FCCP


Catalog No. size PriceQuantity
M6682-2 2mg solid $100
M6682-10 10mg solid $391

Description

Cas:370-86-5

Product Information

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.

 

Chemical Formula: C10H5F3N4O

 

Exact Mass: 254.04155

 

Molecular Weight: 254.17 

 

Elemental Analysis: C, 47.26; H, 1.98; F, 22.42; N, 22.04; O, 6.29

 

Synonym: 

 

FCCP

370-86-5

Carbonyl cyanide p-trifluoromethoxyphenylhydrazone

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone

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

CHEBI:75458

EINECS 206-730-8

BRN 4693268

2-{2-[4-(Trifluoromethoxy)phenyl]hydrazono}malononitrile

CHEMBL457504

{[4-(Trifluoromethoxy)phenyl]-hydrazono}malononitrile

2-[2-[4-(Trifluoromethoxy)phenyl]hydrazono]malononitrile

CARBONYL CYANIDE p-TRIFLUOROMETHOXYPHENYL HYDRAZONE

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

Carbonyl cyanide 4-trifluoromethoxyphenylhydrazone

Carbonyl cyanide, 4-trifluoromethoxyphenylhydrazone

((4-(Trifluoromethoxy)phenyl)hydrazono)malononitrile

[[4-(trifluoromethoxy)phenyl]hydrazono]malononitrile

Mesoxalonitrile, (p-(trifluoromethoxy)phenyl)hydrazone

N-(4-(trifluoromethoxy)phenyl)carbonohydrazonoyl dicyanide

{[4-(trifluoromethoxy)phenyl]hydrazono}malononitrile

(4-(trifluoromethoxy)phenyl)carbonohydrazonoyl dicyanide

[4-(Trifluoromethoxy)phenyl]carbonohydrazonoyl Dicyanide

2-(2-[4-(TRIFLUOROMETHOXY)PHENYL]HYDRAZONO)MALONONITRILE

C10H5F3N4O

trifluoromethoxy carbonylcyanide phenylhydrazone

Cyto10H8

2-[[4-(trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile

Maybridge1_007693

BSPBio_001069

KBioGR_000409

KBioSS_000409

SCHEMBL345231

Carbonyl Cyanide para-Trifluoromethoxyphenylhydrazo

CTK7C4861

HMS563F15

KBio2_000409

KBio2_002977

KBio2_005545

KBio3_000777

KBio3_000778

DTXSID40190494

Bio1_000432

Bio1_000921

Bio1_001410

Bio2_000365

Bio2_000845

HMS1362E11

HMS1792E11

HMS1990E11

HMS3266A16

HMS3403E11

HMS3868H03

ZINC110861

BCP29558

EX-A2029

1-cyano-N-[4-(trifluoromethoxy)phenyl]methanecarbohydrazonoyl cyanide

BDBM50483311

CCG-56026

s8276

SBB101377

AKOS004121079

CS-573

MCULE-4712161118

IDI1_002120

QTL1_000036

NCGC00092274-01

NCGC00092274-02

NCGC00092274-03

NCGC00092274-04

AK546688

LS-52242

PS-10973

HY-100410

B5004

C3463

FT-0610900

NS00041734

[4-(Trifluoromethoxy)phenylhydrazono]malononitrile

Carbonyl cyanide p-(trifluoromethoxy)phenylhydrazone

Carbonyl cyanide-4-(trifluoromethoxy)phenylhydrazone

Q1649579

SR-01000645014-1

SR-01000645014-2

BRD-K14821540-001-02-1

BRD-K14821540-001-03-9

Carbonyl cyanide, 4-(trifluoromethoxy)phenylhydrazone

F9995-2716

2-([4-(Trifluoromethoxy)phenyl]hydrazono)malononitrile #

Mesoxalonitrile, (p-(trifluoromethoxy)phenyl)hydrazone (8CI)

Propanedinitrile, ((4-(trifluoromethoxy)phenyl)hydrazono)- (9CI)

({[4-(trifluoromethoxy)phenyl]amino}azamethylene)methane-1,1-dicarbonitrile

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone, >=98% (TLC), powder

Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazon;Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone; (4-(Trifluoromethoxy)phenyl)hydrazonopropanedinitrile; Carbonyl Cyanide para Trifluoromethoxyphe

 

Chemical Name:

N-(4-(trifluoromethoxy)phenyl)carbonohydrazonoyl dicyanide

 

InChi Key:

BMZRVOVNUMQTIN-UHFFFAOYSA-N

 

InChi Code:  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

 

Smiles Code:

N#C/C(C#N)=N/NC1=CC=C(OC(F)(F)F)C=C1

 

 

Technical Data:

 

Appearance: Solid powder

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life:>2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

 

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.

 

  1. 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.

 

  1. 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.

 

  1. Han YH, Moon HJ, You BR, Kim SZ, Kim SH, Park WH. Effects of carbonyl cyanide p-(trifluoromethoxy) phenylhydrazone on the growth inhibition in human pulmonary adenocarcinoma Calu-6 cells. Toxicology. 2009 Nov 30;265(3):101-7. doi: 10.1016/j.tox.2009.10.001. Epub 2009 Oct 9. PubMed PMID: 19819288.

 

  1. Han YH, Kim SH, Kim SZ, Park WH. Carbonyl cyanide p-(trifluoromethoxy) phenylhydrazone (FCCP) as an O2(*-) generator induces apoptosis via the depletion of intracellular GSH contents in Calu-6 cells. Lung Cancer. 2009 Feb;63(2):201-9. doi: 10.1016/j.lungcan.2008.05.005. Epub 2008 Jun 27. PubMed PMID: 18585819.

 

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

 

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