Synthesis of BODIPY-linked conjugates of cholesterol and FTY720

ORGN 165

Zaiguo Li, nyzli2004@yahoo.com and Robert Bittman, Robert.Bittman@qc.cuny.edu. Department of Chemistry and Biochemistry, Queens College of City University of New York, Flushing, NY 11367-1597
Fluorescent probes are used widely to study biological functions of lipids. Among the many known fluorophores, dipyrrometheneboron difluoride chelate (BODIPY) is a suitable fluorophore for replacing part of the hydrophobic chain of lipids. We synthesized cholesterol and FTY720 analogs containing an ω-azido group and used cuprous iodide catalyzed Huisgen 1,3-dipolar cycloaddition reaction with a terminal alkyne attached to a BODIPY fluorophore to form lipid-fluorophore conjugates with 1,2,3-triazole as the linker.