aspirin-based probe AP (CHEBI:141699)

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ChEBI Name	aspirin-based probe AP

ChEBI ID	CHEBI:141699

Definition	A benzoate ester resulting from the formal condensation of the carboxy group of acetylsalicylic acid with the phenolic hydroxy group of 2-(1,3-benzothiazol-2-yl)-4-fluorophenol. The latter is a fluorophore which is to the aspirin moiety via an H₂O₂-responsive bond. It can be used as probe for imaging H₂O₂ (overproduction of H₂O₂ causes oxidative stress and is characteristic of vascular diseases). In contrast to arylboronat-based probes, it shows high specificity for H₂O₂ over peroxynitrite (which is much more reactive than H₂O₂, but exists at much lower abundance).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Sabrina Toro

Supplier Information

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Formula

C22H14FNO4S

Net Charge

Average Mass

407.416

Monoisotopic Mass

407.06276

InChI

InChI=1S/C22H14FNO4S/c1-13(25)27-18-8-4-2-6-15(18)22(26)28-19-11-10-14(23)12-16(19)21-24-17-7-3-5-9-20(17)29-21/h2-12H,1H3

InChIKey

TVZDIFFVBBTTIJ-UHFFFAOYSA-N

SMILES

C=12C(=CC=CC1)N=C(S2)C=3C=C(C=CC3OC(C=4C(=CC=CC4)OC(C)=O)=O)F

Roles Classification
Application(s):	pharmaceutical Any substance introduced into a living organism with therapeutic or diagnostic purpose.

ChEBI Ontology
Outgoing	aspirin-based probe AP (CHEBI:141699) has functional parent 2-(1,3-benzothiazol-2-yl)-4-fluorophenol (CHEBI:142485) aspirin-based probe AP (CHEBI:141699) has functional parent acetylsalicylic acid (CHEBI:15365) aspirin-based probe AP (CHEBI:141699) has role pharmaceutical (CHEBI:52217) aspirin-based probe AP (CHEBI:141699) is a benzoate ester (CHEBI:36054) aspirin-based probe AP (CHEBI:141699) is a benzothiazoles (CHEBI:37947) aspirin-based probe AP (CHEBI:141699) is a monofluorobenzenes (CHEBI:83575) aspirin-based probe AP (CHEBI:141699) is a salicylates (CHEBI:26596)

IUPAC Names

2-(1,3-benzothiazol-2-yl)-4-fluorophenyl 2-(acetyloxy)benzoate

2-(1,3-benzothiazol-2-yl)-4-fluorophenyl 2-acetoxybenzoate

Synonyms	Sources
2-(1,3-benzothiazol-2-yl)-4-fluorophenyl salicylate	ChEBI
probe AP	SUBMITTER

Citation	Type	Source
29109778	PubMed citation	SUBMITTER

Last Modified

02 November 2018