2-NBDG

2-NBDG

Names
IUPAC name D-Glucose, 2-deoxy-2-((7-nitro-2,1,3-benzoxadiazol-4-yl)amino)-
Other names 2-NBD Glucose
Identifiers
CAS Number	186689-07-6
3D model (Jmol)	Interactive image
ChemSpider	5143305
PubChem	6711157
InChI InChI=1S/C12H14N4O8/c17-3-6(11(20)12(21)8(19)4-18)13-5-1-2-7(16(22)23)10-9(5)14-24-15-10/h1-3,6,8,11-13,18-21H,4H2/t6-,8+,11+,12+/m0/s1 Key: QUTFFEUUGHUPQC-ILWYWAAHSA-N
SMILES O=C([H])[C@H](NC1=CC=C([N+]([O-])=O)C2=NON=C21)[C@H]([C@@H]([C@@H](CO)O)O)O
Properties
Chemical formula	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, the transporter for 2-NBDG is GLUT2.^[5] 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]

Similar to glucose, 2-NBDG is transported according to Michaelis-Menten kinetics. However, transport of 2-NBDG has a lower $V_{\max }$(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.

References

1. 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. PMID 8605231.
2. Yamada K, Saito M, Matsuoka H, Inagaki N (2007). "A real-time method of imaging glucose uptake in single, living mammalian cells". Nat Protoc. 2 (3): 753–62. doi:10.1038/nprot.2007.76. PMID 17406637.
3. Etxeberria E, González P, Tomlinson P, Pozueta-Romero J (2005). "Existence of two parallel mechanisms for glucose uptake in heterotrophic plant cells". J. Exp. Bot. 56 (417): 1905–12. doi:10.1093/jxb/eri185. PMID 15911561.
4. 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.
5. 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.
6. 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.
7. 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.