Sodium glycochenodeoxycholate

• CAS: 16564-43-5
• Catalog Number: ACM16564435-3
• Category: Main Products
• Molecular Weight: 471.6
• Molecular Formula: C26H42NNaO5
• Synonyms: Glycochenodeoxycholic acid sodium salt
• IUPAC Name: Sodium;2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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]acetate
• Canonical SMILES: CC(CCC(=O)NCC(=O)[O-])C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C.[Na+]
• InChI: InChI=1S/C26H43NO5.Na/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29;/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32);/q;+1/p-1/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-;/m1./s1
• InChI Key: AAYACJGHNRIFCT-YRJJIGPTSA-M
• Melting Point: 160-170 °C
• Complexity: 734
• Covalently-Bonded Unit Count: 2
• Defined Atom Stereocenter Count: 10
• Exact Mass: 471.29606772
• Heavy Atom Count: 33
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 3
• Isomeric SMILES: C[C@H](CCC(=O)NCC(=O)[O-])[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C.[Na+]
• Monoisotopic Mass: 471.29606772
• Rotatable Bond Count: 6
• Topological Polar Surface Area: 110 Ų

Case Study

Glycylchenodeoxycholate Promotes Liver Fibrosis in Mice with Hepatocellular Cholestasis

Hohenester, Simon, et al. Cells, 2020, 9(2), 281.

To test the specific contribution of bile salt accumulation to liver fibrosis in cholestatic diseases, this work applied a unique model of inducible hepatocellular cholestasis in bile-salt-fed Atp8b1 G308V/G308V mice. Glycylchenodeoxycholate (GCDCA) was supplemented to humanize the murine bile salt pool.
· Evaluation Methods
Biomarkers associated with cholestasis and liver fibrosis were assessed. Hepatic stellate cells (HSC) obtained from wild-type mice were treated with bile salts, and their proliferation, accumulation, and collagen deposition were analyzed.
· Evaluation Results
Liver fibrosis markers such as increased hepatic αSMA and collagen1a mRNA levels and collagen build-up began to show in cholestatic Atp8b1G308V/G308V mice exclusively with GCDCA supplementation. The number of myofibroblasts and collagen deposition increased when cells were incubated with hydrophobic bile salts according to in vitro studies which found these effects resulted from EGFR and MEK1/2 pathway activation.
· Findings
Chronic hepatocellular cholestasis, independent of biliary damage, can lead to liver fibrosis in mice when exposed to the human bile salt GCDCA. Furthermore, bile salts may exert direct pro-fibrotic effects on HSC, likely involving EGFR and MEK1/2 signaling pathways.

Specificity of Recombinant Bile Salt Hydrolases for Glycine-Conjugated Bile Salts

Li, Chou, et al. Biocatalysis and Biotransformation, 2021, 39(1), 61-70.

Due to their substantial impact on reducing host cholesterol levels and detoxifying intestinal bacteria, further investigation into bile salt hydrolases (BSHs) characteristics and functions is required. Researchers amplified Bifidobacterium bifidum's (ATCC 29521) BSH gene via the GST gene fusion system in this study and assessed its bile salt hydrolysis efficiency quantitatively.
Hydrolysis of BSHs
The hydrolysis efficiency of BSH was assessed using two methods: the ninhydrin coloration technique and high-performance liquid chromatography with an evaporative light scattering detector (HPLC-ELSD). Real-time imaging enabled clear observation of the hydrolysis process. BSH exhibited greater activity on glycine-conjugated bile salts compared to taurine-conjugated ones.
The hydrolysis rates for sodium glycochenodeoxycholate (GCDCA) and sodium glycoursodeoxycholate (GUDCA) exceeded 90% within 60 minutes, whereas sodium taurochenodeoxycholate (TCDCA) and sodium tauroursodeoxycholate (TUDCA) showed hydrolysis rates of only 68% and 43%, respectively, under the same conditions.