Search results for "bile acid"
showing 10 items of 118 documents
Novel two-step synthesis of gold nanoparticles capped with bile acid conjugates
2008
Bile acids and their conjugates are physiologically important molecules. Syntheses and structure elucidation combined with investigation of properties and applications of bile acids and their derivatives are of academic interest. The concept of using bile acids and their conjugates in nanoscience is a novel idea, which opens up fascinating prospects. In this article, an easy and simple route for obtaining N-lithocholyl-L-(cysteine ethyl ester) (3), capable of effectively capping and stabilizing metal nanoparticles, is described. The whole synthetic route needs only two steps giving a moderate to good yield. The gold NPs are characterized by elemental analysis, UV spectroscopy, and TEM. Addi…
3α,3′α-Bis(n-acetoxyphenylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol diesters (n = 2-4):13C NMR chemical shifts, variable-temperature and NOE1H N…
2000
Three novel bile acid-based molecular dimers, 3α,3′α-bis(n-acetoxyphenylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol diesters (n = 2–4), 1–3, were synthesized from lithocholic acid (3α-hydroxy-5β-cholan-24-oic acid) ethane-1,2-diol diester and isomeric n-acetoxybenzoyl chlorides (n = 2–4). Their cleft type conformational preferences were suggested theoretically by PM3 molecular orbital calculations. Molecular weights determined by the matrix-assisted laser desorption/ionization time-of-flight technique and 13C NMR chemical shifts of the 1–3 are also presented. Copyright © 2000 John Wiley & Sons, Ltd.
3α-Hydroxy-N-(3-hydroxypropyl)-5β-cholan-24-amide
2009
The title compound, C27H47NO3, is a (3-hydroxypropyl)amide derivative of naturally occurring enantiopure lithocholic acid (3-hydroxy-5-cholan-24-oic acid). The molecule contains four fused rings: three six-membered rings in chair conformations and one five-membered ring in a half-chair form. The two terminal six-membered rings are cis-fused, while other rings are trans-fused. The structure contains an intramolecular O—H O hydrogen bond and a similar hydrogen-bond framework to the corresponding deoxycholic and chenodeoxycholic acid derivatives. Intermolecular O— H O and N—H O interactions are also present in the crystal. This compound seems to have at least two polymorphic forms from a compa…
Systematic Modulation of the Supramolecular Gelation Properties of Bile Acid Alkyl Amides
2018
The self-assembly properties of nine low-molecular-weight gelators (LMWGs) based on bile acid alkyl amides were studied in detail. Based on the results, the number of hydroxyl groups attached to the steroidal backbone plays a major role in the gelation, although the nature of the aliphatic side chain also modulates the gelation abilities. Of the 50 gel systems studied, 35 are based on lithocholic acid and 15 on cholic acid derivatives. The deoxycholic acid derivatives did not form any gels. The gelation occurred primarily in aromatic solvents and the gels manifested typical fibrous or spherical morphologies. The 13C cross-polarized magic angle spinning (CPMAS) NMR spectra measured on the cr…
Bile acid amidoalcohols: simple organogelators.
2003
Simple bile acid amide synthesis of lithocholic and deoxycholic acids with 2-aminoethanol and 3-aminopropanol are reported. The structural properties of these amides were examined by NMR spectroscopic, ESI-TOF mass spectral, and X-ray crystallographic methods. The gelation properties of these amides in common organic solvents and in three different water solutions were also investigated using Tyndall effect, SEM, TEM, and optical microscopy. 2-Hydroxyethylamides were found to be effective gelators in chlorinated organic solvents and 3-hydroxypropylamides in aromatic solvents. Both derivatives thicken neutral and acidic water solutions.
Bile acid alkylamide derivatives as low molecular weight organogelators: systematic gelation studies and qualitative structural analysis of the syste…
2011
A series of amino- and hydroxyalkyl amides of bile acids have been synthesized and characterized by Fourier transform infrared spectroscopy (FTIR), (1)H and (13)C nuclear magnetic resonance spectroscopy (NMR), as well as electrospray ionization mass spectrometry (ESI-MS) measurements. The ability of the synthesized molecules to promote gel formation was systematically investigated. Out of 396 combinations formed by 11 compounds and 36 different solvents, 22 gel-containing systems were obtained with 1% (w/v) gelator concentration. Apart from one exception, the gelator compounds were lithocholic acid derivatives. This challenges the general trend of bile acid-based physical gelators, accordin…
NR1H4 rs35724 G>C variant modulates liver damage in nonalcoholic fatty liver disease
2021
Background and Aims: Farnesoid X receptor (FXR) plays a key role in bile acid and lipid homeostasis. Experimental evidence suggests that it can modulate liver damage related to nonalcoholic fatty liver disease (NAFLD). We examined the impact of the NR1H4 rs35724 G>C, encoding for FXR, on liver damage in a large cohort of patients at risk of steatohepatitis. Methods: We considered 2,660 consecutive individuals at risk of steatohepatitis with liver histology. The rs35724 G>C polymorphisms were genotyped by TaqMan assays. Gene expression was evaluated by RNASeq in a subset of patients (n = 124). Results: The NR1H4 rs35724 CC genotype, after adjusting for clinic-metabolic and genetic conf…
Synthesis of Both Ionic Species of Ammonium Dithiocarbamate Derived Cholic Acid Moieties
2011
The reaction of 3-aminopropylamide of cholic acid with CS2 produced a bile acid derivative of dithiocarbamic acid which further formed an ammonium salt with another molecule of 3-aminopropylamide of cholic acid. The cationic 3-ammonium propylamide of cholic acid did not react further with CS2 and the formed salt was stable in the reaction mixture, even when excess CS2 was used. When the reaction was carried out in the presence of aqueous sodium hydroxide, only the bile acid derivative of sodium dithiocarbamate was formed. The dithiocarbamate derivatives were characterized by 1H- and 13C-NMR spectroscopy and ESI-TOF mass spectrometry.
Muricholic Acids Promote Resistance to Hypercholesterolemia in Cholesterol-Fed Mice
2021
International audience; Background and aims: Hypercholesterolemia is a major risk factor for atherosclerosis and cardiovascular diseases. Although resistant to hypercholesterolemia, the mouse is a prominent model in cardiovascular research. To assess the contribution of bile acids to this protective phenotype, we explored the impact of a 2-week-long dietary cholesterol overload on cholesterol and bile acid metabolism in mice. Methods: Bile acid, oxysterol, and cholesterol metabolism and transport were assessed by quantitative real-time PCR, western blotting, GC-MS/MS, or enzymatic assays in the liver, the gut, the kidney, as well as in the feces, the blood, and the urine. Results: Plasma tr…
Lean NAFLD: A Distinct Entity Shaped by Differential Metabolic Adaptation
2020
Background and Aims: Nonalcoholic fatty liver disease (NAFLD) affects a quarter of the adult population. A significant subset of patients are lean, but their underlying pathophysiology is not well understood. Approach and Results: We investigated the role of bile acids (BAs) and the gut microbiome in the pathogenesis of lean NAFLD. BA and fibroblast growth factor (FGF) 19 levels (a surrogate for intestinal farnesoid X receptor [FXR] activity), patatin-like phospholipase domain containing 3 (PNPLA3), and transmembrane 6 superfamily member 2 (TM6SF2) variants, and gut microbiota profiles in lean and nonlean NAFLD were investigated in a cohort of Caucasian patients with biopsy-proven NAFLD (n …