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HomeProduct name list5-IODOTUBERCIDIN

5-IODOTUBERCIDIN

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

  • CAS NO.:24386-93-4
  • Empirical Formula: C11H13IN4O4
  • Molecular Weight: 392.15
  • MDL number: MFCD00055131
  • EINECS: 200-001-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-17 16:00:36
5-IODOTUBERCIDIN Structural

What is 5-IODOTUBERCIDIN?

Chemical properties

Tan Solid

The Uses of 5-IODOTUBERCIDIN

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).

The Uses of 5-IODOTUBERCIDIN

An analogue of the antibiotic tubercidin, a pyrrolo[2,3-d]pyrimidine nucleoside antibiotic. A potent inhibitor of adenosine kinase from rat or guinea pig brain. Inhibits uptake of 3H-adenosine into brain slices.

The Uses of 5-IODOTUBERCIDIN

A potent and competitive inhibitor of ERK2, PKA, and ADK.

What are the applications of Application

5-Iodotubercidin is a potent and competitive inhibitor of ERK 2, PKA, and ADK

General Description

solubility: 10 mg/mL in DMSO

Biological Activity

Potent adenosine kinase inhibitor (IC 50 = 26 nM) and nucleoside transporter inhibitor (IC 50 values are 7, 15 and < 25 nM for inhibition of [ 3 H]-uridine, [ 3 H]-formycin B and [ 3 H]-adenosine uptake respectively). Strongly stimulates glycogen synthesis in hepatocytes via activation of glycogen synthase. Also inhibits CK1, insulin receptor tyrosine kinase, phosphorylase kinase, PKA, CK2 and PKC (IC 50 values are 0.4, 3.5, 5-10, 5-10, 10.9 and 27.7 μ M respectively).

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.

storage

Store at -20°C

References

[1]. xin zhang, deyong jia, huijuan liu, et al. identification of 5-iodotubercidin as a genotoxic drug with anti-cancer potential. plos one, 2013, 8(5):e62527.
[2]. jaoek park and radhey s. gupta. adenosine: a key link between metabolism and brain activity: adenosine metabolism, adenosine kinase, and evolution. new york: springer science+business media, 2013.
[3]. garcía-villafranca j. and castro j. effects of 5-iodotubercidin on hepatic fatty acid metabolism mediated by the inhibition of acetyl-coa carboxylase. biochem. pharmacol., 2002, 63(11):1997-2000.
[4]. haiyan chen, ji-ping wang, richard j. santen, et al. adenosine monophosphate activated protein kinase (ampk), a mediator of estradiol-induced apoptosis in long-term estrogen deprived breast cancer cells. apoptosis, 2015, 20:821-830.

Properties of 5-IODOTUBERCIDIN

Melting point: 216-217°C dec.
Boiling point: 701.5±60.0 °C(Predicted)
Density  2.49±0.1 g/cm3(Predicted)
storage temp.  2-8°C
solubility  0.1 M HCl: 0.7 mg/mL
form  solid
pka 12.33±0.70(Predicted)
color  tan
Stability: Store tightly sealed at 4°C; Light Sensitive
CAS DataBase Reference 24386-93-4

Safety information for 5-IODOTUBERCIDIN

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for 5-IODOTUBERCIDIN

InChIKey WHSIXKUPQCKWBY-IOSLPCCCSA-N

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