I100
5-Iodotubercidin
≥85%, solid
동의어(들):
4-Amino-5-iodo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine, 5-Iodotubericidin, 7-Iodo-7-deazaadenosine
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C11H13IN4O4
CAS 번호:
Molecular Weight:
392.15
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
MDL number:
Assay:
≥85%
Form:
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
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
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.
저장 등급
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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
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)
Clara Campàs et al.
Blood, 101(9), 3674-3680 (2003-01-11)
Acadesine, 5-aminoimidazole-4-carboxamide (AICA) riboside, induced apoptosis in B-cell chronic lymphocytic leukemia (B-CLL) cells in all samples tested (n = 70). The half-maximal effective concentration (EC(50)) for B-CLL cells was 380 +/- 60 microM (n = 5). The caspase inhibitor Z-VAD.fmk
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)
문서
Fatty acid synthesis supports cancer cell proliferation, essential for membrane generation, protein modification, and bioenergetics.
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