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| Targets |
The primary target of toringin is the expanded CTG repeat sequence and its associated cytotoxicity. Toringin prevents the cis-effect of expanded CTG repeats in a stable PC12 cell transformant (CTG-250). CTG repeat expansions are associated with a number of neurodegenerative diseases, including myotonic dystrophy type 1 (DM1), where expanded CTG repeats in the DMPK gene cause RNA toxicity and downstream cellular dysfunction. Toringin is able to prevent cytotoxicity and the cis-action of the PC12 converter (CTG-250). The compound's mechanism of action may involve interactions with the expanded repeat RNA or modulation of cellular pathways that mediate repeat-associated toxicity. Toringin also targets caspase pathways, as suggested by its effects on cytotoxicity. Its bioflavonoid structure is characteristic of compounds with antioxidant and neuroprotective properties.
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| ln Vitro |
Toringin demonstrates in vitro activity in preventing CTG repeat-associated cytotoxicity. In studies using a stable PC12 cell transformant (CTG-250), toringin prevents cytotoxicity and the cis-effect of expanded CTG repeats. The compound progressively reduces the cis-effect of expanded CTG repeats. It also reduces cytotoxicity/cell toxicity in these cells. Toringin's effects are observed at concentrations that are not cytotoxic to the cells, indicating a specific mechanism of action. The compound's ability to prevent CTG repeat-associated toxicity makes it a valuable tool for studying the molecular mechanisms of repeat expansion diseases. Its bioflavonoid structure suggests potential antioxidant activity that may contribute to its protective effects. Detailed concentration-response relationships and mechanistic studies have been reported in the literature.
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| ln Vivo |
In vivo activity of toringin has been less extensively characterized compared to its in vitro activity. As a bioflavonoid, toringin would be expected to have oral bioavailability, but comprehensive in vivo studies have not been widely reported. The compound's ability to prevent CTG repeat-associated cytotoxicity in vitro suggests potential for the treatment of repeat expansion diseases such as myotonic dystrophy type 1 (DM1). However, in vivo efficacy studies in animal models of repeat expansion diseases have not been extensively published. The compound is primarily used as a research tool for studying the mechanisms of CTG repeat toxicity and evaluating potential therapeutic strategies. Its bioflavonoid properties suggest that it may have additional activities including antioxidant and anti-inflammatory effects. Further in vivo studies are needed to fully characterize the compound's therapeutic potential.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for toringin are not standard, as the compound is a bioflavonoid with complex biological activities rather than a traditional enzyme inhibitor or receptor ligand. However, the compound's structure and properties can be characterized using analytical chemistry methods. High-performance liquid chromatography (HPLC) and mass spectrometry are used to verify the molecular weight (416.38 g/mol) and chemical composition (C21H20O9). The compound's purity (typically ≥98%) is confirmed by HPLC and NMR analysis. Stability studies may be performed by incubating toringin in various buffer systems and analyzing degradation products over time. The compound's flavonoid structure suggests potential interactions with various cellular targets, but specific receptor binding studies have not been extensively reported. Studies on caspase inhibition have been mentioned in the literature.
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| Cell Assay |
In vitro cellular assays for toringin are performed using PC12 cells or other cell lines expressing expanded CTG repeats. The stable PC12 cell transformant (CTG-250) is cultured in appropriate medium and treated with varying concentrations of toringin for defined time periods. Cytotoxicity is assessed using standard viability assays such as MTT, LDH release, or trypan blue exclusion. The cis-effect of expanded CTG repeats is assessed by measuring reporter gene expression or other readouts of repeat-mediated toxicity. Toringin's ability to prevent CTG repeat-associated cytotoxicity is quantified by comparing cell viability and toxicity markers in treated versus untreated cells. The compound's effects on caspase activity may be measured using fluorogenic caspase substrates. Gene expression changes are analyzed by qRT-PCR or microarray to identify pathways affected by toringin treatment.
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| Animal Protocol |
In vivo animal studies for toringin have not been extensively reported in the public domain. As a bioflavonoid, toringin would be expected to have oral bioavailability, but comprehensive in vivo pharmacokinetic and efficacy studies have not been widely published. The compound is primarily used as a research tool for in vitro studies of CTG repeat toxicity. Animal models of myotonic dystrophy type 1 (DM1) or other repeat expansion diseases could potentially be used to evaluate toringin's in vivo efficacy, but such studies have not been extensively reported. Standard toxicology assessments in animals would include monitoring of body weight, clinical observations, and histopathological examination of tissues. The compound's pharmacokinetic properties in vivo remain to be fully characterized. Further research is needed to determine whether toringin's in vitro protective effects translate to in vivo efficacy.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of toringin have not been extensively characterized in the public domain. As a flavonoid glycoside, toringin would be expected to be metabolized by intestinal microbiota and hepatic enzymes to its aglycone and other metabolites. Flavonoids typically have moderate oral bioavailability and undergo extensive first-pass metabolism. Toringin has a molecular formula of C21H20O9 and a molecular weight of 416.38 g/mol. The compound is soluble in DMSO and other organic solvents. Comprehensive pharmacokinetic parameters including half-life, volume of distribution, clearance, and oral bioavailability have not been reported for toringin. The compound's stability in solution and under various storage conditions has been characterized. Further pharmacokinetic studies are needed to fully understand the compound's absorption, distribution, metabolism, and elimination.
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| Toxicity/Toxicokinetics |
Toringin is intended for laboratory research use only and has not undergone comprehensive toxicology testing. As a bioflavonoid, toringin is a naturally occurring compound found in plants that are consumed in the human diet, suggesting a favorable safety profile. However, the compound's toxicity at research-use concentrations has not been extensively characterized. Standard in vitro cytotoxicity assays in cell lines are typically performed alongside efficacy studies to rule out nonspecific toxicity. In PC12 cells, toringin is able to prevent cytotoxicity at concentrations that are not themselves toxic to the cells. Comprehensive toxicological characterization including genotoxicity, cardiotoxicity, and repeated-dose toxicity studies has not been reported in the public domain. The compound is not approved for human use and is strictly intended for research purposes.
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| References | |
| Additional Infomation |
Toringin belongs to the flavonoid and glycoside classes. 7-Hydroxy-2-phenyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxacyclohexane-2-yl]oxachromen-4-one has been reported in apple (Malus doumeri) and chili pepper (Capsicum annuum), and relevant data are available.
Toringin is a bioflavonoid isolated from the bark of Docyniopsis tschonoski and other plants. Its chemical name is 5-(beta-D-glucopyranosyloxy)-7-hydroxy-2-phenyl-4H-1-benzopyran-4-one, with a molecular formula of C21H20O9 and a molecular weight of 416.38 g/mol. Toringin prevents the cytotoxicity and cis-effect of expanded CTG repeats in PC12 cell transformants (CTG-250). The compound progressively reduces the cis-effect of expanded CTG repeats and also reduces cytotoxicity. This activity makes toringin a potential therapeutic candidate for repeat expansion diseases such as myotonic dystrophy type 1 (DM1). Toringin has not entered clinical trials and has not received regulatory approval for any indication. It is available from research chemical suppliers for non-clinical research purposes only. Toringin is a valuable research tool for studying the molecular mechanisms of CTG repeat toxicity and developing new therapeutic strategies for repeat expansion diseases. |
| Molecular Formula |
C21H20O9
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|---|---|
| Molecular Weight |
416.3781
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| Exact Mass |
416.11
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| CAS # |
1329-10-8
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| PubChem CID |
101686456
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| Appearance |
White to yellow solid powder
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| LogP |
0.7
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
30
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| Complexity |
646
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3OC4C(C(C(C(O4)CO)O)O)O)O
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| InChi Key |
IRHAYEHCEVRWSB-QNDFHXLGSA-N
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| InChi Code |
InChI=1S/C21H20O9/c22-9-16-18(25)19(26)20(27)21(30-16)29-15-7-11(23)6-14-17(15)12(24)8-13(28-14)10-4-2-1-3-5-10/h1-8,16,18-23,25-27H,9H2/t16-,18-,19+,20-,21-/m1/s1
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| Chemical Name |
7-hydroxy-2-phenyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-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 (~240.17 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.00 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.00 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 20.8 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (5.00 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. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4017 mL | 12.0083 mL | 24.0165 mL | |
| 5 mM | 0.4803 mL | 2.4017 mL | 4.8033 mL | |
| 10 mM | 0.2402 mL | 1.2008 mL | 2.4017 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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