Synthesis and Properties of New 4,4-Difluoro-3a,4a-Diaza-s-Indacene (BODIPY)-Labeled Lipids
I. A. Boldyrev and Jul. G. Molotkovsky#
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Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997 Russia
A series of fluorescently labeled fatty acids of various chain lengths with 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl (Me4-BODIPY-8) residue in the ω position were synthesized. These acids were used to prepare new fluorescently labeled phosphatidylcholines, sphingomyelin, and galactosylceramide. The symmetry of the Me4-BODIPY-8 fluorophore suggests that, in most bilayer membrane systems, this fluorophore would be embedded into the bilayer.
Key words: BODIPY, fluorescent lipid probes, synthesis
Received June 30, 2005; in final form, August 4, 2005
Russian Journal of Bioorganic Chemistry 2006, 32 (1):78-83