tlck

Modify Date: 2024-01-14 15:33:39

tlck Structure
tlck structure
Common Name tlck
CAS Number 4272-74-6 Molecular Weight 369.307
Density N/A Boiling Point 509.8ºC at 760 mmHg
Molecular Formula C14H22Cl2N2O3S Melting Point -165ºC (dec.)
MSDS USA Flash Point 262.1ºC
Symbol GHS07
GHS07
Signal Word Warning

 Use of tlck


N-alpha-Tosyl-L-lysine chloromethyl ketone (TLCK), a trypsin like protease inhibitor, sensitizes HeLa cells to Fas-mediated cell death.

 Names

Name (3S)-1-Chloro-3-tosylamido-7-amino-2-heptanone hydrochloride
Synonym More Synonyms

 tlck Biological Activity

Description N-alpha-Tosyl-L-lysine chloromethyl ketone (TLCK), a trypsin like protease inhibitor, sensitizes HeLa cells to Fas-mediated cell death.
Related Catalog
In Vitro N-alpha-Tosyl-L-lysine chloromethyl ketone exhibits an inhibitory effect on IFN-γ activities. The effect of TLCK is studied on the IFN-γ sensitization of HeLa cells towards cell death mediated by anti-Fas. Lower concentration of anti-Fas (10 ng/mL) are used to examine the interaction among the three effectors simultaneously, that is, anti-Fas, TLCK and IFN-γ. TLCK by itself up to 50 μM concentration exhibits a small decrease in cell viability. Beyond 50 μM, a dose dependent decrease in cell viability is observed. IFN-γ slightly reduces cell viability on its own. Addition of anti-Fas (10 ng/mL) results in a slight decrease in cell survival, which is enhanced more than additively in the presence of TLCK, most prominently between 50 and 100 μM. Upon addition of both anti-Fas and IFN-γ, a decrease (≈46%) in cell viability is observed. Moreover, the decrease in cell survival is further enhanced upon addition of higher concentrations of TLCK, 25 μM and more[1].
Cell Assay HeLa cell line (human cervical cancer cells) is cultured in DMEM supplemented with 10% fetal bovine serum (FBS), L-glutamine (300 mg/L), penicillin (100 U/ml) and streptomycin(100 μg/ml) at 37°C in 5% CO2. HT-29 cell line (human colorectal adenocarcinoma) is cultured in RPMI supplemented with 10% fetal bovine serum (FBS), L-glutamine (300 mg/L), penicillin (100 U/mL) and streptomycin (100 μg/mL) at 37°C in 5% CO2. The cells are split every second day to keep the cell growth in logarithmic phase. The cells are routinely tested for mycoplasma. The cells are treated with different concentrations of TPCK or TLCK (5, 10, 25, 50, 100, 150, and 200 μM) for 30 min and/or with different concentrations of IFN-γ for 2 h followed by treatment with different concentrations of anti-Fas for 2 or 4 days for each specific experiment. The control cells are treated with the respective vehicle only. Cell viability analysis of HeLa and HT-29 cells is assessed by their XTT reduction activity. 100 µL of 2×104 cells/mL is incubated with treatments at the indicated time. At the end of the incubation period, 25 µL of 1 mg/mL XTT solution (containing 0.2 mM phenazine methosulphate (PMS) is added and the cells are incubated for an additional 1 h. The OD values are measured using an ELISA reader at 450 nm with a reference wavelength of 650 nm[1].
References

[1]. Shadrin N, et al. Serine protease inhibitors interact with IFN-γ through up-regulation of FasR; a novel therapeutic strategy against cancer. Exp Cell Res. 2015 Jan 15;330(2):233-9.

 Chemical & Physical Properties

Boiling Point 509.8ºC at 760 mmHg
Melting Point -165ºC (dec.)
Molecular Formula C14H22Cl2N2O3S
Molecular Weight 369.307
Flash Point 262.1ºC
Exact Mass 368.072815
PSA 97.64000
LogP 4.55280
Storage condition 2-8°C
Water Solubility H2O: 50 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XT5160000
CHEMICAL NAME :
p-Toluenesulfonamide, N-(5-amino-1-(chloroacetyl)pentyl)-, hydrochloride, L-
CAS REGISTRY NUMBER :
4272-74-6
LAST UPDATED :
199707
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C14-H21-Cl-N2-O3-S.Cl-H
MOLECULAR WEIGHT :
369.34

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravaginal
DOSE :
150 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 19,95,1979

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases 26-36
RIDADR UN 3335
WGK Germany 3
RTECS XT5160000
HS Code 29350090

 Articles16

More Articles
Chemical genetics reveals a complex functional ground state of neural stem cells.

Nat. Chem. Biol. 3(5) , 268-273, (2007)

The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain canc...

Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Nat. Chem. Biol. 5 , 765-71, (2009)

Studies of gene function and molecular mechanisms in Plasmodium falciparum are hampered by difficulties in characterizing and measuring phenotypic differences between individual parasites. We screened...

Lysine acetylation in sexual stage malaria parasites is a target for antimalarial small molecules.

Antimicrob. Agents Chemother. 58(7) , 3666-78, (2014)

Therapies to prevent transmission of malaria parasites to the mosquito vector are a vital part of the global malaria elimination agenda. Primaquine is currently the only drug with such activity; howev...

 Synonyms

MFCD00065395
EINECS 224-266-4
Benzenesulfonamide, N-[(1S)-5-amino-1-(2-chloroacetyl)pentyl]-4-methyl-, hydrochloride (1:1)
N-[(3S)-7-Amino-1-chloro-2-oxoheptan-3-yl]-4-methylbenzenesulfonamide hydrochloride (1:1)
Tosyllysine chloromethyl ketone (hydrochloride)
N-[(3S)-7-Amino-1-chloro-2-oxo-3-heptanyl]-4-methylbenzenesulfonamide hydrochloride (1:1)