5-Iodotubercidin

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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: ≥97% (HPLC)
Datasheet
Citations (6)
Reviews

Biological Activity for 5-Iodotubercidin

5-Iodotubercidin is a 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 for 5-Iodotubercidin

M. Wt 392.15
Formula C11H13IN4O4
Storage Store at -20°C
Purity ≥97% (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.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for 5-Iodotubercidin

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

Preparing Stock Solutions for 5-Iodotubercidin

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

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 5.1 mL 25.5 mL 51 mL
2.5 mM 1.02 mL 5.1 mL 10.2 mL
5 mM 0.51 mL 2.55 mL 5.1 mL
25 mM 0.1 mL 0.51 mL 1.02 mL

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Product Datasheets for 5-Iodotubercidin

Certificate of Analysis / Product Datasheet
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References for 5-Iodotubercidin

References are publications that support the biological activity of the product.

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


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

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6 Citations for 5-Iodotubercidin

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

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

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

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


Do you know of a great paper that uses 5-Iodotubercidin from Tocris? Please let us know.

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