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I100

Sigma-Aldrich

5-Iodotubercidin

≥85%, solid

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Synonym(s):
4-Amino-5-iodo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine, 5-Iodotubericidin, 7-Iodo-7-deazaadenosine
Empirical Formula (Hill Notation):
C11H13IN4O4
CAS Number:
Molecular Weight:
392.15
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
852597A2385567809-M
vibrant-m

I100

5-Iodotubercidin

vibrant-m

852597

5-Iodouridine

vibrant-m

A2385

5-Azacytidine

vibrant-m

567809-M

Src Inhibitor, PP1

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

form

solid

form

powder

form

powder

form

solid

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Retinoblastoma cells are inhibited by aminoimidazole carboxamide ribonucleotide (AICAR) partially through activation of AMP-dependent kinase
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Addition of micromolar concentrations of the adenosine derivative 5-iodotubercidin (Itu) initiates glycogen synthesis in isolated hepatocytes by causing inactivation of phosphorylase and activation of glycogen synthase [Flückiger-Isler and Walter (1993) Biochem. J. 292, 85-91]. We report here that Itu also
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