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Revision as of 19:31, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473824938 of page AEBSF for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 12:54, 9 November 2024 edit Innerstream (talk | contribs)Autopatrolled, Extended confirmed users4,032 editsmNo edit summary 
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{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Refimprove|date=May 2016}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 443657449 | verifiedrevid = 477235294
| ImageFile = AEBSF.png | ImageFile = AEBSF.svg
| ImageSize = | ImageSize =
| ImageFile1 = AEBSF-3D-balls.png
⚫ | IUPACName = 4-(2-Aminoethyl)benzenesulfonyl fluoride
| ImageAlt1 = AEBSF molecule
⚫ | PIN = 4-(2-Aminoethyl)benzene-1-sulfonyl fluoride
| OtherNames = Pefabloc SC | OtherNames = Pefabloc SC
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1638 | ChemSpiderID = 1638
| InChI = 1/C8H10FNO2S/c9-13(11,12)8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2 | InChI = 1/C8H10FNO2S/c9-13(11,12)8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MGSKVZWGBWPBTF-UHFFFAOYSA-N | StdInChIKey = MGSKVZWGBWPBTF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}} | CASNo_Ref = {{cascite|changed|??}}
| CASNo = <!-- blanked - oldvalue: 34284-75-8 --> | CASNo = 34284-75-8
| PubChem = 1701 | CASNo2 = 30827-99-7
| CASNo2_Comment = (hydrochloride salt)
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F5D36L5354
| PubChem = 1701
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB07347 | DrugBank = DB07347
| SMILES = FS(=O)(=O)c1ccc(cc1)CCN | SMILES = FS(=O)(=O)c1ccc(cc1)CCN
| MeSHName = AEBSF | MeSHName = AEBSF
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>8</sub>H<sub>10</sub>FNO<sub>2</sub>S.HCl | Formula = C<sub>8</sub>H<sub>10</sub>FNO<sub>2</sub>S.HCl
| MolarMass = 239.69 g/mol | MolarMass = 239.69 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = 200 mg/mL<ref>{{cite web |title=Pefabloc® SC |url=https://www.pentapharm.com/wp-content/uploads/2019/05/399-01_DSe_Pefabloc-SC.pdf |publisher=Pentapharm |access-date=22 June 2023}}</ref>
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}

'''AEBSF''' or 4-(2-aminoethyl)benzenesulfonyl fluoride hydrochloride is a water-soluble, irreversible ] ] with a molecular weight of 239.5 ] It inhibits ]s like ], ], ], ], and ]. The specificity is similar to the inhibitor ], nevertheless AEBSF is more stable at low pH values. Typical usage is 0.1 - 1.0 mM. AEBSF (marketed as Pefabloc SC from the company ]) was first reported for use in biochemistry in 1993, and came into common use for the inhibition serine proteases and of non-protease enzymes such as acetylhydrolases in the mid 1990s.<ref name="Dentan1996">{{cite journal | last1=Dentan | first1=Christine | last2=Tselepis | first2=Alexandros D. | last3=Chapman | first3=M.John | last4=Ninio | first4=Ewa | title=Pefabloc, 4-benzenesulfonyl fluoride, is a new, potent nontoxic and irreversible inhibitor of PAF-degrading acetylhydrolase | journal=Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism | publisher=Elsevier BV | volume=1299 | issue=3 | year=1996 | issn=0005-2760 | doi=10.1016/0005-2760(95)00226-x | pages=353–357| pmid=8597590 }}</ref>

== Mechanism of action ==
AEBSF is targeted to covalently modify the hydroxyl of serine residues, where it causes an additional 183.0354 ] to be added to each modified residue, but other off-target residues such as ], ], ], and the ], have also been reported.<ref name="ABRF_posts">{{cite web |title=Web-Based Discussion Forum - Protease Inhibitor Cocktail |url=http://www.abrf.org/index.cfm/list.msg/78308?brSort=auth&expand=all&listName=abrf&urlStr= |publisher=The Association of Biomolecular Resource Facilities (ABRF) |access-date=22 June 2023 |archive-date=3 July 2013 |archive-url=https://archive.today/20130703161237/http://www.abrf.org/index.cfm/list.msg/78308?brSort=auth&expand=all&listName=abrf&urlStr= |url-status=bot: unknown }}</ref><ref name="Login 2006 o260">{{cite web | title= Accession #: 276 Aminoethylbenzenesulfonylation | website=Unimod | date=2006-10-16 | url=http://www.unimod.org/modifications_view.php?editid1=276 | access-date=2023-06-21}}</ref> Due to the substantial frequency of modification of these off-target residues in unoptimized protocols, some users recommend not using AEBSF for highly sensitive ] applications, and instead recommend using fresh (and comparatively unstable) ].<ref name="ABRF_posts"></ref> Both AEBSF and ] are ]s and are sulfonylating agents.<ref>{{cite journal | vauthors = Powers JC, Asgian JL, Ekici OD, James KE | title = Irreversible inhibitors of serine, cysteine, and threonine proteases | journal = Chem. Rev. | volume = 102 | issue = 12 | pages = 4735–4736 | year = 2002 | pmid = 12475205 | doi=10.1021/cr010182v}}</ref> Sulfonyl fluorides act by reacting with the ] of the ] ] to form a sulfonyl enzyme derivative. This derivative may be stable for long periods of time except at high pH.<ref>{{cite journal | vauthors = Gold AM, Fahrney D | title = Sulfonyl Fluorides as Inhibitors of Esterases. II. Formation and Reactions of Phenylmethanesulfonyl α-Chymotrypsin | journal = Biochemistry | volume = 3 | pages = 783–791 | year = 1964 | issue = 6 | pmid = 14211616 | doi=10.1021/bi00894a009}}</ref>

== Use in cholesterol regulation studies ==

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.

==See also==
* ]
* ] (diisopropyl fluorophosphate), an analogous fluorophosphonate phosphorylating reagent

==References==
{{Reflist|2}}

==External links==
* The ] online database for peptidases and their inhibitors:
* A Link to the ABRF group usegroup archive with an informative discussion of covalent modifications to proteins resulting from use of AEBSF:

{{DEFAULTSORT:Aebsf}}
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