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24386-93-4

24386-93-4 structure
24386-93-4 structure
Name 5-iodotubercidin
Synonyms 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 5-iodo-7-β-D-ribofuranosyl-
MFCD00055131
5-Iodo-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
5-Iodotubercidin
5-Iodotubericidin
Description 5-Iodotubercidin is a potent adenosine kinase inhibitor with IC50 of 26 nM.
Related Catalog
Target

IC50: 26 nM (adenosine kinase)

In Vitro 5-Iodotubercidin (40 μM) enhances the rate of phosphorylase inactivation and shortens the lag before the activation of glycogen synthase. 5-Iodotubercidin (50 μM) antagonizes the effects of glucagon and vasopressin, but does not affect the basal concentration of free calcium in single hepatocytes[1]. 5-Iodotubercidin (20 μM) causes an important decrease in ATP concentration, and a concomitant smaller increase in AMP concentration. 5-Iodotubercidin decreases the activity of ACC and the rates of synthesis of fatty acids and cholesterol. In line with the iodotubercidin-mediated inhibition of ACC, 5-iodotubercidin induces a marked decrease in the intracellular concentration of malonyl-CoA[3]. 5-Iodotubercidin causes a strong decrease in the immunofluorescence levels of P-T3-H3, and depletion of P-T3-H3 is complete at 10 µM 5-5-iodotubercidin[4].
In Vivo 5-Iodotubercidin (1 mL/kg, i.p.) is in agreement with activity observed against bicuculline-induced seizures following local administration of the AKI into the prepiriform cortex[2].
Kinase Assay AK activity is measured in a radiochemical assay. The final reaction volume is 100 µL and contained 70 mM Tris-maleate (pH 7.0), 0.1% (w/v) bovine serum albumin, 1.0 mM MgCl2, 1.0 mM ATP, 1.0 µM [U-14C]adenosine (400-600 mCi/mmol) and various inhibitor concentrations. Inhibitors are prepared as 10 mM stock solutions in DMSO. The final DMSO concentration in the assay is 5% (v/v). Eleven different concentration of the test solutions ranging from 0.001 to 10.0 µM are utilized to determine a dose response curve of the inhibition of the enzyme. Reactions are started by adding the appropriate amount of purified human recombinant AK and incubated for 20 min at 37°C. The reactions are terminated by addition of the potent AKI GP3269. A 30-µL aliquot of each reaction is spotted on DEAE cellulose filter paper (cut in squares of appr 1×1 cm) and air-dried for 30 min. The dry filters are then washed for 3 min in deionized water to remove residual [U-14C]adenosine, rinsed with ethanol and dried at 90°C for 20 min. The filter papers are counted in 5.5 mL of Ready Safe liquid scintillation cocktail using a Beckman LS3801 scintillation counter. Control AK activity is determined from the amount of [14C]AMP formed in the presence of 5% DMSO. The concentration of inhibitor required to inhibit 50% of the AK activity (IC50) is determined graphically from plots of inhibitor concentration versus percent (%) control enzyme activity.
Cell Assay HeLa cells are grown in DME supplemented with 10% fetal bovine serum (FBS) and 2 mM l-glutamine. Nocodazole is used at a concentration of 3.3 µM unless differently specified. Thymidine (2.5 mM) is used in the asssay. For transfection, FuGENE 6 Transfection Agent is used at a 3:1 ratio with plasmid DNA. Cells are analyzed 24-48 h after transfection.
Animal Admin Male SA rats (100-150 g) are maintained on a 12:12 light:dark cycle in temperaturecontrolled facilities with free access to food and water. One hour prior to seizure testing, the animals are injected intraperitoneally (1 mL/kg) with DMSO vehicle or with test compound dissolved in DMSO. At the time of the test, an electrolyte solution (2% lidocaine in 0.9% sodium chloride) is applied to the eyes. Maximal electroshock seizures are induced by administering a 60-Hz current of 150 mA for 0.2 s via corneal electrodes, using a Wahlquist Model H stimulator. The endpoint measured is suppression of hindlimb tonic extension (HTE) and expressed as percentage of animals in which the response is inhibited. At this supramaximal stimulation level, virtually 100% of control (vehicle-treated) animals show HTE. ED50 values are calculated from a dose-response curve using probit analysis. The N for the screening doses is 6-8; doseresponse determinations are conducted with at least 5 animals/dose.
References

[1]. Massillon D, et al. Identification of the glycogenic compound 5-iodotubercidin as a general protein kinase inhibitor. Biochem J. 1994 Apr 1;299 (Pt 1):123-8.

[2]. Ugarkar BG, et al. Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues. J Med Chem. 2000 Jul 27;43(15):2883-93.

[3]. García-Villafranca J, et al. Effects of 5-iodotubercidin on hepatic fatty acid metabolism mediated by the inhibition of acetyl-CoA carboxylase. Biochem Pharmacol. 2002 Jun 1;63(11):1997-2000.

[4]. De Antoni A, et al. A small-molecule inhibitor of Haspin alters the kinetochore functions of Aurora B. J Cell Biol. 2012 Oct 15;199(2):269-84.

[5]. Acharya MM, et al. Adenosine Kinase Inhibition Protects against Cranial Radiation-Induced Cognitive Dysfunction. Front Mol Neurosci. 2016 Jun 3;9:42.
Density 2.5±0.1 g/cm3
Boiling Point 701.5±60.0 °C at 760 mmHg
Melting Point 216-217ºC dec.
Molecular Formula C11H13IN4O4
Molecular Weight 392.150
Flash Point 378.0±32.9 °C
Exact Mass 391.998138
PSA 126.65000
LogP 0.91
Vapour Pressure 0.0±2.3 mmHg at 25°C
Index of Refraction 1.919
Storage condition 2-8°C
Stability Store tightly sealed at 4°C; Light Sensitive
Water Solubility 0.1 M HCl: 0.7 mg/mL
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2934999090
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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