TPCK

TPCK Basic information
Product Name:TPCK
Synonyms:L-1-TOSYLAMIDE-2-PHENYLETHYL-CHLOROMETHYL KETONE;L-1-P-TOSYLAMINO-2-PHENYLETHYL CHLOROMETHYL KETONE;L-1-CHLORO-3-(4-TOSYLAMIDO)-4-PHENYL-2-BUTANONE;L-1-CHLORO-3-TOSYLAMIDO-4-PHENYL-2-BUTANONE;L-1-4′-TOSYLAMINO-2-PHENYLETHYL CHLOROMETHYL KETONE;N-TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE;N-TOSYL-PHE-CHLOROMETHYLKETONE;N-TOSYLAMIDE PHENETHYL CHLOROMETHYLKETONE
CAS:402-71-1
MF:C17H18ClNO3S
MW:351.85
EINECS:206-954-6
Product Categories:Apoptosis Inhibitors
Mol File:402-71-1.mol
TPCK Structure
TPCK Chemical Properties
Melting point 106-108 °C(lit.)
Boiling point 509.9±60.0 °C(Predicted)
density 1.1350 (rough estimate)
refractive index 1.6100 (estimate)
storage temp. -20°C
solubility DMSO: >10 mg/mL stable for several months at 4°C.
form powder
pka8.71±0.50(Predicted)
color white
BRN 2895215
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
CAS DataBase Reference402-71-1
EPA Substance Registry SystemBenzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl- (402-71-1)
Safety Information
Hazard Codes Xi
Risk Statements 37/38-41
Safety Statements 26-36
RIDADR UN 3335
WGK Germany 3
RTECS XT5613500
10-19-21
TSCA Yes
HS Code 29350090
MSDS Information
ProviderLanguage
ACROSEnglish
SigmaAldrichEnglish
TPCK Usage And Synthesis
DescriptionTPCK (402-71-1) is an irreversible inhibitor of the serine protease chymotrypsin.1 It also inhibits certain cysteine proteases (bromelain, ficin, papain).1 TPCK inhibited (IC50 = 5 μM) the mitogen-induced activation of pp70s6k, a mitogen-regulated serine/threonine kinase involved in the G1 to S phase transition of the cell cycle.2
Chemical Propertieswhite crystalline powder
UsesN-α-Tosyl-L-phenylalanylchloromethane is a proteinase inhibitors with apoptotic function. Studies have shown that it induces caspase-dependent apoptosis in Epstein-Barr virus (EBV)-transformed human B cell lines with release of pro-apoptotic proteins from mitochondria. It also results in down-regulation of the anti-apoptotic proteins and caspase-dependent cleavage of two anti-apoptotic proteins. I t promotes dephosphorylation of p53 on serine residues.
UsesN-α-Tosyl-L-phenylalanylchloromethane is a proteinase inhibitors with apoptotic function. Studies have shown that it induces caspase-dependent apoptosis in Epstein-Barr virus (EBV)-transformed human B cell lines with release of pro-apoptotic proteins from mitochondria. It also results in down-regulation of the anti-apoptotic proteins and caspase-dependent cleavage of two anti-apoptotic proteins. It promotes dephosphorylation of p53 on serine residues.
DefinitionChEBI: The N-tosyl derivative of L-phenylalanyl chloromethyl ketone.
Biochem/physiol ActionsBlocks the LPS- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of iNOS and COX-2 transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli. Also blocks apoptosis initiated by Taxol (in MCF-7 human breast carcinoma cells).
Safety ProfileExperimental reproductive effects. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx, SOx, and Cl-.
References1) Bond and Butler, (1987) Intracellular proteases; Annu. Rev. Biochem., 56 333 2) Grammer and Blenis (1996) The serine protease inhibitors, tosylphenylalanine chloromethylketone and tosyllysine chloromethylketone, potently inhibit pp70s6k activation; J. Biol. Chem., 271 23650
TPCK Preparation Products And Raw materials

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