5-Iodotubercidin

Pricing Availability Delivery Time Qty
Cat.No. 1745 - 5-Iodotubercidin | C11H13IN4O4 | CAS No. 24386-93-4
Description: Potent adenosine kinase inhibitor; also inhibits nucleoside transporters and a range of other kinases
Chemical Name: 5-Iodo-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Purity: ≥90% (HPLC)
Datasheet
Citations (6)
Literature

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
Storage Store at -20°C
Purity ≥90% (HPLC)
CAS Number 24386-93-4
PubChem ID 97297
InChI Key WHSIXKUPQCKWBY-IOSLPCCCSA-N
Smiles O[C@H]([C@H](O)[C@@H](CO)O3)[C@@H]3N1C2=C(C(N)=NC=N2)C(I)=C1

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.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 19.61 50

Preparing Stock Solutions

The following data is based on the product molecular weight 392.15. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.55 mL 12.75 mL 25.5 mL
5 mM 0.51 mL 2.55 mL 5.1 mL
10 mM 0.26 mL 1.28 mL 2.55 mL
50 mM 0.05 mL 0.26 mL 0.51 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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

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

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

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


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6 Citations for 5-Iodotubercidin

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

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

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

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

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 Cell Death Dis 339 886 PMID: 21896918

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

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


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