First synthesis of free cholesterol-BODIPY conjugates.
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 3beta-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.
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
Zaiguo
Z
Li
Evan
E
Mintzer
Robert
R
Bittman
D001896:Boron Compounds / Q000737:chemistry*; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003432:Cross-Linking Reagents; D004952:Esters; D005456:Fluorescent Dyes / Q000737:chemistry; D021962:Membrane Microdomains / Q000737:chemistry; D008567:Membranes, Artificial; D010743:Phospholipids
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D003432:Cross-Linking Reagents; D004952:Esters; D005456:Fluorescent Dyes; D008567:Membranes, Artificial; D010743:Phospholipids; D002784:Cholesterol