Synthesis and Properties of New 4,4-Difluoro-3a,4a-Diaza-s-Indacene (BODIPY)-Labeled Lipids

I. A. Boldyrev and Jul. G. Molotkovsky#

# Phone/fax: +7 (095) 330-6601; e-mail:

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