| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
As a stable isotope-labeled internal standard, Taurolithocholic Acid-d5 does not have a primary pharmacological target in bioanalytical contexts. However, the unlabeled TLCA is a taurine-conjugated secondary bile acid and a major human metabolite that inhibits radioligand binding to muscarinic M1 receptors (but not M2 or M3), and activates TGR5-PI3K/AKT-SREBP2 signaling.
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|---|---|
| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
The unlabeled taurolithocholic acid (TLCA) upregulates FADS2 by activating the TGR5-PI3K/AKT-SREBP2 signaling axis, inhibits SFTSV-induced ferroptosis, viral replication, and viral entry of HBV/HDV, while reducing the release of IL-1beta, lipid ROS, and LDH. The deuterated form is not used for measuring intrinsic biological activity. |
| ln Vivo |
In vivo, unlabeled taurolithocholic acid (TLCA) has been used to induce cholestasis in ex vivo and in vivo animal models of hepatocellular cholestasis. Serum levels of TLCA increase approximately 5-fold within two hours during an oral lipid tolerance test in humans. The deuterated form is used as an internal standard for quantifying these changes.
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| Enzyme Assay |
The unlabeled TLCA is used in ligand binding assays. Membranes from cells expressing human muscarinic receptors (M1, M2, M3) are incubated with a radioligand such as [3H]pirenzepine (M1) or [3H]AF-DX 384 (M2/M3) and varying concentrations of TLCA. After incubation, bound and free ligand are separated by filtration, and radioactivity is counted to determine inhibition constants (Ki).
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| Cell Assay |
No direct cellular activity is reported for the deuterated standard. The unlabeled TLCA is used in cell-based assays, such as treating Hep3B cells transfected with sodium taurocholate cotransporting peptide (NTCP). TLCA (75 uM) increases caspase-3 and -7 activity in these cells, but not in non-transfected controls, demonstrating bile acid-induced apoptosis in hepatocytes.
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| Animal Protocol |
In vivo studies typically use the unlabeled TLCA to induce cholestasis. Rats are administered TLCA at specific doses (e.g., intravenous or intraportal infusion) to model hepatocellular cholestasis. For quantification, deuterated TLCA-d5 is spiked into plasma samples as an internal standard before LC-MS/MS analysis to accurately measure endogenous and induced TLCA levels.
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| ADME/Pharmacokinetics |
Taurolithocholic Acid-d5 is chemically identical to the analyte (TLCA) except for a +5 Da mass shift due to deuterium substitution. It exhibits virtually identical chromatographic retention time, ionization efficiency, and extraction recovery, which are the critical properties for an internal standard. It is stable under standard LC-MS conditions.
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| Toxicity/Toxicokinetics |
No direct toxicity data is reported for the deuterated standard, as it is used at trace levels. The unlabeled TLCA is a well-known cholestatic agent that induces hepatocellular damage and apoptosis at high concentrations. It is toxic to hepatocytes and is used specifically to model cholestatic liver injury in research settings.
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| References |
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| Additional Infomation |
Taurolithocholic Acid-d5 sodium is an essential quality control tool for FDA/EMA bioanalytical method validation. Its stable isotope labeling allows for isotope dilution mass spectrometry (IDMS), which is the gold standard for accurate quantification of endogenous metabolites like TLCA, eliminating the variability that plagues traditional external calibration methods.
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| Molecular Formula |
C26H40D5NNAO5S
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|---|---|
| Molecular Weight |
510.72
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| Exact Mass |
510.315
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| CAS # |
1265476-97-8
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| Related CAS # |
Taurolithocholic acid sodium salt;6042-32-6
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| PubChem CID |
46782976
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
6.22
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
34
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| Complexity |
832
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| Defined Atom Stereocenter Count |
7
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| SMILES |
[Na+].O=S(CCNC(CC[C@H](C1CC[C@H]2[C@@H]3CC[C@@H]4C([C@](C(C[C@]4(C)C3CC[C@]12C)([2H])[2H])([2H])O)([2H])[2H])C)=O)(=O)[O-]
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| InChi Key |
YAERYJYXPRIDTO-SDXLJUFPSA-M
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| InChi Code |
InChI=1S/C26H45NO5S.Na/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3;/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32);/q;+1/p-1/t17-,18-,19-,20+,21?,22+,23?,25+,26-;/m1./s1/i10D2,16D2,19D;
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| Chemical Name |
sodium;2-[[(4R)-4-[(3R,5R,8R,10S,13R,14S)-2,2,3,4,4-pentadeuterio-3-hydroxy-10,13-dimethyl-1,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[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 |
| 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 | 1.9580 mL | 9.7901 mL | 19.5802 mL | |
| 5 mM | 0.3916 mL | 1.9580 mL | 3.9160 mL | |
| 10 mM | 0.1958 mL | 0.9790 mL | 1.9580 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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