I100
5-Iodotubercidin
≥85%, solid
Synonym(s):
4-Amino-5-iodo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine, 5-Iodotubericidin, 7-Iodo-7-deazaadenosine
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About This Item
Empirical Formula (Hill Notation):
C11H13IN4O4
CAS Number:
Molecular Weight:
392.15
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
form:
solid
Assay:
≥85%
Recommended Products
Quality Level
Assay
≥85%
form
solid
storage temp.
2-8°C
SMILES string
Nc1ncnc2n(cc(I)c12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
InChI
1S/C11H13IN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1
InChI key
WHSIXKUPQCKWBY-IOSLPCCCSA-N
General description
5-Iodotubercidin is a purine and modulates cellular adenosine levels by inhibiting the functionality of adenosine kinase. It is an activator for p53 and favors tumor suppression and may serve as a potential chemotherapeutic agent. 5-Iodotubercidin mediated blockade of adenosine to adenosine monophosphate (AMP) conversion results in alleviating antinociceptive effect of AMP. 5-Iodotubercidin is under clinical trial testing for treating epilepsy.
solubility: 10 mg/mL in DMSO
Application
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).
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.
5-Iodotubercidin increases fatty acid oxidation activity and glycogen synthesis in hepatocytes. 5-Iodotubercidin is also a potent inhibitor of adenosine uptake into brain.
Caution
Solutions may be stored frozen. Use promptly when thawed and protect from exposure to light.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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