| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
7-Deazaxanthine (7DX) targets thymidine phosphorylase (TPase), an enzyme that catalyzes the reversible phosphorolysis of thymidine to thymine and 2-deoxy-D-ribose-1-phosphate. TPase is overexpressed in many solid tumors and promotes angiogenesis through the production of 2-deoxy-D-ribose. By inhibiting TPase, 7DX blocks the generation of deoxyribose, thereby reducing endothelial cell migration and tube formation, leading to the suppression of angiogenesis. The compound is a TPase inhibitor with an IC₅0 of 40 uM. It also has structural similarity to xanthine and may interact with xanthine oxidase.
|
|---|---|
| ln Vitro |
In vitro, 7-Deazaxanthine inhibits thymidine phosphorylase (TPase) in a concentration-dependent manner with an IC₅0 value of 40 uM. It has also shown significant angiogenesis inhibition activity. It inhibits the proliferation and tube formation of human umbilical vein endothelial cells (HUVECs) in Matrigel assays. The compound may also have antioxidant properties. It is not cytotoxic at concentrations up to 200 uM in most cancer cell lines.
|
| ln Vivo |
In vivo, 7-Deazaxanthine has potential as an anticancer agent by inhibiting angiogenesis. By blocking TPase, it reduces the production of 2-deoxy-D-ribose, which is a pro-angiogenic factor. This may lead to reduced tumor growth and metastasis. No specific in vivo efficacy data is detailed, but it is a research tool for studying tumor angiogenesis. The compound is not an approved drug.
|
| Enzyme Assay |
The TPase activity is measured by a colorimetric assay. Purified recombinant human TPase (0.1-1 U) is incubated in assay buffer (50 mM potassium phosphate pH 7.4, 1 mM thymidine) with varying concentrations of 7-Deazaxanthine (0.1-1000 uM) at 37degC for 30-60 min. The reaction is terminated by adding 0.2 M NaOH. The formation of thymine is measured by HPLC-UV (260 nm) or by a colorimetric method using 4-aminobenzoic acid. The IC₅0 (40 uM) is calculated from the dose-response curve. For cell-based angiogenesis assays, HUVECs are used.
|
| Cell Assay |
For cell-based studies, human umbilical vein endothelial cells (HUVECs) are seeded in 96-well plates (5,000-10,000 cells/well) in EGM-2 medium. 7-Deazaxanthine (10-200 uM) is added for 24-72 h. Cell viability is measured by MTT assay. For tube formation assays, HUVECs are seeded on Matrigel-coated 96-well plates (2×10⁴ cells/well) in the presence or absence of 7-Deazaxanthine (10-200 uM). After 6-18 h, tube formation is quantified by imaging and measuring total tube length (ImageJ). For anti-proliferative studies, cancer cells (e.g., HCT116, MCF-7) are used.
|
| Animal Protocol |
For in vivo angiogenesis studies, a Matrigel plug assay can be used. Female C57BL/6 mice (6-8 weeks old, n=8/group) are injected subcutaneously with 0.5 mL of Matrigel containing bFGF (500 ng/mL) and heparin (50 U/mL), with or without 7-Deazaxanthine (10-100 uM). After 7-10 days, the Matrigel plugs are excised. Hemoglobin content is measured by Drabkin‘s method to quantify angiogenesis. For tumor xenograft studies, female BALB/c nude mice are subcutaneously inoculated with 5×10⁶ cancer cells. When tumors reach ~100-150 mm3, 7-Deazaxanthine (10-50 mg/kg) is administered intraperitoneally once daily for 2-3 weeks. Tumor volume is measured every 3 days. No specific data is available.
|
| ADME/Pharmacokinetics |
No specific PK data for 7-Deazaxanthine is available. As a small, polar molecule (MW 151.12, LogP ~0), it has moderate water solubility. Following oral administration, it would be absorbed. It is likely metabolized by xanthine oxidase or by conjugation (glucuronidation). The half-life in rodents is expected to be 2-4 hours. For research use, it is stored as a powder at -20degC (powder: -20degC for 3 years, 4degC for 2 years; in solvent: -80degC for 6 months, -20degC for 1 month), protected from light and moisture.
|
| Toxicity/Toxicokinetics |
For 7-Deazaxanthine, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). Storage: at -20degC, sealed, protect from light.
|
| References | |
| Additional Infomation |
Structure in the first source
7-Deazaxanthine (7DX; 7H-Pyrrolo[2,3-d]pyrimidine-2,4-diol; CAS# 39929-79-8) is a research-grade thymidine phosphorylase (TPase) inhibitor (IC₅0 = 40 uM). It is not an FDA-approved drug. It is used as a tool for studying tumor angiogenesis, cancer progression, and as a potential anti-angiogenic agent. For research use only, not for diagnostic or therapeutic applications. |
| Molecular Formula |
C6H5N3O2
|
|---|---|
| Molecular Weight |
151.12
|
| Exact Mass |
151.038
|
| CAS # |
39929-79-8
|
| PubChem CID |
11819216
|
| Appearance |
Brown to gray solid powder
|
| Density |
1.8±0.1 g/cm3
|
| Boiling Point |
607.6±58.0 °C at 760 mmHg
|
| Melting Point |
>250ºC
|
| Flash Point |
321.2±32.3 °C
|
| Vapour Pressure |
0.0±1.8 mmHg at 25°C
|
| Index of Refraction |
1.863
|
| LogP |
-1.03
|
| tPSA |
82.03
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
11
|
| Complexity |
216
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C1C2C([H])=C([H])N([H])C=2N([H])C(N1[H])=O
|
| InChi Key |
HASUWNAFLUMMFI-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C6H5N3O2/c10-5-3-1-2-7-4(3)8-6(11)9-5/h1-2H,(H3,7,8,9,10,11)
|
| Chemical Name |
1,7-dihydropyrrolo[2,3-d]pyrimidine-2,4-dione
|
| Synonyms |
7DX
|
| 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) |
DMSO: ~12.5 mg/mL (~82.7 mM; with ultrasonication and warming by heating to 60°C)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (8.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (12.5 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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: 1.25 mg/mL (8.27 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Suspended solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (12.5 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. Solubility in Formulation 3: 1.25 mg/mL (8.27 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Suspended solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (12.5 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.6173 mL | 33.0863 mL | 66.1726 mL | |
| 5 mM | 1.3235 mL | 6.6173 mL | 13.2345 mL | |
| 10 mM | 0.6617 mL | 3.3086 mL | 6.6173 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
