FCCP

FCCP (Carbonyl cyanide-4-(trifluoromethoxy)phenylhydrazone) is an ionophore that is a mobile ion carrier. It referred to as an uncoupling agent because it disrupts ATP synthesis by transporting hydrogen ions through a cell membrane before they can be used to provide the energy for oxidative phosphorylation. It is a nitrile and hydrazone. FCCP was first described in 1962 by Heytler.

Product information

CAS Number: 370-86-5

Molecular Weight: 254.17

Formula: C10H5F3N4O

Synonym:

LS-52242

PS-10973

HY-100410

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone

FCCP

370-86-5

Carbonyl cyanide p-trifluoromethoxyphenylhydrazone

Propanedinitrile, [[4-(trifluoromethoxy)phenyl]hydrazono]-

Chemical Name: N-(4-(trifluoromethoxy)phenyl)carbonohydrazonoyl dicyanide

Smiles: N#CC(C#N)=NNC1C=CC(=CC=1)OC(F)(F)F

InChiKey: BMZRVOVNUMQTIN-UHFFFAOYSA-N

InChi: InChI=1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

FCCP (5 μM) results in a concentration-dependent decrease in Aβ and APPsβ production in K695sw cells. FCCP inhibits processing of wild-type APP. FCCP does not alter cellular ATP levels at any of the concentrations measured. The effects of FCCP on APP catabolism are independent of secondary effects on oxidative phosphorylation or the result of reduced cell viability. FCCP (5 μM or 500 nM), baf A1, and NH4Cl induce changes in Tf-Tx and Tf-F cellular fluorescence in K695 cells. FCCP (200 nM) protects and enhances the follicle integrity in cat ovarian tissue during short-term in vitro culture. But FCCP does not appear to exert a beneficial or detrimental effect during ovarian tissue cryopreservation.

References:

1. Mlejnek P, Dolezel P. Loss of mitochondrial transmembrane potential and glutathione depletion are not sufficient to account for induction of apoptosis by carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone in human leukemia K562 cells. Chem Biol Interact. 2015 Sep 5;239:100-10. doi: 10.1016/j.cbi.2015.06.033. Epub 2015 Jun 23. PubMed PMID: 26115783.
2. CutroAC, Montich GG, Roveri OA. Effect of carbonylcyanide-4-(trifluoromethoxy)phenylhydrazone (FCCP) on the interaction of 1-anilino-8-naphthalene sulfonate (ANS) with phosphatidylcholine liposomes. J Bioenerg Biomembr. 2014 Apr;46(2):119-25. doi: 10.1007/s10863-014-9545-0. Epub 2014 Feb 26. Erratum in: J Bioenerg Biomembr. 2014 Jun;46(3):243. PubMed PMID: 24570377.
3. Han YH, Park WH. Intracellular glutathione levels are involved in carbonyl cyanide p-(trifluoromethoxy) phenylhydrazone-induced apoptosis in As4.1 juxtaglomerular cells. Int J Mol Med. 2011 Apr;27(4):575-81. doi: 10.3892/ijmm.2011.604. Epub 2011 Jan 21. PubMed PMID: 21258765.

Products are for research use only. Not for human use.