5-Iodotubercidin

Cat. No. 1745

5-Iodotubercidin C11H13IN4O4 [24386-93-4]

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Chemical Name: 5-Iodo-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Biological Activity

Potent adenosine kinase inhibitor (IC50 = 26 nM). Also nucleoside transporter inhibitor (IC50 values are < 25 nM, 7 μM and 15 μM for inhibition of [3H]adenosine, [3H]uridine and [3H]formycin B 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 (IC50 values are 0.4, 3.5, 5-10, 5-10, 10.9 and 27.7 μM respectively). Decreases hippocampal DNA methylation through adenosine kinase inhibition in vivo.

Technical Data

M.Wt:
392.15
Formula:
C11H13IN4O4
Solubility:
Soluble to 50 mM in DMSO
Purity:
>90 %
Storage:
Store at -20°C
CAS No:
24386-93-4

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Product Datasheet / Safety Datasheet

References are publications that support the products' biological activity.

Williams-Karnesky et al (2013) Epigenetic changes induced by adenosine augmentation therapy prevent epileptogenesis. J.Clin.Invest. 123 3552. PMID: 23863710.

Ugarkar et al (2000) Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues. J.Med.Chem. 43 2883. PMID: 10956196.

Parkinson and Geiger (1996) Effects of iodotubercidin on adenosine kinase activity and nucleoside transport in DDT1 MF-2 smooth muscle cells. J.Pharmacol.Exp.Ther. 277 1397. PMID: 8667202.

Massillon et al (1994) Identification of the glycogenic compound 5-iodotubercidin as a general protein kinase inhibitor. Biochem.J. 299 123. PMID: 8166629.

If you know of a relevant reference for 5-Iodotubercidin please let us know.

Citations are publications that use Tocris products. Selected citations for 5-Iodotubercidin include:

Baron et al (2015) The NLRP3 inflammasome is activated by nanoparticles through ATP, ADP and adenosine. Am J Physiol Renal Physiol 6 e1629. PMID: 25654762.

Rüben et al (2015) Selectivity Profiling and Biological Activity of Novel β-Carbolines as Potent and Selective DYRK1 Kinase Inhibitors. PLoS One 10 e0132453. PMID: 26192590.

Prakasam et al (2012) Modulation of bladder function by luminal adenosine turnover and A1 receptor activation. J Neurosci 303 F279. PMID: 22552934.

Visentin et al (2012) Augmentation of reduced folate carrier-mediated folate/antifolate transport through an antiport mechanism with 5-aminoimidazole-4-carboxamide riboside monophosphate. Mol Pharmacol 82 209. PMID: 22554803.

Bumpus and Johnson (2011) 5-Aminoimidazole-4-carboxyamide-ribonucleoside (AICAR)-stimulated hepatic expression of Cyp4a10, Cyp4a14, Cyp4a31, and other peroxisome proliferator-activated receptor α-responsive mouse genes is AICAR 5'-monophosphate-dependent and AMP-activated protein kinase-independent. Cell Death Dis 339 886. PMID: 21896918.

Fassett et al (2011) Adenosine kinase regulation of cardiomyocyte hypertrophy. Am J Physiol Heart Circ Physiol 300 H1722. PMID: 21335462.

Do you know of a great paper that uses 5-Iodotubercidin from Tocris? If so please let us know.show all ▼show less ▲

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Keywords: 5-Iodotubercidin, supplier, Potent, adenosines, kinase, inhibitors, nucleoside, transporters, ENT1, reuptake, Purine, Transporters, Pyrimidine, Equilibrative, Monoamine, Neurotransmitter, ADK, 5-it, inhibits, DNA, methylation, Tocris Bioscience, Adeonsine Kinase Inhibitor products

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