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400035

Sigma-Aldrich

Glucose Transporter Inhibitor II

The Glucose Transporter Inhibitor II controls the biological activity of Glucose Transporter.

Synonym(s):

Glucose Transporter Inhibitor II, ( Z)-5-(4-Hydroxy-3-trifluoromethyl-benzylidene)-3-(4,4,4-trifluoro-2-methyl-2-(2,2,2-trifluoroethyl)-butyl)-thiazolidine-2,4-dione

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About This Item

Empirical Formula (Hill Notation):
C18H14F9NO3S
CAS Number:
Molecular Weight:
495.36
UNSPSC Code:
12352200

Quality Level

assay

≥99% (HPLC)

form

powder

potency

2 μM IC50

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 10 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

O=C1N(CC(CC(F)(F)F)(C)CC(F)(F)F)C(S/C1=C\C2=CC=C(O)C(C(F)(F)F)=C2)=O

General description

A cell-permeable thiazolidinedione compound that is shown to reversibly block glucose uptake in androgen-sensitive human prostate adenocarcinoma (LNCaP) cells transfected with GLUT1 (IC50 = 2 µM). Blocks GLUT3, GLUT4, and GLUT9-mediated transport at higher concentration (IC50 ≥ 5 µM). Binds to GLUT1 at a site that is distinct from the glucose binding site. Selectively reduces proliferation (IC50 = 2.0 µM) and induces apoptosis (IC50 = 2.5 µM) in LNCaP cells without affecting normal human prostate epithelial cells and mammary epithelial cells (~ 10 µM). Shown to elicit energy restriction-associated cellular responses in LNCaP cells, such as β-TrCP facilitated protein degradation, activation of AMP-activated kinase, and endoplasmic reticulum stress.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
glucose transporter
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C. Use only fresh DMSO.

Other Notes

Wang, D-S., et al. 2012, J. Med. Chem.55, 3827.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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