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72987

Sigma-Aldrich

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

≥97% (HPLC)

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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:
186689-07-6
Molecular Weight:
342.26
Beilstein:
7603370
MDL number:
MFCD23135882
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

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A7007A9519SMB00932
2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose ≥97% (HPLC)

Sigma-Aldrich

72987

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

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2-Deoxy-D-glucose 6-phosphate sodium salt ≥98% (HPLC)

Sigma-Aldrich

SMB00932

2-Deoxy-D-glucose 6-phosphate sodium salt

assay

≥97% (HPLC)

assay

≥75%

assay

≥98% (TLC)

assay

≥98% (HPLC)

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

300

Quality Level

200

Quality Level

100

fluorescence

λex 494 nm; λem 551 nm in DMSO

fluorescence

-

fluorescence

-

fluorescence

-

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

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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
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