| Size | Price | |
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| 100mg | ||
| Other Sizes |
| Targets |
Sanguinarine chloride targets multiple proteins: it is a potent, noncompetitive inhibitor of Na+/K+ ATPase. It is a specific inhibitor of protein phosphatase 2C (PP2C) with a Ki of 0.68 μM. It also inhibits mitogen-activated protein kinase phosphatase-1 (MKP-1) with an IC50 of 10 μM. Furthermore, it acts as an allosteric activator of AMPK. It exhibits selectivity for PP2C over PP1, PP2A, and PP2B.
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| ln Vitro |
The activation of JNK and NF-κB signaling pathways is linked to apoptosis inducing sanguinarine (SANG). 22B-cFluc cells were stimulated with varying concentrations of sanguinarine for 24 hours in order to ascertain the impact of sanguinarine on cell viability. Following this, the CKK-8 test was carried out. The administration of sanguinarine exhibited a dose-dependent reduction in the proliferation of 22B cells. In parallel, cellular caspase-3 activity was assessed using the validated caspase-3 substrate Ac-DEVD-pNA in the cytoplasmic extracts of 22B-cFluc cells treated with various dosages of sanguinarine. Greater Sanguinarine-stimulated caspase-3 activity is indicated by a dose-dependent rise in absorbance at 450 nm [1].
Sanguinarine chloride demonstrates potent in vitro cytotoxicity against various cancer cell lines. In human promyelocytic leukemia HL60 cells, it exhibited an IC50 of 0.37 μM and induced apoptosis via a caspase-3/7-dependent mechanism. In PANC-1 human pancreatic cancer cells, it increased ERK and JNK/SAPK phosphorylation. In MDA-MB-231 cells, it caused AMPK and ACC phosphorylation. In LNCaP and DU145 cells, it inhibited cell growth and induced G0/G1 phase arrest and apoptosis. It showed potent toxicity to cancer cells (IC50 1.8-2.3 μM). |
| ln Vivo |
In order to assess the in vivo apoptosis caused by sanguinarine (SANG), a xenograft model was created and one side of nude mice received a subcutaneous inoculation of 22B-cFluc cells. Intravenous sanguinarine (10 mg/kg) was administered to mice as a treatment. Mice were given intraperitoneal injections of 150 mg/kg D-luciferin substrate at 24, 48, and 72 hours post-treatment, followed by bioluminescence imaging. An important rise in luminescence signal was caused by sanguinarine administration as early as 48 hours following the start of treatment. Over the course of the experiment, bioluminescence imaging (BLI) intensity was seen to increase continuously. Tumors were collected 72 hours post-treatment, and apoptosis was evaluated using TUNEL labeling. Increased green signal of sporadic apoptotic cells suggested a considerable increase in apoptosis in the sanguinarine-treated group compared to control tumors [1].
Sanguinarine chloride has demonstrated in vivo antitumor activity. In a study using nude mice, it exhibited potent toxicity to cancer cells. However, specific details of the in vivo models and dosing regimens are not provided in the search results. Its antimicrobial, anti-inflammatory, and antioxidant properties suggest potential for in vivo efficacy in other disease models as well. The compound has also shown antiplaque activity in humans. |
| Enzyme Assay |
The in vitro enzyme inhibition assays typically involve measuring the compound's ability to inhibit the activity of purified enzymes. For PP2C inhibition, the assay uses α-casein as a substrate. Sanguinarine competes with α-casein to inhibit PP2C. The IC50 for MKP-1 inhibition is 10 μM. For MKP-L, the IC50 is 12.5 μM. The compound's selectivity is confirmed by testing against related phosphatases like PP1, PP2A, and PP2B.
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| Cell Assay |
Sanguinarine chloride's activity is evaluated in various cancer cell lines. Cells are treated with the compound, and cell viability is measured using standard assays such as MTT. Apoptosis is assessed through caspase-3/7 activity assays and by measuring the phosphorylation of downstream targets like p38, a PP2C substrate. The compound's effects on cell cycle progression are analyzed using flow cytometry. The IC50 values for different cell lines, such as 0.37 μM for HL60 cells, are determined from dose-response curves.
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| Animal Protocol |
In vivo animal models have been used to study the antitumor effects of Sanguinarine chloride, including xenograft models in nude mice. While specific protocols are not detailed in the provided excerpts, these studies typically involve subcutaneous implantation of cancer cells, followed by treatment with the compound. Tumor growth inhibition and toxicity are monitored. The compound's antiplaque activity has also been studied in humans.
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| ADME/Pharmacokinetics |
Sanguinarine chloride has a molecular weight of 367.8 and a molecular formula of C20H14NO4Cl. It is soluble in methanol, water (slightly), DMSO (10 mM), and ethanol (5 mM). Its melting point is 278-279 °C. The compound is typically stored at 4°C. It is available as a solid and its purity is generally ≥98%.
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| Toxicity/Toxicokinetics |
Sanguinarine chloride is a bioactive alkaloid with multiple mechanisms of action. At concentrations up to 5 μM, it showed very low cytotoxicity to normal human liver LO2 cells (cell survival rate >85%), but exhibited potent toxicity to cancer cells. This suggests a degree of selectivity. However, as a potent inhibitor of Na+/K+ ATPase, it has the potential for significant toxicity, and its use is limited to research applications.
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| References | |
| Additional Infomation |
Sanguinarine chloride is a benzophenanthridine alkaloid with potent and diverse biological activities. It is a noncompetitive inhibitor of Na+/K+ ATPase, a specific inhibitor of PP2C, a selective inhibitor of MKP-1, and an allosteric activator of AMPK. It exhibits antimicrobial, anti-inflammatory, antioxidant, and antitumor properties. It induces apoptosis in cancer cells. Sanguinarine chloride is used as a research tool to study these various pathways.
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| Molecular Formula |
C20H14CLNO4
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|---|---|
| Molecular Weight |
367.78
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| Exact Mass |
367.061
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| CAS # |
5578-73-4
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| Related CAS # |
Sanguinarine;2447-54-3
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| PubChem CID |
68635
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| Appearance |
Orange to red solid powder
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| Melting Point |
287-289 ºC
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| LogP |
0.432
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
26
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| Complexity |
530
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
GIZKAXHWLRYMLE-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C20H14NO4.ClH/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21;/h2-8H,9-10H2,1H3;1H/q+1;/p-1
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| Chemical Name |
24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene;chloride
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| Synonyms |
Sanguinarin chloride Sanguinarium chloride Pseudochelerythrine chloride
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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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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 : ~3.33 mg/mL (~9.05 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.33 mg/mL (0.90 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 3.3 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: ≥ 0.33 mg/mL (0.90 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 3.3 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7190 mL | 13.5951 mL | 27.1902 mL | |
| 5 mM | 0.5438 mL | 2.7190 mL | 5.4380 mL | |
| 10 mM | 0.2719 mL | 1.3595 mL | 2.7190 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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