| Identification | More | [Name]
CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE | [CAS]
555-60-2 | [Synonyms]
[(3-CHLOROPHENYL)HYDRAZONO]PROPANEDINITRILE
BUTTPARK 91\04-41
CARBONYL CYANIDE 3-CHLOROPHENYLHYDRAZONE
CARBONYL CYANIDE M-CHLOROPHENYL-HYDRAZONE
CCCP
M-CL-CCP
MESOXALONITRILE (3-CHLOROPHENYL)HYDRAZONE
TIMTEC-BB SBB003506
((3-chlorophenyl)hydrazono)-propanedinitril
[(3-chlorophenyl)hydrazono]-propanedinitril
m-chlorophenylcarbonylcyanidehydrazone
mesoxalonitrile,(m-chlorophenyl)hydrazone
[(3-chlorophenyl)hydrazono]malononitrile
CARBONYL CYANIDE M-CHLOROPHENYL &
Carbonylcyanide3-chlorophenylhydrazone,98%
Carbonyl cyanide 3-chlorophenylhydrazone, 99+%
Carbonylcyanid-m-chlorphenylhydrazon
m-Cl-CCP, Carbonyl cyanide 3-chlorophenylhydrazone, CCCP, Mesoxalonitrile (3-chlorophenyl)hydrazone, Mesoxalonitrile 3-chlorophenylhydrazone
m-Cl-CCP, CCCP, Mesoxalonitrile 3-chlorophenylhydrazone
Carbonyl cyanide m-chlorophenylhydrazone, 99+% | [EINECS(EC#)]
209-103-7 | [Molecular Formula]
C9H5ClN4 | [MDL Number]
MFCD00001848 | [Molecular Weight]
204.62 | [MOL File]
555-60-2.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to orange-brown crystalline powder | [Melting point ]
170-175 °C (dec.) | [Boiling point ]
333.84°C (rough estimate) | [density ]
1.3807 (rough estimate) | [refractive index ]
1.6110 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
methanol: 10 mg/mL, clear, very deep yellow
| [form ]
powder
| [pka]
6.00±0.10(Predicted) | [color ]
yellow to orange
| [Water Solubility ]
Insoluble in water. Soluble in DMSO (5 mg/ml), ethanol (1 mg/ml) and methanol (10 mg/ml). | [BRN ]
1842102 | [Exposure limits]
NIOSH: IDLH 25 mg/m3 | [InChIKey]
UGTJLJZQQFGTJD-UHFFFAOYSA-N | [CAS DataBase Reference]
555-60-2(CAS DataBase Reference) | [EPA Substance Registry System]
Propanedinitrile, [(3-chlorophenyl)hydrazono]- (555-60-2) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
FG5600000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29280090 |
| Hazard Information | Back Directory | [Description]
CCCP is a protonophore mitochondrial uncoupler that increases membrane permeability to protons, leading to a disruption in the mitochondrial membrane potential.1 It inhibits mitochondrial respiration and ATPase activity when used at concentrations of 110 and 35 nM, respectively.2 CCCP inhibits activation of stimulation of interferon genes (STING), decreasing the expression of downstream STING targets, including IFN-β, TBK1, and IRF3 when used at a concentration of 50 μM in RAW 264.7 cells.3 It induces mitochondrial fission in a manner dependent on the GTPase Drp1. CCCP (4 mg/kg) increases body temperature as well as left ventricular systolic and diastolic dimensions and decreases fractional shortening in rats.4 It also increases myocardial glucose and fatty acid uptake in rats. | [Chemical Properties]
yellow to orange-brown crystalline powder | [Uses]
Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) has been used:
- in the inhibition of efflux pump in clinical Pseudomonas aeruginosa
- to inhibit oxidative phosphorylation activity of mitochondria in human Beas-2B bronchial epithelial cells
- to prepare carbonyl cyanide m-chlorophenylhydrazone solution for oxidative and mitochondrial stress assay and mitophagy induction in Caenorhabditis elegans
| [Uses]
Carbonyl cyanide 3-chlorophenylhydrazone is a widely used uncoupler of oxidative phosphorylation. | [Definition]
ChEBI:CCCP is a member of the class of monochlorobenzenes that is benzene substituted by 2-(1,3-dinitrilopropan-2-ylidene)hydrazinyl and chloro groups at positions 1 and 3, respectively. It is a mitochondrial depolarizing agent that induces reactive oxygen species mediated cell death. It has a role as a geroprotector, an antibacterial agent and an ionophore. It is a nitrile, a hydrazone and a member of monochlorobenzenes. It is functionally related to a hydrazonomalononitrile. | [Biological Activity]
Widely used uncoupler of oxidative phosphorylation. | [Biochem/physiol Actions]
Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) induces mitophagy in mammalian cells. CCCP suppresses the expression of few electron transport chain (ETC) proteins. Protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. Shown to have a number of effects on cellular calcium. Inhibits secretion of hepatic lipase and partially inhibits the pH gradient-activated Cl- uptake and Cl-/Cl- exchange activities in brush-border membrane vesicles. | [in vitro]
a genetic β-galactoside reporter system with a disk diffusion assay on macconkey lactose agar petri plates to monitor maintenance of the bacteriophage λ prophage state and viral induction in escherichia coli k-12. it presented evidence that the phage λ major lytic promoters, pl and pr, are activated via cells containing the reporters following exposure to the energy poison cccp. requirement of expression of the λ lytic promoters in response to cccp is host reca function and an auto-cleavable ci repressor, as does sos induction of the λ prophage occurring by a dna damage-dependent pathway. cccp-mediated activation of the λ lytic promoters required λ cro function. cccp does not modulate an sfi-lacz sos reporter [1]. the uncoupler cccp blocks oxidative phosphorylation by damaging the proton gradient. an anion cccp can bind a proton. but cccp with a delocalized negative charge allows it to cross the lipid bilayer in the unprotonated form, while weak acids cross the hydrophobic membrane only when protonated. many protons can be transported by one molecule of cccp across the inner membrane. it is described that a genetic reporter system to monitor maintenance of the λ prophage state and viral induction, and evidence is presented that it activates the major leftward and rightward lytic promoters of the λ prophage that cells are exposed to the energy poison cccp. | [storage]
Store at 2-8°C | [References]
[1]. thomason lc, court dl. evidence that bacteriophage λ lysogens may induce in response to the proton motive force uncoupler cccp. fems microbiol lett. 2016 feb;363(3). |
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