Glycoursodeoxycholic acid

• CAT Number: R004700
• CAS Number: 64480-66-6
• Molecular Formula: C26H43NO5
• Molecular Weight: 449.62
• Purity: ≥95%
• Synonyms: 2-[[(4R)-4-[(3R,5S,7S,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]acetic acid
• InChI: InChI=1S/C26H43NO5/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)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
• InChIKey: GHCZAUBVMUEKKP-XROMFQGDSA-N
• SMILES: CC(CCC(=O)NCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C

Glycoursodeoxycholic acid, a acyl glycine and a bile acid-glycine conjugate, is a metabolite of ursodeoxycholic acid.
The antioxidant compound glycoursodeoxycholic acid (GUDCA) fully abrogates UCB-induced cytochrome c oxidase inhibition and significantly prevents oxidative stress, metabolic alterations, and cell demise[1].GUDCA has shown therapeutic efficacy in neurodegenerative models and diseases. Increased cytosolic SOD1 inclusions were observed in 4 DIV NSC-34/hSOD1(G93A) cells together with decreased mitochondria viability, caspase-9 activation, and apoptosis[2]. Glycoursodeoxycholic acid shows preventive and restorative effects against unconjugated bilirubin -induced blood-brain barrier disruption and damage to human brain microvascular endothelial cells[3].

Reference

[1]. Vaz AR, et al. Bilirubin selectively inhibits cytochrome c oxidase activity and induces apoptosis in immature cortical neurons: assessment of the protective effects of glycoursodeoxycholic acid. J Neurochem. 2010 Jan;112(1):56-65.
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[2]. Vaz AR, et al. Glycoursodeoxycholic acid reduces matrix metalloproteinase-9 and caspase-9 activation in a cellular model of superoxide dismutase-1 neurodegeneration.
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[3]. Palmela I, et al. Hydrophilic bile acids protect human blood-brain barrier endothelial cells from disruption by unconjugated bilirubin: an in vitro study. Front Neurosci. 2015 Mar 13;9:80.
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