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About This Item
Empirical Formula (Hill Notation):
C12H14N4O8
CAS Number:
Molecular Weight:
342.26
MDL number:
NACRES:
NA.21
Quality Level
Assay
≥97% (HPLC)
form
powder
color
, Faint yellow to dark brown
solubility
H2O: 2 mg/mL, clear (Warmed)
storage temp.
-10 to -25°C
SMILES string
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC(C1=NON=C12)=CC=C2[N+]([O-])=O
Application
2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)-amino]-D-glucose (2-NBDG) may be used as a surrogate reagent to visualize glucose uptake in live cells and tissues for metabolic studies.
Biochem/physiol Actions
2-NBDG, a fluorescent 2-deoxyglucose analog (excitation/emission: ~470/545 nm), supplied as a mixture of α-and β-anomers, enters cells via GLUT transporters, competing with D-glucose. Intracellularly, hexokinase phosphorylates 2-NBDG at C-6, mimicking the first step of glycolysis, before it degrades to a non-fluorescent derivative. This sensitive fluorescent non-toxic tracer illuminates glucose uptake in diverse cell types (e.g., adipocytes, myocytes, tumor cells), offering insights into glycolytic flux, mitochondrial activity, and overall cellular energetics. Compatible with confocal microscopy, flow cytometry, and spectrofluorometry, 2-NBDG (typically used at 10 μM, 37°C, 60 min) enables real-time monitoring of glucose transport kinetics and metabolic dynamics in various biological systems, from insulin-responsive tissues to cancer models.
Features and Benefits
- offers a balance of ease of use
- non-toxicity
- compatibility with common research techniques
- serves as a valuable tool for studying cellular glucose uptake, utilization, and metabolism in various cell types
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Lucas J D'Souza et al.
PloS one, 17(8), e0261801-e0261801 (2022-08-25)
The fluorescent derivative of glucose, 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)-amino]-D-glucose (2NBDG), is a widely used surrogate reagent to visualize glucose uptake in live cells at single cell resolution. Using CRISPR-Cas9 gene editing in 5TGM1 myeloma cells, we demonstrate that ablation of the glucose transporter
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