2-NBDG

vanc changed 2-NBDG 2-NBDG.svg 2-NBDG 2-(7-Nitro-2,1,3-benzoxadiazol-4-yl)-D-glucosamine (2R,3R,4S,5R)-3,4,5,6-Tetrahydroxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanal 2-NBD Glucose correct CAS 186689-07-6 correct FDA JE4F4P486R correct chemspider 6711157 5143305 correct chemspider 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 correct chemspider QUTFFEUUGHUPQC-ILWYWAAHSA-N O=C([H])[C@H](NC1=CC=C([N+]([O-])=O)C2=NON=C21)[C@H]([C@@H]([C@@H](CO)O)O)O C12H14N4O8 342.2646 g/mol 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, 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 10.1016/0304-4165(95)00153-0 8605231 and it is used in cell biology to visualize uptake of glucose by cells.Yamada K, Saito M, Matsuoka H, Inagaki N A real-time method of imaging glucose uptake in single, living mammalian cells Nat Protoc 2 3 753–62 2007 17406637 10.1038/nprot.2007.76 22801727 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 cellsEtxeberria E, González P, Tomlinson P, Pozueta-Romero J Existence of two parallel mechanisms for glucose uptake in heterotrophic plant cells J. Exp. Bot. 56 417 1905–12 2005 15911561 10.1093/jxb/eri185 free Tao J, Diaz RK, Teixeira CR, Hackmann TJ Transport of a Fluorescent Analogue of Glucose (2-NBDG) versus Radiolabeled Sugars by Rumen Bacteria and Escherichia coli Biochemistry 55 18 2578–89 2016 27096355 10.1021/acs.biochem.5b01286 http://www.locus.ufv.br/handle/123456789/18953 subscription 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.Chang HC, Yang SF, Huang CC, Lin TS, Liang PH, Lin CJ, Hsu LC 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 23657801 10.1039/c3mb70060g In mammalian cells, one transporter for 2-NBDG is GLUT2.Yamada K, Nakata M, Horimoto N, Saito M, Matsuoka H, Inagaki N Measurement of glucose uptake and intracellular calcium concentration in single, living pancreatic beta-cells J. Biol. Chem. 275 29 22278–83 2000 10748091 10.1074/jbc.M908048199 free In T cells, 2-NBDG was transported by another, unidentified transporter and it did not match radiolabeled glucose transport.Sinclair LV, Barthelemy C, Cantrell DA Single Cell Glucose Uptake Assays: A Cautionary Tale Immunometabolism 2 4 e200029 2020 32879737 10.20900/immunometab20200029 free 7116014 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.Yoshioka K, Saito M, Oh KB, Nemoto Y, Matsuoka H, Natsume M, Abe H Intracellular fate of 2-NBDG, a fluorescent probe for glucose uptake activity, in Escherichia coli cells Biosci. Biotechnol. Biochem. 60 11 1899–901 1996 8987871 10.1271/bbb.60.1899 free The identity and further metabolism of this non-fluorescent derivative has not been established. References Category:Hexosamines Category:Deoxy sugars Category:Aldohexoses