Search results for "lithocholic acid"
showing 10 items of 24 documents
1H-, 13C-, and 15N-NMR and ESI-TOF+ MS studies of a supramolecular complex of silver(I) and a cholaphane
2003
A novel application of the mixed anhydride procedure for synthesising lithocholic acid piperazine diamide, an important intermediate in designing bile acid-based supramolecular host molecules, is reported. The synthesis of a thiophene-containing cholaphane with transition metal complexation ability and 1H-, 13C-, and 15N-NMR as well as ESI-TOF+ MS spectral characterisation of the ligand and its Ag(I) complex are included. The coordination of the Ag(I) ion as well as an ability of the cholaphane to recognise Ag(I) ion over alkali metal ions, especially potassium ion, is discussed. The possible medical applications are also presented.
Synthesis and characterization of lithocholic acid derived dipyrromethanes: precursors for pyrrole-steroidal macrocycles
2004
Abstract Three steroidal dipyrromethanes, 3,3,24,24-tetrakis(pyrrol-2-yl)-5β-cholane 1 , 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oic acid 2 , and methyl 3,3-bis(pyrrol-2-yl)-5β-cholan-24-oate 3 , have been prepared from 3α-hydroxy-5β-cholan-24-oic acid (lithocholic acid) 4 in good overall yields. The structures of 1 – 3 have been fully characterized by 1 H, 13 C, PFG DQF 1 H– 1 H COSY, 1 H– 1 H ROESY, 13 C DEPT-135, PFG 1 H– 13 C HMQC, PFG 1 H– 13 C HMBC, and PFG 1 H– 15 N HMBC NMR spectra. Their molecular weights and compositions have been determined by ESI-TOF and EI mass spectra, and elemental analyses. The energetically optimised geometry and isotropic 13 C NMR chemical shifts of 3,3,24,24-te…
13C NMR spectral assignments of 3α,3′α-bis(arylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol diesters: new lithocholic acid-based molecular clefts
1999
3α,3′α-Bis(arylcarboxy)-5β-cholan-24-oic acid ethane-1,2-diol diesters (1–3) were synthesized by the reaction of an aroyl chloride (aroyl=2,6-dichlorobenzoyl, 2-naphthoyl and 1-pyrenoyl) with lithocholic acid (3α-hydroxy-5β-cholan-24-oic acid) ethane-1,2-diol diester. The 13C NMR chemical shift assignments of the formed molecular clefts 1–3, pyrene-1-carboxylic acid methyl ester (4) (used as model compound) and 1-pyrenoyl chloride (5) are based on literature data and 13C DEPT-135, 1H,13C HMQC and 1H,13C HMBC experiments. The molecular weights of 1–3 were determined by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Copyright © 1999 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…
Supramolecular architectures formed by co-crystallization of bile acids and melamine
2010
Supramolecular multicomponent crystals constructed from three different bile acids (viz. lithocholic, deoxycholic and cholic acid) and melamine have been prepared and the non-covalent interactions in the crystals studied. Both salts and co-crystals were found. While deoxycholic and cholic acid co-crystallized with melamine as a 1 : 1 isostructural molecular complexes in space group C2, lithocholic acid formed with melamine a 2 : 1 molecular complex in space group P21. This is the first report on a multicomponent crystal structure containing lithocholic acid.
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…
Biocompatible Hydrogelators Based on Bile Acid Ethyl Amides
2016
Four novel bile acid ethyl amides were synthetized using a well-known method. All the four compounds were characterized by IR, SEM, and X-ray crystal analyses. In addition, the cytotoxicity of the compounds was tested. Two of the prepared compounds formed organogels. Lithocholic acid derivative 1 formed hydrogels as 1% and 2% (w/v) in four different aqueous solutions. This is very intriguing regarding possible uses in biomedicine. peerReviewed
Ligand Diversity of Human and Chimpanzee CYP3A4: Activation of Human CYP3A4 by Lithocholic Acid Results from Positive SelectionS⃞
2009
For currently unknown reasons, the evolution of CYP3A4 underwent acceleration in the human lineage after the split from chimpanzee. We investigated the significance of this event by comparing Escherichia coli-expressed CYP3A4 from humans, chimpanzee, and their most recent common ancestor. The expression level of chimpanzee CYP3A4 was ∼50% of the human CYP3A4, whereas ancestral CYP3A4 did not express in E. coli. Steady-state kinetic analysis with 7-benzyloxyquinoline, 7-benzyloxy-4-(trifluoromethyl)coumarin (7-BFC), and testosterone showed no significant differences between human and chimpanzee CYP3A4. Upon addition of α-naphthoflavone (25 μM), human CYP3A4 showed a slightly decreased substr…