370-86-5 Usage
Description
FCCP (Fluoromethylcarbonylcyanide Phenylhydrazone), with the chemical formula C12H8FNO2 and the CAS number 370-86-5, is an extremely potent uncoupler of mitochondrial oxidative phosphorylation. It is a hydrazone derivative, specifically a hydrazonomalononitrile with a p-trifluoromethoxyphenyl group substitution on one of the hydrazine hydrogens. FCCP is cell permeable and has the ability to induce apoptosis in various cell lines. It also inhibits both wild type and mutant beta-amyloid production in certain cell types.
Uses
Used in Cellular Research:
FCCP is used as a potent uncoupler for mitochondrial oxidative phosphorylation in cellular research, disrupting ATP synthesis by transporting protons across cell membranes. This property makes it an important tool for inhibiting mitochondrial membrane potential and studying its effects on cellular processes.
Used in Apoptosis Induction:
FCCP is used as an apoptosis inducer in a variety of cell lines, providing valuable insights into the mechanisms of cell death and potential therapeutic applications.
Used in Beta-Amyloid Production Inhibition:
FCCP is used as an inhibitor of wild type and mutant beta-amyloid production in embryonic kidney 293 cells expressing either wild-type or "Swedish" mutant APP. This application is significant for studying the role of beta-amyloid in neurodegenerative diseases and the development of potential treatments.
Used in Microtubule Depolymerization:
FCCP is used to induce complete depolymerization of microtubules at 40 μM by increasing intracellular pH through the disruption of the mitochondrial H+ gradient and by decreasing the stability of microtubules by impairing the binding of microtubule-associated proteins. This application is useful in studying the role of microtubules in cellular structure and function.
Biological Activity
A very potent uncoupler of oxidative phosphorylation in mitochondria.
Biochem/physiol Actions
FCCP is a protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. It is capable of depolarizing plasma and mitochondrial membranes. FCCP has been shown to have a number of effects on cellular calcium. It also is reported to inhibit a background K+ current and induce a small inward current, reduce pH by 0.1 unit, and induce a rise of intracellular [Na+]. FCCP stimulates Mg2+-ATPase activity, inhibits β-amyloid production, and mimics the effect of selective glutamate agonist N-methyl-D-aspartate (NMDA) on mitochondrial superoxide production.
in vitro
fccp increases the rate of cellular o2 consumption. in pc-3 and du-145 prostate cancer cells, the compound could significantly decrease hypoxic as well as normoxic hif-1 transcriptional activity which was in part mediated by down-regulation of the oxygen labile hif-1α and hif-2α protein levels. during hypoxic as well as normoxic, it decreases the expression of hif target genes, vegf and vegf receptor-2. [2]
in vivo
fccp reduces mitochondrial membrane potential and atp production in 8-cell mouse embryos. also, the number of inner cell mass cells decrease within blastocysts with unchanged blastocyst development. this perturbed embryonic mitochondrial function is concomitant with reduced birth weight in female offspring following embryo transfer, which persists until weaning. although fccp-treated males also exhibits reduced glucose tolerance as female, their insulin sensitivity and adiposity gain between 4 and 14 weeks is unchanged. reducing mitochondrial function and, thus, decreasing atp output in the precompacting embryo can influence offspring phenotype. [3]
References
1) Benz R & McLaughlin S, (1983). The molecular mechanism of action of the proton ionophore FCCP (carbonylcyanide p-trifluoromethoxyphenylhydrazone).; Biophys J 41 381
2) Gautier et al. (2000), A moderate but not total decrease of mitochondrial membrane potential triggers apoptosis in neuron-like cells.; Neuroreport 11 2953
3) Connop et al. (1999), Novel effects of FCCP [carbonyl cyanide p-(trifluoromethoxy)phenylhydrazone] on amyloid precursor protein processing; J. Neurochem. 72 1457
4) Collins et al. (2000), Inositol 1,4,5-trisphosphate-induced Ca2+ release in inhibited by mitochondrial depolarization.; Biochem. J. 347 593
Check Digit Verification of cas no
The CAS Registry Mumber 370-86-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,7 and 0 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 370-86:
(5*3)+(4*7)+(3*0)+(2*8)+(1*6)=65
65 % 10 = 5
So 370-86-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H
370-86-5Relevant articles and documents
Simultaneous imaging of protonated and deprotonated carbonylcyanide p-trifluoromethoxyphenylhydrazone in live cells by Raman microscopy
Yamakoshi, Hiroyuki,Palonpon, Almar F.,Dodo, Kosuke,Ando, Jun,Kawata, Satoshi,Fujita, Katsumasa,Sodeoka, Mikiko
, p. 1341 - 1343 (2014)
We report the simultaneous imaging of protonated and deprotonated forms of carbonylcyanide p-trifluoromethoxy-phenylhydrazone (FCCP) molecules in live cells by Raman microscopy. Nitriles, structure-sensitive Raman tags, are used to detect the two distinct
