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Tetrahydroxyquinone monohydrate exerts its biological effects primarily through redox cycling. The compound participates in redox cycles with semiquinone radicals, leading to the formation of reactive oxygen species (ROS). This ROS generation triggers oxidative stress and activates downstream signaling pathways. The compound induces apoptosis in cancer cells through a mechanism involving caspase 3 activation, DNA fragmentation, and phosphatidylserine exposure. As a redox-active benzoquinone, it can also cause oxidative damage to cellular components including lipids, proteins, and DNA. Its activity as an anticataract agent is attributed to its redox properties and ability to modulate oxidative stress in the lens.
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| ln Vitro |
Tetrahydroxyquinone (100-500 μM; 24 hours; HL60 cells) treatment exhibits cytotoxicity for HL60 leukemia cells as measured by MTT assay (IC50 of 45 µM), total protein content (IC50 of 20 µM), or phosphatase activity (IC50 of 40 µM). In HL60 leukaemia cells, tetrahydroxyquinone effectively induces the generation of ROS[1]. At concentrations greater than 25 µM, tetrahydroxyquinone effectively activates caspase 3, induces DNA fragmentation at the same concentration, and causes exposure to phosphatidylserine[1]. Even at 25 µM concentration, tetrahydroxyquinone causes the mitochondria to release cytochrome c. Moreover, treatment with tetrahydroxyquinone increases protein kinase B's phosphorylation of Ser473 (the Bad kinase for Ser112)[1].
In vitro, tetrahydroxyquinone monohydrate has been shown to efficiently induce ROS production in HL60 leukemia cells. The compound activates caspase 3 at concentrations exceeding 25 µM, stimulates DNA fragmentation at the same concentration, and provokes phosphatidylserine exposure, indicating induction of apoptosis. Its redox-active properties allow it to participate in redox cycles with semiquinone radicals, generating ROS that can cause oxidative damage to cellular components. The compound's ability to induce apoptosis in cancer cells makes it relevant for anticancer research. Its activity as an anticataract agent has also been studied in vitro using lens epithelial cell models. |
| ln Vivo |
In vivo, tetrahydroxyquinone monohydrate has been studied primarily for its anticataract activity. The compound's redox-active properties and ability to generate ROS are relevant for understanding its effects in animal models of cataract formation. However, detailed in vivo efficacy and safety data are limited. The compound's ability to induce apoptosis suggests potential anticancer activity that could be explored in tumor models. Its use as an anticataract agent indicates that it has been evaluated in ocular disease models. Further research is needed to fully characterize its in vivo biological activity, therapeutic potential, and safety profile. Researchers should consult the primary literature for available in vivo data.
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| Enzyme Assay |
For in vitro biochemical assays, tetrahydroxyquinone monohydrate is evaluated for its redox activity and ROS-generating capacity. ROS production is measured using fluorescent probes such as DCFH-DA or chemiluminescence-based assays. Redox cycling activity is assessed by measuring the compound's ability to reduce electron acceptors or generate superoxide. Antioxidant activity can be evaluated using DPPH, ABTS, or FRAP assays. Caspase activity is measured using fluorogenic substrates. DNA fragmentation is assessed using gel electrophoresis or TUNEL assays. Phosphatidylserine exposure is detected using Annexin V binding. These cell-free and cell-based assays help characterize the compound's redox properties and pro-apoptotic activity.
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| Cell Assay |
In vitro cellular assays for tetrahydroxyquinone monohydrate are performed using various cell lines including HL60 leukemia cells. Cells are cultured in standard media and treated with the compound at concentrations ranging from 0.1 to 100 µM for 24-72 hours. ROS production is measured using DCFH-DA fluorescent probes. Apoptosis is assessed by measuring caspase 3/7 activity using fluorogenic substrates, DNA fragmentation using gel electrophoresis or TUNEL assays, and phosphatidylserine exposure using Annexin V/PI staining and flow cytometry. Cell viability is measured using MTT or trypan blue exclusion assays. Oxidative stress markers such as lipid peroxidation and protein carbonylation are also measured. These cellular assays help validate the compound's pro-apoptotic and redox-active properties.
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| Animal Protocol |
In vivo animal experiments with tetrahydroxyquinone monohydrate are primarily conducted in models of cataract formation. Animal models of cataract include those induced by oxidative stress, diabetes, or genetic mutations. The compound is administered via topical ocular application, intraperitoneal injection, or oral gavage. Efficacy is assessed by monitoring cataract progression using slit-lamp microscopy or by measuring lens opacity. Biochemical analyses of lens tissues include measurement of ROS levels, antioxidant enzyme activities, and markers of oxidative damage. For potential anticancer studies, tumor xenograft models could be used, with efficacy assessed by tumor growth inhibition. Detailed protocols for in vivo studies are described in the primary literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of tetrahydroxyquinone monohydrate are not extensively documented. As a small redox-active benzoquinone, it is expected to have moderate oral bioavailability and good tissue distribution. The compound's ability to participate in redox cycling may affect its stability and metabolism. Its use as an anticataract agent suggests that it can reach the lens following systemic or topical administration. Detailed PK parameters such as half-life, Cmax, Tmax, AUC, volume of distribution, and clearance are not available in the literature. Researchers should consult the primary literature for any available pharmacokinetic data. The compound's redox activity may complicate its pharmacokinetic characterization due to rapid metabolism and interactions with cellular antioxidants.
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| Toxicity/Toxicokinetics |
The toxicological profile of tetrahydroxyquinone monohydrate is related to its redox-active properties and ability to generate ROS. Excessive ROS production can lead to oxidative damage to cellular components, potentially causing cytotoxicity and tissue injury. The compound's pro-apoptotic activity may contribute to its toxicity at high concentrations. Its use as an anticataract agent suggests that it has been evaluated for safety in ocular applications. However, comprehensive toxicity studies including acute, subchronic, and chronic toxicity assessments are limited. The compound is intended for research use only and not for human therapeutic applications without appropriate safety evaluation. Researchers should follow standard laboratory safety practices when handling tetrahydroxyquinone monohydrate.
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| References |
[1]. Alexandre D Martins Cavagis, et al. Tetrahydroxyquinone induces apoptosis of leukemia cells through diminished survival signaling. Exp Hematol. 2006 Feb;34(2):188-96.
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| Additional Infomation |
Tetrahydroxyquinone monohydrate is a valuable research tool for studying oxidative stress, redox biology, and apoptosis. Its ability to generate ROS through redox cycling makes it useful for investigating the mechanisms of oxidative damage and the cellular responses to oxidative stress. The compound's pro-apoptotic activity provides opportunities for studying apoptosis signaling pathways and evaluating potential anticancer strategies. Its use as an anticataract agent makes it relevant for research on age-related and oxidative stress-induced cataract formation. Tetrahydroxyquinone monohydrate can also be employed to study the role of redox cycling in drug toxicity and to develop antioxidants for protecting against oxidative damage. The compound serves as a model for understanding the biological effects of quinone-based redox-active compounds.
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| Molecular Formula |
C6H6O7
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| Molecular Weight |
190.107642650604
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| Exact Mass |
190.011
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| CAS # |
1215458-51-7
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| Related CAS # |
Tetrahydroxyquinone;319-89-1
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| PubChem CID |
6420048
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| Appearance |
Brown to black solid powder
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
13
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| Complexity |
272
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1(=C(C(=O)C(=C(C1=O)O)O)O)O.O
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| InChi Key |
CJFTUKFVMMYYHH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H4O6.H2O/c7-1-2(8)4(10)6(12)5(11)3(1)9;/h7-8,11-12H;1H2
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| Chemical Name |
2,3,5,6-tetrahydroxycyclohexa-2,5-diene-1,4-dione;hydrate
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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 (526.01 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.15 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 (13.15 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 | 5.2601 mL | 26.3006 mL | 52.6011 mL | |
| 5 mM | 1.0520 mL | 5.2601 mL | 10.5202 mL | |
| 10 mM | 0.5260 mL | 2.6301 mL | 5.2601 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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