5-Iodotubercidin

Cayman Chemical Item Number 10010375

NSC 113939; Itu (CAS 24386-93-4)

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Description

5-Iodotubercidin (Itu) is an adenosine derivative that initiates glycogen synthesis in hepatocytes by causing inactivation of phosphorylase α and activation of glycogen synthase α (maximal effects with ~20 µM Itu).1 Itu can inhibit a broad range of PKs including PKA (IC50 = 5-10 µM), phosphorylase kinase (IC50 = 5-10 µM), casein kinase I (IC50 = 0.4 µM) and II (IC50 = 10.9 µM), and PKC (IC50 = 0.4 µM), which appears to account for its glycogenic action.2 Itu is also a highly potent inhibitor of ERK2 (Ki = 525 nM), a protein kinase with important roles in cell proliferation.3 Mediated by the inhibition of acetyl-CoA carboxylase, Itu increases fatty acid oxidation activity of the liver at the expense of lipogenesis.4

1. Flückiger-Isler, R.E., and Walter, P. Stimulation of rat liver glycogen synthesis by the adenosine kinase inhibitor 5-iodotubercidin. Biochem J 292 85-91 (1993).

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

3. Fox, T., Coll, J.T., Xie, X., et al. A single amino acid substitution makes ERK2 susceptible to pyridinyl imidazole inhibitors of p38 MAP kinase. Protein Sci 7 2249-2255 (1998).

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).

Synonyms
  • NSC 113939
  • Itu
Formal Name 5-​iodo-​7-​β-​D-​ribofuranosyl-​7H-​pyrrolo[2,​3-​d]pyrimidin-​4-​amine
CAS Number 24386-93-4
Molecular Formula C11H13IN4O4
Formula Weight 392.2
Formulation A solution in ethanol
Purity ≥95%
λmax 207, 284 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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IC1=CN([C@H]​2[C@H]​(O)​[C@H]​(O)​[C@@H]​(CO)​O2)​C3=C1C(N)​=NC=N3
InCHI Code
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​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
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WHSIXKUPQCKWBY-IOSLPCCCSA-N

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Size Price Quantity Subtotal
100 µg $13.00 $0.00
250 µg $29.00 $0.00
1 mg $78.00 $0.00
5 mg $260.00 $0.00
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