2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose
[CAS# 186689-07-6]

Identification

• Classification: API >> Water, electrolyte and acid-base balance regulator >> Glucose drug
• Name: 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose
• Synonyms: 2-NBDG
• Molecular Formula: C₁₂H₁₄N₄O₈
• Molecular Weight: 342.26
• CAS Registry Number: 186689-07-6
• EC Number: 811-648-6
• 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

Properties

• Solubility: Very slightly soluble (0.48 g/L) (25 ºC), Calc.^*
• Density: 1.750±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 740.0±70.0 ºC 760 mmHg (Calc.)^*
• Flash point: 401.3±35.7 ºC (Calc.)^*
• Index of refraction: 1.73 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose is a fluorescent glucose derivative commonly used in biochemical and cellular research to study glucose uptake and metabolism. This compound is structurally based on D-glucose, with the substitution of a 7-nitro-2,1,3-benzoxadiazol-4-yl (NBD) fluorescent moiety attached via an amino linkage at the 2-position in place of the hydroxyl group. This modification enables the molecule to retain properties similar to natural glucose while providing a fluorescent signal for detection.

The compound was developed to provide a sensitive and specific probe for monitoring glucose transport in living cells and tissues. The presence of the NBD group allows the compound to be visualized using fluorescence microscopy or fluorometry, facilitating real-time observation of glucose uptake dynamics. Because glucose transport is fundamental to cellular energy metabolism and is altered in many diseases, including cancer and diabetes, this compound has become a valuable tool in biomedical research.

In application, 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose is frequently used in studies involving glucose transporter function, metabolic activity assays, and the investigation of glucose uptake under various physiological and pathological conditions. It serves as a non-metabolizable glucose analog, meaning that once inside the cell, it is not further processed through glycolysis, allowing researchers to track uptake without confounding downstream metabolic effects.

Its use extends to high-throughput screening of compounds that affect glucose transport, aiding in drug discovery efforts targeting metabolic diseases. The compound is also applied in cancer research, where altered glucose uptake by tumor cells, known as the Warburg effect, can be examined with high spatial and temporal resolution.

The discovery and commercialization of this fluorescent glucose derivative have provided an essential tool for advancing the understanding of glucose biology at the cellular level. Its chemical design ensures compatibility with live-cell imaging techniques and minimal interference with normal cellular processes, making it suitable for both in vitro and in vivo experiments.

Overall, 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose has become a standard reagent in the study of glucose transport mechanisms, metabolic regulation, and disease pathology related to energy metabolism.

References

1996. Evaluation of 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-D-glucose, a new fluorescent derivative of glucose, for viability assessment of yeast Candida albicans. Applied Microbiology and Biotechnology, 46(4).
DOI: 10.1007/bf00166236

2001. Confocal microscopy study of the different patterns of 2-NBDG uptake in rabbit enterocytes in the apical and basal zone. Pfl�gers Archiv - European Journal of Physiology, 443(2).
DOI: 10.1007/s004240100677

2023. Autofluorescence imaging of endogenous metabolic cofactors in response to cytokine stimulation of classically activated macrophages. Cancer & Metabolism, 11(1).
DOI: 10.1186/s40170-023-00325-z