5-IODOTUBERCIDIN
Synonym(s):4-Amino-5-iodo-7-(β-D -ribofuranosyl)pyrrolo[2,3-d]pyrimidine;5-Iodotubericidin;7-Iodo-7-deazaadenosine
- CAS NO.:24386-93-4
- Empirical Formula: C11H13IN4O4
- Molecular Weight: 392.15
- MDL number: MFCD00055131
- EINECS: 200-001-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-17 16:00:36
What is 5-IODOTUBERCIDIN?
Chemical properties
Tan Solid
The Uses of 5-IODOTUBERCIDIN
5-Iodotubercidin has been used for the inhibition of retinoblastoma cells, astroglial cultures and for the inhibition of adenosine kinase in human umbilical vein endothelial cells (HUVECs).
The Uses of 5-IODOTUBERCIDIN
An analogue of the antibiotic tubercidin, a pyrrolo[2,3-d]pyrimidine nucleoside antibiotic. A potent inhibitor of adenosine kinase from rat or guinea pig brain. Inhibits uptake of 3H-adenosine into brain slices.
The Uses of 5-IODOTUBERCIDIN
A potent and competitive inhibitor of ERK2, PKA, and ADK.
What are the applications of Application
5-Iodotubercidin is a potent and competitive inhibitor of ERK 2, PKA, and ADK
General Description
solubility: 10 mg/mL in DMSO
Biological Activity
Potent adenosine kinase inhibitor (IC 50 = 26 nM) and nucleoside transporter inhibitor (IC 50 values are 7, 15 and < 25 nM for inhibition of [ 3 H]-uridine, [ 3 H]-formycin B and [ 3 H]-adenosine uptake respectively). Strongly stimulates glycogen synthesis in hepatocytes via activation of glycogen synthase. Also inhibits CK1, insulin receptor tyrosine kinase, phosphorylase kinase, PKA, CK2 and PKC (IC 50 values are 0.4, 3.5, 5-10, 5-10, 10.9 and 27.7 μ M respectively).
Biochem/physiol Actions
Potent inhibitor of adenosine uptake into brain, and of adenosine kinase and subsequent metabolism of adenine nucleotides. In cultured rat hepatocytes, 5-iodotubercidin inhibits both acetyl-CoA carboxylase and de novo synthesis of fatty acids and cholesterol.
storage
Store at -20°C
References
[1]. xin zhang, deyong jia, huijuan liu, et al. identification of 5-iodotubercidin as a genotoxic drug with anti-cancer potential. plos one, 2013, 8(5):e62527.
[2]. jaoek park and radhey s. gupta. adenosine: a key link between metabolism and brain activity: adenosine metabolism, adenosine kinase, and evolution. new york: springer science+business media, 2013.
[3]. garcía-villafranca j. and castro j. effects of 5-iodotubercidin on hepatic fatty acid metabolism mediated by the inhibition of acetyl-coa carboxylase. biochem. pharmacol., 2002, 63(11):1997-2000.
[4]. haiyan chen, ji-ping wang, richard j. santen, et al. adenosine monophosphate activated protein kinase (ampk), a mediator of estradiol-induced apoptosis in long-term estrogen deprived breast cancer cells. apoptosis, 2015, 20:821-830.
Properties of 5-IODOTUBERCIDIN
Melting point: | 216-217°C dec. |
Boiling point: | 701.5±60.0 °C(Predicted) |
Density | 2.49±0.1 g/cm3(Predicted) |
storage temp. | 2-8°C |
solubility | 0.1 M HCl: 0.7 mg/mL |
form | solid |
pka | 12.33±0.70(Predicted) |
color | tan |
Stability: | Store tightly sealed at 4°C; Light Sensitive |
CAS DataBase Reference | 24386-93-4 |
Safety information for 5-IODOTUBERCIDIN
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for 5-IODOTUBERCIDIN
InChIKey | WHSIXKUPQCKWBY-IOSLPCCCSA-N |
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