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5.04817

UK-5099

Name: UK-5099
Brand: MM

≥99% (HPLC), solid, mitochondrial pyruvate carrier inhibitor, Calbiochem

Synonym(s):

Mitochondrial Pyruvate Carrier Inhibitor, UK5099, ( E)-2-Cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid, ( E)-2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic acid, MPC Inhibitor, PF-1005023, (E)-2-Cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid, (E)-2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic acid, MPC Inhibitor, PF-1005023

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₁₂N₂O₂

CAS Number:

56396-35-1

Molecular Weight:

288.30

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD19443867

Assay:

≥99% (HPLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze, protect from light

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Properties

Product Name

Mitochondrial Pyruvate Carrier Inhibitor, UK5099,

assay

≥99% (HPLC)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

bright yellow

solubility

DMSO: 100 mg/mL

storage temp.

2-8°C

SMILES string

[n]2(c3c(c(c2)\C=C(\C(=O)O)/C#N)cccc3)c1ccccc1

InChI

1S/C18H12N2O2/c19-11-13(18(21)22)10-14-12-20(15-6-2-1-3-7-15)17-9-5-4-8-16(14)17/h1-10,12H,(H,21,22)/b13-10+

InChI key

BIZNHCWFGNKBBZ-JLHYYAGUSA-N

Description

General description

A cell-permeable α-cyanocinnamate compound that acts as a rapid, active site thiol modifying, time-dependent and non-competitive inhibitor of bi-directional pyruvate transport across plasma membranes in yeast, bacteria, Drosophila, and humans (IC₅₀ = 50 nM in rat heart mitochondria; K_i ≤ 1 µM) with excellent selectivity over monocarboxylates and anions. Shown to significantly decrease pyruvate-driven respiration, enhance glucose uptake and activate AMPK (2 µM in human myocytes and skeletal muscle myotubes).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
mitochondria

Reversible: no

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C or -70°C). Stock solutions are stable for up to 2 weeks at -20°C or for up to 6 weeks at -70°C.

Use only fresh DMSO for reconstitution.

Other Notes

Divakaruni, A.S., et al. 2013. Proc. Natl. acad. Sci. USA110, 5422.
Bricker, D.K., et al. 2012. Science337, 96.
Herzig, S., et al. 2012. Science337, 93.
Hinoi, E., et al. 2006. Mol. Pharmacol.70, 925.
Hildyard, J.C.W., et al. 2005. Biochim. Biophys. Acta1707, 221.
Halestrap, A.P. 1978. Biochem. J.172, 377.
Halestrap, A.P. 1975. Biochem. J.145, 85.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c