AEBSF

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AEBSF

Names

IUPAC name
4-(2-Aminoethyl)benzenesulfonyl fluoride

Other names
Pefabloc SC

Identifiers

CAS Number

34284-75-8 N

3D model (Jmol)
Interactive image

ChEMBL
ChEMBL1096339 Y

ChemSpider
1638 Y

DrugBank
DB07347 Y

MeSH
AEBSF

PubChem
1701

InChI

InChI=1S/C8H10FNO2S/c9-13(11,12)8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2 Y
Key: MGSKVZWGBWPBTF-UHFFFAOYSA-N Y

InChI=1/C8H10FNO2S/c9-13(11,12)8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2
Key: MGSKVZWGBWPBTF-UHFFFAOYAK

SMILES

FS(=O)(=O)c1ccc(cc1)CCN

Properties

Chemical formula

C8H10FNO2S.HCl

Molar mass
239.69 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

AEBSF or 4-(2-aminoethyl)benzenesulfonyl fluoride hydrochloride is a water-soluble, irreversible serine protease inhibitor with a molecular weight of 239.5 Da. It inhibits proteases like chymotrypsin, kallikrein, plasmin, thrombin, and trypsin. The specificity is similar to the inhibitor PMSF, nevertheless AEBSF is more stable at low pH values. Typical usage is 0.1 – 1.0 mM.

Contents

1 Mechanism of action
2 Use in cholesterol regulation studies
3 External links
4 References

Mechanism of action[edit]
Both AEBSF and PMSF are sulfonyl fluorides and are sulfonylating agents.[1] Sulfonyl fluorides act by reacting with the hydroxy group of the active site serine residue to form a sulfonyl enzyme derivative. This derivative may be stable for long periods of time except at high pH.[2]
Use in cholesterol regulation studies[edit]
AEBSF is extensively used in studies aiming to describe cholesterol regulatory genes due to its potent ability to inhibit Site-1-protease (S1P). This serine protease, located in the Golgi apparatus, is responsible for activating the sterol regulatory element-binding proteins (SREBP). By selectively inhibiting S1P, AEBSF can be used to characterize the downstream result of SREBP inhibition and its influence on cholesterol regulation.
External links[edit]

The MEROPS online database for peptidases and their inhibitors: AEBSF
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