Sodium Tauroursodeoxycholate (TUDC)water soluble bile salt CAS# 35807-85-3 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 35807-85-3 | SDF | Download SDF |
| PubChem ID | 46782978 | Appearance | Powder |
| Formula | C26H44NNaO6S | M.Wt | 521.69 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Sodium tauroursodeoxycholate; Tauroursodeoxycholic acid sodium salt | ||
| Solubility | H2O : 100 mg/mL (191.68 mM; Need ultrasonic) DMSO : 100 mg/mL (191.68 mM; Need ultrasonic) | ||
| Chemical Name | sodium;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]ethanesulfonate | ||
| SMILES | CC(CCC(=O)NCCS(=O)(=O)[O-])C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C.[Na+] | ||
| Standard InChIKey | IYPNVUSIMGAJFC-JUWYWQLMSA-M | ||
| Standard InChI | InChI=1S/C26H45NO6S.Na/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29;/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33);/q;+1/p-1/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-;/m1./s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Tauroursodeoxycholate Sodium is an endoplasmic reticulum (ER) stress inhibitor. Tauroursodeoxycholate significantly reduces expression of apoptosis molecules, such as caspase-3 and caspase-12. Tauroursodeoxycholate also inhibits ERK.In Vitro:Tauroursodeoxycholate (TUDCA) suppresses both viability and migration of vascular smooth muscle cells (VSMCs) through inhibition of ERK phosphorylation, by induction of mitogen-activated protein kinase phosphatase-1 (MKP-1) via PKCα. Tauroursodeoxycholate inhibits both the proliferation and migration of VSMCs via inhibition of ERK, through Ca2+-dependent PKCα translocation. Tauroursodeoxycholate prevents platelet-derived growth factor (PDGF) and vascular injury-induced MMP-9 expression. The knock-down of MKP-1 using specific si-RNA restores the reduced VSMC viability by Tauroursodeoxycholate (200 μM), which suggests that anti-proliferative effect of Tauroursodeoxycholate depended on the MKP-1 expression[1].In Vivo:The effects of Tauroursodeoxycholate (TUDCA) on proliferation and apoptosis of VSMCs in vivo are examined using immunohistochemistry for proliferating cell nuclear antigen (PCNA) and the transferase dUTP nick-end labelling (TUNEL) assay. Tauroursodeoxycholate (10, 50, and 100 mg/kg) increases the caspase 3 activity of injured tissues in a dose-dependent manner, indicating that Tauroursodeoxycholate induces apoptosis of VSMCs in the neointima. Using the injured tissues, further examination and comparison of the phosphorylation level of ERK and MMP-9 expression is performed at 1 week after injury, compared with normal controls. Balloon injury increased both the phosphorylation of ERK and expression of MMP-9 in the tissues. Tauroursodeoxycholate (10, 50, and 100 mg/kg) inhibits phosphorylation of ERK and MMP-9 expression in a dose-dependent manner[1]. Tauroursodeoxycholate (TUDCA) is a hydrophilic bile acid. Tauroursodeoxycholate as a cytoprotective agent improves liver function and can prevent hepatocellular carcinoma by reducing ER stress and apoptosis. Tauroursodeoxycholate significantly reduces expression of apoptosis molecules, such as caspase-3, caspase-12, C/EBP homologous protein, c-Jun N-terminal kinase (JNK), activating transcription factor 4 (ATF4), X-box binding protein (XBP), and eukaryotic initiation factor 2α (eIF2α) in Ang II induced ApoE-/- mice (p<0.05). Tauroursodeoxycholate reduces Angiotensin (Ang) II induced abdominal aortic aneurysm (AAA) formation in ApoE-/- mice. Tauroursodeoxycholate is used at a dose of 0.5 g/kg/day in treating Ang II induced ApoE-/- mice (ER stress inhibitor group). Systolic blood pressure (141.3±5.6 mmHg vs 145.9±8.9 mmHg; p>0.05) and total cholesterol levels (663.6±88.7 mg/dL vs 655.7±65.4 mg/dL; p>0 .05) do not differ between the AAA model group and Tauroursodeoxycholate group. In addition, maximum aortic diameter is significantly smaller in those in Tauroursodeoxycholate group compared with those in the AAA model group (0.95±0.03 mm vs 1.79±0.04 mm; p<0.05). AAA lesion areas are also smaller in those in Tauroursodeoxycholate group than in those in the AAA model group (0.37±0.03 mm2 vs 1.51±0.06 mm2; p<0.05)[2]. References: | |||||
Sodium Tauroursodeoxycholate (TUDC) Dilution Calculator
Sodium Tauroursodeoxycholate (TUDC) Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9168 mL | 9.5842 mL | 19.1685 mL | 38.3369 mL | 47.9212 mL |
| 5 mM | 0.3834 mL | 1.9168 mL | 3.8337 mL | 7.6674 mL | 9.5842 mL |
| 10 mM | 0.1917 mL | 0.9584 mL | 1.9168 mL | 3.8337 mL | 4.7921 mL |
| 50 mM | 0.0383 mL | 0.1917 mL | 0.3834 mL | 0.7667 mL | 0.9584 mL |
| 100 mM | 0.0192 mL | 0.0958 mL | 0.1917 mL | 0.3834 mL | 0.4792 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Sodium tauroursodeoxycholate (TUDC) shows therapeutic effect on cholestasis [1, 2]. In human erythrocytes, it inhibited 2’,7’-bis-(carboxypropyl)-5(6)-carboxyfluorescein (BCPCF) efflux induced by bile salts with an IC50 value of 560 µM [3].
Cholestasis is the syndrome resulted from the impairment of the formation of bile, a vital function [4].
cVA-of-CLF means the canalicular vacuolar accumulation of cholyllysylfluorescein [1]. cVA of CLF is a parameter to indicate overall biliary secretion [5]. Incubation with 17βEG dose-dependently decreased the cVA-of-CLF in cells. 17βEG at a concentration of 50 µM decreased cVA-of-CLF by 40%. The simultaneous incubation with TUDC and 17βEG improved the decreased cVA by 24%. The simultaneous incubation with SAMe and 17βEG improved the decreased cVA by 18%. The simultaneous incubation with TUDC, SAMe and 17βEG improved the decreased cVA by 28%. But the effect of TUDC + SAMe was not significantly greater than the effect of either protectant alone [1].
In rats, intrahepatic cholestasis was induced by the administration of phalloidin at an i.p. dose of 500 µg/kg for 7 days. In these treated rats, bile flow was decreased, and activities of glutamic pyruvic transaminase, leucine aminopeptidase, serum alkaline phosphatase, and concentrations of bile acid, phospholipid and cholesterol were increased. But these effects were significantly suppressed by tauroursodeoxycholate. In these rats, excretion rates of biliary cholesterol and phospholipid were significantly improved by tauroursodeoxycholate [2].
References:
[1]. Milkiewicz P, Roma MG, Cardenas R, et al. Effect of tauroursodeoxycholate and S-adenosyl-l-methionine on 17β-estradiol glucuronide-induced cholestasis. Journal of hepatology, 2001, 34(2): 184-191.
[2]. Ishizaki K, Kinbara S, Hirabayashi N, et al. Effect of sodium tauroursodeoxycholate on phalloidin-induced cholestasis in rats. European journal of pharmacology, 2001, 421(1): 55-60.
[3]. Mrowczynska L, Bobrowska-Hgerstrand M, Wrobel A, et al. Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts. Anticancer research, 2005, 25(5): 3173-3178.
[4]. Trauner M, Meier PJ, Boyer JL. Molecular pathogenesis of cholestasis. New England Journal of Medicine, 1998, 339(17): 1217-1227.
[5]. Milkiewicz P, Roma MG, Elias E, et al. Hepatoprotection with tauroursodeoxycholate and β muricholate against taurolithocholate induced cholestasis: involvement of signal transduction pathways. Gut, 2002, 51(1): 113-119.
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