Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone（FCCP） - Moligand™, ≥98%(TLC) , CAS No.370-86-5

CAS: 370-86-5 Cat. No.: C169970 Molecular Weight: 254.17 Beilstein Registry Number: 664446 EC Number: 206-730-8

GRADE & PURITY Moligand™, ≥98%(TLC)

Synonyms

Mesoxalonitrile, (p-(trifluoromethoxy)phenyl)hydrazone | SR-01000645014-2 | [4-(Trifluoromethoxy)phenylhydrazono]malononitrile | Carbonyl cyanide, 4-(trifluoromethoxy)phenylhydrazone | AKOS004121079 | C74911 | Carbonyl cyanide 4-trifluoromethoxyphenylhydr

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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 several effects on cellular calcium. It is also 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.

Specifications

Synonyms

Mesoxalonitrile, (p-(trifluoromethoxy)phenyl)hydrazone | SR-01000645014-2 | [4-(Trifluoromethoxy)phenylhydrazono]malononitrile | Carbonyl cyanide, 4-(trifluoromethoxy)phenylhydrazone | AKOS004121079 | C74911 | Carbonyl cyanide 4-trifluoromethoxyphenylhydr

Specifications & Purity

Moligand™, ≥98%(TLC)

Biochemical and Physiological Mechanisms

Potent mitochondrial oxidative phosphorylation uncoupler (IC 50 = 20 nM). Disrupts ATP synthesis by transporting protons across mitochondrial inner membranes. Depolarises mitochondrial membrane potential.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(TLC)

Names and Identifiers

• Pubchem Sid: 504750658
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750658
• Canonical Smiles: C1=CC(=CC=C1NN=C(C#N)C#N)OC(F)(F)F
• IUPAC Name: 2-[[4-(trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile
• InChIKey: BMZRVOVNUMQTIN-UHFFFAOYSA-N
• 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
• Isomeric SMILES: C1=CC(=CC=C1NN=C(C#N)C#N)OC(F)(F)F
• WGK Germany: 3
• RTECS: FG5775000
• Molecular Weight: 254.17
• Beilstein: 664446
• Reaxy-Rn: 4693268
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4693268&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Phenylhydrazines

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Phenylhydrazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylhydrazines
• Alternative Parents: Phenoxy compounds Phenol ethers Trihalomethanes Nitriles Hydrazones Organopnictogen compounds Organooxygen compounds Organofluorides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Phenol ether - Phenylhydrazine - Trihalomethane - Hydrazone - Carbonitrile - Nitrile - Alkyl fluoride - Hydrocarbon derivative - Halomethane - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylhydrazines. These are compounds containing a phenylhydrazide moiety, which consists of a hydrazide substituent attached to a phenyl group.
• External Descriptors: organofluorine compound - aromatic ether - nitrile - hydrazone

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

VDR Tclin Vitamin D receptor (26531 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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CCRF-CEM (65223 Activities)

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HL-60 (67320 Activities)

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MCF7 (126967 Activities)

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SH-SY5Y (11521 Activities)

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T47D (39041 Activities)

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HCT-116 (91556 Activities)

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MDA-MB-231 (73002 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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Liver (3974 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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TRAP1 Tchem Heat shock protein 75 kDa, mitochondrial (274 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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BLM Tchem Bloom syndrome protein (4248 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

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PRKAA2 Tchem AMP-activated protein kinase, AMPK (12273 Activities)

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HIF1A Tchem Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha (820 Activities)

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GM15850 (303 Activities)

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GM16216 (129 Activities)

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Hep 3B2 (2332 Activities)

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KOPN-8 (317 Activities)

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Associated Targets(non-human)

Cruzipain (33337 Activities)

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Leishmania infantum (5912 Activities)

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Leishmania amazonensis (3813 Activities)

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Leishmania braziliensis (1091 Activities)

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Leishmania donovani (89745 Activities)

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Leishmania major (2877 Activities)

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Trypanosoma cruzi (99888 Activities)

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Plasmodium berghei (192651 Activities)

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lef Anthrax lethal factor (7585 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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FTL Ferritin light chain (43324 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: 95% ethanol: soluble
• Melt Point(°C): 156 °C(dec.)
• Molecular Weight: 254.170 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 254.042 Da
• Monoisotopic Mass: 254.042 Da
• Topological Polar Surface Area: 81.200 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 388.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xu Zhang, Wei Xiong, Ling-Li Chen, Jia-Qiang Huang, Xin Gen Lei.  (2020)  Selenoprotein V protects against endoplasmic reticulum stress and oxidative injury induced by pro-oxidants.  FREE RADICAL BIOLOGY AND MEDICINE,      [PMID:32846216] [10.1016/j.freeradbiomed.2020.08.011]

2. Mengyun Peng, Xiao-Qiang Wang, Yu Zhang, Chu-Xin Li, Mingkang Zhang, Han Cheng, Xian-Zheng Zhang.  (2019)  Mitochondria-Targeting Thermosensitive Initiator with Enhanced Anticancer Efficiency.  ACS Applied Bio Materials,      [PMID:35021424] [10.1021/acsabm.9b00739]