Isodiospyrin is a natural dimeric naphthoquinone and a human DNA topoisomerase I (Topoisomerase) inhibitor. Isodiospyrin prevents DNA relaxation and the kinase activity of human topoisomerase I. Isodiospyrin has anticancer, antibacterial and antifungal activities.

Physicochemical Properties

Molecular Formula	C22H14O6
Molecular Weight	374.34
Exact Mass	374.079
CAS #	20175-84-2
PubChem CID	99298
Appearance	Orange to red solid powder
Density	1.5±0.1 g/cm3
Boiling Point	712.0±60.0 °C at 760 mmHg
Flash Point	398.3±29.4 °C
Vapour Pressure	0.0±2.4 mmHg at 25°C
Index of Refraction	1.707
LogP	3.83
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Heavy Atom Count	28
Complexity	795
Defined Atom Stereocenter Count	0
InChi Key	OEEOHKZVBKYMBA-UHFFFAOYSA-N
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
Chemical Name	5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxonaphthalen-1-yl)-7-methylnaphthalene-1,4-dione
HS Tariff Code	2934.99.9001
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)

Biological Activity

Targets	Topoisomerase I
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].
References	[1]. Isodiospyrin as a novel human DNA topoisomerase I inhibitor. Biochem Pharmacol. 2003 Nov 15;66(10):1981-91. [2]. Antibacterial activity of diospyrin, isodiospyrin and bisisodiospyrin from the root of Diospyros piscatoria (Gurke) (Ebenaceae). Phytother Res. 2000 Mar;14(2):112-7. [3]. Antifungal metabolites from the roots of Diospyros virginiana by overpressure layer chromatography. Chem Biodivers. 2011 Dec;8(12):2331-40.
Additional Infomation	Isodiospyrin is a member of biphenyls. Isodiospyrin has been reported in Diospyros morrisiana, Diospyros oleifera, and other organisms with data available.

Solubility Data

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

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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (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.