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PubMed1991

Dissolution of bile duct stones by a hydrophilized glyceromonooctanoin-bile-acid-EDTA emulsion.

The clinical suitability of conventional glyceromonooctanoin (GMOC) and ethylenediaminetetraacetic acid (EDTA) containing solvents for the dissolution of common bile duct stones is questionable. To improve the solvent-stone contact and the miscibility with bile, GMOC was hydrophilized by the addition of polyethyleneglycol-caprylglyceride, polyethyleneglycol-sorbitan-etheroleyl-ester, and polyethyleneglycol-sorbitanlauryl-ester (PEG-GMOC). This product was mixed with a bile acid-EDTA (BA-EDTA) solution in a ratio of 1:2 (v/v) for cholesterol solubilizing and calcium complexing capacities. To determine clinical efficiency, the new solvent was infused via a nasobiliary tube in 16 patients with endoscopically nonextractable common bile duct stones and compared with a group of 16 patients treated with an alternating GMOC/BA-EDTA regimen. Continuous perfusion with PEG-GMOC-BA-EDTA led to a total (12 patients) or partial (3 patients) disappearance of the stones within 2-15 days. Similarly, alternating GMOC and BA-EDTA treatment dissolved the stones in 12 patients. The average volume of PEG-GMOC-BA-EDTA infused contained only 27% of the GMOC applied during the alternating therapeutic regime. This reduction of the GMOC dose was associated with a significant reduction of adverse effects such as emesis, diarrhea and biliary pain. We concluded that GMOC is equally efficient in the new hydrophilized form but it is clearly superior as far as side effects are concerned. In all, this supports its clinical suitability for the dissolution treatment of common bile duct stones.

Aged↗
PubMed1985

Total serum bile acids and the bile acid profile as tests of liver function.

Total serum bile acid assay for the evaluation of liver function has been available for many years but its application has been limited primarily by factors such as methodology, equipment and cost. New and improved methods for bile acid assay such as the radioimmunoassay or the hydroxysteroid dehydrogenase techniques have brought the assay for bile acids into the realm of the clinical laboratory. The efficacy of bile acids for clinical diagnostic use in the evaluation of liver function has not been firmly established. Newer methods using high pressure liquid chromatography to develop a profile of the different bile acids may clarify its usefulness and define its role among the many available tests of liver function in animals.

Bile Acids and Salts↗
PubMed1977

Diffusion coefficients of single bile salt and bile salt-mixed lipid micelles in aqueous solution measured by quasielastic laser light scattering.

Diffusion coefficients of single bile salt micelles and mixed binary micelles consisting of single bile salts and phosphatidylcholine in the molar ratio 3 : 1 have been measured using quasielastic laser light scattering spectroscopy. Among single systems, marked concentration dependence of the diffusion coefficient was observed only in those containing sodium taurodeoxycholate. Micellar size correlates with bile salt molecular structure in a manner similar to that observed by earlier workers with some minor differences to towards a more consistent ordering. Phosphatidylcholine produces small increases in micellar size in most systems depending on bile salt structure, and seems most plausibly interpreted as simple swelling of the single species micelles. In some systems, when phosphatidylcholine is added, size or shape changes are indicated. Diffusion coefficients were also studied in the ternary systems bile salt-phosphatidylcholine-cholesterol which were saturated and metastably super-saturated with respect to cholesterol. The Stokes radii in both systems were the same within experimental error, 35 A. Our results indicate that intermicellar interactions significantly contributed to the measured diffusion coefficients in the ternary systems as well as in the single sodium taurodeoxycholate and binary sodium taurodeoxycholate-phosphatidylcholine systems in the concentration range studied.

Bile Acids and Salts↗
PubMed1979

Distinct effects of three bile salts on cholesterol solubilization by oleate-monoolein-bile salt micelles.

Micellar cholesterol solubilities in bile salt-monoolein-oleic acid systems have been determined. Whatever the bile salt/oleyl compounds ratio, taurochenodeoxycholate solubilizes more cholesterol than taurocholate and much more than tauroursodeoxycholate. At pH 6.7, the cholesterol solubility limit is about the same with either oleate or monoolein. Cholesterol solubility falls in oleate-bile acid mixtures as the pH is raised. The capacity for supersaturation with cholesterol is greater for bile salt-monoolein than for bile salt-oleate micelles. For the latter it decreases as pH increases.

Bile Acids and Salts↗
PubMed1993

Fatty acid composition of lecithin is a key factor in bile metastability in supersaturated model bile systems.

We studied the effect of fatty acid saturation of biliary lecithin on bile metastability, determined by nucleation time, using model bile solutions with identical lipid compositions except for the lecithin species (total lipid concentration, 9 g/dl; cholesterol, 12 mM; lecithin, 31 mM, bile salts, 116 mM). Gel permeation chromatographic studies revealed that nonmicellar cholesterol distribution was inversely related to the degree of unsaturation of the lecithin species. Differential interference contrast microscopy and cholesterol crystal growth assay showed that a lower degree of saturation of the lecithin species was associated with a faster nucleation time and crystal growth rate. These results suggest that vesicular lecithin containing more unsaturated fatty acyl chains binds less tightly to cholesterol as compared with lecithin containing predominantly saturated fatty acids and that the biliary lecithin species modulates cholesterol crystal nucleation in bile. Also, the high ratio of cholesterol to lecithin (more than 1.0) was found in the crystal forming model biles, although the vesicle aggregation was not always observed prior to the cholesterol crystal formation. These findings indicated that there are different processes in cholesterol crystal nucleation, with or without vesicle aggregation, and that such processes depend, in part, on lecithin species in vesicles.

Bile↗
PubMed1996

Alpha-naphthylisothiocyanate-induced elevation of serum bile acids: lack of causative effect on bile acid transport.

In recent years chemicals including chlorinated solvents have been found to interfere with the transport of bile acids (BA) by hepatocytes, which probably accounts for the raised serum bile acids (SBA) after exposure. However, the known cholestatic agent, alpha-naphthylisothiocyanate (ANIT) has never been fully examined for its effect on these processes. Accordingly, the direct effects in vitro and the effects of in vivo treatment on bile acid transport have been investigated in this study. Direct addition of ANIT (5-100 microns) to hepatocytes isolated from untreated rats did not result in any change in uptake or efflux of taurocholic acid (TC), one of the most obviously elevated SBA in ANIT-treated rats. Additionally, accumulation of TC over an extended incubation period was not affected by ANIT. In vivo treatment with ANIT (50 mumol/kg i.p. on each of 3 consecutive days) resulted in a marked elevation of total serum bile acids (TSBA) and a slight increase in the activity of serum alkaline phosphatase (ALP) and a very mild hyperbilirubinemia, while other markers of liver injury were unaltered. In hepatocytes isolated from these rats, Km and Vmax for uptake and V0 for efflux were no different between ANIT and vehicle-treated animals. In conclusion, ANIT showed no effects on transport of BA on in vitro exposure or after treatment in vivo where SBA were clearly elevated. The lack of effects of ANIT on transport of bile acids is consistent with other postulated mechanisms of action. Furthermore, this indicates that the effects noted with solvents are not necessarily replicated by substances known to cause histopathological cholestasis.

1-Naphthylisothiocyanate↗
PubMed1985

Influence of microbial bile salt desulfation upon the fecal excretion of bile salts in gnotobiotic rats.

The fecal excretion of intraperitoneally injected 24-14C-labeled taurocholate (TCA), taurolithocholate (TLCA) and the respective 3-sulfate esters (TCA-3-S; TLCA-3-S), were compared in germfree (GF) rats, conventional (CV) rats, and in gnotobiotic rats associated with Clostridium Cl-8 or this same strain Cl-8 plus the bile desulfating Clostridium S1, respectively. TCA and TLCA were about two times more rapidly excreted by CV animals than by GF animals; the time required for 50% excretion of total label injected (t 1/2) was 6.6 days vs 14.9 for TCA, and 4.4 vs 8.9 for TLCA. In GF and in CV animals, TCA-3-S and TLCA-3-S were excreted more rapidly than their nonsulfated analogues; the t 1/2 values of TCA-3-S and TCA were 2.7 days vs 14.9 in GF rats, and 3.1 vs 6.6 days in CV animals. The t 1/2 values of TLCA-3-S and TLCA were 2.7 days vs 8.9 in GF rats, and 1.5 vs 4.4 days in CV rats. In gnotobiotic rats associated with Clostridium strains S1 + Cl-8, fecal bile salts were nearly 100% deconjugated and desulfated and the 50% excretion times of TCA-3-S and TLCA-3-S approximated to those of TCA and TLCA in GF animals. T 1/2 of TCA-3-S in gnotobiotic S1 + Cl-8 animals was 12.2 days vs 14.9 for TCA in GF animals. In gnotobiotic S1 + Cl-8 animals the t 1/2 of TLCA and TLCA-3-S was 12.5 and 11.0 days, respectively. These results illustrate clearly the important effect the intestinal microflora has upon the metabolic half-life of bile salts. Moreover, they demonstrate that desulfation of bile salts by the intestinal microflora takes place in intestinal segments from where a certain degree of reabsorption is still possible, and thus point to the fact that microbial desulfation is an important variable in the overall elimination of bile salts.

Animals↗
PubMed1995

Bile salt secretion by hepatocytes incubated with bile salts and liposomes or low density lipoproteins.

The purpose of this work was to determine the effect of exogenous unesterified cholesterol provided in either artificial liposomes or LDL on bile salt synthesis by isolated rat hepatocytes. Rates of de novo synthesis were determined in the presence of 300 or 600 microM taurocholate, 600 microM taurodehydrocholate, cholate, deoxycholate or chenodeoxycholate. There was no significant difference between the cholesterol uptake by hepatocytes when the degree of hydrophobicity of the bile salts changed (cholate vs deoxycholate or chenodeoxycholate). Compared to taurocholate, taurodehydrocholate lowered the hepatic incorporation of unesterified cholesterol for the first 60 minutes; compared to control, taurocholate stimulated the cholesterol incorporation for the first 20 minutes. A possible explanation for this finding would be an interaction between bile salts and exogenous cholesterol, depending on the kind of conjugated bile salt. Taurocholate increased the exchange of cholesterol between liposomes or LDL and hepatocyte membranes. It resulted in a significant increase of bile salt synthesis and secretion. This phenomenon was not observed with taurodehydrocholate.

Animals↗
PubMed1979

Bile acid sulfates. III. Synthesis of 7- and 12-monosulfates of bile acids and their conjugates using a sulfur trioxide-triethylamine complex.

The 7- and 12-monosulfates of chenodeoxycholic acid, deoxycholic acid, and cholic acid were prepared by sulfation of the protected bile acids with sulfur trioxide-triethylamine in pyridine overnight and were isolated by precipitation as the p-toluidinium salt after removing the protecting group(s). The taurine conjugates were obtained by conjugating the bile acid sulfates with taurine in hot dimethylformamide (DMF) in the presence of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ). A new procedure of preparing glycine conjugated bile acid sulfates by direct conjugation of the bile acid sulfate triethylammonium salt with ethyl glycinate in boiling chloroform in the presence of EEDQ is also described. The advantage of these procedures over other procedures are their simplicity and their higher yields (tyically above 90%) The thin layer chromatographic mobilities of these sulfates are presented. The influence of side chain and hydroxyl group configurations on the properties of bile acid sulfates is briefly discussed.

Bile Acids and Salts↗
PubMed2006

Design of novel synthetic MTS conjugates of bile acids for site-directed sulfhydryl labeling of cysteine residues in bile acid binding and transporting proteins.

The purpose of this study was to design bile acid-containing methanethiosulfonate (MTS) agents with appropriate physical attributes to effectively modify the cysteine residues present in the human apical sodium-dependent bile acid transporter. Four physical properties including surface area, molecular volume, ClogP, and dipole moment were calculated for each semiempirically optimized structure of MTS compounds. The specificity of the synthesized bile acid-MTS conjugate toward native cysteines and putative bile acid interacting domains of hASBT was supported by the effect of 1mM cholyl-MTS, cholylglycyl-MTS, and 3-amino-cholyl-MTS on uptake activity, that displayed a significant decrease in TCA affinity (K(T)=69.9+/-4.5, 69.01+/-6.2, and 63.24+/-0.26 microM and J(max)=35.8+/-0.3, 24.03+/-1.22, 46.49+/-5.01 pmol mg protein min(-1), respectively). These compounds prove to be effective tools in probing the structural and functional effects of cysteine residues in bile acid binding and transporting proteins.

Amino Acid Substitution↗
PubMed2005

Synthesis of bile acid coenzyme a thioesters in the amino acid conjugation of bile acids.

Bile acids are converted to their glycine and taurine N-acyl amidates by enzymes in the liver in a two-step process. This conjugation reaction increases the aqueous solubility of bile acids, particularly in the acidic environment of the initial portion of the small intestine. In the first step, bile acid coenzyme A (CoA) thioesters are formed by a bile acid CoA ligase (BAL). This chapter describes the methods used to purify BAL from rat liver microsomes and to isolate and clone the cDNAs encoding BAL from a rat liver cDNA library, the expression of BAL, the assays used to measure its activities, and the chemical synthesis of bile acid CoA thioesters.

Amino Acid Sequence↗
PubMed1997

The crystal structure of bovine bile salt activated lipase: insights into the bile salt activation mechanism.

BACKGROUND: The intestinally located pancreatic enzyme, bile salt activated lipase (BAL), possesses unique activities for digesting different kinds of lipids. It also differs from other lipases in a requirement of bile salts for activity. A structure-based explanation for these unique properties has not been reached so far due to the absence of a three-dimensional structure. RESULTS: The crystal structures of bovine BAL and its complex with taurocholate have been determined at 2.8 A resolution. The overall structure of BAL belongs to the alpha/beta hydrolase fold family. Two bile salt binding sites were found in each BAL molecule within the BAL-taurocholate complex structure. One of these sites is located close to a hairpin loop near the active site. Upon the binding of taurocholate, this loop becomes less mobile and assumes a different conformation. The other bile salt binding site is located remote from the active site. In both structures, BAL forms similar dimers with the active sites facing each other. CONCLUSIONS: Bile salts activate BAL by binding to a relatively short ten-residue loop near the active site, and stabilize the loop in an open conformation. Presumably, this conformational change leads to the formation of the substrate-binding site, as suggested from kinetic data. The BAL dimer observed in the crystal structure may also play a functional role under physiological conditions.

Animals↗
PubMed2001

High prevalence of TT virus in human bile juice samples: importance of secretion through bile into feces.

TT virus (TTV) is much more prevalent than we once imagined. With the use of primers designed from the noncoding regions, a more than 90% rate of TTV infection in the general population by polymerase chain reaction (PCR) has been reported, showing that nonparenteral transmission must play an important role to its epidemiology. We considered that TTV may be secreted through bile juice into feces to establish nonparenteral infection. Paired bile juice and serum samples were obtained from 26 patients who were receiving bile drainage. Feces were also recovered after the drainage tube was removed. TTV DNA was detected from 22 patients in serum (84.6%), and they were all TTV DNA positive in bile juice. Most feces samples recovered from TTV-positive patients were also TTV DNA positive. Secretion of TTV into bile juice appears to be common, and this could play an important role to its transmission and its epidemiology.

Bile↗
PubMed1968

Comparative studies of bile salts. Bile salts of sturgeons (Acipenseridae) and of the paddlefish Polyodon spathula: a new partial synthesis of 5 beta-cyprinol.

1. Bile salts of the sturgeons Acipenser guldenstaedti Brandt, Acipenser stellatus Pall and Huso huso L. and of the paddlefish Polyodon spathula Walbaum are shown to be closely similar, consisting mainly of taurocholate with minor amounts of tauroallocholate and the monosulphates of bile alcohols. The bile alcohols, comprising less than 10% of the bile salts, are mixtures with high proportions of substances resembling C(27) tetrols and of C(27) pentols, including 5beta-cyprinol and (probably) 5alpha-cyprinol. 2. 5beta-Cyprinol (3alpha,7alpha,12alpha,26,27-pentahydroxy-5beta-cholestane) was made from cholic acid via 3alpha,7alpha,12alpha-triacetoxy-5beta-cholan-24-ol in an overall yield of about 0.8%. 3. The chemical nature of chondrostean bile salts agrees with the systematic position of the fishes and suggests further correspondence between evolution at the morphological and molecular levels.

Animals↗
PubMed1976

Bile acids of snakes of the subfamily Viperinae and the biosynthesis of C-23-hydroxylated bile acids in liver homogenate fractions from the adder, Vipera berus (Linn.).

1. Analysis of bile salts of four snakes of the subfamily Viperinae showed that their bile acids consisted mainly of C-23-hydroxylated bile acids. 2. Incubations of 14C-labelled sodium cholate (3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholan-24-oate) and deoxycholate (3 alpha, 12 alpha-dihydroxy-5 beta-cholan-24-oate) with whole and fractionated adder liver homogenates were carried out in the presence of molecular oxygen and NADPH or an NADPH-generating system. The formation of C-23-hydroxylated bile acids, namely bitocholic acid (3 alpha, 12 alpha, 23xi-trihydroxy-5 beta-cholan-24-oic acid) and 3 alpha, 7 alpha, 12 alpha, 23 xi-tetrahydroxy-cholanic acid (3 alpha, 7 alpha, 12 alpha, 23 xi-tetrahydroxy-5 beta-cholan-24-oic acid), was observed mainly in the microsomal fraction and partly in the mitochondrial fraction. 3. Biosynthetic pathways of C-23-hydroxylated bile acids are discussed.

Animals↗
PubMed1986

Application of a rapid and efficient h.p.l.c. method to measure bilirubin and its conjugates from native bile and in model bile systems. Potential use as a tool for kinetic reactions and as an aid in diagnosis of hepatobiliary disease.

We have developed an extremely rapid and efficient reverse-phase h.p.l.c. method for the measurement of bilirubin and its conjugates in human bile and in model bile systems. Our method involves the use of a Perkin-Elmer 3 mu C18 column and a methanol/sodium acetate/aq. ammonium acetate buffer system. Three isomers of bilirubin diglucuronide (BDG), two isomers of bilirubin monoglucuronide (BMG), three isomers of unconjugated bilirubin (UCB) and minor conjugates containing glucose and xylose were separated in 12 min. Initial quantification of BDG and BMG was based on the use of the ethyl anthranilate azo derivative of bilirubin (AZO UCB); however, the standard curves for BDG, BMG and UCB were similar enough to permit quantification to be later based on the UCB standard curve only, thereby simplifying the quantification process. Routine direct injection of 6 or 10 microliter of crude undiluted or diluted (1:1) bile sample was sufficient for analysis. The method was helpful in diagnosing biliary-tract obstruction in a newborn and a partial deficiency state of bilirubin conjugation (Crigler-Najjar syndrome) in a 10-year-old male. When the method was applied to biles of patients both with and without gallstones, levels of UCB were less than 2% of total pigment, consistent with previous reports. Because of its speed and efficiency, this method has the potential for a broad range of applications including enzymic, kinetic and bile sample analyses.

Animals↗
PubMed1995

Comparative studies on bile flow and biliary lipid excretion after bile-acid loading in normal and partially hepatectomized rats.

This study was performed to investigate sequential changes in bile secretion and biliary lipids after taurocholic acid (TCA) loading of regenerating rat liver. TCA was administered intravenously at stepwise-increasing doses to groups of non-operated control and partially hepatectomized rats, 24, 72 and 168 h after surgery. Bile flow, bile-acid output (BAO) and phospholipid output (PLO) (expressed per gram of liver) in partially hepatectomized rats increased more than in the controls. Using an isolated perfusion rat-liver system, TCA infusion was also carried out on groups of non-operated control and hepatectomized rats 72 h after operation. Again bile flow, BAO and PLO (expressed per gram of liver) were significantly higher in the partial hepatectomy case, mirroring the results obtained in vivo. When horseradish peroxidase (HRP) was pulse-loaded in isolated perfusion preparations, the second peak of biliary HRP secretion in hepatectomized rats was significantly higher than in controls. We conclude that increased bile-acid flow in partially hepatectomized rats is dependent upon acceleration of vesicular transport accompanying or following proliferation in regenerating livers.

Animals↗
PubMed2000

Isolation and characterization of a Lactobacillus amylovorus mutant depleted in conjugated bile salt hydrolase activity: relation between activity and bile salt resistance.

Growth experiments were conducted on Lactobacillus amylovorus DN-112 053 in batch culture, with or without pH regulation. Conjugated bile salt hydrolase (CBSH) activity was examined as a function of culture growth. The CBSH activity increased during growth but its course depended on bile salts type and culture conditions. A Lact. amylovorus mutant was isolated from the wild-type strain of Lact. amylovorus DN-112 053 after mutagenesis with N-methyl-N'-nitro-N-nitrosoguanidine. An agar plate assay was used to detect mutants without CBSH activity. In resting cell experiments, the strain showed reduced activity. Differences between growth parameters determined for wild-type and mutant strains were not detected. Comparative native gel electrophoresis followed by CBSH activity staining demonstrated the loss of proteins harbouring this activity in the mutant. Four protein bands corresponding to CBSH were observed in the wild-type strain but only one was detected in the mutant. The specific growth rate of the mutant strain was affected more by bile salts than the wild-type strain. Nevertheless, bile was more toxic for the wild-type strain. In viability studies in the presence of nutrients, it was demonstrated that glycodeoxycholic acid exerted a higher toxicity than taurodeoxycholic acid in a pH-dependent manner. No difference was apparent between the two strains. In the absence of nutrients, the wild-type strain died after 2 h whereas no effect was observed for the mutant. The de-energization experiments performed using the ionophores nigericin and valinomycin suggested that the chemical potential of protons (ZDeltapH) was involved in Lactobacillus bile salt resistance.

Amidohydrolases↗