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PubMed1999

Antimicrobial activities of amine- and guanidine-functionalized cholic acid derivatives.

Compounds in a series of cholic acid derivatives, designed to mimic the activities of polymyxin B and its derivatives, act as both potent antibiotics and effective permeabilizers of the outer membranes of gram-negative bacteria. Some of these compounds rival polymyxin B in antibacterial activity against gram-negative bacteria and are also very active against gram-positive organisms. Other compounds interact synergistically with hydrophobic antibiotics to inhibit bacterial growth.

Anti-Bacterial Agents↗
PubMed2003

Physiological characteristics of allo-cholic acid.

The physiological characterstics of allo-cholic acid (ACA), a typically fetal bile acid that reappears during liver regeneration and carcinogenesis were investigated. [(14)C] Tauro-ACA (TACA) uptake by Chinese hamster ovary cells expressing rat organic anion transporter polypeptide (Oatp)1 or sodium-taurocholate cotransporter polypeptide (Ntcp) was lower than that of [(14)C]taurocholic acid (TCA). Although TACA inhibited ATP-dependent TCA transport across plasma membrane vesicles from Sf9 cells expressing rat or mouse bile salt export pump (Bsep), no ATP-dependent TACA transport was found. In rats, TACA was secreted into bile with no major biotransformation and it had lower clearance and longer half-life than TCA. In mice, TACA bile output was lower (-50%) than that of TCA, whereas TACA induced 9-fold higher bile flow than TCA. Even though the intracellular levels were lower for TACA, translocation into the hepatocyte nucleus was higher for TACA than for TCA; however, rate of DNA synthesis, expression levels of alpha-fetoprotein, albumin, Ntcp, and Bsep, cell viability, and apoptosis in rat hepatocytes were similarly affected by both isomers. In conclusion, TACA partly shares hepatocellular uptake system(s) for TCA. Furthermore, in contrast to other "flat" bile acids, TACA is efficiently secreted into bile via transport system(s) other than Bsep and is highly choleretic, hence its appearance during certain situations may prevent accumulation of cholestatic precursors.

ATP Binding Cassette Transporter, Subfamily B, Mem↗
PubMed1979

The degradation of cholic acid by Pseudomonas sp. N.C.I.B. 10590.

The microbial degradation of cholic acid by Pseudomonas sp. N.C.I.B. 10590 was studied, and two major products were isolated and identified as 7 alpha, 12 beta-dihydroxyandrosta-1,4-diene-3,17-dione and 7 alpha, 12 alpha-dihydroxy-3-oxopregna-1,4-diene-20-carboxylic acid. Four minor products were isolated and evidence is given for the following structures: 7 alpha, 12 alpha-dihydroxyandrosta-1,4-diene-3,17-dione, 12 beta-hydroxyandrosta-1,4,6-triene-3,17-dione, 7 alpha, 12 beta, 17 beta-trihydroxyandrosta-1,4-dien-3-one and 7 alpha, 12 alpha-dihydroxy-3-oxopregn-4-ene-20-carboxylic acid. The significance of the production of the steroid products is discussed, along with the possible enzymic mechanisms responsible for their production.

Androstadienes↗
PubMed2002

Elucidation of solid-state complexation in ground mixtures of cholic acid and guest compounds.

The solid-state complexation between cholic acid (CA) and either methyl p-hydroxybenzoate (MPB) or ibuprofen (IBP) was investigated. Powder X-ray diffractometry, IR spectroscopy and thermal analysis suggested the complex formation between CA and MPB as well as between CA and IBP by co-grinding method. The stoichiometry of CA-MPB was 1 : 1 while that of CA-IBP was 2 : 1, reflecting the effect of guest size on complex formation. The guest compounds were assumed to be included in the channel of complexes formed by hydrogen bonds among CA molecules.

Calorimetry, Differential Scanning↗
PubMed2006

Simultaneous determination of geniposide, baicalin, cholic acid and hyodeoxycholic acid in rat serum for the pharmacokinetic investigations by high performance liquid chromatography-tandem mass spectrometry.

A simple, rapid, and specific analytical method for simultaneous determination of geniposide, baicalin, cholic acid and hyodeoxycholic acid in 50 microL samples of rat serum was developed by high performance liquid chromatography-tandem mass spectrometry. The quantification of the target compounds was determined by multiple reaction monitoring (MRM) mode using electrospray ionization (ESI). The correlation coefficients of the calibration curves were better than 0.997. The intra- and inter-day accuracy, precision, and linear range had been investigated in detail. This method was subsequently applied to pharmacokinetic studies of geniposide, baicalin, cholic acid and hyodeoxycholic acid in rats successfully.

Animals↗
PubMed1984

Estriol and cholic acid in maternal serum in induced labor.

Prostaglandin E2 (PGE2), but not oxytocin, treatment to induce parturition brought about an increase (p less than 0.001) in maternal serum levels of total estrogens (conjugated and nonconjugated estriol). There was no increase in nonconjugated estriol. To explore if the changes were related to an altered enterohepatic circulation, cholic acid assay in maternal serum was used. There were no changes in cholic acid which parallelled those in total estrogens. It is concluded that PGE2 does not appear to affect enterohepatic circulation of steroids, and it is suggested that the increase in total estrogens may be caused by changes in the kidney excretion of estriol.

Adolescent↗
PubMed1979

[Kinetics of 14C-cholic acid in the baboon under normal conditions and in cholestasis. Description and validity of a multicompartmental model].

A multicompartmental model was applied to the study of the plasmatic and biliary kinetics of the 14C-Cholic acid intravenously injected into a baboon in normal and cholestatic condition. For the evaluation of transfer rates FORTAN IV procedures were used, utilizing Powell method. The degree of fitting was: in normal condition in serum 7% for free and 35% for conjugated Cholic acid, while in bile 5% and 4% respectively; in serum in cholestatic condition 7% for free and 12% for conjugates. The high degree of fitting and reliable estimation of transfer rates suggest that the multicompartmental model applied represents most likely the physio-pathological conditions studied.

Animals↗
PubMed2003

Conversion of cholic acid to methyl 3alpha-carbethoxy-12alpha-acetoxy-6-oxo-5beta-chol-7-en-24-oate.

A new and efficient method for preparation of a 7-en-6-one derivative of cholic acid is described. Acetylation of the known methyl 3alpha-carbethoxy-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate (3) at 12 position and reduction of its 7-oxo group yield the 12alpha-acetoxy-7alpha-hydroxy derivative 5. Dehydration of the 7alpha-hydroxy group in 5 followed by allylic oxidation provide methyl 3alpha-carbethoxy-12alpha-acetoxy-6-oxo-5beta-chol-7-en-24-oate (7) in good yield.

Chemistry, Organic↗
PubMed2005

Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids.

A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3beta-hydroxy-Delta(5)- or a Delta(4)-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3beta-acetoxy-pregn-5-en-20-carboxylic acid. The obtained compounds are useful as standards for studies of cholic acids. Construction of the side chain was achieved by linkage of steroidal 23-iodides to sulfones prepared from (2R)- and (2S)-3-hydroxy-2-methylpropanoates. Oxidation of intermediate 26-alcohols into the corresponding carboxylic acids ensuring preservation of stereochemistry at C-25 and functional groups in the cyclic part was achieved with sodium chlorite catalyzed by TEMPO and bleach.

Alcohols↗
PubMed1995

Further investigation of the effect of cholic acid on the induction, growth characteristics and stability of aberrant crypt foci in rat colon.

We previously reported that the colons of animals injected with azoxymethane (AOM) and fed a diet containing cholic acid (CHA) had lower numbers of aberrant crypt foci (ACF) than those in animals fed a control diet. To follow up on this observation, a series of studies was conducted to determine whether CHA affects the development of ACF in a dose- and time-dependent manner, and the possible mechanism(s) involved. Sprague Dawley male rats were injected with AOM (20 mg/kg s.c.), and one week later randomly allocated to groups fed diets containing 0, 0.05, 0.1 or 0.2% CHA by weight, for 4 weeks. Their colons were scored for the number size and location of ACF, number of crypts per ACF, and mitotic activity. It was observed that the number and size of ACF decreased with increasing levels of CHA. Mitotic activity was higher (P < 0.05) in the 0.2% CHA diet (CHA-diet) group compared to the 0% CHA group. To determine if timing of intervention with the CHA-diet was critical, rats were allocated to the CHA-diet before or after AOM injection. The ACF-reducing effect of 0.2% CHA diet was evident (P < or = 0.05) only after AOM injection. Intervention with the CHA-diet 4 weeks after AOM injection demonstrated that the diet eliminated and/or remodelled a large proportion (50%) of ACF which had developed within 4 weeks and inhibited the growth of those ACF that persisted. This effect was also associated with higher (P < or = 0.05) mitotic activity in the colon. Discontinuing the treatment of rats with the CHA-diet resulted in a rapid increase in the number of ACF in their colons, establishing that the growth inhibitory effect of the CHA-diet on ACF was reversible. In conclusion, it was demonstrated that the CHA-diet modulated the number of ACF by inhibiting their development and growth and by eliminating or remodelling a selected population of ACF.

Animals↗
PubMed2005

Hydrogen-bonded aggregations of oxo-cholic acids.

The crystal structures of six new crystals of oxo-cholic acids (oxo-CA) are reported: (I) 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholan-24-oic acid; (II) 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid; (III) 7alpha-hydroxy-3,12-dioxo-5beta-cholan-24-oic acid; (IV-alpha) and (IV-beta) 12alpha-hydroxy-3,7-dioxo-5beta-cholan-24-oic acid; (V) 3,7,12-trihydroxy-5beta-cholan-24-oic acid. (IV-beta) is a pseudopolymorphic solvated form of (IV-alpha) and contains small channels which can trap disordered water molecules. In all the structures the four saturated cycles, forming the common alicyclic skeleton, have the same conformation, while the carboxylic side chain adopts flexible conformations in order to produce the most efficient crystal aggregations. The structures display a variety of supramolecular architectures dominated by networks of cooperative O-H...O hydrogen bonds forming different packing motifs often supported by weaker C-H...O interactions.

Cholic Acids↗
PubMed2001

Evaluation of polymeric nanoparticles composed of cholic acid and methoxy poly(ethylene glycol).

Amphiphilic polymeric conjugate based on cholic acid (CA) as the hydrophobic component and methoxy poly(ethylene glycol) (MPEG) as the hydrophilic component was synthesized using a 1,1'-carbonyldiimidazole (CDI) mediated conjugation. Fluorescence spectroscopy measurements suggested that CA and MPEG (abbreviated as CE) conjugate was associated in water to form polymeric core-shell type nanoparticles with a critical association concentration (CAC) value of 0.063 g l(-1). From the transmission electron microscope (TEM) observation, CE nanoparticles were almost spherical with a size range of approximately 10-30 nm in the dried state, which was in agreement with the result from particle size measurement using photon correlation spectroscopy (PCS). Clonazepam (CNZ) was physically loaded into the CE nanoparticles with a 16.2 wt.% loading. CNZ release was pseudo zero-order in kinetic terms for up to 3 days.

Cholic Acid↗
PubMed2005

Cholic-acid-based fluorescent sensor for dicarboxylates and acidic amino acids in aqueous solutions.

[structure: see text] The binding affinities of a cholic-acid-based fluorescent neutral receptor toward dicarboxylate anions and amino acids have been investigated in a CH3OH/H2O system (1:1, 0.01 M HEPES buffer, pH = 7.4) by fluorescence titration experiments. The synthetic host bearing four convergent functionalities strongly binds glutamate via multiple hydrogen bonds with a binding constant of (5.57 +/- 0.88) x 10(6).

Amino Acids, Acidic↗
PubMed1998

Retrograded high-amylose corn starch reduces cholic acid excretion from the small bowel in ileostomy subjects.

OBJECTIVE: To study the short-term effect of resistant starch (RS) from retrograded high-amylose corn starch (HACS) on the excretion of bile acids and nutrients from the small bowel in humans. DESIGN: Seven healthy ileostomists were given a controlled, constant diet during three days. On days 2 and 3, 100 g/d of one of two test-products--drum-dried ordinary corn starch and autoclaved retrograded HACS, providing 5 and 39 g RS/d, respectively--was given, in random order. Ileostomy effluents were collected for 24 h per day and analysed for wet weight, dry weight, energy, bile acids and nutrients. SETTINGS: In-patient study at the metabolic ward, Department of Clinical Nutrition, Sahlgrenska University Hospital, Göteborg. RESULTS: Consumption of retrograded HACS caused (1) a 42% lower mean excretion of cholic acid (P = 0.024); (2) a 42% lower mean wet weight concentration of bile acids (P < 0.001); (3) a 70% increased excretion of dry weight (P = 0.001); and (4) a 41% increased excretion of energy (P= 0.036) compared with consumption of drum-dried ordinary corn starch. CONCLUSION: The reduced ileal excretion and concentration of cholic acid would be protective regarding colon cancer risk in addition to the increased fermentation substrate provided by RS and other energy-yielding components.

Adult↗
PubMed1969

Bacterial 7-dehydroxylation of cholic acid and allocholic acid.

An obligate anaerobic organism capable of dehydroxylating cholic acid to deoxycholic acid and allocholic acid to allodeoxycholic acid was isolated from feces of the rabbit. It was a member of the bacteroides group (Gram-variable, nonsporulating anaerobes). The growth of the organism was inhibited by neomycin, 10-20 micro g/ml. The existence of this organism affords a satisfactory explanation for the development of gallstones in the cholestanol-fed rabbit and for their absence in rabbits simultaneously treated with neomycin.

Animals↗
PubMed2006

Imitation of artificial membrane system via mobile phases with Tween-80 and cholic acid in biopartitioning micellar chromatography.

The chromatographic behaviour of compounds of biomedical significance was studied using micellar mobile phases modified with polyoxyethylene (20) sorbitan monooleate (Tween-80). The influence of the surfactant within the 0.75-4% concentration range on the retention factor of model compounds was investigated. The biological surfactant cholic acid was introduced into the mobile phases in order to approach to the structure of natural membranes, viz. erythrocyte and cytoplasmatic membranes. It was found that curves of dependence of retention factor vs concentration of Tween-80 in the absence and presence of cholic acid in the mobile phase considerably diverge with one another, especially in the 2-3% concentration range of Tween-80 using C18-type support. Increasing the concentration of Tween-80 resulted in the increase of retention factors using phenyl-coated stationary phase.

Cholic Acid↗