UK 5099
| Code | Size | Price |
|---|
| AG-CR1-3691-M001 | 1 mg | £40.00 |
Quantity:
| AG-CR1-3691-M005 | 5 mg | £100.00 |
Quantity:
| AG-CR1-3691-M010 | 10 mg | £145.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Target Species: Universal
Shipping:
AMBIENT
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
PF-1005023; 2-Cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic acid
Appearance:
Off-white to yellow solid.
CAS:
56396-35-1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Keep cool and dry.Protect from light.
Hazards:
H312, H317, H319, H335
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)/b13-10+
InChiKey:
BIZNHCWFGNKBBZ-JLHYYAGUSA-N
Long Description:
Chemical. CAS: 56396-35-1. Formula: C18H12N2O2. MW: 288.3. . Potent and specific inhibitor of the mitochondrial pyruvate carrier (MPC), blocking pyruvate from entering the mitochondria, consequently promoting lactate production. Inhibitor of tricarboxylic acid (TCA) cycle. Plasma membrane monocarboxylate transporters (MCTs) inhibitor, but with Ki values some two or three orders of magnitude higher than those for the inhibition of the MPC. Inhibits mitochondrial lactate and pyruvate transport. Decreases glycolysis. Useful agent for immunometabolism research.
MDL:
MFCD19443867
Molecular Formula:
C18H12N2O2
Molecular Weight:
288.3
Package Type:
Vial
Precautions:
P302+P352, P304+P340, P305+P351+P338
Product Description:
Potent and specific inhibitor of the mitochondrial pyruvate carrier (MPC), blocking pyruvate from entering the mitochondria, consequently promoting lactate production. Inhibitor of tricarboxylic acid (TCA) cycle. Plasma membrane monocarboxylate transporters (MCTs) inhibitor, but with Ki values some two or three orders of magnitude higher than those for the inhibition of the MPC. Inhibits mitochondrial lactate and pyruvate transport. Decreases glycolysis. Useful agent for immunometabolism research.
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
N#C/C(C(O)=O)=CC1=CN(C2=CC=CC=C2)C3=CC=CC=C31
Solubility Chemicals:
Soluble in DMSO (20mg/ml) or DMF (10mg/ml). Sparingly soluble in aqueous buffers.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
The concentration of the mitochondrial pyruvate carrier in rat liver and heart mitochondria determined with alpha-cyano-beta-(1-phenylindol-3-yl)acrylate: M.S. Shearman & A.P. Halestrap; Biochem. J. 223, 673 (1984) | The inhibition of pyruvate transport across the plasma membrane of the bloodstream form of Trypanosoma brucei and its metabolic implications: E.A. Wiemer, et al.; Biochem. J. 312, 479 (1995) | Identification of the mitochondrial pyruvate carrier in Saccharomyces cerevisiae: J.C.W. Hildyard, et al.; Biochem, J. 374, 607 (2003) | A molecular mechanism of pyruvate protection against cytotoxicity of reactive oxygen species in osteoblasts: E. Hinoi, et al.; Mol. Pharmacol. 70, 925 (2006) | Thiazolidinediones are acute, specific inhibitors of the mitochondrial pyruvate carrier: A.S. Divakaruni, et al.; PNAS 110, 5422 (2013) | Mitochondrial metabolism of pyruvate is essential for regulating glucose-stimulated insulin secretion: J.N. Patterson, et al.; J. Biol. Chem. 289, 13335 (2014) | Application of mitochondrial pyruvate carrier blocker UK5099 creates metabolic reprogram and greater stem-like properties in LnCap prostate cancer cells in vitro: Y. Zhong, et al.; Oncotarget 6, 37758 (2015) | A guide to immunometabolism for immunologists: L.A. O'Neill, et al.; Nat. Rev. Immunol. 16, 553 (2016) (Review) | ERRalpha-Regulated Lactate Metabolism Contributes to Resistance to Targeted Therapies in Breast Cancer: S. Park, et al.; Cell Rep. 15, 323 (2016) | Inhibition of the mitochondrial pyruvate carrier protects from excitotoxic neuronal death: A.S. Divakaruni, et al.; J. Cell Biol. 216, 1091 (2017) | Lactate dehydrogenase activity drives hair follicle stem cell activation: A. Flores, et al.; Nat. Cell Biol. 19, 1017 (2017) | E3 Ligase VHL Promotes Group 2 Innate Lymphoid Cell Maturation and Function via Glycolysis Inhibition and Induction of Interleukin-33 Receptor: Q. Li, et al.; Immunity 48, 258 (2018)
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