Chemistry:2-NBDG
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| Names | |
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| IUPAC name
2-(7-Nitro-2,1,3-benzoxadiazol-4-yl)-D-glucosamine
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| Systematic IUPAC name
(2R,3R,4S,5R)-3,4,5,6-Tetrahydroxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanal | |
| Other names
2-NBD Glucose
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
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| Properties | |
| C12H14N4O8 | |
| 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). | |
| Infobox references | |
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,[1] and it is used in cell biology to visualize uptake of glucose by cells.[2] 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[2]
The compound is taken up by a variety of mammalian, plant, and microbial cells[2][3][4] In mammalian cells, one transporter for 2-NBDG is supposed to be GLUT2.,[5] but this has been recently challenged (see below). In bacterial cells, the predominant transporter is the mannose phosphotransferase system.[4] Cells that lack these or other compatible transporters do not take up 2-NBDG.[4][6]
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.[4]
Once taken up, the compound is metabolized to a non-fluorescent derivative, as shown in Escherichia coli.[7] 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[8]
References
- ↑ 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.
- ↑ 2.0 2.1 2.2 "A real-time method of imaging glucose uptake in single, living mammalian cells". Nat Protoc 2 (3): 753–62. 2007. doi:10.1038/nprot.2007.76. PMID 17406637.
- ↑ "Existence of two parallel mechanisms for glucose uptake in heterotrophic plant cells". J. Exp. Bot. 56 (417): 1905–12. 2005. doi:10.1093/jxb/eri185. PMID 15911561.
- ↑ 4.0 4.1 4.2 4.3 "Transport of a Fluorescent Analogue of Glucose (2-NBDG) versus Radiolabeled Sugars by Rumen Bacteria and Escherichia coli". Biochemistry 55 (18): 2578–89. 2016. doi:10.1021/acs.biochem.5b01286. PMID 27096355. http://www.locus.ufv.br/handle/123456789/18953.
- ↑ "Measurement of glucose uptake and intracellular calcium concentration in single, living pancreatic beta-cells". J. Biol. Chem. 275 (29): 22278–83. 2000. doi:10.1074/jbc.M908048199. PMID 10748091.
- ↑ "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. 2013. doi:10.1039/c3mb70060g. PMID 23657801.
- ↑ "Intracellular fate of 2-NBDG, a fluorescent probe for glucose uptake activity, in Escherichia coli cells". Biosci. Biotechnol. Biochem. 60 (11): 1899–901. 1996. doi:10.1271/bbb.60.1899. PMID 8987871.
- ↑ "Single Cell Glucose Uptake Assays: A Cautionary Tale". Immunometabolism 2 (4): e200029. 2020. doi:10.20900/immunometab20200029. PMID 32879737.
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