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Merck
CN

SML4177

2-NBDG

new

≥97% (HPLC), powder, fluorescent glucose analog

Synonym(s):

(2R,3R,4S,5R)-3,4,5,6-Tetrahydroxy-2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)hexanal, 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose, 2 NBDG, 2NBDG

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About This Item

Empirical Formula (Hill Notation):
C12H14N4O8
CAS Number:
186689-07-6
Molecular Weight:
342.26
MDL number:
MFCD23135882

Key Documents

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Quality Level

100

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

General description

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 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.

Application

2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)-amino]-D-glucose (2-NBDG)maybe used as a surrogate reagent to visualize glucose uptake in live cells andtissues for metabolic studies.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000453751
0000453751
0000443372
0000443372

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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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