title: Synthesis and characterization of a fluorescent probe for α-tocopherol suitable for fluorescence microscopy.
abstract: Previously prepared fluorescent derivatives of α-tocopherol have shown tremendous utility in both in vitro exploration of the mechanism of ligand transfer by the α-tocopherol transfer protein (α-TTP) and the intracellular transport of α-tocopherol in cells and tissues. We report here the synthesis of a 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) containing α-tocopherol analog having extended conjugation with an alkenyl thiophene group that extends the absorption and emission maxima to longer wavelengths (λex=571nm and λem=583nm). The final fluorophore thienyl-ene-BODIPY-α-tocopherol, 2, binds to recombinant human α-TTP with a Kd=8.7±1.1nM and is a suitable probe for monitoring the secretion of α-tocopherol from cultured Mcf7#189 cells.
authors.affiliation: Department of Chemistry, Brock University, St. Catharines, ON L2S 3A1, Canada.
authors.forename: Mikel
authors.initials: M
authors.lastname: Ghelfi
authors.affiliation: Department of Nutrition, School of Medicine, Case Western Reserve University, Cleveland, OH 44106, USA.
authors.forename: Lynn
authors.initials: L
authors.lastname: Ulatowski
authors.affiliation: Department of Nutrition, School of Medicine, Case Western Reserve University, Cleveland, OH 44106, USA.
authors.forename: Danny
authors.initials: D
authors.lastname: Manor
authors.affiliation: Department of Chemistry, Brock University, St. Catharines, ON L2S 3A1, Canada. Electronic address: jatkinson@brocku.ca.
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Atkinson
mesh_terms: D000818:Animals; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D002352:Carrier Proteins / Q000378:metabolism; D002460:Cell Line; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D008856:Microscopy, Fluorescence / Q000379:methods*; D011485:Protein Binding; D051381:Rats; D024502:alpha-Tocopherol / Q000031:analogs & derivatives* / Q000032:analysis* / Q000378:metabolism
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D002352:Carrier Proteins; D005456:Fluorescent Dyes; C017763:alpha-tocopherol transfer protein; D024502:alpha-Tocopherol
keywords: BODIPY; Fluorescent ligand; Vitamin E; α-Tocopherol; α-Tocopherol transfer protein