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I100

Sigma-Aldrich

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:
24386-93-4
Molecular Weight:
392.15
MDL number:
MFCD00055131
UNSPSC Code:
12352202
PubChem Substance ID:
329815331
NACRES:
NA.77

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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AMPK inhibits oxidative stress induced caveolin-1 phosphorylation and endocytosis by suppressing the dissociation between c-Abl and prdx1 in endothelial cells
Takeuchi K, et al.
The Journal of Biological Chemistry, jbc-M113 (2013)
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)
Identification of 5-iodotubercidin as a genotoxic drug with anti-cancer potential
Zhang X, et al.
PLoS ONE, 8(5), e62527-e62527 (2013)
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)
Opposite modulation of astroglial proliferation by adenosine 5?-O-(2-thio)-diphosphate and 2-methylthioadenosine-5?-diphosphate: mechanisms involved
Quintas C, et al.
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