title: Evaluation of the effect of fluorination on the property of monofluorinated dimyristoylphosphatidylcholines.
abstract: The synthesis of three monofluorinated dimyristoylphosphatidylcholines (F-DMPC's), with the fluorine atom located at the extremities of the acyl chain in position 2 of the glycerol (sn-2), is described. The synthetic strategy relies on the coupling of 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (14:0 lyso-PC) and three different fluorinated fatty acids. FTIR results suggest that the presence of the fluorine atom does not significantly perturb the lipid phase transition temperature and conformational order even though a small increase in the phase transition temperature is observed for the 14F derivative. Overall, comparison with previously reported F-DMPC's where the fluorine atom is located in the middle or close from either side supports the fact that monofluorination of the acyl chain in sn-2 brings minimal perturbation to the lipid bilayer. F-DMPC's could therefore potentially be used as NMR probes for the investigation at the molecular level of the interaction between drugs or peptides and lipid membranes and for the study of membrane topology.
authors.affiliation: Department of Chemistry, PROTEO, CERMA, 1045 avenue de la Médecine, Université Laval, Québec, Canada. Michele.auger@chm.ulaval.ca.
authors.forename: Marie-Claude
authors.initials: MC
authors.lastname: Gagnon
authors.forename: Bianka
authors.initials: B
authors.lastname: Turgeon
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Savoie
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Parent
authors.forename: Michèle
authors.initials: M
authors.lastname: Auger
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin
mesh_terms: D004134:Dimyristoylphosphatidylcholine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D005227:Fatty Acids / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D005990:Glycerol / Q000737:chemistry; D054879:Halogenation; D008051:Lipid Bilayers / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015335:Molecular Probes / Q000138:chemical synthesis*; D044367:Phase Transition; D013696:Temperature
chemical_list: D005227:Fatty Acids; D008051:Lipid Bilayers; D015335:Molecular Probes; D005461:Fluorine; D005990:Glycerol; D004134:Dimyristoylphosphatidylcholine