TPCK

Synonym(s):(S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone;(S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone;N^α-Tosyl-Phe Chloromethyl Ketone;Tosyl-L-phenylalanyl-chloromethane;TPCK

CAS NO.：402-71-1
Empirical Formula: C17H18ClNO3S
Molecular Weight: 351.85
MDL number: MFCD00000935
EINECS: 206-954-6
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-08 20:21:46

What is TPCK?

Description

TPCK (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 properties

white crystalline powder

The Uses of TPCK

N-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.

The Uses of TPCK

N-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.

Definition

ChEBI: The N-tosyl derivative of L-phenylalanyl chloromethyl ketone.

What are the applications of Application

TPCK is a serine/cysteine protease inhibitor, which acts as an alkylating agent that interferes with translation

Biochem/physiol Actions

Blocks 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 Profile

Experimental reproductive effects. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx, SOx, and Cl-.

References

1) 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

Properties of TPCK

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
pka	8.71±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 Reference	402-71-1
EPA Substance Registry System	Benzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl- (402-71-1)

Safety information for TPCK

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water.