Polyene-lipids: A new tool to image lipids

Nature Methods

Volumn 2, Issue 1, 2005, Pages 39-45

  Kuerschner, Lars ^a   Ejsing, Christer S ^a   Ekroos, Kim ^b   Shevchenko, Andrej ^a   Anderson, Kurt I ^a   Thiele, Christoph ^a  

^a MAX PLANCK INSTITUTE OF MOLECULAR CELL BIOLOGY AND GENETICS   (Germany)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

POLYENE; 4 CHLORO 7 NITROBENZOFURAZAN; 4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON DERIVATIVE; DETERGENT; FLUORESCENT DYE; LIPID;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; BIOPHYSICS; BRAIN FUNCTION; CELL METABOLISM; CELLULAR DISTRIBUTION; CONJUGATION; CONTROLLED STUDY; FLUORESCENCE MICROSCOPY; FREQUENCY ANALYSIS; IMAGE ANALYSIS; LIPID ANALYSIS; LIPOGENESIS; MAMMAL CELL; MICROSCOPY; MOUSE; NONHUMAN; PHASE PARTITIONING; PRIORITY JOURNAL; STRUCTURE ANALYSIS; ANIMAL; BRAIN; CELL LINE; CELL STRAIN 3T3; CELL STRAIN COS1; CHEMISTRY; IMAGE PROCESSING; KIDNEY; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; THIN LAYER CHROMATOGRAPHY;

ANIMALIA; MAMMALIA;

3T3-L1 CELLS; 4-CHLORO-7-NITROBENZOFURAZAN; ANIMALS; BORON COMPOUNDS; BRAIN; CELL LINE; CHROMATOGRAPHY, THIN LAYER; COS CELLS; DETERGENTS; FLUORESCENT DYES; IMAGE PROCESSING, COMPUTER-ASSISTED; KIDNEY; LIPIDS; MASS SPECTROMETRY; MICE; MICROSCOPY; MICROSCOPY, FLUORESCENCE; POLYENES;

EID: 18744387424     PISSN: 15487091     EISSN: None     Source Type: Journal    
DOI: 10.1038/nmeth728     Document Type: Article

References (43)

1. Simons, K. & Ikonen, E. Functional rafts in cell membranes. Nature 387, 569-572 (1997).
2. Brown, D.A. & London, E. Structure and origin of ordered lipid domains in biological membranes. J. Membr. Biol. 164, 103-114 (1998).
3. Magee, T., Pirinen, N., Adler, J., Pagakis, S.N. & Parmryd, I. Lipid rafts: cell surface platforms for T cell signaling. Biol. Res. 35, 127-131 (2002).
4. Holthuis, J.C., van Meer, G. & Huitema, K. Lipid microdomains, lipid translocation and the organization of intracellular membrane transport (Review). Mol. Membr. Biol. 20, 231-241 (2003).
5. Maier, O., Oberle, V. & Hoekstra, D. Fluorescent lipid probes: some properties and applications (Review). Chem. Phys. Lipids 116, 3-18 (2002).
6. Ishitsuka, R., Yamaji-Hasegawa, A., Makino, A., Hirabayashi, Y. & Kobayashi, T. A lipid-specific toxin reveals heterogeneity of sphingomyelin-containing membranes. Biophys. J. 86, 296-307 (2004).
7. Chattopadhyay, A. Chemistry and biology of N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)-labeled lipids: fluorescent probes of biological and model membranes. Chem. Phys. Lipids 53, 1-15 (1990).
8. Pagano, R.E., Martin, O.C., Kang, H.C. & Haugland, R.P. A novel fluorescent ceramide analogue for studying membrane traffic in animal cells: accumulation at the Golgi apparatus results in altered spectral properties of the sphingolipid precursor. J. Cell Biol. 113, 1267-1279 (1991).
9. Stoffel, W. & Michaelis, G. Chemical syntheses of novel fluorescent-labelled fatty acids, phosphatidylcholines and cholesterol esters. Hoppe-Seyler's Z. Physiol. Chem. 357, 7-19 (1976).
10. Somerharju, P. Pyrene-labeled lipids as tools in membrane biophysics and cell biology. Chem. Phys. Lipids 116, 57-74 (2002).
11. Antes, P., Schwarzmann, G. & Sandhoff, K. Distribution and metabolism of fluorescent sphingosines and corresponding ceramides bearing the diphenythexatrienyl (DPH) fluorophore in cultured human fibroblasts. Eur. J. Cell Biol. 59, 27-36 (1992).
12. Pagano, R.E. & Sleight, R.G. Defining lipid transport pathways in animal cells. Science 229, 1051-1057 (1985).
13. Kaiser, R.D. & London, E. Determination of the depth of BODIPY probes in model membranes by parallax analysis of fluorescence quenching. Biochim. Biophys. Acta 1375, 13-22 (1998).
14. Wang, T.Y. & Silvius, J.R. Different sphingolipids show differential partitioning into sphingolipid/cholesterol-rich domains in lipid bilayers. Biophys. J. 79, 1478-1489 (2000).
15. Sklar, L.A., Hudson, B.S. & Simoni, R.D. Conjugated polyene fatty acids as membrane probes: preliminary characterization. Proc. Natl. Acad. Sci. USA 72, 1649-1653 (1975).
16. Lentz, B.R. Use of fluorescent probes to monitor molecular order and motions within liposome bilayers. Chem. Phys. Lipids 64, 99-116 (1993).
17. Mateo, C.R., Souto, A.A., Amat-Guerri, F. & Acuna, A.U. New fluorescent octadecapentaenoic acids as probes of lipid membranes and protein-lipid interactions. Biophys. J. 71, 2177-2191 (1996).
18. Quesada, E., Acuna, A.U. & Amat-Guerri, F. New transmembrane polyene bolaamphiphiles as fluorescent probes in lipid bilayers. Angew. Chem. Int. Edn. Engl. 40, 2095-2097 (2001).
19. Quesada, E., Acuna, A.U. & Amat-Guerri, F. Synthesis of carboxyl-tethered symmetric conjugated polyenes as fluorescent transmembrane probes of lipid bilayers. Eur. J. Org. Chem. 2003, 1308-1318 (2003).
20. Souto, A.A., Ulises Acuna, A. & Amat-Guerri, F. A general and practical synthesis of linear conjugated pentaenoic acids. Tetrahedr. Lett. 35, 5907-5910 (1994).
21. London, E. & Feigenson, G.W. Fluorescence quenching in model membranes. 1. Characterization of quenching caused by a spin-labeled phospholipid. Biochemistry 20, 1932-1938 (1981).
22. Ahmed, S.N., Brown, D.A. & London, E. On the origin of sphingolipid/cholesterol-rich detergent-insoluble cell membranes: physiological concentrations of cholesterol and sphingolipid induce formation of a detergent-insoluble, liquid-ordered lipid phase in model membranes. Biochemistry 36, 10944-10953 (1997).
23. Brown, D.A. & Rose, J.K. Sorting of GPI-Anchored proteins to glycolipid-enriched membrane subdomains during transport to the apical cell surface. Cell 68, 533-544 (1992).
24. Roper, K., Corbeil, D. & Huttner, W.B. Retention of prominin in microvilli reveals distinct cholesterol-based lipid micro-domains in the apical plasma membrane. Nat. Cell Biol. 2, 582-592 (2000).
25. Nagan, N. & Zoeller, R.A. Plasmalogens: biosynthesis and functions. Prog. Lipid Res. 40, 199-229 (2001).
26. Tanhuanpaa, K. & Somerharju, P. Gamma-cyclodextrins greatly enhance translocation of hydrophobic fluorescent phospholipids from vesicles to cells in culture. Importance of molecular hydrophobicity in phospholipid trafficking studies. J. Biol. Chem. 274, 35359-35366 (1999).
27. Ekroos, K. et al. Charting molecular composition of phosphatidylcholines by fatty acid scanning and ion trap MS3 fragmentation. J. Lipid Res. 44, 2181-2192 (2003).
28. Denk, W., Strickler, J.H. & Webb, W.W. Two-photon laser scanning fluorescence microscopy. Science 248, 73-76 (1990).
29. Campbell, R.E. et al. A monomeric red fluorescent protein. Proc. Natl. Acad. Sci. USA 99, 7877-7882 (2002).
30. Huang, H., Starodub, O., McIntosh, A., Kier, A.B. & Schroeder F. Liver fatty acid-binding protein targets fatty acids to the nucleus Real time confocal and multiphoton fluorescence imaging in living cells. J. Biol. Chem. 277, 29139-29151 (2002).
31. Lipsky, N.G. & Pagano, R.E. A vital stain for the Golgi apparatus. Science 228, 745-747 (1985).
32. Bielawska, A., Crane, H.M., Liotta, D., Obeid, L.M. & Hannun, Y.A. Selectivity of ceramide-mediated biology. Lack of activity of erythro-dihydroceramide. J. Biol. Chem. 268, 26226-26232 (1993).
33. Li, L., Tang, X., Taylor, K.G., DuPre, D.B. & Yappert, M.C. Conformational characterization of ceramides by nuclear magnetic resonance spectroscopy. Biophys. J. 82, 2067-2080 (2002).
34. Mukherjee, S. & Maxfield, F.R. Role of membrane organization and membrane domains in endocytic lipid trafficking. Traffic 1, 203-211 (2000).
35. Brugger, B., Erben, G., Sandhoff, R., Wieland, F.T. & Lehmann, W.D. Quantitative analysis of biological membrane lipids at the low picomole level by nano-electrospray ionization tandem mass spectrometry. Proc. Natl. Acod. Sci. USA 94, 2339-2344 (1997).
36. Sprong, H., van der Sluijs, P. & van Meer, G. How proteins move lipids and lipids move proteins. Nat. Rev. Mol. Cell Biol. 2, 504-513 (2001).
37. Pagano, R.E., Sepanski, M.A. & Martin, O.C. Molecular trapping of a fluorescent ceramide analogue at the Golgi apparatus of fixed cells: Interaction with endogenous lipids provides a trans-Golgi marker for both light and electron microscopy. J. Cell Biol. 109, 2067-2079 (1989).
38. Rodemer, C. et al. Inactivation of ether lipid biosynthesis causes male infertility, defects in eye development and optic nerve hypoplasia in mice. Hum. Mol. Genet. 12, 1881-1895 (2003).
39. Tanhuanpaa, K., Virtanen, J. & Somerharju, P. Fluorescence imaging of pyrene-labeled lipids in living cells. Biochim. Biophys. Acta 1497, 308-320 (2000).
40. Thiele, C., Hannah, M.J., Fahrenholz, F. & Huttner, W.B. Cholesterol binds to synaptophysin and is required for biogenesis of synaptic vesicles. Nat. Cell Biol. 2, 42-49 (2000).
41. Bligh, E.G. & Dyer, W.J. A rapid method for total lipid extraction and purifiaction. Can. J. Biochem. Physiol. 37, 911-917 (1959).
42. Dasgupta, S. & Hogan, E.L. Chromatographic resolution and quantitative assay of CNS tissue sphingoids and sphingolipids. J. Lipid Res. 42, 301-308 (2001).
43. Ekroos, K., Chemushevich, I.V., Simons, K. & Shevchenko, A. Quantitative profiling of phospholipids by multiple precursor ion scanning on a hybrid quadrupole time-of-flight mass spectrometer. Anal. Chem. 74, 941-949 (2002).