2-cyano-3-(1-phenylindol-3-yl)acrylate Property

Melting point:

235-238°C

Boiling point:

448.6±45.0 °C(Predicted)

Density 

1.20

storage temp. 

2-8°C

solubility 

DMSO: >20mg/mL

form 

powder

pka

1.49±0.19(Predicted)

color 

yellow to tan

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

InChIKey

BIZNHCWFGNKBBZ-JLHYYAGUSA-M

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

2-cyano-3-(1-phenylindol-3-yl)acrylate Chemical Properties,Usage,Production

Description

UK-5099 (56396-35-1) is a potent inhibitor of the mitochondrial pyruvate carrier (MPC).1?Rapidly increases glucose uptake in human monocytes.2?Attenuates mitochondrial oxidative phosphorylation and increases glycolysis creating greater stem-like properties in LnCap prostate cancer cells.3?Blocks the neuroprotective action of L-lactate or pyruvate during glutamate-induced excitotoxicity.4?Inhibits pyruvate transport across the plasma membrane of trypanosomes (Ki=49 μM).5

Chemical Properties

Yellow Solid

Uses

Pyruvate transport into mitochondria is facilitated by mitochondrial pyruvate carrier (MPC) 1 and 2, two small transmembrane proteins that are part of a larger 150 kDa protein transport complex in the inner mitochondrial membrane. UK 5099 is a specific and potent inhibitor of MPC carrier activity. It potently inhibits pyruvate-dependent oxygen consumption by rat heart mitochondria with an IC50 value of 50 nM.

Uses

UK-5099 has been used:

• as a mitochondrial pyruvate blocker to reduce pyruvate transportation into mitochondria in Roswell park memorial institute (RPMI) 1640 medium for prostatic cancer cell line culture
• in dimethyl sulfoxide (DMSO) stock, to study the effect of inhibiting pyruvate transport into mitochondria on pro-inflammatory responses in lipopolysaccharide activated macrophages
• in topical treatment in order to study its effect on hair cycle induction in experimental mice

Uses

Inhibitor of plasma membrane monocarboxylate transporters (MCTs) and the mitochondrial pyruvate carrier (MPC).

Biochem/physiol Actions

UK-5099 induces lactate generation.

storage

Store at +4°C

References

1) Shearman and Halestrap (1984), The concentration of the mitochondrial pyruvate carrier in rat liver and heart mitochondria determined with alpha-cyano-beta-(1-phenylindol-3-yl)acrylate; Biochem. J.,?223?673 2) Divakaruni?et al.?(2013),?Thiazolidinediones are acute, specific inhibitors of the mitochondrial pyruvate carrier.; Proc. Natl. Acad. Sci. USA,?110?5422 3) Zhong?et al. (2015),?Application of mitochondrial pyruvate carrier blocker UK5099 creates metabolic reprogram and greater stem-like properties in LnCap prostate cancer cells in vitro; Oncotarget,?6?37758 4) Jourdain?et al. (2016),?L-Lactate protects neurons against excitotoxicity: implication of an ATP-mediated signaling cascade; Sci. Rep.,?6?21250 5) Wiemer?et al.?(1995),?The inhibition of pyruvate transport across the plasma membrane of the bloodstream form of Trypanosoma brucei and its metabolic implications; Biochem. J.,?312?479