Accéder au contenu
Merck
Toutes les photos(1)

Documents

I100

Sigma-Aldrich

5-Iodotubercidin

≥85%, solid

Synonyme(s) :

4-Amino-5-iodo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine, 5-Iodotubericidin, 7-Iodo-7-deazaadenosine

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

About This Item

Formule empirique (notation de Hill):
C11H13IN4O4
Numéro CAS:
24386-93-4
Poids moléculaire :
392.15
Numéro MDL:
MFCD00055131
Code UNSPSC :
12352202
ID de substance PubChem :
329815331
Nomenclature NACRES :
NA.77

Pureté

≥85%

Forme

solid

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

WHSIXKUPQCKWBY-IOSLPCCCSA-N

Description générale

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).

Actions biochimiques/physiologiques

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.

Attention

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)
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
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)
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)
Afficher tous les articles scientifiques apparentés

Articles

Fatty Acid Synthesis in Cancer Cells

Fatty acid synthesis supports cancer cell proliferation, essential for membrane generation, protein modification, and bioenergetics.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique