Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

72987

Sigma-Aldrich

2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose

≥97% (HPLC)

Synonym(s):

2-NBDG, 2-[N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-D-glucose

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C12H14N4O8
CAS Number:
186689-07-6
Molecular Weight:
342.26
Beilstein:
7603370
MDL number:
MFCD23135882
UNSPSC Code:
12352108
PubChem Substance ID:
329764517
NACRES:
NA.32

biological source

synthetic

Quality Level

100

Assay

≥97% (HPLC)

form

powder

fluorescence

λex 494 nm; λem 551 nm in DMSO

application(s)

cell analysis

storage temp.

−20°C

SMILES string

OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](Nc1ccc([N+]([O-])=O)c2nonc12)C=O

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

General description

2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl) amino]-D-glucose, also known as 2-NBDG, is a fluorescent D-glucose analog. The consequent fluorescent activity is detected by flow cytometry. 2-NBDG is incubated directly with the test sample for uptake, followed by measurement.

Application

2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl) amino]-D-glucose is used as a fluorescent indicator for direct glucose uptake measurement. 2-NBDG is used as a fluorescent deoxyglucose analog to study the tumor cells. For in vivo imaging of epileptic activity experiments, 2-NBDG is used as a fluorescent deoxyglucose analog.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Roger G O'Neil et al.
Molecular imaging and biology, 7(6), 388-392 (2005-11-15)
A new fluorescent analog of D -glucose was recently developed by [Yoshioka K, Takahashi H, Homma T, Sato M, Ki Bong O, Nemoto Y, Matsuoka H (1996) A novel fluorescent derivative of glucose applicable to the assessment of glucose uptake
Terumasa Umemoto et al.
The Journal of experimental medicine, 215(8), 2097-2113 (2018-06-28)
Most of the hematopoietic stem cells (HSCs) within the bone marrow (BM) show quiescent state with a low mitochondrial membrane potential (ΔΨm). In contrast, upon stress hematopoiesis, HSCs actively start to divide. However, the underlying mechanism for the initiation of
Han-Wei Tan et al.
International journal of cancer, 145(7), 1860-1873 (2019-03-06)
Accumulating evidence illustrates the significance of cell plasticity in the molecular biology of liver cancer. Reprogramming of mature parenchymal cells to a less differentiated state by key molecular targets contributes to the pathogenesis of hepatocellular carcinoma (HCC). Hereby, we investigated
Vassiliy Tsytsarev et al.
Journal of neuroscience methods, 203(1), 136-140 (2011-09-24)
Accurately locating epileptic foci has great importance in advancing the treatment of epilepsy. In this study, epileptic seizures were first induced by intracortical injection of 4-aminopyridine in rats. A fluorescent deoxyglucose substitute, 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose (2-NBDG), was then continuously injected via the
Chenhui Zou et al.
Journal of biochemical and biophysical methods, 64(3), 207-215 (2005-09-27)
Evaluation of glucose uptake ability in cells plays a fundamental role in diabetes mellitus research. In this study, we describe a sensitive and non-radioactive assay for direct and rapid measuring glucose uptake in single, living cells. The assay is based
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service