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
Empirical Formula (Hill Notation):
C12H14N4O8
CAS Number:
Molecular Weight:
342.26
Beilstein/REAXYS Number:
7603370
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

biological source

synthetic

assay

≥97% (HPLC)

form

powder

application(s)

cell analysis: suitable

fluorescence

λex 494 nm; λem 551 nm in DMSO

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

Related Categories

Application

fluorescent indicator for monotoring of glucose uptake into living cells

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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...
Danna Bai et al.
Scientific reports, 6, 22068-22068 (2016-02-26)
The leading cause of death in diabetic patients is diabetic cardiomyopathy, in which alteration of Akt signal plays an important role. Inpp5f is recently found to be a negative regulator of Akt signaling, while its expression and function in diabetic...
Stephanie Denk et al.
Journal of immunology (Baltimore, Md. : 1950), 198(12), 4846-4854 (2017-05-12)
During sepsis, excessive activation of the complement system with generation of the anaphylatoxin C5a results in profound disturbances in crucial neutrophil functions. Moreover, because neutrophil activity is highly dependent on intracellular pH (pH
Ai Ushiyama et al.
Biology of reproduction, 100(6), 1482-1491 (2019-02-06)
Despite knowledge that glucose metabolism is essential for the regulation of signaling cascades in the sperm that are pre-assembled into specific areas and function at multistage for fertilization, the physiological roles of glucose in avian sperm are poorly understood. Accumulated...

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