| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
Na+/K+-ATPase (sodium-potassium adenosine triphosphatase). Digoxigenin monodigitoxoside is a cardiac glycoside that binds to and inhibits the Na+/K+-ATPase, a transmembrane enzyme that pumps sodium out of and potassium into cells. The compound's aglycone (digoxigenin) and monosaccharide structure is sufficient for high-affinity binding. By inhibiting this pump, it causes an increase in intracellular sodium, which secondarily reduces the activity of the sodium-calcium exchanger, leading to an accumulation of intracellular calcium. This increase in calcium enhances cardiac muscle contraction (positive inotropy).
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| ln Vitro |
In cell-free biochemical assays, digoxigenin monodigitoxoside directly inhibits the Na+/K+-ATPase enzyme. Its binding affinity is often studied using a competition binding assay with [3H]-ouabain, a well-known cardiac glycoside. Purified lamb kidney or pig brain Na+/K+-ATPase is incubated with a fixed concentration of [3H]-ouabain and varying concentrations of the unlabeled test compound (0.1 nM-100 uM). After incubation, bound and free radioligand are separated by filtration, and radioactivity is counted. The relative binding affinity is often reported; for this compound, it has a binding affinity of 0.829 relative to [3H]-ouabain. The inhibitory potency for ATPase activity is 1.07 relative to ouabain.
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| ln Vivo |
In cell-based assays, the inhibition of the Na+/K+-ATPase pump by digoxigenin monodigitoxoside leads to an increase in intracellular calcium, activation of signaling pathways, and potentially, the induction of cell death in certain cancer cell lines. In cardiomyocytes, this results in increased contractility. In cancer research, it is studied for its ability to induce apoptosis and inhibit cell proliferation. It is also used as a tool to study the structure-activity relationship of cardiac glycosides, as the presence of one sugar molecule is sufficient for potent activity, unlike digoxin which has three digitoxose sugars.
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| Enzyme Assay |
To measure inhibition of Na+/K+-ATPase activity, an ATPase assay is performed. Purified Na+/K+-ATPase is incubated in a buffer containing 100 mM NaCl, 20 mM KCl, 3 mM MgCl2, 3 mM ATP, and varying concentrations of digoxigenin monodigitoxoside (0.001-100 uM). The reaction is initiated by adding ATP and incubated at 37degC for 30 minutes. The amount of inorganic phosphate (Pi) released is measured using a colorimetric (malachite green) or luminescent (e.g., PiPer Phosphate Assay) detection system. The IC50 is the concentration that inhibits 50% of the specific ATPase activity. Ouabain is used as a positive control. For binding affinity, a [3H]-ouabain competition assay is performed as described above.
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| Cell Assay |
Cellular assays involve measuring the effect of the compound on intracellular calcium levels using fluorescent dyes such as Fura-2 AM or Fluo-4 AM. Cells (e.g., cardiomyocytes, HeLa, or HEK293) are seeded in 96-well plates and loaded with the calcium dye. They are then treated with digoxigenin monodigitoxoside (0.1-100 uM), and the fluorescence signal (excitation/emission) is monitored in real-time on a fluorescence plate reader. The increase in intracellular calcium is measured as the fold-change over baseline. For cell viability, MTT or CellTiter-Glo assays are performed after 48-72 hours of treatment. Apoptosis is assessed by measuring caspase-3/7 activity.
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| Animal Protocol |
In vivo animal studies for digoxigenin monodigitoxoside are not commonly reported, as it is primarily a research tool for studying Na+/K+-ATPase inhibition. However, as a metabolite of digoxin, its pharmacokinetic and pharmacodynamic properties can be extrapolated. In animal models, intravenous administration of the compound would produce positive inotropic effects (increased cardiac contractility) measured by echocardiography. In rodent studies, it could be administered at doses typically ranging from 0.1-1 mg/kg IV, and blood pressure, heart rate, and ECG parameters (e.g., QT interval) would be monitored. For cardiotoxicity, a therapeutic window would be established based on lethal doses.
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| ADME/Pharmacokinetics |
Digoxigenin monodigitoxoside is a metabolite of digoxin, and its pharmacokinetics are informed by the parent drug's profile. Following oral administration of digoxin, this metabolite is formed by the sequential cleavage of sugar residues by gut bacteria and possibly by hepatic metabolism. It has a much shorter half-life than digoxin (approximately 1-2 days vs. 36-48 hours) and is less polar, leading to potentially better tissue penetration. It is eliminated primarily by the kidneys as unchanged drug or conjugated metabolites. For research use, the compound is typically dissolved in DMSO or ethanol for in vitro studies. For in vivo administration, a formulation of DMSO:PEG300:Tween80:saline is used.
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| Toxicity/Toxicokinetics |
The toxicity of digoxigenin monodigitoxoside is typical of cardiac glycosides. Acute toxicity manifests as nausea, vomiting, arrhythmias, and visual disturbances. The compound has a narrow therapeutic index; overdose leads to severe cardiac toxicity, including ventricular tachycardia, bradycardia, and cardiac arrest. Chronic toxicity can cause gynecomastia and neurological effects. In cell-based assays, it is cytotoxic at higher concentrations. For research purposes, the compound should be handled with caution as a potent cardiotoxin. It is not approved for human use as a separate compound, although it is a metabolite of the FDA-approved drug digoxin.
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| References | |
| Additional Infomation |
Digoxigenin monoDigoxigenin is a steroidal saponin composed of a Digoxigeninyl group with a Digoxigeninyl residue linked at the 3-position. It is a metabolite. It is a cardiac glycoside, Digoxigenin glycoside, monosaccharide derivative, and steroidal saponin. Functionally, it is related to Digoxigenin.
Digoxigenin monodigitoxoside (CAS 5352-63-6) is a valuable research tool for studying the structure-activity relationships of cardiac glycosides, particularly the role of the sugar moiety. It is a metabolite of digoxin and digitoxin, and it can be used as an internal standard for LC-MS/MS bioanalysis of digoxin and its metabolites. This compound is also used to study the role of Na+/K+-ATPase inhibition in heart failure and cancer biology. It is typically provided as a solid powder with a purity of ≥98% and should be stored at -20degC. It is not approved for therapeutic use. |
| Molecular Formula |
C29H44O8
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|---|---|
| Molecular Weight |
520.65486
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| Exact Mass |
520.304
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| CAS # |
5352-63-6
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| PubChem CID |
93001
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| Appearance |
White to off-white solid powder
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| Density |
1.31g/cm3
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| Boiling Point |
708.3ºC at 760mmHg
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| Melting Point |
228-230ºC
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| Flash Point |
230.5ºC
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| LogP |
2.456
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
37
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| Complexity |
952
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| Defined Atom Stereocenter Count |
13
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| SMILES |
C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3C[C@H]([C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)O
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| InChi Key |
JFSXBMIFXZFKHD-ZDDLGXCGSA-N
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| InChi Code |
InChI=1S/C29H44O8/c1-15-26(33)22(30)13-25(36-15)37-18-6-8-27(2)17(11-18)4-5-20-21(27)12-23(31)28(3)19(7-9-29(20,28)34)16-10-24(32)35-14-16/h10,15,17-23,25-26,30-31,33-34H,4-9,11-14H2,1-3H3/t15-,17-,18+,19-,20-,21+,22+,23-,25+,26-,27+,28+,29+/m1/s1
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| Chemical Name |
3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
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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) |
DMSO : ~100 mg/mL (~192.07 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 50.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9207 mL | 9.6034 mL | 19.2068 mL | |
| 5 mM | 0.3841 mL | 1.9207 mL | 3.8414 mL | |
| 10 mM | 0.1921 mL | 0.9603 mL | 1.9207 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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