| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
|
||
| Other Sizes |
| Targets |
2,6-Dithiopurine acts as a nucleophilic scavenger targeting electrophilic carcinogens. It eliminates the formation of DNA adducts and impedes the initiation of carcinogenesis. It may also inhibit the enzyme thymidylate synthase, blocking DNA and RNA synthesis. It interacts with its targets through intersystem crossing, leading to population of reactive triplet states in cancer cells.
|
|---|---|
| ln Vitro |
In vitro, 2,6-Dithiopurine acts as a nucleophilic scavenger of electrophilic carcinogens, preventing DNA adduct formation. It shows anti-carcinogenic activity by blocking the initiation of carcinogenesis. It may also inhibit cell proliferation through thymidylate synthase inhibition. It has immunosuppressive activity used to prevent organ transplant rejection.
|
| ln Vivo |
In vivo, 2,6-Dithiopurine has immunosuppressive effects and is used to prevent organ transplant rejection. It blocks the synthesis of DNA and RNA in cells by inhibiting thymidylate synthase. Its nucleophilic scavenging activity may contribute to chemopreventive effects by reducing carcinogen-DNA adduct formation.
|
| Enzyme Assay |
Cell-free assays for 2,6-Dithiopurine: thymidylate synthase inhibition is measured using [3H]-dUMP as substrate, monitoring tritium release. Nucleophilic scavenging activity is assessed by reacting the compound with electrophilic carcinogens (e.g., benzo[a]pyrene diol epoxide) and measuring adduct formation by HPLC or mass spectrometry. DNA adduct formation is quantified by 32P-postlabeling.
|
| Cell Assay |
Cellular assays for 2,6-Dithiopurine: cancer cell lines or lymphocytes are cultured in RPMI 1640 with 10% FBS and treated with 2,6-Dithiopurine (0.1-100 µM) for 24-72 hours. Cell proliferation is measured by MTT or [3H]-thymidine incorporation. DNA synthesis is assessed by BrdU incorporation. DNA adduct formation is measured in cells exposed to carcinogens with and without the compound.
|
| Animal Protocol |
In vivo animal studies for 2,6-Dithiopurine: rodent models of organ transplantation are used to evaluate immunosuppressive effects. Animals are administered 2,6-Dithiopurine orally or intraperitoneally at doses of 1-10 mg/kg. Graft survival and immune responses are monitored. Chemopreventive effects are evaluated in carcinogen-induced cancer models by measuring tumor incidence and DNA adduct levels.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2,6-Dithiopurine: as a purine analog, it is likely well absorbed orally. It is metabolized in the liver by xanthine oxidase and other enzymes. The compound may have a short half-life due to rapid metabolism. Its immunosuppressive and anti-carcinogenic activities depend on adequate tissue concentrations.
|
| Toxicity/Toxicokinetics |
Toxicity of 2,6-Dithiopurine: as an immunosuppressive agent, it may have significant toxicity including myelosuppression, hepatotoxicity, and gastrointestinal effects. It is a potent compound and should be handled with caution. It is used as an immunosuppressive drug but has been largely replaced by newer agents. The compound is for research use in modern applications.
|
| References |
[1]. Stephen Boulware, et al. 2,6-Dithiopurine, a nucleophilic scavenger, protects against mutagenesis in mouse skin treated in vivo with 2-(chloroethyl) ethyl sulfide, a mustard gas analog. Toxicol Appl Pharmacol. 2012 Sep 1;263(2):203-9.
|
| Additional Infomation |
2,6-Dithiopurine (2,6-Dimercaptopurine) is an immunosuppressive drug used to prevent organ transplant rejection. It blocks DNA and RNA synthesis by inhibiting thymidylate synthase. It also acts as a nucleophilic scavenger of electrophilic carcinogens. It has been used clinically but has largely been replaced by newer immunosuppressants. It is available as a research compound.
|
| Molecular Formula |
C5H4N4S2
|
|---|---|
| Molecular Weight |
184.2421
|
| Exact Mass |
183.987
|
| CAS # |
5437-25-2
|
| PubChem CID |
1268252
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.8±0.1 g/cm3
|
| Boiling Point |
496.2±37.0 °C at 760 mmHg
|
| Melting Point |
>350 °C(lit.)
|
| Flash Point |
253.9±26.5 °C
|
| Vapour Pressure |
0.0±1.3 mmHg at 25°C
|
| Index of Refraction |
1.89
|
| LogP |
0.5
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
11
|
| Complexity |
217
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
VQPMXSMUUILNFZ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C5H4N4S2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
|
| Chemical Name |
3,7-dihydropurine-2,6-dithione
|
| 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 |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| 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
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 | 5.4277 mL | 27.1385 mL | 54.2770 mL | |
| 5 mM | 1.0855 mL | 5.4277 mL | 10.8554 mL | |
| 10 mM | 0.5428 mL | 2.7139 mL | 5.4277 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
