe procedure for the attempted dissolution of retained common bile duct stones.

Adult↗

PubMed1999

Effect of Sublytic Concentrations of Sodium Cholate on Phospholipase C Hydrolysis of Phospholipid Bilayers.

Phospholipase C activity has been assayed with phosphatidylcholine as substrate in the presence of sodium cholate at concentrations well below those producing lipid solubilization. With short-chain phosphatidylcholine, which exists in monomeric form in aqueous solution, cholate has little or no effect. However, when the substrate is egg phosphatidylcholine in the form of bilayers, small cholate concentrations (below 1 mM, corresponding to an effective surfactant:lipid ratio below 0.05) increase the maximum enzyme rates by about threefold, while decreasing drastically the latency periods of enzyme activity. Previous studies from this laboratory have associated the phospholipase enhancing activity of a variety of amphiphiles to their ability to facilitate the formation of inverted hexagonal phospholipid structures, yet sodium cholate has the opposite effect, stabilizing the lamellar versus the inverted hexagonal phase. This suggests that cholate is activating phospholipase C through a hitherto undescribed mechanism. Sodium cholate concentrations above 1 mM decrease further the enzyme lag time, but they are less effective in enhancing enzyme rates. These observations may be pertinent in the analysis of biochemical data with purified lipases, as well as in physiological studies of biliary function. Copyright 1999 Academic Press.

Journal Article↗

PubMed1984

Apolipoprotein B: removal of lipids by sodium cholate and reassociation of a lipid-free apoprotein with dipalmitoyl phosphatidylcholine.

Apolipoprotein B (apoB) of human plasma low-density lipoprotein has been solubilized with sodium cholate added in an amount highly above its critical micellar concentration. During isolation by gel exclusion chromatography on Sepharose CL-4B, the apoB forms mixed micelles of protein and detergent that are free of endogenous lipids. The circular dichroic spectra of the sodium cholate-solubilized apoB indicate significant heterogeneity within the fractions obtained by gel chromatography. The peak position fraction of apoB taken from the column was used for reassociation with dipalmitoyl phosphatidylcholine (DPPC). A soluble apoB-DPPC complex has been prepared by incubation of apoB-sodium cholate and DPPC-sodium cholate solutions at 42 degrees C, followed with detergent removal by extensive dialysis in the presence of a XAD-2 ion-exchange resin. Data from negative-stain electron microscopy suggests the incorporation of solubilized apoB into single-bilayer phospholipid vesicles. Upon reassociation with phospholipid, a shift (to shorter wavelengths) occurs in the intrinsic fluorescence of the apoB, thus indicating a transfer of tryptophan residues to a more hydrophobic environment. Sodium dodecylsulfate-polyacrylamide electrophoresis gives a single band (apparent Mr 370,000) for apoB after solubilization, purification and interaction with the phospholipid.

Apolipoproteins B↗

PubMed1985

Self-association of sodium cholate in isotonic saline solutions.

The self-association of dialyzed solutions of sodium cholate in isotonic saline solutions has been studied by vapor pressure osmometry and sedimentation equilibrium. These studies were carried out at 25, 31 and 37 degrees C. In all experiments the self-association could be described as a two-equilibrium constant, indefinite self-association in which odd species beyond monomer were absent. The plots of M1/Mna or M1/Mwa vs. c were quite smooth with no sharp breaks; this suggested that there were no critical phenomena. The temperature dependence of the self-association was quite small. Our results are in accord with other studies on sodium cholate which indicate that the self-association involves several species, and that it is not a monomer-n-mer self-association.

Centrifugation↗

PubMed1986

Effect of sodium taurocholate and sodium cholate on short-circuit current on amphibian membranes.

The effects of the bile salts, sodium taurocholate (NaTc) and sodium cholate (NaCh), and toad bile gallbladder (bile) on short-circuit current (SCC) across isolated skin, and sodium taurocholate (NaTc) on isolated bladder of Bufo arenarum toads were tested. Sodium taurocholate (NaTc), sodium cholate (NaCh) and toad bile gallbladder (bile) promoted an increase in SCC, when added to the external side. The stimulatory effect was reversible after rinsing the preparation for 60 min. Implications on in vivo renal function of these results are discussed.

Animals↗

PubMed2001

Separation and selectivity of benzophenones in micellar electrokinetic chromatography using sodium dodecyl sulfate micelles or sodium cholate modified mixed micelles.

The separation and selectivity of nine benzophenones in micellar electrokinetic chromatography (MEKC) using sodium dodecyl sulfate (SDS) micelles or sodium cholate (SC) modified mixed micelles were investigated in the pH range 6.5-8.0. The results indicate that the combined effects of buffer pH and SC concentration can greatly affect the separation and selectivity of benzophenones, particularly for benzophenones possessing a hydroxyl substituent at the 4-position of the aromatic ring with respect to the carbonyl moiety when using SDS-SC mixed micelles. Better separability can be obtained with SDS-SC mixed micelles than with SDS micelles. Complete separation of nine benzophenones in MEKC can be achieved with an appropriate choice of buffer pH and the concentration of SDS micelles or SC modified mixed micelles. The dependence of the migration order of those benzophenones based on their structures and solute-micelle interactions is discussed.

Benzophenones↗

PubMed1996

Purification of fibroblast growth factor-2 from human placenta using tri(n-butyl)phosphate and sodium cholate.

Tri(n-butyl)phosphate (TNBP) and sodium cholate (SC) mixtures have been used to inactivate lipid-enveloped viruses like HIV and hepatitis B. We exploited the use of this combination to purify fibroblast growth factor-2 (FGF-2) from human placenta. Human placentas were extracted in the presence of 0.3% TNBP/0.2% SC and the clarified homogenate was adsorbed to S-Sepharose. The active fractions were further loaded onto a heparin-Sepharose column and purified FGF-2 was eluted with 2.0 M NaCl. FGF-2 purified this way was indistinguishable from FGF-2 purified without TNBP/SC in the extraction step in terms of yield, specific activity and biological response. The lipid-enveloped vaccinia virus was used in a parallel experiment to evaluate the inactivation capacity of our protocol. Under the conditions described here, the combined use of TNBP/SC did not eliminate but reduced significantly the number of vaccinia virus PFUs by log 2-3.

3T3 Cells↗