| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Tetroquinone is a redox-active molecule that generates reactive oxygen species (ROS) through redox cycling with semiquinone radicals. By generating ROS, the compound may exert oxidative stress on cells and tissues. This mechanism was exploited for its anticataract activity, although the compound is no longer widely used for this indication. Its redox properties make it a tool for studying oxidative stress and ROS biology.
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| ln Vitro |
The cytotoxic cells exhibited action against HL60 leukemia when treated with tetrahydroxyquinone (100-500 μM) for 24 hours. The activity was assessed by total protein content (IC50 of 20 µM), phosphatase activity (IC50 of 40 µM), or MTT assay (IC50 of 45 µM). In HL60 leukemia cells, tetrahydroxyquinone is a strong inducer of ROS generation [1]. At concentrations higher than 25 µM, tetrahydroxyquinone efficiently activates caspase 3, which in turn promotes DNA fragmentation and phosphatidylserine exposure at the same concentration [1]. At as low as 25 µM, tetrahydroxyquinone causes the release of cytochrome c from mitochondria. Increased phosphorylation of Ser473 in protein kinase B (the Bad kinase of Ser112) is another effect of tetrahydroxyquinone therapy [1].
In vitro, tetroquinone is a redox-active molecule that can participate in redox cycles with semiquinone radicals, leading to the formation of reactive oxygen species (ROS). Its ability to generate ROS has been studied in cell-free and cell-based systems. The compound's redox properties are assessed by electron paramagnetic resonance (EPR) or by measuring ROS production using fluorescent probes. |
| ln Vivo |
In vivo, tetroquinone was used as an anticataract drug. Its mechanism involved the generation of ROS, which may have been intended to modify lens proteins or to exert other effects on the lens. The compound is no longer widely used for this indication. It has also been studied for its potential effects on other conditions involving oxidative stress.
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| Enzyme Assay |
In vitro enzyme assays for tetroquinone measure its redox activity and ability to generate reactive oxygen species. The compound is incubated with reducing agents or in the presence of oxygen, and ROS production is measured using probes such as DCFH-DA or by electron paramagnetic resonance (EPR) spectroscopy. The redox cycling between tetroquinone and semiquinone radicals is characterized by electrochemical methods.
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| Cell Assay |
Cell viability assay [1]
Cell Types: HL60 leukemia cells Tested Concentrations: 100 μM, 200 μM, 300 μM, 400 μM, 500 μM Incubation Duration: 24 hrs (hours) Experimental Results: Cytotoxic to HL60 leukemia cells. In vitro cell-based assays for tetroquinone assess its effects on cellular oxidative stress. Cells are treated with serial dilutions of the compound, and ROS production is measured using fluorescent probes such as DCFH-DA. Cellular viability is assessed using MTT or other assays. The compound's effects on antioxidant defense systems, including glutathione levels and enzyme activities, are also evaluated. |
| Animal Protocol |
In vivo animal models for tetroquinone include models of cataract formation. The compound was evaluated for its ability to prevent or reverse cataract formation in animal models. Other models of oxidative stress-related diseases may be used to study the compound's effects. However, tetroquinone is no longer widely used as a therapeutic agent.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of tetroquinone are not well characterized. As a small redox-active molecule, it is expected to be absorbed and distributed to tissues. The compound's redox activity may contribute to its metabolism and elimination. Its use as an anticataract drug was primarily topical, with limited systemic exposure.
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| Toxicity/Toxicokinetics |
Toxicity data for tetroquinone are available from its use as a drug. As a redox-active compound that generates ROS, it may cause oxidative stress and cellular damage. High concentrations may be cytotoxic. The compound should be handled with appropriate safety precautions. Its use as a drug has been largely discontinued due to limited efficacy and potential toxicity.
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| References | |
| Additional Infomation |
Tetrahydroxy-1,4-benzoquinone is a hydroxybenzoquinone in which all four protons in its benzoquinone structure are replaced by hydroxyl groups. It is a systemic keratolytic agent, usually supplied in hydrated form (CHEBI:137471). It is a keratolytic drug.
Tetroquinone is a redox-active benzoquinone compound best known as a primitive anticataract drug. It is also known as tetrahydroxyquinone or tetrahydroxy-1,4-benzoquinone. The compound can participate in redox cycles with semiquinone radicals, leading to the formation of reactive oxygen species (ROS). It is used as a research tool for studying oxidative stress and redox biology. |
| Molecular Formula |
C6H4O6
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|---|---|
| Molecular Weight |
172.09
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| Exact Mass |
172.001
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| CAS # |
319-89-1
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| Related CAS # |
Tetrahydroxyquinone monohydrate;1215458-51-7
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| PubChem CID |
5424
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| Appearance |
Light brown to black solid powder
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| Density |
0.79
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| Boiling Point |
148 °C / 15mmHg
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| Melting Point |
300ºC
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| Index of Refraction |
2.023
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| LogP |
-0.6
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
12
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| Complexity |
272
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C(O)=C(O)C(C(O)=C1O)=O
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| InChi Key |
DGQOCLATAPFASR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H4O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h7-8,11-12H
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| Chemical Name |
2,3,5,6-tetrahydroxycyclohexa-2,5-diene-1,4-dione
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| Synonyms |
Tetroquinonum; Tetroquinona; Tetroquinone
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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 (~581.09 mM)
H2O : ~1 mg/mL (~5.81 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.53 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 25.0 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: ≥ 2.5 mg/mL (14.53 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 25.0 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.8109 mL | 29.0546 mL | 58.1091 mL | |
| 5 mM | 1.1622 mL | 5.8109 mL | 11.6218 mL | |
| 10 mM | 0.5811 mL | 2.9055 mL | 5.8109 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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