title: Benzophenone-containing fatty acids and their related photosensitive fluorescent new probes: design, physico-chemical properties and preliminary functional investigations.
abstract: Hydrophobic photoaffinity labeling is a powerful strategy to identify hydrophobic segments within molecules, in particular membrane proteins. Here we report the design and synthesis of a novel family of fluorescent and photosensitive lipid tools, which have a common amino acid scaffold functionalized by three groups: (i) a first fatty acid chain grafted with a photoactivatable benzophenone moiety (Fatty Acid BenzoPhenone, FABP), (ii) a second fatty acid chain to ensure anchoring into a half-bilayer or hydrophobic environment, and (iii) a fluorescent carboxytetramethylrhodamine headgroup (CTMR) to detect the photolabeled compound. We present data of the synthesis and characterization of three lipid tools whose benzophenone ring is situated at various distances from the central scaffold. We could therefore establish structure/properties relationships dependent upon the depth of insertion of benzophenone into the membrane. Our lipid tools were extensively characterized both physico- and bio-chemically, and we assessed their functionality in vitro using bacterioRhodopsin (bR). We thus provide the scientific community with novel and reliable tools for the identification and study of hydrophobic regions in proteins.
authors: UMR 7199 CNRS/Université de Strasbourg, Equipe de Biovectorologie, Faculté de Pharmacie, 74 route du Rhin, 67401 Illkirch Cedex, France.
authors: Benoît
authors: B
authors: Hilbold
authors: Marie
authors: M
authors: Perrault
authors: Christophe
authors: C
authors: Ehret
authors: Song-Lin
authors: SL
authors: Niu
authors: Benoît
authors: B
authors: Frisch
authors: Eve-Isabelle
authors: EI
authors: Pécheur
authors: Line
authors: L
authors: Bourel-Bonnet
mesh_terms: D001436:Bacteriorhodopsins / Q000032:analysis; D001577:Benzophenones / Q000138:chemical synthesis / Q000737:chemistry*; D005227:Fatty Acids / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D019617:Halobacterium salinarum / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D012235:Rhodamines / Q000737:chemistry; D013050:Spectrometry, Fluorescence
chemical_list: C437523:5-carboxytetramethylrhodamine; D001577:Benzophenones; D005227:Fatty Acids; D005456:Fluorescent Dyes; D012235:Rhodamines; D001436:Bacteriorhodopsins; C047723:benzophenone