Sodium taurodeoxycholate hydrate [207737-97-1]

Sodium taurodeoxycholate hydrate is a bile salt-related anionic detergent. Sodium taurodeoxycholate hydrate is formed in the liver by conjugation of deoxycholate with Taurine (HY-B0351). Sodium taurodeoxycholate hydrate is used for isolation of membrane proteins including inner mitochondrial membrane proteins. Taurodeoxycholate-d₆ (TDCA) exhibits anti-inflammatory and neuroprotective effects^{[1][2][3][9][10]}.

Sodium taurodeoxycholate hydrate (Taurodeoxycholic acid form) shows agonist activity at human TGR5 expressed in CHO cells by luciferase assay, with an EC₅₀ of 0.79 μM^[4].
Sodium taurodeoxycholate hydrate (Taurodeoxycholic acid form, 16 h) shows agonist activity at wild type and Y89A mutant human TGR5 expressed in HEK293 cells assessed as rise in intracellular cAMP level, with EC₅₀s of 0.68 and 8.9 μM, respectively^[5].
Sodium taurodeoxycholate hydrate (Taurodeoxycholic acid form, 50 μM, 100 μM; 4 h) increases oligonucleosomal DNA cleavage and apoptotic nuclei in primary human hepatocytes^[6].
Sodium taurodeoxycholate hydrate (Taurodeoxycholic acid form, 400 μM, 18-24 h) increases DNA fragmentation and PARP cleavage in human liver-derived cell line Huh7 cells, thus induces apoptosis^[8].
Sodium taurodeoxycholate hydrate (0.05-1.00 mM; 1-6 days) stimulates intestinal epithelial cell proliferation^[8].
Sodium taurodeoxycholate hydrate (0.05-1.00 mM; 24 h) induces a significant increase in S-phase concentration and a significant decrease in G1-phase concentration of the cell cycle, increases c-myc protein and mRNA expression in IEC-6 cells^[8].
Sodium taurodeoxycholate hydrate (25-400 ng/mL, with a four-fold dilution, 3 h) inhibits the activation of NF-κB in lipopolysaccharide-activated bone marrow-derived macrophages (BMDMs) by activating the cAMP-PKA axis^[9].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Sodium taurodeoxycholate hydrate (1.25-5 mg/kg, p.o., 6 days) ameliorates dextran sodium sulfate (DSS)-induced colitis in mice^[9].
Sodium taurodeoxycholate hydrate (Taurodeoxycholic acid form, 50 mg/kg; i.p.; once daliy for 34 d) prevents neuropathology and associated behavioral deficits in the 3-nitropropionic acid rat model of Huntington's disease (HD) ^[10].
Sodium taurodeoxycholate hydrate (Taurodeoxycholic acid form, 500 mg/kg; s.c.; once every 3 d for 7 weeks) leads to a significant reduction in striatal neuropathology of the R6/2 transgenic HD mouse^[11].
Sodium taurodeoxycholate hydrate (0.5 mg/kg; i.v., once) confers protection to C57BL/6N mice with sepsis, but does not protect TGR5 KO mice under sepsis^[12].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

C₂₆H₄₄NNaO₆S·xH₂O

207737-97-1

Solid

White to off-white

C[C@@]12[C@](CC[C@]2(20)[C@H](C)CCC(NCCS(=O)(O[Na])=O)=O)(20)[C@@]3(20)[C@@](C[C@@H]1O)(20)[C@@]4([C@](C[C@@H](CC4)O)(20)CC3)C.O.[x]

Room temperature in continental US; may vary elsewhere.

4°C, sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

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  [2]. Kispal G, et al. Isolation and characterization of 3-hydroxyacyl coenzyme A dehydrogenase-binding protein from pig heart inner mitochondrial membrane. J Biol Chem. 1986 Oct 25;261(30):14209-13.  [Content Brief]

  [3]. Choi HJ, et al. Evaluation of acute and subacute toxicity of sodium Taurodeoxycholate in rats. Drug Chem Toxicol. 2021 May;44(3):268-276.  [Content Brief]

  [4]. Sato H, et al. Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies. J Med Chem. 2008 Mar 27;51(6):1831-41.  [Content Brief]

  [5]. Gertzen CG, et al. Mutational mapping of the transmembrane binding site of the G-protein coupled receptor TGR5 and binding mode prediction of TGR5 agonists. Eur J Med Chem. 2015 Nov 2;104:57-72.  [Content Brief]

  [6]. 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.  [Content Brief]

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

  [8]. Yamaguchi J, et al. Taurodeoxycholate increases intestinal epithelial cell proliferation through c-myc expression. Surgery. 2004 Feb;135(2):215-21.  [Content Brief]

  [9]. Zou Y, et al. Taurodeoxycholate ameliorates DSS-induced colitis in mice. Int Immunopharmacol. 2023 Sep;122:110628.  [Content Brief]

  [10]. 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.  [Content Brief]

  [11]. 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.  [Content Brief]

  [12]. Chang S, et al. Taurodeoxycholate Increases the Number of Myeloid-Derived Suppressor Cells That Ameliorate Sepsis in Mice. Front Immunol. 2018 Sep 18;9:1984.  [Content Brief]