An adenosine kinase inhibitor
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5-Iodotubercidin

Item No. 10010375

Technical Information
Formal Name
5-iodo-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
CAS Number
24386-93-4
Synonyms
  • Itu
  • NSC 113939
Molecular Formula
C11H13IN4O4
Formula Weight
Purity
≥95%
A solid
DMSO: 10 mg/ml
λmax
207, 284 nm
SMILES
IC1=CN([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)C3=C1C(N)=NC=N3
InChi Code
InChI=1S/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
InChi Key
WHSIXKUPQCKWBY-IOSLPCCCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    5-Iodotubercidin is an inhibitor of adenosine kinase (IC50 = 0.026 µM).1 It inhibits protein kinase A (PKA), phosphorylase kinase, casein kinase 1 (CK1), CK2, and PKC (IC50s = 5-10, 5-10, 0.4, 10.9, and 0.4 µM, respectively).2 5-Iodotubercidin is also an inhibitor of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) RNA-dependent RNA polymerase (RdRp; EC50 = 0.75 µM).3 It decreases fatty acid synthesis and increases fatty acid oxidation in isolated rat hepatocytes when used at a concentration of 20 µM.4 In vivo, 5-iodotubercidin reduces the number of seizures in a rat model of seizures induced by maximum electroshock (MES; ED50 = 6 mg/kg).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ugarkar, B.G., DaRe, J.M., Kopcho, J.J., et alAdenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues. J. Med. Chem. 43(15), 2883-2893 (2000).

    2. Massillon, D., Stalmans, W., van de Werve, G., et alIdentification of the glycogenic compound 5-iodotubercidin as a general protein kinase inhibitor. Biochem. J. 299, 123-128 (1994).

    3. Zhao, J., Liu, Q., Yi, D., et al5-Iodotubercidin inhibits SARS-CoV-2 RNA synthesis. Antiviral Res. 198, 105254 (2022).

    4. 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. 63, 1997-2000 (2002).