| Identification | Back Directory | [Name]
2-cyano-3-(1-phenylindol-3-yl)acrylate | [CAS]
56396-35-1 | [Synonyms]
CS-748
UK 5099
PF-1005023
PF-06340678
BIZNHCWFGNKBBZ-JLHYYAGUSA-N
2-cyano-3-(1-phenylindol-3-yl)acrylate
Mitochondrial Pyruvate Carrier Inhibitor, UK5099
PF-1005023; UK5099; UK 5099; PF1005023; PF 1005023
(E)-2-cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid
2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoicacid
2-Propenoic acid, 2-cyano-3-(1-phenyl-1H-indol-3-yl)-
Mitochondrial Pyruvate Carrier Inhibitor, UK5099 - CAS 56396-35-1 - Calbiochem | [Molecular Formula]
C18H12N2O2 | [MDL Number]
MFCD19443867 | [MOL File]
56396-35-1.mol | [Molecular Weight]
288.3 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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]
Inhibitor of plasma membrane monocarboxylate transporters (MCTs) and the mitochondrial pyruvate carrier (MPC). | [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. | [Biochem/physiol Actions]
UK-5099 induces lactate generation. | [storage]
Store at -20°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 |
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