| Size | Price | |
|---|---|---|
| 1mg | ||
| Other Sizes |
| Targets |
Lithocholic acid Metabolite; Biochemical Assay Reagent; The primary targets of Lithocholic acid 3-sulfate disodium include the GPR39 receptor and the RORγt nuclear receptor. As a GPR39 agonist, it exhibits EC₅₀ values of 41 μM and 42.4 μM in M39-20 and hGPR39-2 cells (in the absence of Zn²⁺), and 0.88 μM and 0.97 μM (in the presence of Zn²⁺), activating GPR39 receptor and initiating intracellular calcium signaling independent of Zn²⁺-binding sites H17 and H19. Additionally, this compound acts as an RORγt ligand, selectively inhibiting Th17 cell differentiation. It is also a metabolite of lithocholic acid, participating in bile acid metabolism and transport regulation.
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| ln Vitro |
In cell-free and cellular systems, Lithocholic acid 3-sulfate disodium exhibits multiple biological activities. It selectively inhibits the replication of human immunodeficiency virus type 1 (HIV-1), completely protecting MT-4 cells against HIV-1-induced cytopathogenicity at 100 μg/ml, with no host cell toxicity observed at 200 μg/ml. It also inhibits HIV-1 antigen expression in HIV-1-infected CEM cells, partially inhibits virus adsorption, and exhibits inhibitory activity against HIV-1-associated reverse transcriptase. Furthermore, as an RORγt ligand, this compound selectively inhibits Th17 cell differentiation. As a GPR39 agonist, its potency for receptor activation is significantly enhanced in the presence of Zn²⁺ (EC₅₀ reduced from approximately 40 μM to approximately 0.9 μM).
Lithocholic acid 3-sulfate disodium is the 3-sulfated form of Lithocholic acid. |
| ln Vivo |
In vivo activity of Lithocholic acid 3-sulfate disodium is primarily studied through its metabolic and excretory properties. In a rat diabetes model induced by streptozotocin, biliary secretion of lithocholic acid 3-sulfate is increased under diabetic conditions. This compound is a key metabolite in the hepatic detoxification pathway of lithocholic acid, increasing water solubility through sulfation modification, thereby promoting its excretion via bile and reducing toxic accumulation of lithocholic acid in the liver. In gallbladder disease research, this compound participates in the regulation of bile composition as a bile acid metabolite. The immunomodulatory effects of its stereoisomers suggest that this compound may be involved in regulating the Th17/Treg balance.
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| Enzyme Assay |
Binding of Lithocholic acid 3-sulfate disodium to the GPR39 receptor can be assessed using 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 Lithocholic acid 3-sulfate disodium (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 RORγt binding assays, fluorescence resonance energy transfer (FRET) or time-resolved fluorescence resonance energy transfer (TR-FRET) competition binding assays can be used to determine the binding affinity of the compound to the RORγt ligand-binding domain.
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| Cell Assay |
Lithocholic acid 3-sulfate disodium can be used in cellular assays to study anti-HIV-1 activity or immunomodulatory functions. A typical protocol (anti-HIV-1 activity assay): MT-4 cells are seeded in 96-well plates, treated with varying concentrations of Lithocholic acid 3-sulfate disodium (e.g., 25, 50, 100, 200 μg/ml), and then infected with HIV-1 virus. After 5-7 days of culture, cell viability is assessed by MTT assay or trypan blue staining, and inhibition of viral replication is evaluated by detecting HIV-1 antigen expression or reverse transcriptase activity. For Th17 differentiation inhibition assays (based on RORγt ligand activity): CD4+ T cells are isolated from mouse spleens, cultured under Th17-polarizing conditions (IL-6 and TGF-β) with Lithocholic acid 3-sulfate disodium (1-20 μM), and after 72-96 hours, Th17 cell proportions are assessed by detecting IL-17A expression via flow cytometry.
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| Animal Protocol |
In vivo studies of Lithocholic acid 3-sulfate disodium typically employ metabolic disease animal models. A typical protocol (diabetic rat model): Male rats are administered streptozotocin (STZ, 50-60 mg/kg) intraperitoneally to induce diabetes. After successful model establishment, bile is collected via bile duct cannulation, and levels of Lithocholic acid 3-sulfate disodium and other bile acid sulfates in bile are detected by HPLC-MS/MS to compare secretory differences between diabetic and normal states. For cholestatic liver disease studies, rats can be fed a lithocholic acid-containing diet to induce liver injury, followed by intervention with Lithocholic acid 3-sulfate disodium, and serum liver function indicators (ALT, AST, ALP) and liver histopathological changes are examined.
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| ADME/Pharmacokinetics |
As a sulfated metabolite of lithocholic acid, the pharmacokinetic behavior of Lithocholic acid 3-sulfate disodium follows the enterohepatic circulation pattern of bile acids. This compound is the primary water-soluble metabolite generated from lithocholic acid via sulfation catalyzed by sulfotransferase (SULT2A1) in the liver, subsequently excreted into the intestine through bile. In diabetic rat models, its biliary secretion rate is significantly increased. Predicted physicochemical properties: LogP is approximately 4.67, polar surface area (tPSA) is 124.17 Ų, hydrogen bond donor count is 2, hydrogen bond acceptor count is 6, and rotatable bond count is 6. This compound exhibits good water solubility (as the disodium salt) and is primarily used in bile acid metabolism research. Storage conditions: The powder is stable for 3 years at -20°C and 2 years at 4°C; once dissolved, it can be stored for 6 months at -80°C and 1 month at -20°C.
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| Toxicity/Toxicokinetics |
As the sulfated detoxification product of lithocholic acid, Lithocholic acid 3-sulfate disodium exhibits significantly lower toxicity compared to its parent compound lithocholic acid. Lithocholic acid is a toxic secondary bile acid that can induce intrahepatic cholestasis and promote tumorigenesis. 3-Sulfation is the primary detoxification pathway for hepatic clearance of lithocholic acid, reducing its cytotoxicity. Nevertheless, this compound can still induce cell damage. In in vitro studies, this compound shows no toxicity to MT-4 cells at concentrations up to 200 μg/ml. This product is for research use only and not for human or veterinary use. When handling, it should be used by technically qualified persons following standard laboratory practices, wearing personal protective equipment.
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| References |
[1]. Synthesis and identification of lithocholic acid 3-sulfate as RORγt ligand to inhibit Th17 cell differentiation. J Leukoc Biol. 2022 Oct;112(4):835-843.
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| Additional Infomation |
Lithocholic acid sulfate is a steroidal sulfate, a derivative of lithocholic acid in which the hydroxyl hydrogen at the 3-position is replaced by a sulfonic acid group. It is functionally related to lithocholic acid. It is the conjugate acid of the lithocholic acid sulfate (2-) group.
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| Molecular Formula |
C24H38NA2O6S
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|---|---|
| Molecular Weight |
500.60
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| Exact Mass |
518.229
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| CAS # |
64936-81-8
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| Related CAS # |
Lithocholic acid 3-sulfate-d4 disodium; 434-13-9
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| PubChem CID |
451489
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| Appearance |
White to off-white solid powder
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| LogP |
4.673
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
31
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| Complexity |
790
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| Defined Atom Stereocenter Count |
9
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| SMILES |
O.[Na+].[Na+].O=C(CC[C@H]([C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](CC[C@]4(C)[C@H]3CC[C@]12C)OS([O-])(=O)=O)C)[O-]
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| InChi Key |
AXDXVEYHEODSPN-HVATVPOCSA-N
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| InChi Code |
InChI=1S/C24H40O6S/c1-15(4-9-22(25)26)19-7-8-20-18-6-5-16-14-17(30-31(27,28)29)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21H,4-14H2,1-3H3,(H,25,26)(H,27,28,29)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
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| Chemical Name |
(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-sulfooxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
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| Synonyms |
64936-81-8; 3ALPHA-HYDROXY-5BETA-CHOLAN-24-OIC ACID 3-SULFATE DISODIUM SALT HYDRATE; Disodium;(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]pentanoate;hydrate; CDTNUTIRRLVRHG-PBICEZGRSA-L; DB-266732; Sodium (3alpha,5beta)-3-(sulfonatooxy)cholan-24-oate hydrate (2:1:1)
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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 Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9976 mL | 9.9880 mL | 19.9760 mL | |
| 5 mM | 0.3995 mL | 1.9976 mL | 3.9952 mL | |
| 10 mM | 0.1998 mL | 0.9988 mL | 1.9976 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.
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