2-cyano-3-(1-phenylindol-3-yl)acrylate
- Product Name
- 2-cyano-3-(1-phenylindol-3-yl)acrylate
- CAS No.
- 56396-35-1
- Chemical Name
- 2-cyano-3-(1-phenylindol-3-yl)acrylate
- Synonyms
- CS-748;UK 5099;PF-1005023;PF-06340678;UK-5099 (PF-1005023);BIZNHCWFGNKBBZ-JLHYYAGUSA-N;2-cyano-3-(1-phenylindol-3-yl)acrylate;2-Cyano-3-(1-phenyl-1H-indol-3-yl)acrylic acid;Mitochondrial Pyruvate Carrier Inhibitor, UK5099;(E)-2-cyano-3-(1-phenylindol-3-yl)prop-2-enoicaci
- CBNumber
- CB11396725
- Molecular Formula
- C18H12N2O2
- Formula Weight
- 288.3
- MOL File
- 56396-35-1.mol
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
N-Bromosuccinimide Price
- Product number
- PZ0160
- Product name
- UK-5099
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $139
- Updated
- 2024/03/01
- Product number
- PZ0160
- Product name
- UK-5099
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $519
- Updated
- 2024/03/01
- Product number
- 5.04817
- Product name
- Mitochondrial Pyruvate Carrier Inhibitor, UK5099 - CAS 56396-35-1 - Calbiochem
- Packaging
- 5mg
- Price
- $111
- Updated
- 2024/03/01
- Product number
- 5.04817
- Product name
- Mitochondrial Pyruvate Carrier Inhibitor, UK5099 - CAS 56396-35-1 - Calbiochem
- Packaging
- 25MG
- Price
- $378
- Updated
- 2024/03/01
- Product number
- 16980
- Product name
- UK 5099
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
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
2-cyano-3-(1-phenylindol-3-yl)acrylate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2-cyano-3-(1-phenylindol-3-yl)acrylate manufacturers
- Product
- 2-cyano-3-(1-phenylindol-3-yl)acrylate 56396-35-1
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 40%-99%
- Supply Ability
- 1000kg
- Release date
- 2018-08-20