|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||342.2646 g/mol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
2-NBDG is a fluorescent tracer used for monitoring glucose uptake into living cells; it consists of a glucosamine molecule substituted with a 7-nitrobenzofurazan fluorophore at its amine group. It is widely referred to a fluorescent derivative of glucose, and it is used in cell biology to visualize uptake of glucose by cells. Cells that have taken up the compound fluoresce green.
2-NBDG is similar to radiolabeled glucose in that both can be used to detect glucose transport. Unlike radiolabeled glucose, 2-NBDG is compatible with fluorescence techniques such as a fluorescent microscopy, flow cytometry, and fluorimetry
The compound is taken up by a variety of mammalian, plant, and microbial cells In mammalian cells, one transporter for 2-NBDG is supposed to be GLUT2., but this has been recently challenged (see below). In bacterial cells, the predominant transporter is the mannose phosphotransferase system. Cells that lack these or other compatible transporters do not take up 2-NBDG.
Like glucose, 2-NBDG is transported according to Michaelis–Menten kinetics. However, transport of 2-NBDG has a lower Vmax (maximum rate), and thus the rate of transport is generally slower than glucose.
Once taken up, the compound is metabolized to a non-fluorescent derivative, as shown in Escherichia coli. The identity and further metabolism of this non-fluorescent derivative has not been established.
Three articles published between 2020 and 2022 indicate that the uptake of 2-NBDG is independent of Glut transporters and as such, it does not reflect true glucose intake like radiolabeled glucose would
- Yoshioka, K; Takahashi, H; Homma, T; Saito, M; Oh, K; Nemoto, Y; Matsuoka, H (1996). "A novel fluorescent derivative of glucose applicable to the assessment of glucose uptake activity of Escherichia coli". Biochim Biophys Acta. 1289 (1): 5–9. doi:10.1016/0304-4165(95)00153-0. PMID 8605231.
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- Tao J, Diaz RK, Teixeira CR, Hackmann TJ (2016). "Transport of a Fluorescent Analogue of Glucose (2-NBDG) versus Radiolabeled Sugars by Rumen Bacteria and Escherichia coli". Biochemistry. 55 (18): 2578–89. doi:10.1021/acs.biochem.5b01286. PMID 27096355.
- Yamada K, Nakata M, Horimoto N, Saito M, Matsuoka H, Inagaki N (2000). "Measurement of glucose uptake and intracellular calcium concentration in single, living pancreatic beta-cells". J. Biol. Chem. 275 (29): 22278–83. doi:10.1074/jbc.M908048199. PMID 10748091.
- Chang HC, Yang SF, Huang CC, Lin TS, Liang PH, Lin CJ, Hsu LC (2013). "Development of a novel non-radioactive cell-based method for the screening of SGLT1 and SGLT2 inhibitors using 1-NBDG". Mol Biosyst. 9 (8): 2010–20. doi:10.1039/c3mb70060g. PMID 23657801.
- Yoshioka K, Saito M, Oh KB, Nemoto Y, Matsuoka H, Natsume M, Abe H (1996). "Intracellular fate of 2-NBDG, a fluorescent probe for glucose uptake activity, in Escherichia coli cells". Biosci. Biotechnol. Biochem. 60 (11): 1899–901. doi:10.1271/bbb.60.1899. PMID 8987871.
- Sinclair LV, Barthelemy C, Cantrell DA (2020). "Single Cell Glucose Uptake Assays: A Cautionary Tale". Immunometabolism. 2 (4): e200029. doi:10.20900/immunometab20200029. PMID 32879737.