First synthesis of free cholesterol− BODIPY conjugates

Z Li, E Mintzer, R Bittman - The Journal of organic chemistry, 2006 - ACS Publications
Z Li, E Mintzer, R Bittman
The Journal of organic chemistry, 2006ACS Publications
Analogues of cholesterol (compounds 1 and 2) and coprostanol (compound 3) containing
the BODIPY fluorophore in the aliphatic tail of the free sterol have been synthesized starting
with bisnorcholenic acid, cholenic acid 3β-acetate, and lithocholic acid, respectively. An
ester linkage joining the fluorophore to the sterol nucleus interfered with the ability of the
fluorescent sterol to pack with phospholipids in monolayers. However, an analogue in which
the linker was devoid of polar atoms exhibited a substantially similar physical behavior to …
Analogues of cholesterol (compounds 1 and 2) and coprostanol (compound 3) containing the BODIPY fluorophore in the aliphatic tail of the free sterol have been synthesized starting with bisnorcholenic acid, cholenic acid 3β-acetate, and lithocholic acid, respectively. An ester linkage joining the fluorophore to the sterol nucleus interfered with the ability of the fluorescent sterol to pack with phospholipids in monolayers. However, an analogue in which the linker was devoid of polar atoms exhibited a substantially similar physical behavior to cholesterol in model membranes with respect to localization in raft domains.
ACS Publications