5-Iodotubercidin (Synonyms: Itu, NSC 113939) |
| Katalog-Nr.GC14801 |
An adenosine kinase inhibitor
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 24386-93-4
Sample solution is provided at 25 µL, 10mM.
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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 μmol/g cell wet mass, respectively; while control incubation at 0.27 ± 0.05 and 2.25 ± 0.33 μmol/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]. 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., 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.
| Cell experiment [1]: | |
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Cell lines |
MEFs and HCT116 cells |
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Preparation method |
The solubility of this compound in DMSO is > 10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months. |
|
Reacting condition |
0 ~ 2.5 μM; 8 hrs |
|
Applications |
In both MEFs and HCT116 cells, 5-Iodotubercidin up-regulated p53 expression. Moreover, dosage experiments indicated that 5-Iodotubercidin was able to up-regulate p53 expression at the concentration as low as 0.25 μM. In HCT116 cells with ADK knocked out, the decrease of ADK levels did not significantly change the protein levels of p53, which indicated that 5-Iodotubercidin-induced p53 upregulation was not contributed to direct inhibition of ADK. |
| Animal experiment [1]: | |
|
Animal models |
Nude mice bearing HCT116 cells |
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Dosage form |
0.625 or 2.5 mg/kg; i.p. |
|
Applications |
In nude mice bearing HCT116 cells, 5-Iodotubercidin at 2.5 mg/kg induced rapid tumor regression. However, 5-Iodotubercidin treatment also decreased the body weight of mice (a reduction of 6% at the end of treatment). Moreover, 5-Iodotubercidin showed inhibition on p53-/- HCT116-initiated tumors as well. At a lower dose of 0.625 mg/kg, 5-Iodotubercidin still showed an inhibition effect on tumor growth but p53-/- HCT116 exhibited resistance to 5-Iodotubercidin. |
|
Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
|
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. | |
| Cas No. | 24386-93-4 | SDF | |
| Überlieferungen | Itu, NSC 113939 | ||
| Chemical Name | (2R,3R,4S,5R)-2-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol | ||
| Canonical SMILES | C1=C(C2=C(N1C3C(C(C(O3)CO)O)O)N=CN=C2N)I | ||
| Formula | C11H13IN4O4 | M.Wt | 392.15 |
| Löslichkeit | <0.78 mg/mL in DMSO, <2.91 mg/mL in EtOH, <2.28 mg/mL in Water | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.55 mL | 12.7502 mL | 25.5004 mL |
| 5 mM | 0.51 mL | 2.55 mL | 5.1001 mL |
| 10 mM | 0.255 mL | 1.275 mL | 2.55 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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