Glycochenodeoxycholic Acid

Synonyme: Glycochenodeoxycholic acid, GCDCA, Chenodeoxycholylglycine, 3α,7α-Dihydroxy-5β-cholan-24-oylglycine, N-[(3α,5β,7α)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine, Glycine chenodeoxycholate

Glycochenodeoxycholic acid belongs to the family of glycine-conjugated bile acids, characterized by a 5β-cholane skeleton with hydroxyl groups at C-3 and C-7 and a glycine moiety linked via an amide bond at C-24. This amphipathic structure underpins its role as a physiological detergent, facilitating the emulsification and absorption of dietary lipids and fat-soluble vitamins in the small intestine. As a major constituent of human bile, GCDCA is also a key signaling molecule that activates the farnesoid X receptor (FXR) and G protein-coupled bile acid receptor 1 (TGR5), influencing glucose and lipid metabolism, energy homeostasis, and inflammatory responses.

Industrially, GCDCA is produced through chemical conjugation of chenodeoxycholic acid with glycine or by enzymatic synthesis using bile acid-CoA:amino acid N-acyltransferase. It is available in high-purity grades, typically ≥98% as determined by HPLC, and finds extensive use as a reference standard in clinical diagnostics, a critical component in cell culture media for hepatocyte and intestinal models, and a precursor in pharmaceutical research targeting cholestatic liver diseases and metabolic disorders.

Beyond its physiological functions, GCDCA serves as a valuable tool in drug discovery and development. Its ability to modulate bile acid receptors and transporters makes it a subject of interest in studies on non-alcoholic steatohepatitis (NASH), type 2 diabetes, and bile acid diarrhea. The compound is also employed in the formulation of liposomal drug delivery systems to enhance the oral bioavailability of poorly soluble drugs. With a well-defined impurity profile and consistent batch-to-batch quality, GCDCA from LyvBio meets the rigorous demands of pharmaceutical and biotech customers worldwide.

Chemical Structure & Properties

Glycochenodeoxycholic acid features a steroid nucleus with a cis A/B ring junction, two α-oriented hydroxyl groups at positions 3 and 7, and a side chain terminated by a glycine conjugate. The molecule is amphiphilic, with a hydrophobic convex face and a hydrophilic concave face, which drives its self-assembly into micelles above the critical micellar concentration (CMC) of approximately 2-5 mM in aqueous buffer. Its sodium salt forms are more water-soluble and are often used in physiological studies. The compound is stable under normal storage conditions but should be protected from prolonged exposure to light and moisture to prevent degradation.

Mechanism of Action

• FXR activation: GCDCA binds to and activates the nuclear receptor FXR, leading to downregulation of cholesterol 7α-hydroxylase (CYP7A1) and modulation of bile acid synthesis.
• TGR5 agonism: It stimulates the membrane receptor TGR5, triggering cAMP signaling and influencing energy expenditure and glucose metabolism.
• Membrane disruption: As a detergent, GCDCA can disrupt cellular membranes at high concentrations, a property exploited in permeabilization studies but also linked to cholestatic injury.
• Inflammation modulation: GCDCA activates the NLRP3 inflammasome in macrophages, contributing to sterile inflammation in liver diseases.
• Drug transporter interaction: It interacts with apical sodium-dependent bile acid transporter (ASBT) and multidrug resistance-associated protein 2 (MRP2), affecting drug absorption and biliary excretion.

Quality Specifications

Supply & Documentation

• Capacity: 500 kg per month
• Lieferzeit: 3–5 Werktage (Lagerware)
• Dokumentation: COA, MSDS, TDS, and custom analytical reports available upon request
• Verpackung: 1 kg, 5 kg, and 25 kg fiber drums with double polyethylene liners; customized packaging options for sensitive applications

Angebotsanfrage

• LyvBio GmbH. — E-Mail: info@lyvbio.com