N1-Fluoroalkyltryptophan analogues: synthesis and in vitro study as potential substrates for indoleamine 2,3-dioxygenase

Henrottin, Jean; Zervosen, Astrid; Lemaire, Christian; Sapunaric, Frédéric; Laurent, Sophie; Van den Eynde, Benoit; Goldman, Serge; Plenevaux, Alain; Luxen, André

doi:10.1021/ml500385d

Article (Scientific journals)

N1-Fluoroalkyltryptophan analogues: synthesis and in vitro study as potential substrates for indoleamine 2,3-dioxygenase

Henrottin, Jean; Zervosen, Astrid; Lemaire, Christian et al.

2015 • In ACS Medicinal Chemistry Letters, 6, p. 260-265

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https://hdl.handle.net/2268/177411

DOI
10.1021/ml500385d

PubMed
25815143

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Keywords :

Tryptophan; Indoleamine 2,3-dioxygenase; Kynurenine; 1-(2-fluoroethyl)-Tryptophan; Tryptophan 2,3-Dioxygenase; Positron Emission Tomography

Abstract :

[en] ABSTRACT: Indoleamine 2,3-dioxygenase (hIDO) is an enzyme that catalyzes the oxidative cleavage of the indole ring of L-tryptophan through the kynurenine pathway, thereby exerting immunosuppressive properties in inflammatory and tumoral tissues. The syntheses of 1-(2-fluoroethyl)-tryptophan (1-FETrp) and 1-((1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl)methyl)-tryptophan, two N1-fluoroalkylated tryptophan derivatives, are described here. In vitro enzymatic assays with these two new potential substrates of hIDO show that 1-FETrp is a good and specific substrate of hIDO. Therefore, its radioactive isotopomer, 1-[18F]FETrp, should be a molecule of choice to visualize tumoral and inflammatory tissues and/or to validate new potential inhibitors.

Disciplines :

Chemistry

Author, co-author :

Henrottin, Jean ; Université de Liège - ULiège > Centre de recherches du cyclotron

Zervosen, Astrid ; Université de Liège - ULiège > Centre de recherches du cyclotron

Lemaire, Christian ; Université de Liège - ULiège > Centre de recherches du cyclotron

Sapunaric, Frédéric

Laurent, Sophie

Van den Eynde, Benoit

Goldman, Serge

Plenevaux, Alain ; Université de Liège - ULiège > Centre de recherches du cyclotron

Luxen, André ; Université de Liège - ULiège > Département de chimie (sciences) > Laboratoire de chimie organique de synthèse

Language :

English

Title :

N1-Fluoroalkyltryptophan analogues: synthesis and in vitro study as potential substrates for indoleamine 2,3-dioxygenase

Publication date :

January 2015

Journal title :

ACS Medicinal Chemistry Letters

eISSN :

1948-5875

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

Pages :

260-265

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 26 January 2015

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