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Key Documents

I100

Sigma-Aldrich

5-Iodotubercidin

≥85%, solid

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C11H13IN4O4
Numero CAS:
Peso molecolare:
392.15
Numero MDL:
Codice UNSPSC:
12352202
ID PubChem:
NACRES:
NA.77

Saggio

≥85%

Forma fisica

solid

Temperatura di conservazione

2-8°C

Stringa SMILE

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
WHSIXKUPQCKWBY-IOSLPCCCSA-N

Descrizione generale

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

Applicazioni

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).

Azioni biochim/fisiol

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.

Avvertenza

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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

Articoli

Information on fatty acid synthesis and metabolism in cancer cells. Learn how proliferatively active cells require fatty acids for functions such as membrane generation, protein modification, and bioenergetic requirements. These fatty acids are derived either from dietary sources or are synthesized by the cell.

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