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| | 5-IODOTUBERCIDIN Basic information |
| | 5-IODOTUBERCIDIN Chemical Properties |
| Melting point | 216-217°C dec. | | Boiling point | 701.5±60.0 °C(Predicted) | | density | 2.49±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | 0.1 M HCl: 0.7 mg/mL | | pka | 12.33±0.70(Predicted) | | form | solid | | color | tan | | Stability: | Store tightly sealed at 4°C; Light Sensitive | | InChIKey | WHSIXKUPQCKWBY-IOSLPCCCSA-N | | CAS DataBase Reference | 24386-93-4 |
| WGK Germany | 3 | | HS Code | 29349990 |
| | 5-IODOTUBERCIDIN Usage And Synthesis |
| Chemical Properties | Tan Solid | | Uses | An analogue of the antibiotic tubercidin, a pyrrolo[2,3-d]pyrimidine nucleoside antibiotic. A potent inhibitor of adenosine kinase from rat or guinea pig brain. Inhibits uptake of 3H-adenosine into brain slices. | | Uses | A potent and competitive inhibitor of ERK2, PKA, and ADK. | | Uses | 5-Iodotubercidin has been used for the inhibition of retinoblastoma cells, astroglial cultures and for the inhibition of adenosine kinase in human umbilical vein endothelial cells (HUVECs). | | General Description | solubility: 10 mg/mL in DMSO | | Biological Activity | Potent adenosine kinase inhibitor (IC 50 = 26 nM) and nucleoside transporter inhibitor (IC 50 values are 7, 15 and < 25 nM for inhibition of [ 3 H]-uridine, [ 3 H]-formycin B and [ 3 H]-adenosine uptake respectively). Strongly stimulates glycogen synthesis in hepatocytes via activation of glycogen synthase. Also inhibits CK1, insulin receptor tyrosine kinase, phosphorylase kinase, PKA, CK2 and PKC (IC 50 values are 0.4, 3.5, 5-10, 5-10, 10.9 and 27.7 μ M respectively). | | Biochem/physiol Actions | Potent inhibitor of adenosine uptake into brain, and of adenosine kinase and subsequent metabolism of adenine nucleotides. In cultured rat hepatocytes, 5-iodotubercidin inhibits both acetyl-CoA carboxylase and de novo synthesis of fatty acids and cholesterol. | | storage | Store at -20°C | | 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. |
| | 5-IODOTUBERCIDIN Preparation Products And Raw materials |
| Raw materials | α-D-Ribofuranosyl chloride, 5-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)--->7H-Pyrrolo[2,3-d]pyrimidine,4-chloro-5-iodo-7-b-D-ribofuranosyl--->4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine-->5-O-TERT-BUTYLDIMETHYLSILYL-2,3-O-ISOPROPYLIDENE-D-RIBOFURANOSE-->7H-Pyrrolo[2,3-d]pyriMidine, 4-chloro-5-iodo-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)--->TUBERCIDIN-->4-Chloro-7H-pyrrolo[2,3-d]pyrimidine |
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