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| 5mg |
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| Targets |
Metabolite of Taurolithocholic Acid; The primary targets of Taurolithocholic acid 3-sulfate disodium include the GPR39 receptor and the CD95 death receptor. As a GPR39 agonist, it stimulates GPR39 receptors to initiate intracellular calcium signaling in M39-20 and hGPR39-2 cells, with EC₅₀ values of 71.6 and 69.4 μM (in the absence of Zn²⁺) and 9 and 9.6 μM (in the presence of Zn²⁺), independent of Zn²⁺ binding sites H17 and H19. Furthermore, this compound induces oxidative stress and EGFR tyrosine phosphorylation, triggering CD95 tyrosine phosphorylation, CD95 membrane targeting, and death-inducing signaling complex (DISC) formation, mediating hepatocyte apoptosis. The compound also promotes CD95 trafficking to the plasma membrane via sustained activation of c-Jun N-terminal kinase (JNK).
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| ln Vitro |
In cell-free and cellular systems, Taurolithocholic acid 3-sulfate disodium exhibits multiple biological activities. In cultured rat hepatocytes, 100 μM of this compound induces activation of caspase-8, caspase-9, and caspase-3, leading to hepatocyte apoptosis as evidenced by PARP cleavage, Annexin-V staining positivity, and TUNEL reaction positivity. The apoptotic effects induced by this compound can be abolished by tauroursodeoxycholate (TUDC), and this protective effect is independent of PI3K/PKB, p38MAPK, and Erk-2 pathways. At the molecular mechanism level, TLCS leads to sustained JNK activation and CD95 trafficking to the plasma membrane, and inhibition of JNK1 or protein kinase C prevents TLCS-induced CD95 membrane trafficking and blunts the apoptotic response. Additionally, this compound has been used to assess the electrophysiological effects of bile acids on pancreatic acinar cells.
Taurolithocholic Acid 3-sulfate is a metabolite of Taurolithocholic Acid |
| ln Vivo |
In vivo activity of Taurolithocholic acid 3-sulfate disodium is primarily studied using animal models. In cholestasis-related research, this compound, as a representative hydrophobic bile acid, induces intrahepatic cholestasis and hepatocyte apoptosis. Both isolated perfused rat liver models and in vivo bile duct-ligated rat liver models have confirmed that this compound induces CD95-dependent hepatocyte apoptosis involving oxidative stress, EGFR activation, and JNK signaling pathways. Studies demonstrate that the apoptotic potency of this compound correlates with its ability to induce sustained JNK activation. In gallbladder disease research, this compound serves as a GPR39 agonist and can be used to explore the mechanisms of bile acid signaling pathways in gallbladder disease.
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| Enzyme Assay |
Binding of Taurolithocholic acid 3-sulfate disodium to the GPR39 receptor can be assessed using cell-based calcium flux assays. A typical protocol: GPR39-expressing cells (e.g., M39-20 cells or hGPR39-2 cells) are seeded in 96-well plates and loaded with a calcium-sensitive dye (e.g., Fluo-4 AM). Varying concentrations of TLCS (0.1-100 μM) are added in the presence or absence of Zn²⁺ (10 μM), and the increase in fluorescence intensity resulting from changes in intracellular calcium concentration is monitored using a fluorescence plate reader to calculate EC₅₀ values. For EGFR phosphorylation detection, cultured rat hepatocytes can be treated with TLCS, and EGFR tyrosine phosphorylation levels are detected by immunoprecipitation and Western blotting.
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| Cell Assay |
Taurolithocholic acid 3-sulfate disodium is widely used in cellular assays to study the mechanisms of bile acid-induced hepatocyte apoptosis. A typical protocol: Isolated 24-hour cultured rat hepatocytes are treated with 100 μM TLCS and collected at various time points (0-24 hours). Apoptosis is assessed by PARP cleavage detection via Western blotting; apoptotic cell proportion is quantified by Annexin-V staining and TUNEL reaction using flow cytometry or fluorescence microscopy; activation of the apoptotic pathway is assessed by measuring caspase-3, caspase-8, and caspase-9 activities. For signaling pathway studies, cells can be pretreated with JNK inhibitors (e.g., SP600125) or PKC inhibitors to examine their effects on TLCS-induced CD95 membrane trafficking and apoptosis. Additionally, this compound has been used to investigate the mechanisms underlying the inhibition of bile acid-induced apoptosis by cyclic AMP in rat hepatocytes.
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| Animal Protocol |
In vivo studies of Taurolithocholic acid 3-sulfate disodium primarily employ rat cholestasis and apoptosis models. A typical protocol: Male Wistar rats (200-250 g) undergo common bile duct cannulation, TLCS is administered via intravenous or biliary routes (dose to be determined based on experimental objectives), bile and blood samples are collected, and liver function indicators (ALT, AST, ALP) and bile flow are measured. In isolated perfused rat liver models, perfusion solution containing TLCS is used to assess bile secretion and hepatocyte injury. For apoptosis studies, animals are euthanized, liver tissues are collected, apoptotic cells are detected by TUNEL staining, and activation of CD95, caspase-8, and caspase-3 is detected by Western blotting. Bile duct-ligated rat models can also be used to study the mechanisms of bile acid-induced hepatocyte apoptosis.
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| ADME/Pharmacokinetics |
As a taurine-conjugated sulfated bile acid, the pharmacokinetic behavior of Taurolithocholic acid 3-sulfate disodium follows the enterohepatic circulation pattern of bile acids. This compound has a molecular weight of 607.73 g/mol, with purity ≥90.0% (TLC) and impurities ≤3%. Predicted physicochemical properties: hydrogen bond donor count is 2, hydrogen bond acceptor count is 8, and rotatable bond count is 9. This compound exists as a disodium salt with good water solubility. Storage conditions: The powder should be kept dry and sealed at -20°C, avoiding repeated freeze-thaw cycles. The WGK Germany classification is 3 (hazardous to water). This product is for research use only and not for human or veterinary use.
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| Toxicity/Toxicokinetics |
As a sulfated derivative of a hydrophobic bile acid, Taurolithocholic acid 3-sulfate disodium exhibits toxic effects including the induction of hepatocyte apoptosis and cholestasis. In cultured rat hepatocytes, 100 μM TLCS induces significant apoptosis, characterized by caspase cascade activation and PARP cleavage. Its toxic mechanism involves oxidative stress-induced EGFR activation, sustained JNK activation, and CD95 death receptor membrane trafficking and activation. According to the Material Safety Data Sheet, this compound is an anionic detergent, and personal protective equipment (such as N95-type dust mask, Eyeshields, and Gloves) is recommended during handling. The WGK Germany classification is 3 (hazardous to water). This product is for research use only and not for human or veterinary use.
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| Molecular Formula |
C26H43NNA2O8S2
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| Molecular Weight |
607.73
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| Exact Mass |
607.223
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| CAS # |
64936-83-0
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| Related CAS # |
Taurolithocholic Acid-3-Sulfate-d4 （disodium salt）
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| PubChem CID |
92043494
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| Appearance |
White to off-white solid powder
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| LogP |
6.12
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
39
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| Complexity |
1020
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| Defined Atom Stereocenter Count |
9
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| SMILES |
C[C@H](CCC(=NCCS(=O)(=O)[O-])[O-])C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)OS(=O)(=O)O.[Na+].[Na+]
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| InChi Key |
YHTVOGLKSGJIDL-RLHFEMFKSA-L
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| InChi Code |
InChI=1S/C26H45NO8S2.2Na/c1-17(4-9-24(28)27-14-15-36(29,30)31)21-7-8-22-20-6-5-18-16-19(35-37(32,33)34)10-12-25(18,2)23(20)11-13-26(21,22)3;;/h17-23H,4-16H2,1-3H3,(H,27,28)(H,29,30,31)(H,32,33,34);;/q;2*+1/p-2/t17-,18-,19-,20+,21-,22+,23+,25+,26-;;/m1../s1
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| Chemical Name |
disodium;2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-sulfonatooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonate
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| Synonyms |
64936-83-0; Taurolithocholic Acid Sulfate Disodium Salt; 3ALPHA-HYDROXY-5BETA-CHOLAN-24-OIC ACID N-[2-SULFOETHYL]AMIDE 3-SULFATE DISODIUM SALT; Disodium;2-[[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-sulfonatooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonate;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6455 mL | 8.2273 mL | 16.4547 mL | |
| 5 mM | 0.3291 mL | 1.6455 mL | 3.2909 mL | |
| 10 mM | 0.1645 mL | 0.8227 mL | 1.6455 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
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