Fluorescent BODIPY-labelled GM1 gangliosides designed for exploring lipid membrane properties and specific membrane-target interactions

Chemistry and Physics of Lipids

Volumn 159, Issue 1, 2009, Pages 38-44

  Mikhalyov, Ilya ^b   Gretskaya, Natalia ^b   Johansson, Lennart B Å ^a  

^a UMEÅ UNIVERSITY   (Sweden)

^b SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

BODIPY labelled gangliosides; F rster energy transfer; GM1 ganglioside

Indexed keywords

FLUORESCENT DYE; GANGLIOSIDE GM1;

ARTICLE; CONTROLLED STUDY; DEPOLARIZATION; DNA PROBE; DYNAMIC EXERCISE; ELECTRON TRANSPORT; ENERGY TRANSFER; HYDROPHOBICITY; LIPID ANALYSIS; LIPID BILAYER; LIPID MEMBRANE; MOLECULE; PRIORITY JOURNAL; PROTEIN LIPID INTERACTION; SPATIAL DISCRIMINATION; SPECTROSCOPY;

BORON COMPOUNDS; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; G(M1) GANGLIOSIDE; LIPID BILAYERS; SPECTROMETRY, FLUORESCENCE; STAINING AND LABELING;

EID: 63649109490     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2009.01.005     Document Type: Article

References (26)

1. Abrami L., Fivaz M., and van der Goot F.G. Adventures of a pore-forming toxin at the target cell surface. Trends Microbiol. 8 (2000) 168-172
2. Acquotti D., Sonnino S., Masserini M., Gasella L., Fronza G., and Tettamanti G. A new chemical procedure for the preparation of gangliosides carrying fluorescent or paramagnetic probes on the lipid moiety. Chem. Phys. Lipids 40 (1986) 71-86
3. Aman A.T., Fraser S., Merritt E.A., Rodigherio C., Kenny M., Ahn M., Hol W.G.J., Williams N.A., Lencer W.I., and Hirst T.R. A mutant cholera toxin B subunit that binds GM1-ganglioside but lacks immunomodulatory or toxic activity. Proc. Natl. Acad. Sci. 98 (2001) 8536-8541
4. Andrey A.V., Samsonov V., Mihalyov I., and Cohen F.S. Characterization of cholesterol-sphingomyelin domains and their dynamics in bilayer membranes. Biophys. J. 81 (2001) 1486-1500
5. Bacia K., Schwille P., and Kurzchalia T. Sterol structure determines the separation of phases and the curvature of the liquid-ordered phase in model membranes. PNAS 102 (2005) 3272-3277
6. Bagatolli L.A., Sanchez S.A., Hazlett T., and Gratton E. Giant Vesicles, Laurdan, and Two-Photon Fluorescence Microscopy: evidence of lipid lateral separation in bilayers. Methods Enzymol. 360 (2003) 481-500
7. Bergström F., Mikhalyov I., Hägglöf P., Wortmann R., Ny T., and Johansson L.B.-A. Dimers of dipyrrometheneboron difluoride (BODIPY) with light spectroscopic applications in chemistry and biology. J. Am. Chem. Soc. 124 (2002) 196-204
8. Bogen S.-T., de Korte-Kool G., Lindblom G., and Johansson L.B.-A. Aggregation of an α-helical transmembrane peptide in lipid phases studied by time resolved fluorescence spectroscopy. J. Phys. Chem. B 103 (1999) 8344-8352
9. Bokvist M., Lindström F., Watts A., and Gröbner G. Two types of Alzheimer's beta-amyloid (1-40) peptide membrane interactions: aggregation preventing transmembrane anchoring versus accelerated surface fibril formation. J. Mol. Biol. 335 (2004) 1039-1049
10. Brown D.A., and London E. Structure and function of sphingolipid- and cholesterol-rich membrane rafts. J. Biol. Chem. 275 (2000) 17221-17224
11. Curatolo W. The physical properties of glycolipids. Biochim. Biophys. Acta 906 (1987) 111-136
12. García-Sáeza A.J., and Schwille P. Fluorescence correlation spectroscopy for the study of membrane dynamics and protein/lipid interactions. Methods 46 (2008) 116-122
13. Grechishnikova I.V., Johansson L.B.-A., and Molotkovsky J.G. Synthesis of new bifluorophoric probes adapted to studies of donor-donor electronic energy transfer in lipid systems. Chem. Phys. Lipids 81 (1996) 87-98
14. Heyn M.P. Determination of lipid order parameters and rotational correlation times from fluorescence depolarisation experiments. FEBS Lett. 108 (1979) 359-364
15. Marushchak D., Gretskaya N., Mikhalyov I., and Johansson L.B.-A. Self-aggregation-an intrinsic property of GM1 in lipid bilayers. Mol. Membr. Biol. 24 (2007) 102-112
16. Mikhalyov I., Gretskaya N., Bergström F., and Johansson L.B.-A. Electronic ground and excited state properties of dipyrrometheneboron difluoride (BODIPY): dimers with application to biosciences. Phys. Chem. Chem. Phys. 4 (2002) 5663-5670
17. Neubauer H., Gaiko N., Berger S., Schaffer J., Eggeling C., Verdier L., Seidel C.A.M., and Volkmer G.C.A. Orientational and dynamical heterogeneity of Rhodamine 6G terminally attached to a DNA Helix revealed by NMR and single-molecule fluorescence spectroscopy. J. Am. Chem. Soc. 129 (2007) 12746-12755
18. Sarah S.L., Veatch L., and Keller S.L. Separation of liquid phases in giant vesicles of ternary mixtures of phospholipids and cholesterol. Biophys. J. 85 (2003) 3074-3083
19. Sonnino S., Kirschner G., Ghidoni R., Acquotti D., and Tettamanti G. Preparation of GM1 ganglioside molecular species having homogeneous fatty acid and long chain base moieties. J. Lipid Res. 26 (1985) 248-257
20. Sonnino S., Cantù L., Corti M., Acquotti D., and Venerando B. Aggregative properties of gangliosides in solution. Chem. Phys. Lipids 71 (1994) 21-45
21. Stanley P., Koronakis V., and Hughes C. Acylation of Escherichia coli hemolysin: a unique protein lipidation mechanism underlaying toxin function. Microbiol. Mol. Biol. Rev. 62 (1998) 309-333
22. Svennerholm L. Gangliosides. Isolation. Methods Carbohyd. Chem. 6 (1974) 464-474
23. Tachiya M. Application of a generating function to reaction kinetics in micelles kinetics of quenching of lumuniscence probes in micelles. Chem. Phys. Lett. 33 (1975) 289-292
24. Yip C.M., and McLaurin J. Amyloid-beta peptide assembly: a critical step in fibrillogenesis and membrane disruption. Biophys. J. 80 (2001) 1359-1371
25. Zander C., Enderlein J., and Keller R.A. Single-Molecule Detection in Solution-Methods and Applications (2002), VCH-Wiley, Berlin/New York
26. Zhang R.G., Westbrook M.L., Westbrook E.M., Scott D.L., Otwinowski Z., Maulik P.R., Reed R.A., and Shipley G.G. The 2.4 Å crystal structure of cholera toxin B-subunit pentamer-choleragenoid. J. Mol. Biol. 251 (1995) 550-562