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SML0621

Sigma-Aldrich

WZB-117

≥98% (HPLC)

Synonym(s):

3-Fluoro-1,2-phenylene bis(3-hydroxybenzoate), 3-Hydroxy-benzoic acid 1,1′-(3-fluoro-1,2-phenylene) ester

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About This Item

Empirical Formula (Hill Notation):
C20H13FO6
CAS Number:
1223397-11-2
Molecular Weight:
368.31
MDL number:
MFCD24387113
UNSPSC Code:
12352200
PubChem Substance ID:
329825570
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(C1=CC=CC(O)=C1)OC2=C(F)C=CC=C2OC(C3=CC(O)=CC=C3)=O

InChI

1S/C20H13FO6/c21-16-8-3-9-17(26-19(24)12-4-1-6-14(22)10-12)18(16)27-20(25)13-5-2-7-15(23)11-13/h1-11,22-23H

InChI key

FRSWCCBXIHFKKY-UHFFFAOYSA-N

Application

WZB-117 has been used to study its tumor initiating ability in cancer stem cells. It has also been used to study the effect of glucose antagonists on 2-NBDG (2-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)Amino)-2-Deoxyglucose) uptake.

Biochem/physiol Actions

WBZ 117 is an inhibitor of basal glucose transport in H1299 lung and other cancer cells.
WZB-117 is an irreversible inhibitor. In cancer cells, WZB-117 prevents cell growth by stimulating apoptosis in any glucose concentration. It targets self-renewal and tumor-initiating capacity in cancer stem cells.

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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Masaki Tsuchiya et al.
Communications biology, 7(1), 459-459 (2024-04-17)
Cellular glucose uptake is a key feature reflecting metabolic demand of cells in physiopathological conditions. Fluorophore-conjugated sugar derivatives are widely used for monitoring glucose transporter (GLUT) activity at the single-cell level, but have limitations in in vivo applications. Here, we
Stroma-derived HGF drives metabolic adaptation of colorectal cancer to angiogenesis inhibitors.
Mira A, et al.
Oncotarget, 8(24), 38193-38193 (2017)
Modulation of Glucose Takeup by Glucose Transport on the Isolated OHCs.
Cheng X T, et al.
Neural Plast., 2018, 7-7 (2018)
Lucas J D'Souza et al.
PloS one, 17(8), e0261801-e0261801 (2022-08-25)
The fluorescent derivative of glucose, 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)-amino]-D-glucose (2NBDG), is a widely used surrogate reagent to visualize glucose uptake in live cells at single cell resolution. Using CRISPR-Cas9 gene editing in 5TGM1 myeloma cells, we demonstrate that ablation of the glucose transporter
Meng Wei et al.
Biochemical and biophysical research communications, 503(2), 1154-1159 (2018-06-29)
Like tumour cells, during intraerythrocytic stage, Plasmodium-infected erythrocytes rely completely on glucose absorption from the blood circulation for energy metabolism. Glucose is taken up by glucose transporter 1 (GLUT1) on human red blood cells (RBCs) and glucose transporter 4 (GLUT4)
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