Fluorescent sterols and cholesteryl esters as probes for intracellular cholesterol transport

Katarzyna A. Solanko, Maciej Modzel, Lukasz M. Solanko, Daniel Wüstner*

*Corresponding author for this work

Research output: Contribution to journalReviewResearchpeer-review

Abstract

Cholesterol transport between cellular organelles comprised vesicular trafficking and nonvesicular exchange; these processes are often studied by quantitative fluorescence microscopy. A major challenge for using this approach is producing analogs of cholesterol with suitable brightness and structural and chemical properties comparable with those of cholesterol. This review surveys currently used fluorescent sterols with respect to their behavior in model membranes, their photophysical properties, as well as their transport and metabolism in cells. In the first part, several intrinsically fluorescent sterols, such as dehydroergosterol or cholestatrienol, are discussed. These polyene sterols (P-sterols) contain three conjugated double bonds in the steroid ring system, giving them slight fluorescence in ultraviolet light. We discuss the properties of P-sterols relative to cholesterol, outline their chemical synthesis, and explain how to image them in living cells and organisms. In particular, we show that P-sterol esters inserted into low-density lipoprotein can be tracked in the fibroblasts of Niemann-Pick disease using high-resolution deconvolution microscopy. We also describe fluorophore-tagged cholesterol probes, such as BODIPY-, NBD-, Dansyl-, or Pyrene-tagged cholesterol, and eventual esters of these analogs. Finally, we survey the latest developments in the synthesis and use of alkyne cholesterol analogs to be labeled with fluorophores by click chemistry and discuss the potential of all approaches for future applications .

Original languageEnglish
JournalLipid Insights
Volume8s1
Pages (from-to)95-114
Number of pages20
ISSN1178-6353
DOIs
Publication statusPublished - 1. Jan 2015

Fingerprint

Cholesterol Esters
Sterols
Cholesterol
Polyenes
Fluorophores
Alkynes
Fluorescence microscopy
Deconvolution
Fibroblasts
LDL Lipoproteins
Metabolism
Transport properties
Chemical properties
Structural properties
Luminance
Microscopic examination
Esters
Fluorescence
Steroids
Cells

Keywords

  • Endocytosis
  • Fluorescent sterols
  • Imaging
  • Metabolism
  • Optical microscopy
  • Sterol trafficking

Cite this

Solanko, Katarzyna A. ; Modzel, Maciej ; Solanko, Lukasz M. ; Wüstner, Daniel. / Fluorescent sterols and cholesteryl esters as probes for intracellular cholesterol transport. In: Lipid Insights. 2015 ; Vol. 8s1. pp. 95-114.
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abstract = "Cholesterol transport between cellular organelles comprised vesicular trafficking and nonvesicular exchange; these processes are often studied by quantitative fluorescence microscopy. A major challenge for using this approach is producing analogs of cholesterol with suitable brightness and structural and chemical properties comparable with those of cholesterol. This review surveys currently used fluorescent sterols with respect to their behavior in model membranes, their photophysical properties, as well as their transport and metabolism in cells. In the first part, several intrinsically fluorescent sterols, such as dehydroergosterol or cholestatrienol, are discussed. These polyene sterols (P-sterols) contain three conjugated double bonds in the steroid ring system, giving them slight fluorescence in ultraviolet light. We discuss the properties of P-sterols relative to cholesterol, outline their chemical synthesis, and explain how to image them in living cells and organisms. In particular, we show that P-sterol esters inserted into low-density lipoprotein can be tracked in the fibroblasts of Niemann-Pick disease using high-resolution deconvolution microscopy. We also describe fluorophore-tagged cholesterol probes, such as BODIPY-, NBD-, Dansyl-, or Pyrene-tagged cholesterol, and eventual esters of these analogs. Finally, we survey the latest developments in the synthesis and use of alkyne cholesterol analogs to be labeled with fluorophores by click chemistry and discuss the potential of all approaches for future applications .",
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Fluorescent sterols and cholesteryl esters as probes for intracellular cholesterol transport. / Solanko, Katarzyna A.; Modzel, Maciej; Solanko, Lukasz M.; Wüstner, Daniel.

In: Lipid Insights, Vol. 8s1, 01.01.2015, p. 95-114.

Research output: Contribution to journalReviewResearchpeer-review

TY - JOUR

T1 - Fluorescent sterols and cholesteryl esters as probes for intracellular cholesterol transport

AU - Solanko, Katarzyna A.

AU - Modzel, Maciej

AU - Solanko, Lukasz M.

AU - Wüstner, Daniel

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AB - Cholesterol transport between cellular organelles comprised vesicular trafficking and nonvesicular exchange; these processes are often studied by quantitative fluorescence microscopy. A major challenge for using this approach is producing analogs of cholesterol with suitable brightness and structural and chemical properties comparable with those of cholesterol. This review surveys currently used fluorescent sterols with respect to their behavior in model membranes, their photophysical properties, as well as their transport and metabolism in cells. In the first part, several intrinsically fluorescent sterols, such as dehydroergosterol or cholestatrienol, are discussed. These polyene sterols (P-sterols) contain three conjugated double bonds in the steroid ring system, giving them slight fluorescence in ultraviolet light. We discuss the properties of P-sterols relative to cholesterol, outline their chemical synthesis, and explain how to image them in living cells and organisms. In particular, we show that P-sterol esters inserted into low-density lipoprotein can be tracked in the fibroblasts of Niemann-Pick disease using high-resolution deconvolution microscopy. We also describe fluorophore-tagged cholesterol probes, such as BODIPY-, NBD-, Dansyl-, or Pyrene-tagged cholesterol, and eventual esters of these analogs. Finally, we survey the latest developments in the synthesis and use of alkyne cholesterol analogs to be labeled with fluorophores by click chemistry and discuss the potential of all approaches for future applications .

KW - Endocytosis

KW - Fluorescent sterols

KW - Imaging

KW - Metabolism

KW - Optical microscopy

KW - Sterol trafficking

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