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Tosyl phenylalanyl chloromethyl ketone

Names

[ CAS No. ]:
402-71-1

[ Name ]:
Tosyl phenylalanyl chloromethyl ketone

[Synonym ]:
(S)-N-(4-Chloro-3-oxo-1-phenyl-2-butyl)-p-toluenesulfonamide
MFCD00000935
TPCK
Benzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-
N-[(2S)-4-Chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
Benzenesulfonamide, N-(3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-, (S)-
N-(p-Toluenesulfonyl)-L-phenylalanyl Chloromethyl Ketone
L-1-4‘-Tosylamino-2-phenylethyl chloromethyl ketone
Tosyl phenylalanyl chloromethyl ketone
EINECS 206-954-6
N-[(2S)-4-Chloro-3-oxo-1-phenyl-2-butanyl]-4-methylbenzenesulfonamide
Tosyl-L-phenylalanyl-chloromethane
N-p-Tosyl-L-phenylalanine chloromethyl ketone
Benzenesulfonamide, N-((1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-
N-Tosyl-L-phenylalanyl Chloromethyl Ketone
L-1-4′-Tosylamino-2-phenylethyl chloromethyl ketone
N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK)

Biological Activity

[Description]:

TPCK (L-1-Tosylamido-2-phenylethyl chloromethyl ketone; L-TPCK) is a potent serine protease inhibitor that reacts with the retinoblastoma protein (RB)-binding core of HPV-18 E7 protein and abolish its RB-binding capability. TPCK is able to modify E7 protein in live keratinocytes following its addition to the culture medium[1].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Ser/Thr Protease
Research Areas >> Cancer
Research Areas >> Inflammation/Immunology

[References]

[1]. H Stöppler, et al. The serine protease inhibitors TLCK and TPCK react with the RB-binding core of HPV-18 E7 protein and abolish its RB-binding capability. Virology. 1996 Mar 15;217(2):542-53.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
509.9±60.0 °C at 760 mmHg

[ Melting Point ]:
106-108ºC(lit.)

[ Molecular Formula ]:
C17H18ClNO3S

[ Molecular Weight ]:
351.848

[ Flash Point ]:
262.2±32.9 °C

[ Exact Mass ]:
351.069580

[ PSA ]:
71.62000

[ LogP ]:
3.98

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.583

[ Storage condition ]:
−20°C

[ Water Solubility ]:
DMSO: >10 mg/mL stable for several months at 4°C.

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XT5613500
CHEMICAL NAME :
p-Toluenesulfonamide, N-(alpha-(chloroacetyl)phenethyl)-, (-)-
CAS REGISTRY NUMBER :
402-71-1
LAST UPDATED :
199701
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C17-H18-Cl-N-O3-S
MOLECULAR WEIGHT :
351.87

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intrauterine
DOSE :
160 mg/kg
SEX/DURATION :
female 2 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 25,954,1974

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H318-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
UN 3335

[ WGK Germany ]:
3

[ RTECS ]:
XT5613500

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