5-Iodotubercidin

Short Summary : Adenosine kinase inhibitor,potent

Category : GPCR/G protein|Adenosine Kinase

Purity : 0.9826

CAS Number : 24386-93-4

Formula : C11H13IN4O4

Molecular Weight : 392.15

SMILE : C1=C(C2=C(N1C3C(C(C(O3)CO)O)O)N=CN=C2N)I

Solubility : Soluble in DMSO > 10 mM

Storage : Store at -20°C

Description : 5-Iodotubercidin (Itu) is a purine derivative and hence an inhibitor of adenosine kinase with an IC50 value of 26 nM [1]. Adenosine kinase is important in regulating the intracellular and extracellular concentrations of adenosine and hence diverse physiological actions of adenosine [2]. In various cells such as cancer cells, persisted AMPK activation could result in apoptosis [4]. In nude mice with colon carcinoma xenograft, Itu at a dose of 2.5 mg/kg resulted in rapid tumor regression compared with the control group. At the dose of 0.625 mg/kg, Itu still inhibited tumor growth, but p53-/- tumors were resistant to Itu at this lowered dose [1]. In male Wistar rat hepatocytes, incubation with Itu resulted in concentrations of AMP and ATP at 0.39 0.06 and 1.51 0.10 mol/g cell wet mass, respectively; while control incubation at 0.27 0.05 and 2.25 0.33 mol/g cell wet mass, respectively. Addition of 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR) and Itu simultaneously resulted in almost the same effect of Itu alone. It was probable that Itu inhibited adenosine kinase and blocked the synthesis of 5-aminoimidazole-4-carboxamide ribonucleotide (ZMP) from AICAR. ZAM is a structural AMP analogue and hence mimics the effect of AMP on the AMP-activated protein kinase (AMPK) activation [3]. References: [1]. Xin Zhang, Deyong Jia, Huijuan Liu, et al. Identification of 5-Iodotubercidin as a Genotoxic Drug with Anti-Cancer Potential. PLOS ONE, 2013, 8(5):e62527.[2]. Jaoek Park and Radhey S. Gupta. Adenosine: A Key Link between Metabolism and Brain Activity: Adenosine Metabolism, Adenosine Kinase, and Evolution. New York: Springer Science+Business Media, 2013.[3]. Garca-Villafranca J. and Castro J. Effects of 5-iodotubercidin on hepatic fatty acid metabolism mediated by the inhibition of acetyl-CoA carboxylase. Biochem. Pharmacol., 2002, 63(11):1997-2000.[4]. Haiyan Chen, Ji-ping Wang, Richard J. Santen, et al. Adenosine monophosphate activated protein kinase (AMPK), a mediator of estradiol-induced apoptosis in long-term estrogen deprived breast cancer cells. Apoptosis, 2015, 20:821-830.

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