Tauroursodeoxycholic acid
Tauroursodeoxycholic acid
CAS: 14605-22-2
Molecular Formula: C26H45NO6S
Tauroursodeoxycholic acid - Names and Identifiers
| Name | Tauroursodeoxycholic acid |
| Synonyms | yl)amino)- TUDCA Soduim Salt Ursodeoxycholyltaurin ursodeoxycholyltaurine Tauroursodeoxycholic acid tauroursodeoxycholic acid sodium 9,10-secocholesta-5,7,10-trien-3-ol 3α,7β-dihydroxy-5β-cholan-24-oic acid n-(2-sulfoethyl)amide 3a,7b-Dihydroxy-5b-cholan-24-oic Acid N-(2-Sulfoethyl)amide 2-{[(3alpha,5beta,7beta)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid 2-{[(3alpha,5beta,7beta,8xi,9xi,14xi)-3,7-dihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid |
| CAS | 14605-22-2 |
| EINECS | 1308068-626-2 |
| InChI | InChI=1/C26H45NO6S/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)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1 |
| InChIKey | BHTRKEVKTKCXOH-LBSADWJPSA-N |
Tauroursodeoxycholic acid - Physico-chemical Properties
| Molecular Formula | C26H45NO6S |
| Molar Mass | 499.7 |
| Density | 1.216±0.06 g/cm3(Predicted) |
| Melting Point | 173-175°C |
| Boling Point | 496.4°C at 760mmHg |
| Specific Rotation(α) | (C=1, EtOH)+46 |
| Solubility | Organic solvents such as DMSO and ethanol |
| Appearance | Powder |
| Color | White |
| pKa | 1.42±0.50(Predicted) |
| Storage Condition | +15C to +30C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| Refractive Index | 46 ° (C=1, EtOH) |
| MDL | MFCD00069496 |
| In vitro study | 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 Ca 2+ -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. |
| In vivo study | 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. 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 mm 2 vs 1.51±0.06 mm 2 ; p<0.05). |
Tauroursodeoxycholic acid - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | KI7372500 |
| HS Code | 29242990 |
Tauroursodeoxycholic acid - Reference
| Reference Show more | 1. Yang Jinwei, Zhao Can, Liu Xiu, Wu Yongjun, Yu Rong. Effect of Zuogui Jiangtang Shuxin Recipe Drug-containing Plasma on Foaming and Apoptosis of Mouse Macrophages Induced by ox-LDL [J]. Journal of Nanjing University of Traditional Chinese Medicine, 2020,36(03):370-375. 2. Cao Yan, Li Ting, Chang Anqi, Jiang Zhenzhen, Yu Juan, Tu Pengfei, Song Yuelin. Analysis of Bile Acids in Snake Gallbladder [J]. Chinese journal of traditional Chinese medicine, 2021,46(01):130-138. 3. Wang, Tianyang, et al. "Metabolomic profile perturbations of serum, lung, bronchoalveolar lavage fluid, spleen and feces in LPS-induced acute lung injury rats based on HPLC-ESI-QTOF-MS." Analytical and bioanalytical chemistry 412.5 (2020): 1215-1234. 4. Song Lin, Tian-yang Wang, Hua-rong Xu, Xin-nong Zhang, qi Wang, Ran Liu, Qing Li, Kai-shun Bi,A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induce 5. [IF = 3.361] Qingqing Song et al. "Polarity-extended quantitative analysis of bear bile and its analogs using serially coupled reversed phase-hydrophilic interaction liquid chromatography-tailored multiple reaction monitoring." Rsc Adv. 2017 Nov;7(83):52822-52831 6. [IF = 8.322] Hou Yonghui et al. "Tauroursodeoxycholic acid alleviates secondary injury in spinal cord injury mice by reducing oxidative stress, apoptosis, and inflammatory response." J Neuroinflamm. 2021 Dec;18(1):1-13 7. [IF = 6.558] Qingqing Song et al. "Binary code, A flexible tool for diagnostic metabolite sequencing of medicinal plants." Anal Chim Acta. 2019 Dec;1088:89 8. [IF = 5.878] Min Wen et al. "Geniposide suppresses liver injury in a mouse model of DDC-induced sclerosing cholangitis." Phytother Res. 2021 Jul;35(7):3799-3811 9. [IF = 5.396] Shiming Huang et al. "A sulfated polysaccharide from Gracilaria Lemaneiformis regulates cholesterol and bile acid metabolism in high-fat diet mICE." Food Funct. 2019 Jun;10(6):3224-3236 10. [IF = 5.396] Cong Liang et al. "Lactiplantibacillus plantarum H-87 prevents high-fat diet-induced obesity by regulating bile acid metabolism in c57bl/6j mice." food funct. 2021 may; 12(10):4315-4324 11. [IF = 3.935] Song Lin et al. "A systemic combined nontargeted and targeted LC-MS based metabolomic strategy of plasma and liver on pathology exploration of alpha-naphthylisothiocyanate induced cholestatic liver injury in mice." J Pharmaceut Biomed. 2019 Jul;171:180 12. [IF = 0.252] Yi Dong et al. "Mechanism of tauroursodeoxycholic acid-mediated neuronal protection after acute spinal cord injury through AKT signaling pathway in rats." Int J Clin Exp Patho. 2020; 13(9): 2218-2227 13. [IF = 5.396] Juan Wu et al. "Sargassum fusiforme polysaccharide is a potential auxiliary substance for metformin in the management of diabetes." Food Funct. 2022 Feb;: 14. [IF = 6.558] Yan Cao et al. "Widely quasi-quantitative analysis enables temporal bile acids-targeted metabolomics in rat after oral administration of ursodeoxycholic acid." ANALYTICA CHIMICA ACTA. 2022 Jun;1212:339885 |
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