Fluorescent BODIPY-labelled GM1 gangliosides designed for exploring lipid membrane properties and specific membrane-target interactions |
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| Authors: | Ilya Mikhalyov,Lennart B.-Å . Johansson |
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| Affiliation: | a Department of Chemistry, Biophysical Chemistry, Umeå University, S-901 87 Umeå, Sweden
b Shemyakin & Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow 117871, Russia |
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| Abstract: | New fluorophore-labelled GM1 gangliosides have been synthesised and spectroscopically characterised. Spectroscopically different BODIPY groups were covalently linked, specifically to either the polar or the hydrophobic part of the ganglioside molecule. The absorption and fluorescence spectroscopic properties are reported for 564/571-BODIPY- and 581/591-BODIPY-labelled GM1. Each of the different BODIPY groups is highly fluorescent and depolarisation experiments provide molecular information about the spatial distribution in lipid bilayers, as well as order and dynamics. From experiments performed on two spectroscopically different BODIPY:s, specific interactions can be revealed by monitoring the rate/efficiency of donor-acceptor electronic energy transfer. Systems of particular interest for applying these probes are e.g. mixtures of lipids, and peptides/proteins interacting with lipid membranes. |
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| Keywords: | BODIPY-FL-GM1, N-(BODIPY-FL-pentanoyl)-ganglioside 564/570-BODIPY-C5-GM1(p), N-(BODIPY-564/570-pentanoyl)-neuraminosyl-ganglioside GM1 labelled in the polar (p) head group 564/570-BODIPY-C5-GM1(np), N-(BODIPY-564/570-pentanoyl)-ganglioside GM1 labelled in the non-polar (np) region 564/570-BODIPY-C5-asialo GM1, N-(BODIPY-564/570-pentanoyl)-asialo-ganglioside GM1 labelled in the non-polar region 581/591-BODIPY-C5-GM1(p), N-(BODIPY-581/591-pentanoyl)-neuraminosyl-ganglioside GM1 labelled in the polar (p) head group 581/591-BODIPY-C11-GM1, N-(BODIPY-581/591-undecanoic)-ganglioside GM1 labelled in the non-polar (np) region DOPC, 1,2-dioleoyl-sn-glycero-3-phosphocholine eSM, egg sphingomyelin GM1, ganglioside GM1 r, steady-state fluorescence anisotropy r(t), time-resolved fluorescence anisotropy τ, the fluorescence lifetime |
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