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Glycocholic acid

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Glycocholic acid is a bile acid glycine conjugate having cholic acid as the bile acid component. It has a role as a human metabolite. It derives from a cholic acid and a glycochenodeoxycholic acid. It is a conjugate acid of a glycocholate.

Category

Other Unnatural Amino Acids

Catalog number

BAT-007690

CAS number

475-31-0

Molecular Formula

C26H43NO6

Molecular Weight

465.63

Specification
Reference Reading

IUPAC Name

2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid

Synonyms

Cholylglycine hydrate; N-[(3α,5β,7α,12α)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine; 3α,7α,12α-Trihydroxy-5β-cholan-24-oylglycine; 3α,7α,12α-Trihydroxy-5β-cholanic acid-24-glycine; 3α,7α,12α-Trihydroxy-N-(carboxymethyl)-5β-cholan-24-amide; Cholylglycine; Glycine Cholate; N-Choloylglycine; 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid

Appearance

White to Off-White Solid

Purity

≥ 99% (HPLC)

Density

1.134 g/cm3 (Predicted)

Melting Point

128 °C

Boiling Point

692.0 °C at 760 mmHg

Storage

Store at -20°C

Solubility

Soluble in Ethanol

Application

Labelled Glycocholic Acid. The product of conjugation of cholic acid with glycine; chief ingredient of the bile of herbivorous animals. In the weakly alkaline bile fluid glycocholic acid exists as the sodium salt.

InChI

InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1

InChI Key

RFDAIACWWDREDC-FRVQLJSFSA-N

Canonical SMILES

CC(CCC(=O)NCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C

1.Macromolecular crowding agents-assisted imprinted polymers for analysis of Glycocholic acid in human plasma and urine.

Li QF1, Zhan YM1, Zhong YG1, Zhang B1, Ge CQ1. Biomed Chromatogr. 2016 Apr 8. doi: 10.1002/bmc.3737. [Epub ahead of print]

Glycocholic acid (GCA) is a new identification of biomarker for hepatocellular carcinoma (HCC) patients. In this study, a method based on macromolecular crowding strategy has been applied for preparation of molecularly imprinted polymer (MIP), which possesses high adsorption capacity for GCA. Polymethyl methacrylate (PMMA) was used as macromolecular crowding agent, N-(3-aminopropyl)-methacrylamide hydrochloride (APMA · HCl) as functional monomer, ethylene dimethacrylate (EDMA) as cross-linker. The morphology and binding characteristics of MIP were assessed by scanning electron microscopy and absorption experiments. The MIP was used as an adsorbent material to separate GCA, and the molecularly imprinted solid-phase extraction (MISPE) was carefully optimized. The MISPE combined with high performance liquid chromatography (HPLC) analysis was successfully used to determine the GCA in plasma and urine samples. When spiked levels ranged from 0.

2.Safety, beneficial and technological properties of Enterococcus faecium isolated from Brazilian cheeses.

Dos Santos KM1, Vieira AD2, Salles HO3, Oliveira Jda S3, Rocha CR4, Borges Mde F5, Bruno LM5, Franco BD6, Todorov SD6. Braz J Microbiol. 2015 Mar 1;46(1):237-49. doi: 10.1590/S1517-838246120131245. eCollection 2015.

This study aimed to characterize the safety and technological properties of Enterococcus faecium strains isolated from Brazilian Coalho cheeses. High levels of co-aggregation were observed between Enterococcus faecium strains EM485 and EM925 and both Escherichia coli and Clostridium perfringens . Both strains presented low levels of hydrophobicity. E. faecium EM485 and EM925 were both able to grow in the presence of 0.5% of the sodium salts of taurocholic acid (TC), taurodeoxycholic acid (TDC), glycocholic acid (GC), and glycodeoxycholic acid (GDC), although they showed the ability to deconjugate only GDC and TDC. Both strains showed good survival when exposed to conditions simulating the gastro intestinal tract (GIT). When tested for the presence of virulence genes, only tyrosine decarboxylase and vancomycin B generated positive PCR results.

3.Radiosynthesis of N-11C-Methyl-Taurine-Conjugated Bile Acids and Biodistribution Studies in Pigs by PET/CT.

Schacht AC1, Sørensen M2, Munk OL1, Frisch K3. J Nucl Med. 2016 Apr;57(4):628-33. doi: 10.2967/jnumed.115.161711. Epub 2015 Dec 23.

During cholestasis, accumulation of conjugated bile acids may occur in the liver and lead to hepatocellular damage. Inspired by our recent development ofN-(11)C-methyl-glycocholic acid-that is,(11)C-cholylsarcosine-a tracer for PET of the endogenous glycine conjugate of cholic acid, we report here a radiosynthesis ofN-(11)C-methyl-taurine-conjugated bile acids and biodistribution studies in pigs by PET/CT.

4.Metabolomics Coupled with Multivariate Data and Pathway Analysis on Potential Biomarkers in Cholestasis and Intervention Effect of Paeonia lactiflora Pall.

Ma X1, Chi YH2, Niu M3, Zhu Y4, Zhao YL5, Chen Z1, Wang JB3, Zhang CE6, Li JY4, Wang LF4, Gong M4, Wei SZ1, Chen C1, Zhang L1, Wu MQ1, Xiao XH3. Front Pharmacol. 2016 Feb 4;7:14. doi: 10.3389/fphar.2016.00014. eCollection 2016.

BACKGROUND: The dried root of Paeonia lactiflora Pall. (PLP) is a classical Chinese herbal medicine that has been used to treat hepatic disease for 1000s of years. Our previous work suggested that PLP can be used to treat hepatitis with severe cholestasis. This study explored the mechanism by which PLP affects ANIT-induced cholestasis in rats using a metabolomics approach.