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| Targets |
Topoisomerase I
Human DNA topoisomerase I (Topoisomerase). Isodiospyrin is a human DNA topoisomerase I inhibitor. It prevents both DNA relaxation and the kinase activity of human topoisomerase I. Topoisomerase I is an enzyme that relieves torsional stress in DNA during replication and transcription by introducing transient single-strand breaks. Inhibition of topoisomerase I leads to DNA damage and cell death, making it a target for anticancer agents. |
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| ln Vitro |
Covalent complexes between human topoisomerase I (htopo I) and DNA are not induced by isodiospyrin (10–40 μM). Isodiospyrin, however, inhibited the DNA breakage that was caused by camptothecin-mediated htopo I. Homo I is bound by isodiospyrin, but DNA is not. Isodiospyrin significantly inhibits the kinase activity of htopo I on splicing factor 2/alternative splicing factors in the absence of DNA [1]. The MICs of isodiospyrin against bacteria that are Gram-positive vary from 0.78 to 50 μg/mL. Concentrations of isodiospyrin against Salmonella typhi and Pseudomonas aeruginosa ATCC 15443 range from 50 to 100 μg/mL. For M. chelonae, the MIC ranges from 6.25 to 25 μg/mL [2]. Isodiospyrin (30 μM; 120-144 hours) inhibited P. obscurans growth by 81.4%. 30 μM isodiospyrin has 57.7% antifungal efficacy against P. viticola[3].
In vitro, Isodiospyrin exhibits cytotoxic activity against tumor cell lines. It prevents DNA relaxation and the kinase activity of human topoisomerase I. The compound also demonstrates antibacterial activity with minimum inhibitory concentrations (MICs) against Gram-positive bacteria ranging from 0.78 to 50 microg/mL. It exhibits high antifungal activity against various fungal strains. Isodiospyrin also exhibits antioxidant effects in vitro. |
| ln Vivo |
In vivo studies of Isodiospyrin are limited as the compound is primarily used as a research tool. Its anticancer activity has been suggested based on its topoisomerase I inhibitory and cytotoxic activities. The compound's antibacterial and antifungal activities have been characterized in vitro, but in vivo efficacy studies are limited. Further in vivo studies are needed to fully characterize its therapeutic potential.
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| Enzyme Assay |
In vitro topoisomerase I inhibition assays for Isodiospyrin measure the compound's ability to prevent DNA relaxation. The assay uses purified human topoisomerase I and supercoiled plasmid DNA as substrate. Varying concentrations of Isodiospyrin are incubated with topoisomerase I and supercoiled DNA in reaction buffer. After incubation at 37degC for 30 minutes, the reaction is stopped with SDS and proteinase K. DNA products are separated by agarose gel electrophoresis. Relaxed DNA (slower migrating) and supercoiled DNA (faster migrating) are visualized by ethidium bromide staining. Inhibition is measured as the concentration that prevents relaxation of supercoiled DNA.
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| Cell Assay |
In vitro cell-based assays for Isodiospyrin use human tumor cell lines. Cells are cultured in appropriate media and treated with varying concentrations of the compound (typically 0.1-100 microM) for 24-72 hours. Cell viability is measured using MTT, XTT, or CCK-8 assays. IC50 values are calculated from dose-response curves. Apoptosis is evaluated using Annexin V/PI staining or caspase-3/7 activity assays. DNA damage can be assessed by gamma-H2AX staining. Antibacterial activity is evaluated using standard broth microdilution methods to determine MICs against Gram-positive and Gram-negative bacteria.
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| Animal Protocol |
In vivo animal studies for Isodiospyrin are limited. If performed, typical protocols would involve murine xenograft models of human cancers to evaluate antitumor efficacy. Mice would be implanted subcutaneously with tumor cells and treated with Isodiospyrin at various doses via intraperitoneal or intravenous administration. Tumor volumes would be measured with calipers, and tumor growth inhibition would be calculated. However, such studies are not extensively reported in the literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Isodiospyrin are characteristic of natural naphthoquinone compounds. With a molecular weight of 374.34, the compound is likely to have moderate lipophilicity and may have limited oral bioavailability. The compound is a natural product used as a research tool. Standard pharmacokinetic parameters could be determined in preclinical species if needed for research purposes. Storage at -20degC is recommended.
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| Toxicity/Toxicokinetics |
Toxicological data for Isodiospyrin are limited as the compound is used for research purposes only. As a natural product with topoisomerase I inhibitory activity, it may have potential for cytotoxicity at higher concentrations. Standard safety precautions for handling chemical compounds apply. The compound is intended for research use only and not for human therapeutic use.
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| References |
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| Additional Infomation |
Isodiospyrin is a member of the biphenyl class of compounds. It has been reported to exist in persimmon (Diospyros morrisiana), oil persimmon (Diospyros oleifera), and other organisms with relevant data.
Isodiospyrin is a research-grade natural dimeric naphthoquinone and human DNA topoisomerase I inhibitor. It is found in plants of the genus Diospyros. The compound has a molecular formula of C22H14O6 and molecular weight of 374.34. It prevents both DNA relaxation and kinase activities of human topoisomerase I. Isodiospyrin exhibits cytotoxic activity against tumor cell lines, antibacterial activity against Gram-positive bacteria (MIC 0.78-50 microg/mL), and antifungal activity. It is used as a research tool to study topoisomerase I inhibition and anticancer mechanisms. Not approved for clinical use. |
| Molecular Formula |
C22H14O6
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| Molecular Weight |
374.34
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| Exact Mass |
374.079
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| CAS # |
20175-84-2
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| PubChem CID |
99298
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| Appearance |
Orange to red solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
712.0±60.0 °C at 760 mmHg
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| Flash Point |
398.3±29.4 °C
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| Vapour Pressure |
0.0±2.4 mmHg at 25°C
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| Index of Refraction |
1.707
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| LogP |
3.83
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
28
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| Complexity |
795
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
OEEOHKZVBKYMBA-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C22H14O6/c1-9-7-11-12(23)3-4-13(24)19(11)22(28)18(9)17-10(2)8-16(27)20-14(25)5-6-15(26)21(17)20/h3-8,27-28H,1-2H3
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| Chemical Name |
5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxonaphthalen-1-yl)-7-methylnaphthalene-1,4-dione
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 2.6714 mL | 13.3568 mL | 26.7137 mL | |
| 5 mM | 0.5343 mL | 2.6714 mL | 5.3427 mL | |
| 10 mM | 0.2671 mL | 1.3357 mL | 2.6714 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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