2-NBDG

2-NBDG 2-NBDG is a fluorescently-labeled deoxyglucose analog that is used primarily to directly monitor glucose uptake by living cells and tissues. It is also used as a topical contrast reagent for the detection of neoplasia. 2-NBDG can be used in real-time confocal, high-resolution, or wide-field fluorescence microscopy as well as in flow cytometry. The probe can be excited by the Argon laser at 488 nm to give the environment-sensitive fluorescence. It has lower photostability than the rhodamine-based fluorescent probes. Fluorescently-labeled deoxyglucose analog, used to directly monitor glucose uptake by living cells and tissues. Also used as a topical contrast reagent for the detection of neoplasia. Uptake can be monitored by real-time confocal, high-resolution or wide-field fluorescence microscopy and flow cytometry. 2-NBDG is a fluorescent derivative of glucose whose uptake is competitively inhibited by D-glucose, but not L-glucose or sucrose, in E. coli. It has been used to monitor glucose uptake by bacteria and live mammalian cells and in tumor biopsies. 2-NBDG displays excitation/emission maxima of 475/550 nm, respectively. 2-NBDG is a fluorescent derivative of glucose whose uptake is competitively inhibited by D-glucose, but not L-glucose or sucrose, in E. coli. It has been used to monitor glucose uptake by bacteria and live mammalian cells and in tumor biopsies. CAS Number 186689-07-6 Product Name (2R,3R,4S,5R)-3,4,5,6-Tetrahydroxy-2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanal IUPAC Name (2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanal Molecular Formula C12H14N4O8 Molecular Weight 342.26 g/mol 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 InChI Key QUTFFEUUGHUPQC-ILWYWAAHSA-N SMILES C1=C(C2=NON=C2C(=C1)[N+](=O)[O-])NC(C=O)C(C(C(CO)O)O)O Solubility Soluble in DMSO Synonyms 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxy-D-glucose, 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose, 2-deoxy-2-((7-nitro-2,1,3-benzoxadiazol-4-yl)amino)-D-glucose, 2-NBDG Canonical SMILES C1=C(C2=NON=C2C(=C1)[N+](=O)[O-])NC(C=O)C(C(C(CO)O)O)O Isomeric SMILES C1=C(C2=NON=C2C(=C1)[N+](=O)[O-])N[C@@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O