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taurodeoxycholic acid

Names

[ CAS No. ]:
516-50-7

[ Name ]:
taurodeoxycholic acid

[Synonym ]:
taurochenodeoxycholic acid
Deoxycholyltaurine
2-[4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-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]pentanoylamino]ethanesulfonic acid
Tudcabil
Taurodeoxychloic Acid
[3H]-Deoxycholyltaurine
Taurodesoxycholic Acid
Deoxytaurocholic Acid
N-(3a,12a-Dihydroxy-5-cholan-24-oyl)taurine
2-[[(3a,5,12)-3,12-Dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic Acid

Biological Activity

[Description]:

Taurodeoxycholic acid, a bile acid, stabilizes the mitochondrial membrane, decreases free radical formation. Taurodeoxycholic acid inhibits apoptosis by blocking a calcium-mediated apoptotic pathway as well as caspase-12 activation. Taurodeoxycholic acid exhibits neuroprotective effect in 3-nitropropionic acid induced mouse model or genetic mouse model of Huntington's disease (HD)[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Neurological Disease

[Target]

Microbial Metabolite


[In Vitro]

Taurodeoxycholic acid (50 μM,100 μM;4 h) 增加原代人肝细胞中寡核体 DNA 切割和细胞核凋亡[1]。 Taurodeoxycholic acid (400 μM;18-24 h) 在人肝来源的 Huh7 细胞中增加 DNA 碎片和 PARP 切割,诱导凋亡[2]。

[In Vivo]

Taurodeoxycholic acid (50 mg/kg;腹腔注射;每天 1 次,共 34 天) 预防亨廷顿舞蹈病 (HD) 大鼠模型的神经病理和相关的行为缺陷[3]。 Taurodeoxycholic acid (500 mg/kg;皮下注射;每 3 天 1 次,共 7 周) 导致 R6/2 转基因 HD 小鼠纹状体神经病理的显著降低[4]。 Animal Model: Huntington's disease model in mouse[3] Dosage: 50 mg/kg Administration: Intraperitoneal injection; once daliy for 34 d, injected 3-NP at 6 hr after Taurodeoxycholic acid treatment Result: Reduced striatal atrophy, decreased striatal apoptosis, as well as fewer and smaller size ubiquitinated neuronal intranuclear huntingtin inclusions. Significantly improved locomotor and sensorimotor deficits.

[References]

[1]. Benz C, et al. Effect of tauroursodeoxycholic acid on bile acid-induced apoptosis in primary human hepatocytes. Eur J Clin Invest. 2000 Mar;30(3):203-9.  

[2]. Xie Q, et al. Effect of tauroursodeoxycholic acid on endoplasmic reticulum stress-induced caspase-12 activation. Hepatology. 2002 Sep;36(3):592-601.  

[3]. Keene CD, et al. A bile acid protects against motor and cognitive deficits and reduces striatal degeneration in the 3-nitropropionic acid model of Huntington's disease. Exp Neurol. 2001 Oct;171(2):351-60.  

[4]. Keene CD, et al. Tauroursodeoxycholic acid, a bile acid, is neuroprotective in a transgenic animal model of Huntington's disease. Proc Natl Acad Sci U S A. 2002 Aug 6;99(16):10671-6.  

Chemical & Physical Properties

[ Molecular Formula ]:
C26H45NO6S

[ Molecular Weight ]:
499.70400

[ Exact Mass ]:
499.29700

[ PSA ]:
132.31000

[ LogP ]:
4.86900

Synthetic Route

Precursor & DownStream


Related Compounds