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

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.

InChI

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)

InChIKey

BIZNHCWFGNKBBZ-JLHYYAGUSA-M

SMILES

C(O)(=O)C(C#N)=CC1C2=C(N(C3=CC=CC=C3)C=1)C=CC=C2

Safety Information

WGK Germany 

3

Storage Class

11 - Combustible Solids

2-cyano-3-(1-phenylindol-3-yl)acrylate Usage And Synthesis

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] M S SHEARMAN  A P H. The concentration of the mitochondrial pyruvate carrier in rat liver and heart mitochondria determined with alpha-cyano-beta-(1-phenylindol-3-yl)acrylate.[J]. Biochemical Journal, 1984, 223 3: 673-676. DOI:10.1042/bj2230673
[2] AJIT S DIVAKARUNI. Thiazolidinediones are acute, specific inhibitors of the mitochondrial pyruvate carrier.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2013, 110 14: 5422-5427. DOI:10.1073/pnas.1303360110
[3] YALI ZHONG. Application of mitochondrial pyruvate carrier blocker UK5099 creates metabolic reprogram and greater stem-like properties in LnCap prostate cancer cells in vitro.[J]. Oncotarget, 2015, 6 35: 37758-37769. DOI:10.18632/oncotarget.5386
[4] P. JOURDAIN. L-Lactate protects neurons against excitotoxicity: implication of an ATP-mediated signaling cascade[J]. Scientific Reports, 2016, 6 1. DOI:10.1038/srep21250
[5] E A WIEMER  F R O  P A Michels. The inhibition of pyruvate transport across the plasma membrane of the bloodstream form of Trypanosoma brucei and its metabolic implications.[J]. Biochemical Journal, 1995, 312 ( Pt 2): 479-484. DOI:10.1042/bj3120479

2-cyano-3-(1-phenylindol-3-yl)acrylate(56396-35-1)Related Product Information

• MITOQ
• 2-HEPTYL-4-HYDROXYQUINOLINE N-OXIDE
• Vanillylidenacetone
• UK-371804