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. Author manuscript; available in PMC: 2016 Mar 2.
Published in final edited form as: Chembiochem. 2015 Feb 6;16(4):611–617. doi: 10.1002/cbic.201402715

Figure 1. 19-ethynylcholesterol (eChol) is a functional bioorthogonal analog of cholesterol (Chol).

Figure 1

(A) Structures of cholesterol (Chol) and eChol, a Chol analog in which a terminal alkyne group replaces the axial methyl at position C-19 of the sterol molecule. After labeling cells, eChol can be imaged by fluorescence microscopy, following copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) with fluorescein-azide.

(B) Chol auxotrophic M19 CHO cells were grown for 4 days in media containing delipidated serum supplemented with oleic acid (35 μM), and in the presence or absence of Chol (10 μM) or eChol (35 μM), added as soluble methyl β-cyclodextrin (MCD) complexes. Representative fields of cells were photographed on days 1, 2 and 3 after plating. M19 CHO cells cannot proliferate in the absence of sterols; proliferation is completely rescued by eChol or Chol.