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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

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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’.

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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
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
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
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
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