[CAS NO. 24386-93-4] 5-Iodotubercidin
PRODUCTS SPECIFICATIONS [24386-93-4]
DESCRIPTION [24386-93-4]
Overview
| MDL | MFCD00055131 |
|---|---|
| Molecular Weight | 392.15 |
| Molecular Formula | C11H13IN4O4 |
| SMILES | NC1=C2C(N([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C=C2I)=NC=N1 |
4 Publications Citing Use of MCE
Summary
5-Iodotubercidin (NSC 113939), an ATP mimetic, is a potent adenosine kinase inhibitor with an IC 50 of 26 nM. 5-Iodotubercidin (NSC 113939) initiates glycogen synthesis in isolated hepatocytes by causing inactivation of phosphorylase and activation of glycogen synthase. 5-Iodotubercidin (NSC 113939) also inhibits CK1 , insulin receptor tyrosine kinase, phosphorylase kinase, PKA , CK2 , PKC and Haspin [1] [2] [3] .
IC50 & Target
IC50: 26 nM (adenosine kinase)
In Vitro
5-Iodotubercidin (NSC 113939) inhibits CK1, insulin receptor tyrosine kinase, phosphorylase kinase, PKA, CK2 and PKC, and the IC
50
values are 0.4, 3.5, 5-10, 5-10, 10.9 and 27.7 μM respectively
[1]
.
5-Iodotubercidin (20 μM) causes an important decrease in ATP concentration, and a concomitant smaller increase in AMP concentration. 5-Iodotubercidin decreases the activity of ACC and the rates of synthesis of fatty acids and cholesterol. In line with the iodotubercidin-mediated inhibition of ACC, 5-iodotubercidin induces a marked decrease in the intracellular concentration of malonyl-CoA
[4]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
5-Iodotubercidin (1 mL/kg, i.p.) is in agreement with activity observed against bicuculline-induced seizures following local administration of the AKI into the prepiriform cortex [2] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
DMSO : ≥ 49 mg/mL ( 124.95 mM )
* "≥" means soluble, but saturation unknown.
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 2.5500 mL | 12.7502 mL | 25.5004 mL |
| 5 mM | 0.5100 mL | 2.5500 mL | 5.1001 mL |
| 10 mM | 0.2550 mL | 1.2750 mL | 2.5500 mL |
-
1.
-
2.
Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)
Solubility: ≥ 2.5 mg/mL (6.38 mM); Clear solution
-
3.
Add each solvent one by one: 10% DMSO >> 90% corn oil
Solubility: ≥ 2.5 mg/mL (6.38 mM); Clear solution
-
4.
-
5.
Add each solvent one by one: 5% DMSO >> 95% (20% SBE-β-CD in saline)
Solubility: ≥ 2.5 mg/mL (6.38 mM); Clear solution
-
6.
Add each solvent one by one: 1% DMSO >> 99% saline
Solubility: ≥ 0.5 mg/mL (1.28 mM); Clear solution
References
- [1] Massillon D, et al. Identification of the glycogenic compound 5-iodotubercidin as a general protein kinase inhibitor. Biochem J. 1994 Apr 1;299 (Pt 1):123-8.
- [2] Ugarkar BG, et al. Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues. J Med Chem. 2000 Jul 27;43(15):2883-93.
- [3] García-Villafranca J, et al. Effects of 5-iodotubercidin on hepatic fatty acid metabolism mediated by the inhibition of acetyl-CoA carboxylase. Biochem Pharmacol. 2002 Jun 1;63(11):1997-2000.
- [4] De Antoni A, et al. A small-molecule inhibitor of Haspin alters the kinetochore functions of Aurora B. J Cell Biol. 2012 Oct 15;199(2):269-84.
- [5] Acharya MM, et al. Adenosine Kinase Inhibition Protects against Cranial Radiation-Induced Cognitive Dysfunction. Front Mol Neurosci. 2016 Jun 3;9:42.
Synonyms