title: Synthesis of fluorinated agonist of sphingosine-1-phosphate receptor 1.
abstract: The bioactive metabolite sphingosine-1-phosphate (S1P), a product of sphingosine kinases (SphKs), mediates diverse biological processes such as cell differentiation, proliferation, survival and angiogenesis. A fluorinated analogue of S1P receptor agonist has been synthesized by utilizing a ring opening reaction of oxacycles by a lithiated difluoromethylphosphonate anion as the key reaction. In vitro activity of this S1P analogue is also reported.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507 & FR3038, ENSICAEN, Normandie Université, Université de Caen Basse-Normandie, 6 Bd du Maréchal Juin, Caen 14050, France; Normandie Université, COBRA, UMR 6014 & FR 3038; Université de Rouen; INSA Rouen; CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Lucie
authors.initials: L
authors.lastname: Aliouane
authors.affiliation: Normandie Université, COBRA, UMR 6014 & FR 3038; Université de Rouen; INSA Rouen; CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Sovy
authors.initials: S
authors.lastname: Chao
authors.affiliation: CNRS, Institut de Pharmacologie et de Biologie Structurale, 205 Route de Narbonne, 31077 Toulouse, France; Université de Toulouse, UPS, IPBS, 205 Route de Narbonne, 31077 Toulouse, France.
authors.forename: Leyre
authors.initials: L
authors.lastname: Brizuela
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507 & FR3038, ENSICAEN, Normandie Université, Université de Caen Basse-Normandie, 6 Bd du Maréchal Juin, Caen 14050, France.
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Pfund
authors.affiliation: CNRS, Institut de Pharmacologie et de Biologie Structurale, 205 Route de Narbonne, 31077 Toulouse, France; Université de Toulouse, UPS, IPBS, 205 Route de Narbonne, 31077 Toulouse, France.
authors.forename: Olivier
authors.initials: O
authors.lastname: Cuvillier
authors.affiliation: Normandie Université, COBRA, UMR 6014 & FR 3038; Université de Rouen; INSA Rouen; CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France.
authors.forename: Ludovic
authors.initials: L
authors.lastname: Jean
authors.affiliation: Normandie Université, COBRA, UMR 6014 & FR 3038; Université de Rouen; INSA Rouen; CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France. Electronic address: pierre-yves.renard@univ-rouen.fr.
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Renard
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507 & FR3038, ENSICAEN, Normandie Université, Université de Caen Basse-Normandie, 6 Bd du Maréchal Juin, Caen 14050, France. Electronic address: thierry.lequeux@ensicaen.fr.
authors.forename: Thierry
authors.initials: T
authors.lastname: Lequeux
mesh_terms: D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D054879:Halogenation; D006801:Humans; D008297:Male; D015394:Molecular Structure; D010755:Organophosphates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049349:Receptors, Lysosphingolipid / Q000819:agonists*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000081025:Sphingosine-1-Phosphate Receptors; D013329:Structure-Activity Relationship
chemical_list: C525008:FTY 720P; D010755:Organophosphates; D049349:Receptors, Lysosphingolipid; C477362:S1PR1 protein, human; D000081025:Sphingosine-1-Phosphate Receptors; D013110:Sphingosine
keywords: Agonist; Difluorophosphonate; Fluorine; Sphingosine-1-phosphate