AEBSF HCl

Names

[ Name ]:
AEBSF HCl

[Synonym ]:
4-(2-Aminoethyl)benzene-1-sulfonyl fluoride hydrochloride
Benzenesulfonyl fluoride, 4-(2-aminoethyl)-, hydrochloride (1:1)
4-(2-Aminoethyl)benzenesulfonyl fluoride hydrochloride
2-[4-(fluorosulfonyl)phenyl]ethanaminium chloride
AEBSF
AEBSF hydrochloride
4-(2-Aminoethyl)benzenesulphonyl fluoride hydrochloride
4-(2-Aminoethyl)benzenesulfonyl fluoride, hydrochloride
MFCD00132962
Pefabloc SC
4-(2-Aminoethyl)benzenesulfonyl fluoride hydrochloride (1:1)
Benzenesulfonyl fluoride hydrochloride, 4-(2-aminoethyl)-
4-(2-Aminoethyl)-benzenesulfonylfluoride hydrochloride
AEBSF HCl

Biological Activity

[Description]:

AEBSF is an irreversible inhibitor of serine proteases, such as chymotrypsin, kallikrein, plasmin, thrombin, and trypsin.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Thrombin

Research Areas >> Others

[In Vitro]

AEBSF inhibits the constitutive production of Aβ by directly inhibiting β-secretase in five different human cell lines, both neural and nonneural[1]. AEBSF, as a serine protease inhibitor, inhibits the lysis of leukemic cells by human macrophages without inhibiting macrophage secretion of TNF-α and IL-1β[2]. AEBSF also disturbs the growth of blastocysts on endometrial cells and inhibit the adhesion of HeLa cells on HUVECs by altering the protein secretion pattern[4].

[In Vivo]

AEBSF (76.8 mg/kg daily, i.p.) results in prolongation of the survival of mice that have been given a lethal T. gondii infection[3]. AEBSF also reduces airway response and underlying inflammation in cockroach allergen-induced murine model[4].

[Cell Assay]

The HeLa cells suspended in RPMI-1640 media containing 10% FCS are plated into each well of a 96-well microplate (5×103 cells/200 μL/well). After incubation for 24 h at 37°C, cells are treated with different doses of AEBSF (0, 25, 50, 100 μg/mL) for 48 h. Then, 20 μL fresh 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-diphenytetrazoliumromide (MTT) reagent (5 μg/μL) is added into each well, and cells are cultured at 37°C in 5% CO2 for another 4 h. The media are discarded carefully, and 150 μL DMSO is added. Absorbance is read on a microplate reader at dual wavelengths of 540 and 620 nm.

[Animal admin]

Mice injected with 2.5×103 parasites are randomLy assigned to one of the treatment groups according to the treatment given: without drugs (control group), vehicle alone (vehicle control group), pyrimethamine alone at different doses, LY311727 alone at different doses, AEBSF alone at different doses or AEBSF 76.8 mg/kg plus pyrimethamine 10 mg/kg. Each treatment group consists of 10 animals. Treatment is initiated 24 h after parasite inoculation and is continued for seven consecutive days. Mouse survival is monitored daily and continued in live mice until 15 days post-infection. All experiments are performed three times and the data shown represent the cumulative results.

[References]

[1]. Citron M, et al. Inhibition of amyloid beta-protein production in neural cells by the serine protease inhibitor AEBSF. Neuron. 1996 Jul;17(1):171-9

[2]. Nakabo Y, et al. Lysis of leukemic cells by human macrophages: inhibition by 4-(2-aminoethyl)-benzenesulfonyl fluoride (AEBSF), a serine protease inhibitor. J Leukoc Biol. 1996 Sep;60(3):328-36.

[3]. Buitrago-Rey R, et al. Evaluation of two inhibitors of invasion: LY311727 [3-(3-acetamide-1-benzyl-2-ethyl-indolyl-5-oxy)propane phosphonic acid] and AEBSF [4-(2-aminoethyl)-benzenesulphonyl fluoride] in acute murine toxoplasmosis. J Antimicrob Chemother.

[4]. Jiang YH, et al. Serine protease inhibitor 4-(2-aminoethyl)benzenesulfonyl fluoride hydrochloride (AEBSF) inhibits the rat embryo implantation in vivo and interferes with cell adhesion in vitro. Contraception. 2011 Dec;84(6):642-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
292.5ºC at 760 mmHg

[ Melting Point ]:
175-177 °C

[ Molecular Formula ]:
C₈H₁₁ClFNO₂S

[ Molecular Weight ]:
239.695

[ Flash Point ]:
130.7ºC

[ Exact Mass ]:
239.018311

[ PSA ]:
68.54000

[ LogP ]:
3.42910

[ Storage condition ]:
0-6°C

[ Water Solubility ]:
10 g/L (20 ºC)

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H314

[ Precautionary Statements ]:
P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
C:Corrosive;

[ Risk Phrases ]:
R34

[ Safety Phrases ]:
S45-S36/37/39-S26

[ RIDADR ]:
UN 3261

[ Packaging Group ]:
II

[ Hazard Class ]:
8

[ HS Code ]:
2921499090

Customs

[ HS Code ]: 2921499090

[ Summary ]:
2921499090 other aromatic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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