I100

5-Iodotubercidin

Name: 5-Iodotubercidin
Brand: SIGMA

≥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:

24386-93-4

Molecular Weight:

392.15

NACRES:

NA.77

PubChem Substance ID:

329815331

UNSPSC Code:

12352202

MDL number:

MFCD00055131

Product Name

5-Iodotubercidin, ≥85%, solid

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

SMILES string

Nc1ncnc2n(cc(I)c12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI key

WHSIXKUPQCKWBY-IOSLPCCCSA-N

assay

≥85%

form

solid

storage temp.

2-8°C

Quality Level

100

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

5-Iodotubercidin increases fatty acid oxidation activity and glycogen synthesis in hepatocytes. 5-Iodotubercidin is also a potent inhibitor of adenosine uptake into brain.

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.

Disclaimer

Solutions may be stored frozen. Use promptly when thawed and protect from exposure to light.

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Understanding the basic mechanisms underlying seizures in mesial temporal lobe epilepsy and possible therapeutic targets: a review

O'dell CM, et al.

Journal of Neuroscience Research, 90(5), 913-924 (2012)

Ecto-5?-nucleotidase (CD73) inhibits nociception by hydrolyzing AMP to adenosine in nociceptive circuits

Sowa NA, et al.

The Journal of Neuroscience, 30(6), 2235-2244 (2010)

Opposite modulation of astroglial proliferation by adenosine 5?-O-(2-thio)-diphosphate and 2-methylthioadenosine-5?-diphosphate: mechanisms involved

Quintas C, et al.

Neuroscience, 182(8), 32-42 (2011)

Retinoblastoma cells are inhibited by aminoimidazole carboxamide ribonucleotide (AICAR) partially through activation of AMP-dependent kinase

Theodoropoulou S, et al.

Faseb Journal, 24(8), 2620-2630 (2010)

Identification of the glycogenic compound 5-iodotubercidin as a general protein kinase inhibitor.

D Massillon et al.

The Biochemical journal, 299 ( Pt 1), 123-128 (1994-04-01)

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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