2-NBDG
2-NBDG is a fluorescence-labeled 2-deoxy-glucose analog useful as a tracer for evaluation of cellular glucose metabolism.
Glucose is a necessary source of energy for sustaining cell activities and homeostasis in tissues. Glucose metabolism is an important target in many diseases and changed with the pathological condition, therefore, evaluation of glucose metabolism can be a significant indication in disease progressions.
2-NBDG can be used in many kinds of cells in vitro, such as HepG2 human hepatocarcinoma cells, L6 rat skeletal muscle cells, MCF-7 breast cancer epithelial cells and astrocytes, it is also used in disease models, epilepsy rat, hyperglycemia, diabetes or mouse xenograft model of cancer.
2-NBDG enters cells through glucose transporters and is subsequently phosphorylated by hexokinase and trapped inside cells. Flow cytometric detection of fluorescence produced by cells can be performed to examine 2-NBDG uptake into living cells, and the intracellular concentration of transported 2-NBDG can be measured with a fluorescence microplate assay. It can be detected with a fluorescence imaging microscopy or CCD camera simply as well.
References:
[1]. Zou C, Wang Y, Shen Z. 2-NBDG as a fluorescent indicator for direct glucose uptake measurement[J]. Journal of biochemical and biophysical methods, 2005, 64(3): 207-215.
[2]. O’Neil R G, Wu L, Mullani N. Uptake of a fluorescent deoxyglucose analog (2-NBDG) in tumor cells[J]. Molecular Imaging and Biology, 2005, 7(6): 388-392.
[3]. Tsytsarev V, Maslov K I, Yao J, et al. In vivo imaging of epileptic activity using 2-NBDG, a fluorescent deoxyglucose analog[J]. Journal of neuroscience methods, 2012, 203(1): 136-140.
[4]. Yan Chen, Junjian Zhang, Xiang-yang Zhang, 2-NBDG as a Marker for Detecting Glucose Uptake in Reactive Astrocytes Exposed to Oxygen-Glucose Deprivation In Vitro. J Mol Neurosci (2015) 55:126–130.
[5]. Vassiliy Tsytsareva,b,1,2, Konstantin I. Maslova,1,3, Junjie Yaoa,1,3, et al, In vivo imaging of epileptic activity using 2-NBDG, a fluorescent deoxyglucose analog, J Neurosci Methods. 2012 Jan 15;203(1):136-40.
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| Physical Appearance | A crystalline solid |
| Storage | Store at -20°C |
| M.Wt | 342.26 |
| Cas No. | 186689-07-6 |
| Formula | C12H14N4O8 |
| Solubility | insoluble in DMSO; ≥17.1 mg/mL in H2O with ultrasonic; ≥2.93 mg/mL in EtOH with gentle warming and ultrasonic |
| Chemical Name | (3R,4R,5S,6R)-6-(hydroxymethyl)-3-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)tetrahydro-2H-pyran-2,4,5-triol |
| SDF | Download SDF |
| Canonical SMILES | OC[C@](O1)([H])[C@](O)([H])[C@@](O)([H])[C@](NC2=CC=C(N(=O)=O)C3=NON=C23)([H])C1([H])O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1,2]: | |
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Cell lines |
HepG2 human hepatocarcinoma cells, L6 rat skeletal muscle cells, MCF-7 breast cancer epithelial cells |
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Preparation method |
General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
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Reacting condition |
10 μM for 10 min |
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Applications |
In HepG2 human hepatocarcinoma cells and L6 rat skeletal muscle cells, 2-NBDG concentrations higher than 0.25 mM might show a high degree of self-quenching. 2-NBDG could be used as a fluorescent indicator for direct glucose uptake measurement. In the MCF-7 breast cancer cells, 2-NBDG uptake displayed rapid uptake for the first one to five minutes, then slowed, reaching an apparent maximum uptake near 20–30 minutes. |
| Animal experiment [3]: | |
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Animal models |
Sprague–Dawley male adult rat |
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Dosage form |
200 mg |
|
Application |
2-NBDG can be used for localizing epileptic foci. |
|
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. |
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References: [1]. Zou C, Wang Y, Shen Z. 2-NBDG as a fluorescent indicator for direct glucose uptake measurement[J]. Journal of biochemical and biophysical methods, 2005, 64(3): 207-215. [2]. O’Neil R G, Wu L, Mullani N. Uptake of a fluorescent deoxyglucose analog (2-NBDG) in tumor cells[J]. Molecular Imaging and Biology, 2005, 7(6): 388-392. [3]. Tsytsarev V, Maslov K I, Yao J, et al. In vivo imaging of epileptic activity using 2-NBDG, a fluorescent deoxyglucose analog[J]. Journal of neuroscience methods, 2012, 203(1): 136-140. |
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