BODIPY-Cholesterol (Synonyms: BCh2)

BODIPY-Cholesterol is cholesterol tagged with a boron dipyrromethene difluoride (BODIPY) fluorophore used for monitoring sterol uptake and inter-organelle sterol flux in cells with excitation of 480 nm and emission of 508 nm.^[1] The excretion of BODIPY cholesterol from late endoplasmic organelles depends on acidic lipase and Niemann pickc1 protein.^[6]

In vitro, treatment with Bodipy-cholesterol in cells, prominent PM labeling is observed at 2–5 min; however, upon ≥30 min incubations, it is also observed the fluorescence labeling of intracellular structures.^[2] In vitro efficacy test it suggested that accumulation of BODIPY-cholesterol in the media gave more reproducible values than assaying for the loss of the compound from the cells.^[3] With 1 μg BODIPY-cholesterol analogs show a similar cellular localization in HeLa cells and exhibit similar cholesterol efflux properties from THP1 cells to HDL acceptors.^[4] BODIPY-cholesterol efflux clearly increased when treatment of fibroblasts with the Hh pathway agonist SAG, which enhances Ptc protein expression, or over-expression of human Ptc in yeast.^[5] Treatment with miR-758 inhibitor obviously increased ABCA1-dependent cholesterol efflux by BODIPY-Cholesterol efflux assay.^[7] Micrographs of EPCs incubated with HDL labeld bodipy-cholesterol (50 µg/ml) 30 min, small cytoplasmic vesicles as well as large positive MVBs containing intraluminal microvesicles, tightly-packed with reaction products could be displayed. The internalized-HDL-derived bodipy-cholesterol was also spread within many of the stacked Golgi cisterns and the TGN.^[8]

References:
[1].Wüstner D, et al. Potential of BODIPY-cholesterol for analysis of cholesterol transport and diffusion in living cells. Chem Phys Lipids. 2016 Jan;194:12-28.
[2].Hölttä-Vuori M, et al. BODIPY-cholesterol: a new tool to visualize sterol trafficking in living cells and organisms. Traffic. 2008 Nov;9(11):1839-49.
[3].Sankaranarayanan S, et al. A sensitive assay for ABCA1-mediated cholesterol efflux using BODIPY-cholesterol. J Lipid Res. 2011 Dec;52(12):2332-2340.
[4].Liu Z, et al. Synthesis of cholesterol analogues bearing BODIPY fluorophores by Suzuki or Liebeskind-Srogl cross-coupling and evaluation of their potential for visualization of cholesterol pools. Chembiochem. 2014 Sep 22;15(14):2087-96.
[5].Bidet M, et al. The hedgehog receptor patched is involved in cholesterol transport. PLoS One. 2011;6(9):e23834.
[6].Kanerva K, et al. LDL cholesterol recycles to the plasma membrane via a Rab8a-Myosin5b-actin-dependent membrane transport route. Dev Cell. 2013 Nov 11;27(3):249-62.
[7].Yao Y, et al. Glucagon-like peptide-1 contributes to increases ABCA1 expression by downregulating miR-758 to regulate cholesterol homeostasis. Biochem Biophys Res Commun. 2018 Mar 4;497(2):652-658.
[8].Srisen K, et al. Human endothelial progenitor cells internalize high-density lipoprotein. PLoS One. 2013 Dec 30;8(12):e83189.