title: N (1)-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase.
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 N (1)-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-[(18)F]FETrp, should be a molecule of choice to visualize tumoral and inflammatory tissues and/or to validate new potential inhibitors.
authors: Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium ; Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium.
authors: Jean
authors: J
authors: Henrottin
authors: Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium.
authors: Astrid
authors: A
authors: Zervosen
authors: Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium.
authors: Christian
authors: C
authors: Lemaire
authors: Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium.
authors: Frédéric
authors: F
authors: Sapunaric
authors: Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium.
authors: Sophie
authors: S
authors: Laurent
authors: Ludwig Institute for Cancer Research, Brussels Branch and de Duve Institute, Université Catholique de Louvain , B-1200 Brussels, Belgium.
authors: Benoit
authors: B
authors: Van den Eynde
authors: PET/Biomedical Cyclotron Unit and Department of Nuclear Medicine, Erasme Hospital, Université Libre de Bruxelles , B-1070 Brussels, Belgium ; Center for Microscopy and Molecular Imaging , Rue Adrienne Bolland 8, B-6041 Gosselies, Belgium.
authors: Serge
authors: S
authors: Goldman
authors: Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium.
authors: Alain
authors: A
authors: Plenevaux
authors: Cyclotron Research Center, Department of Chemistry, and Macromolécules Biologiques, Center for Protein Engineering, Université de Liège, Sart-Tilman , B-4000 Liège, Belgium.
authors: André
authors: A
authors: Luxen
keywords: 1-(2-fluoroethyl)-tryptophan; Tryptophan; indoleamine 2,3-dioxygenase; kynurenine; positron emission tomography; tryptophan 2,3-dioxygenase