Synthesis and characterization of a fluorescent probe for α-tocopherol suitable for fluorescence microscopy. Issue 12 (15th June 2016)

• Record Type: Journal Article
• Authors: Ghelfi, Mikel; Ulatowski, Lynn; Manor, Danny; Atkinson, Jeffrey
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 12(2016)
• Page Start: 2754
• Page End: 2761
• Publication Date: 2016-06-15
• Subjects: Vitamin E -- α-Tocopherol -- Fluorescent ligand -- α-Tocopherol transfer protein -- BODIPY; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2016.04.044
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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 ( λ ex = 571 nm and λ em = 583 nm). The final fluorophore thienyl-ene-BODIPY-α-tocopherol, 2, binds to recombinant human α-TTP with a K d = 8.7 ± 1.1 nM and is a suitable probe for monitoring the secretion of α-tocopherol from cultured Mcf7#189 cells.