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Merck

72987

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
UNSPSC Code:
12352108
NACRES:
NA.32
PubChem Substance ID:
329764517
MDL number:
MFCD23135882
Beilstein/REAXYS Number:
7603370

Key Documents

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Product Name

2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose, ≥97% (HPLC)

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

SMILES string

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

InChI key

QUTFFEUUGHUPQC-ILWYWAAHSA-N

biological source

synthetic

assay

≥97% (HPLC)

form

powder

fluorescence

λex 494 nm; λem 551 nm in DMSO

application(s)

cell analysis

storage temp.

−20°C

Quality Level

100

Related Categories

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.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF5523V
WXBF4712V
WXBF3617V
WXBF2242V
BCCK7452

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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
Xiumei Wei et al.
Journal of immunology (Baltimore, Md. : 1950), 203(5), 1172-1188 (2019-07-28)
T cells suddenly appeared in jawed fish ∼450 million years ago. Biological studies of fish T cells may provide helpful evidence to understand evolution of adaptive immune systems. To this end, using a Nile tilapia (Oreochromis niloticus) model, we revealed
Sun-Young Yoon et al.
Bioorganic chemistry, 90, 103087-103087 (2019-07-10)
Natural products as antidiabetic agents have been shown to stimulate insulin signaling via the inhibition of the protein tyrosine phosphatases relevant to insulin resistance. Previously, we have identified PTPN9 and DUSP9 as potential antidiabetic targets and a multi-targeting natural product
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
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