title: Synthesis of cholesterol analogues bearing BODIPY fluorophores by Suzuki or Liebeskind-Srogl cross-coupling and evaluation of their potential for visualization of cholesterol pools.
abstract: We report a synthetic route to BODIPY-cholesterol conjugates in which the key steps were Suzuki or Liebeskind-Srogl cross-coupling of cholesterol phenyl moieties with structurally diverse BODIPY scaffolds. All conjugates feature single-bonded and hydrophobic linkages between the fluorophore and sterol that are devoid of heteroatoms. Using HeLa cells, we show that these BODIPY-cholesterol analogues can be used simultaneously with the parent BODIPY-cholesterol for cell imaging and flow cytometry. The BODIPY-cholesterol analogues exhibit similar cellular localization in HeLa cells and show similar cholesterol efflux properties from THP-1 cells to HDL acceptors. These results demonstrate that the red-shifted BODIPY-cholesterol analogues behave in a manner similar to unlabeled cholesterol and are useful probes for simultaneous visualization of intracellular cholesterol pools and for monitoring cholesterol efflux from cells to extracellular acceptors.
authors.affiliation: Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, NY 11367 (USA).
authors.forename: Zheng
authors.initials: Z
authors.lastname: Liu
authors.forename: Seth G
authors.initials: SG
authors.lastname: Thacker
authors.forename: Sara
authors.initials: S
authors.lastname: Fernandez-Castillejo
authors.forename: Edward B
authors.initials: EB
authors.lastname: Neufeld
authors.forename: Alan T
authors.initials: AT
authors.lastname: Remaley
authors.forename: Robert
authors.initials: R
authors.lastname: Bittman
mesh_terms: D001896:Boron Compounds / Q000032:analysis*; D002784:Cholesterol / Q000031:analogs & derivatives / Q000032:analysis*; D005434:Flow Cytometry; D005456:Fluorescent Dyes / Q000032:analysis*; D006367:HeLa Cells; D006801:Humans; D061848:Optical Imaging
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D002784:Cholesterol
keywords: BODIPY-cholesterol; Liebeskind-Srogl coupling; Suzuki coupling; confocal microscopy; fluorescence imaging