24386-93-4

Basic information

• Product Name: 5-IODOTUBERCIDIN
• Synonyms: 7-IODO-7-DEAZAADENOSINE;5-IODOTUBERCIDIN;5-IODOTUBERICIDIN;4-AMINO-5-IODO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE;IODOTUBERCIDIN;ITU;Iodotubercidin,Itu;4-Amino-5-iodo-7-(b-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• CAS NO: 24386-93-4
• Molecular Formula: C₁₁H₁₃IN₄O₄
• Molecular Weight: 392.15
• EINECS: 200-001-2
• Product Categories: Miscellaneous Natural Products;Bases & Related Reagents;Inhibitors;Nucleotides;Protein Kinase Inhibitors and Activators
• Mol File: 24386-93-4.mol

Chemical Properties

• Melting Point: 216-217°C dec.
• Boiling Point: 701.5 °C at 760 mmHg
• Flash Point: 378 °C
• Appearance: tan/solid
• Density: 2.495 g/cm³
• Vapor Pressure: 1.18E-20mmHg at 25°C
• Refractive Index: 1.918
• Storage Temp.: 2-8°C
• Solubility: 0.1 M HCl: 0.7 mg/mL
• PKA: 12.33±0.70(Predicted)
• Stability: Store tightly sealed at 4°C; Light Sensitive
• CAS DataBase Reference: 5-IODOTUBERCIDIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-IODOTUBERCIDIN(24386-93-4)
• EPA Substance Registry System: 5-IODOTUBERCIDIN(24386-93-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 24386-93-4(Hazardous Substances Data)

Usage

Uses

Used in Enzyme Inhibition:
5-Iodotubercidin is used as a potent inhibitor for adenosine kinase, ERK2, PKA, and ADK. Its application in this area is crucial for understanding the roles these enzymes play in various biological processes and for developing potential therapeutic strategies targeting these enzymes.
Used in Cancer Research:
In the field of oncology, 5-Iodotubercidin is used as an inhibitor of retinoblastoma cells, astroglial cultures, and adenosine kinase in human umbilical vein endothelial cells (HUVECs). Its ability to inhibit these cells and enzymes makes it a valuable tool in the study of cancer biology and the development of novel cancer treatments.
Used in Neurobiology Research:
5-Iodotubercidin is also used in neurobiological research as a potent inhibitor of adenosine kinase from rat or guinea pig brain. This application aids in the study of adenosine signaling in the brain and its potential implications in neurological disorders and cognitive functions.
Used in Cellular and Molecular Biology:
As a competitive inhibitor, 5-Iodotubercidin is employed in cellular and molecular biology research to investigate the roles of various kinases and other cellular targets in cell signaling, proliferation, and differentiation. This helps researchers understand the underlying mechanisms of these processes and develop targeted therapies for various diseases.

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.

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.

InChI:InChI=1/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

Upstream product

• 480439-89-2 4-chloro-5-iodo-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 24386-91-2 4-chloro-5-iodo-7-(α-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 64609-53-6 7-methyl-7-deazaadenosine 
• 69-33-0 tubercidin 
• 76319-89-6 4-amino-5-stryryl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 

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