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TLCK

Product Name
TLCK
CAS No.
4272-74-6
Chemical Name
TLCK
Synonyms
TLCK;TLCK HCL;(s)-lorid;TOS-LYS-CMK;TOSYL-LYS-CMK;TLCK USP/EP/BP;TOS-LYS-CMK HCL;Tos-L-Lys-CMK·HCl;TLCK HYDROCHLORIDE;Tos-Lys-chloromethylketone
CBNumber
CB1197729
Molecular Formula
C14H21ClN2O3S.ClH
Formula Weight
369.31
MOL File
4272-74-6.mol
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TLCK Property

Melting point:
~165 °C (dec.)
storage temp. 
-20°C
solubility 
H2O: 50 mg/mL
form 
powder
color 
white to pink
optical activity
[α]20/D 7.8±0.5°, c = 2% in H2O
BRN 
7106867
CAS DataBase Reference
4272-74-6
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
RIDADR 
UN 3335
WGK Germany 
3
RTECS 
XT5160000
F 
10-21
HS Code 
29350090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
90182
Product name
Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride
Purity
≥99.0% (AT)
Packaging
100mg
Price
$183
Updated
2024/03/01
Sigma-Aldrich
Product number
90182
Product name
Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride
Purity
≥99.0% (AT)
Packaging
500mg
Price
$724
Updated
2024/03/01
Cayman Chemical
Product number
13074
Product name
Tosyllysine Chloromethyl Ketone (hydrochloride)
Purity
≥98%
Packaging
50mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
13074
Product name
Tosyllysine Chloromethyl Ketone (hydrochloride)
Purity
≥98%
Packaging
100mg
Price
$107
Updated
2024/03/01
Sigma-Aldrich
Product number
T7254
Product name
Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride
Purity
≥96% (TLC), powder
Packaging
100mg
Price
$160
Updated
2024/03/01
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TLCK Chemical Properties,Usage,Production

Chemical Properties

white to light beige powder

Uses

Tosyllysine chloromethylketone (TLCK) is an active site-directed agent that inhibits serine proteinases with trypsin-like activity. TLCK may also act non-selectively with thiol groups and thereby inhibit cysteine proteinases and other enzymes. To prevent proteolytic degradation, TLCK may be used in protein purification protocols. TLCK selectively inactiviates clostripain obtained from C. histolyticum.

Uses

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride has been used:

  • in chymotrypsin purification to prevent binding of trypsins to the affinity support by inhibiting them in the crude extract
  • as a protease inhibitor in tissue and cell homogenization
  • as a trypsin inhibitor to determine the specific protease activity levels

Biological Activity

tosyllysine chloromethyl ketone (hydrochloride) is a protease inhibitor [1][2][3].l-1-chloro-3-[4-tosylamido]-7-amino-2-heptanone-hcl (tlck) is a protease inhibitor. tlck is an active site-directed agent that inhibits serine proteinases with trypsin-like activity. tlck also interacts non-selectively with thiol groups and thereby inhibits cysteine proteinases and other enzymes. in lps-activated rat alveolar macrophages, tlck at 1-100 μm inhibited nox- accumulation and inducible inos expression in a concentration-dependent way [1]. to prevent proteolytic degradation, tlck may be used in protein purification protocols [2]. tlck significantly increased the cytotoxic activity of c. histolyticum supernatant towards human epithelial hela cells probably by hindering natural defence mechanisms of cells. 30 min incubation with bacterial supernatant increased toxicity in both concentrations (200 and 1000 μm) from 18 ± 3% to 39 ± 3% and 57 ± 8%, respectively. tlck also blocked clostripain enzymatic activity obtained from c. histolyticum. so tlck might be used to treat diseases complicated by concurrent c. histolyticum infection [3].

Biochem/physiol Actions

Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride (TLCK) blocks the lipopolysaccharide (LPS)- or cytokine-induced activation of nuclear factor κB (NF-κB), which, in turn, blocks the induction of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis in cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli.

Purification Methods

The hydrochloride slowly crystallises from a concentrated solution in absolute EtOH, thinned with EtOH/Et2O for collection and dried in vacuo. It is a suicide enzyme inhibitor of serine proteases, e.g. trypsin and clostripain. [Matsuda et al. Chem Pharm Bull Jpn 30 2512 1982, Shaw et al. Biochemistry 4 2219 1965].

References

[1]. griscavage jm, wilk s, ignarro lj. serine and cysteine proteinase inhibitors prevent nitric oxide production by activated macrophages by interfering with transcription of the inducible no synthase gene. biochem biophys res commun. 1995 oct 13;215(2):721-9.
[2]. urban mk, franklin sg, zweidler a. isolation and characterization of the histone variants in chicken erythrocytes. biochemistry. 1979 sep 4;18(18):3952-60.
[3]. józwiak, j.,komar, a.,jankowska, e., et al. determination of the cytotoxic effect of clostridiumhistolyticum culture supernatant on hela cells in the presence of protease inhibitors. fems immunology & medical microbiology 45(2):137-42 (2005).

TLCK Preparation Products And Raw materials

Raw materials

Preparation Products

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TLCK Suppliers

Belgium 1 China 48 Germany 3 India 2 Switzerland 1 United Kingdom 2 United States 18 Global 75
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Chemsky (shanghai) International Co.,Ltd
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
15402
Advantage
60
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
meilunui@163.com
Country
China
ProdList
4727
Advantage
58
Thermo Fisher Scientific
Tel
800-810-5118
Fax
+86-10-84193589
Email
cnchemical@thermofisher.com
Country
China
ProdList
17770
Advantage
75
Beijing innoChem Science & Technology Co.,Ltd.
Tel
400-810-7969 010-59572699
Fax
010-59572688
Email
ningzi.li@inno-chem.com.cn
Country
China
ProdList
6134
Advantage
55
9ding chemical ( Shanghai) Limited
Tel
4009209199
Fax
86-021-52271987
Email
sales@9dingchem.com
Country
China
ProdList
22514
Advantage
55
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
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View Lastest Price from TLCK manufacturers

Career Henan Chemical Co
Product
(3S)-1-Chloro-3-tosylamido-7-amino-2-heptanone hydrochloride 4272-74-6
Price
US $1.00/kg
Min. Order
1kg
Purity
95%-99%
Supply Ability
1000kg
Release date
2018-12-25

4272-74-6, TLCKRelated Search:

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  • N-TOSYL-LYS-CHLOROMETHYLKETONE
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  • TOS-LYS-CMK
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  • TOSYL-LYS-CMK
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  • N-ALPHA-TOSYL-L-LYSINE CHLOROMETHYL KETONE (TLCK)
  • N-ALPHA-TOSYL-L-LYSINE CHLOROMETHYL KETONE
  • Nα-Tosyl-L-lysine chloromethyl ketone
  • (3S)-1-Chloro-3-tosylamido-7-amino-2-heptanone HCl
  • TLCK USP/EP/BP
  • N-alpha-Tosyl-L-lysine chloromethyl ketone HCl
  • Nα-Tosyl-L-lysine chloromethyl ketone hydrochloride
  • Inhibitor,inhibit,N alpha Tosyl L lysine chloromethyl ketone hydrochloride,NalphaTosylLlysine chloromethyl ketone hydrochloride
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  • 4272-74-6
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