TPCK Property

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

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-36

RIDADR 

UN 3335

WGK Germany 

3

RTECS 

XT5613500

F 

10-19-21

TSCA 

Yes

HS Code 

29350090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

TPCK Chemical Properties,Usage,Production

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

Uses

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.

Definition

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

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