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| Targets |
The primary target of desacetylcinobufagin is Na⁺/K⁺-ATPase, a membrane-bound enzyme that maintains the electrochemical gradient of sodium and potassium ions across the cell membrane. Na⁺/K⁺-ATPase is a critical enzyme for cellular homeostasis, and its inhibition leads to increased intracellular sodium and calcium concentrations. This disruption of ion homeostasis triggers downstream signaling pathways that lead to apoptosis in cancer cells. Desacetylcinobufagin's inhibition of Na⁺/K⁺-ATPase is similar to that of other cardiotonic steroids such as ouabain and digoxin. The compound also serves as an isoform-specific probe for UGT1A4 and UGT1A3, enzymes involved in glucuronidation and drug metabolism. Its ability to inhibit prostaglandin synthesis suggests additional anti-inflammatory targets.
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| ln Vitro |
In vitro, desacetylcinobufagin demonstrates cytotoxicity against various human cancer cell lines. It is cytotoxic to HepG2 (human hepatoma) with an IC₅₀ of 51.2 µM, K562 (human leukemia) with an IC₅₀ of 50.1 µM, and HL-60 (human leukemia) with an IC₅₀ of 7.5 µM. The compound also shows activity against human cervical carcinoma cells (HeLa) and malignant melanoma cells (A375). Its antitumor effects are primarily mediated through inhibition of Na⁺/K⁺-ATPase activity and modulation of downstream signaling pathways, leading to apoptosis. The compound also has anti-inflammatory properties, which may be due to its ability to inhibit prostaglandin synthesis. Its activity as an isoform-specific probe for UGT1A4 and UGT1A3 makes it valuable for studying glucuronidation pathways.
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| ln Vivo |
In vivo, desacetylcinobufagin is the main urinary metabolite of cinobufagin, a cardiotonic steroid derived from toad venom. As a metabolite, it contributes to the overall pharmacological effects of cinobufagin. The compound's antitumor effects, mediated through Na⁺/K⁺-ATPase inhibition and downstream signaling modulation, would be expected to translate to in vivo antitumor activity. Its anti-inflammatory properties may also contribute to its in vivo effects. However, comprehensive in vivo efficacy studies specifically for desacetylcinobufagin are not extensively reported in the publicly available literature. The compound's role as a UGT1A4 and UGT1A3 probe suggests it may be useful for studying drug metabolism and interactions in vivo.
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| Enzyme Assay |
In vitro enzyme assays for desacetylcinobufagin measure its ability to inhibit Na⁺/K⁺-ATPase activity. In these assays, purified Na⁺/K⁺-ATPase enzyme is incubated with ATP and the compound, and the release of inorganic phosphate is measured using a colorimetric method. The compound's inhibition of Na⁺/K⁺-ATPase activity is quantified and compared to that of known inhibitors. Additionally, desacetylcinobufagin can be used as an isoform-specific probe for UGT1A4 and UGT1A3 in glucuronidation assays, where the compound's glucuronidation by these enzymes is measured using LC-MS/MS. These assays are essential for characterizing the compound's mechanism of action and its role in drug metabolism.
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| Cell Assay |
In vitro cell-based assays for desacetylcinobufagin evaluate its cytotoxic activity and mechanism of action in cancer cells. Cancer cell lines including HepG2, K562, HL-60, HeLa, and A375 are treated with varying concentrations of the compound, and cell viability is assessed using standard assays such as MTT, CellTiter-Glo, or sulforhodamine B. IC₅₀ values are determined from dose-response curves. Apoptosis is quantified using Annexin V/PI staining or caspase activity assays. The compound's effects on Na⁺/K⁺-ATPase activity can be assessed by measuring intracellular sodium and calcium concentrations using fluorescent indicators. These assays confirm the compound's mechanism of action and provide functional data on its cellular activity.
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| Animal Protocol |
In vivo animal studies for desacetylcinobufagin are typically conducted in the context of cinobufagin pharmacology, as desacetylcinobufagin is a metabolite of the parent compound. Studies would involve administering cinobufagin to animals and measuring desacetylcinobufagin levels in urine and other tissues. Antitumor efficacy studies could be conducted using xenograft models with cancer cell lines sensitive to desacetylcinobufagin, such as HepG2 or HL-60. However, comprehensive in vivo studies specifically for desacetylcinobufagin are not extensively reported. The compound's role as a UGT1A4 and UGT1A3 probe suggests it may be used in studies of drug metabolism and interactions.
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| ADME/Pharmacokinetics |
Desacetylcinobufagin has a molecular weight of approximately 400.51 g/mol and a chemical formula of C₂₄H₃₂O₅. As a cardiotonic steroid metabolite, it is a lipophilic compound that is primarily excreted in urine following glucuronidation. The compound's metabolism involves glucuronidation by UGT1A4 and UGT1A3, making it a useful probe for studying these enzymes. Detailed pharmacokinetic parameters such as half-life, volume of distribution, and bioavailability are not extensively reported in the publicly available literature for desacetylcinobufagin specifically, but would be similar to those of other cardiotonic steroids.
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| Toxicity/Toxicokinetics |
Desacetylcinobufagin is cytotoxic to cancer cells and inhibits Na⁺/K⁺-ATPase activity. As a cardiotonic steroid, it may have cardiovascular effects similar to other compounds in this class, including effects on cardiac contractility and rhythm. The compound's anti-inflammatory properties may also contribute to its overall safety profile. Comprehensive toxicology data for desacetylcinobufagin specifically is not extensively reported, but related cardiotonic steroids are known to have narrow therapeutic windows. The compound is classified as a research-grade chemical and is not intended for human use. Standard laboratory safety precautions should be followed when handling desacetylcinobufagin.
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| References | |
| Additional Infomation |
Reports indicate that deacetylbufotalin has been found in Bufo gargarizans and Bufo bufo, and relevant data is available for reference.
Desacetylcinobufagin (CAS# 4026-95-3) is an active metabolite of the cardiotonic steroid cinobufagin. It inhibits Na⁺/K⁺-ATPase activity and induces apoptosis in cancer cells. The compound is cytotoxic to HepG2, K562, HL-60, HeLa, and A375 cancer cell lines. It serves as an isoform-specific probe for UGT1A4 and UGT1A3. It is the main urinary metabolite of cinobufagin and has anti-inflammatory properties. The compound has not received FDA approval for any indication. |
| Molecular Formula |
C24H32O5
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|---|---|
| Molecular Weight |
400.515
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| Exact Mass |
400.224
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| CAS # |
4026-95-3
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| PubChem CID |
11877495
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| Appearance |
White to light yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
601.9±55.0 °C at 760 mmHg
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| Melting Point |
278-280ºC
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| Flash Point |
208.1±25.0 °C
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| Vapour Pressure |
0.0±3.9 mmHg at 25°C
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| Index of Refraction |
1.619
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| LogP |
2
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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 |
1
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| Heavy Atom Count |
29
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| Complexity |
818
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| Defined Atom Stereocenter Count |
10
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| SMILES |
C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@]35[C@H](O5)[C@@H]([C@@H]4C6=COC(=O)C=C6)O)C)O
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| InChi Key |
IXZHDDUFQVXHIL-UOAIQHMYSA-N
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| InChi Code |
InChI=1S/C24H32O5/c1-22-9-7-15(25)11-14(22)4-5-17-16(22)8-10-23(2)19(13-3-6-18(26)28-12-13)20(27)21-24(17,23)29-21/h3,6,12,14-17,19-21,25,27H,4-5,7-11H2,1-2H3/t14-,15+,16+,17-,19+,20-,21-,22+,23-,24-/m1/s1
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| Chemical Name |
5-[(1R,2S,4R,5R,6R,7R,10S,11S,14S,16R)-5,14-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-one
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| Synonyms |
Cinobufagin, deacetyl- (6CI); Desacetylcinobufagin; Desacetylcinobufagin
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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 : ≥ 26 mg/mL (~64.92 mM)
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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 | 2.4968 mL | 12.4838 mL | 24.9675 mL | |
| 5 mM | 0.4994 mL | 2.4968 mL | 4.9935 mL | |
| 10 mM | 0.2497 mL | 1.2484 mL | 2.4968 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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