Skip to main content
Top

2013 | OriginalPaper | Chapter

3-Hydroxychromone Probes Precisely Located and Oriented in Lipid Bilayers: A Toolkit for Biomembrane Research

Authors : Andrey S. Klymchenko, Guy Duportail, Yves Mély

Published in: Fluorescent Methods to Study Biological Membranes

Publisher: Springer Berlin Heidelberg

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Environment-sensitive dyes due to the sensitivity of their spectra to the physicochemical properties of their environment are unique tools for probing model and biological membranes. Here, we describe a particular class of environment-sensitive dyes based on 3-hydroxychromones. These dyes exhibit excited-state intramolecular proton transfer resulting in dual emission, highly sensitive to environment polarity and hydration. Appropriate molecular design of the new probes allows precise localization and orientation of their fluorophore in the lipid bilayers, which confer high specificity to particular membrane properties. In this respect, interface localization of the probes allows monitoring lipid order, while vertical orientation is required to achieve sensitivity to dipole and transmembrane potentials. Finally, biological applications of these probes for sensing lipid domains (rafts) and apoptosis are shown.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference Demchenko AP, Mely Y, Duportail G, Klymchenko AS (2009) Monitoring biophysical properties of lipid membranes by environment-sensitive fluorescent probes. Biophys J 96(9):3461CrossRef Demchenko AP, Mely Y, Duportail G, Klymchenko AS (2009) Monitoring biophysical properties of lipid membranes by environment-sensitive fluorescent probes. Biophys J 96(9):3461CrossRef
2.
go back to reference Klymchenko AS (2012) Solvatochromic fluorescent dyes as universal tools for biological research. Actual Chim 359:20–26 Klymchenko AS (2012) Solvatochromic fluorescent dyes as universal tools for biological research. Actual Chim 359:20–26
3.
go back to reference Loving GS, Sainlos M, Imperiali B (2010) Monitoring protein interactions and dynamics with solvatochromic fluorophores. Trends Biotechnol 28(2):73–83CrossRef Loving GS, Sainlos M, Imperiali B (2010) Monitoring protein interactions and dynamics with solvatochromic fluorophores. Trends Biotechnol 28(2):73–83CrossRef
4.
go back to reference Haidekker MA, Theodorakis EA (2007) Molecular rotors – fluorescent biosensors for viscosity and flow. Org Biomol Chem 5(11):1669–1678CrossRef Haidekker MA, Theodorakis EA (2007) Molecular rotors – fluorescent biosensors for viscosity and flow. Org Biomol Chem 5(11):1669–1678CrossRef
5.
go back to reference Hwan MK, Byeong HJ, Hyon JY, Myoung JA, Mun SS, Jin HH, Lee KJ, Chul HK, Joo T, Hong SC, Bong RC (2008) Two-photon fluorescent turn-on probe for lipid rafts in live cell and tissue. J Am Chem Soc 130(13):4246–4247CrossRef Hwan MK, Byeong HJ, Hyon JY, Myoung JA, Mun SS, Jin HH, Lee KJ, Chul HK, Joo T, Hong SC, Bong RC (2008) Two-photon fluorescent turn-on probe for lipid rafts in live cell and tissue. J Am Chem Soc 130(13):4246–4247CrossRef
6.
go back to reference Kuimova MK, Yahioglu G, Levitt JA, Suhling K (2008) Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging. J Am Chem Soc 130(21):6672–6673CrossRef Kuimova MK, Yahioglu G, Levitt JA, Suhling K (2008) Molecular rotor measures viscosity of live cells via fluorescence lifetime imaging. J Am Chem Soc 130(21):6672–6673CrossRef
7.
go back to reference Suhling K, Levitt JA, Chung PH, Kuimova MK, Yahioglu G (2012) Fluorescence lifetime imaging of molecular rotors in living cells. J Visual Exper (60): e2925 Suhling K, Levitt JA, Chung PH, Kuimova MK, Yahioglu G (2012) Fluorescence lifetime imaging of molecular rotors in living cells. J Visual Exper (60): e2925
8.
go back to reference Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94(8):2319–2358CrossRef Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94(8):2319–2358CrossRef
9.
go back to reference Lippert EL (1975) Laser-spectroscopic studies of reorientation and other relaxation processes in solution. In: Birks JB (ed) Organic and biomolecular chemistry, vol 2. Wiley, New York, pp 1–31 Lippert EL (1975) Laser-spectroscopic studies of reorientation and other relaxation processes in solution. In: Birks JB (ed) Organic and biomolecular chemistry, vol 2. Wiley, New York, pp 1–31
10.
go back to reference Slavik J (1982) Anilinonaphthalene sulfonate as a probe of membrane-composition and function. Biochim Biophys Acta 694(1):1–25CrossRef Slavik J (1982) Anilinonaphthalene sulfonate as a probe of membrane-composition and function. Biochim Biophys Acta 694(1):1–25CrossRef
11.
go back to reference Krishna MMG (1999) Excited-state kinetics of the hydrophobic probe Nile red in membranes and micelles. J Phys Chem A 103(19):x1CrossRef Krishna MMG (1999) Excited-state kinetics of the hydrophobic probe Nile red in membranes and micelles. J Phys Chem A 103(19):x1CrossRef
12.
go back to reference Sykora J, Jurkiewicz P, Epand RM, Kraayenhof R, Langner M, Hof M (2005) Influence of the curvature on the water structure in the headgroup region of phospholipid bilayer studied by the solvent relaxation technique. Chem Phys Lipids 135(2):213–221CrossRef Sykora J, Jurkiewicz P, Epand RM, Kraayenhof R, Langner M, Hof M (2005) Influence of the curvature on the water structure in the headgroup region of phospholipid bilayer studied by the solvent relaxation technique. Chem Phys Lipids 135(2):213–221CrossRef
13.
go back to reference Chong PL (1988) Effects of hydrostatic pressure on the location of Prodan in lipid bilayers and cellular membranes. Biochemistry 27(1):399CrossRef Chong PL (1988) Effects of hydrostatic pressure on the location of Prodan in lipid bilayers and cellular membranes. Biochemistry 27(1):399CrossRef
14.
go back to reference Jurkiewicz P, Olzynska A, Langner M, Hof M (2006) Headgroup hydration and mobility of DOTAP/DOPC bilayers: a fluorescence solvent relaxation study. Langmuir 22(21):8741–8749CrossRef Jurkiewicz P, Olzynska A, Langner M, Hof M (2006) Headgroup hydration and mobility of DOTAP/DOPC bilayers: a fluorescence solvent relaxation study. Langmuir 22(21):8741–8749CrossRef
15.
go back to reference Rowe BA, Neal SL (2006) Photokinetic analysis of prodan and laurdan in large unilamellar vesicles from multivariate frequency-domain fluorescence. J Phys Chem B 110(30):15021–15028CrossRef Rowe BA, Neal SL (2006) Photokinetic analysis of prodan and laurdan in large unilamellar vesicles from multivariate frequency-domain fluorescence. J Phys Chem B 110(30):15021–15028CrossRef
16.
go back to reference Barucha-Kraszewska J, Kraszewski S, Jurkiewicz P, Ramseyer C, Hof M (2010) Numerical studies of the membrane fluorescent dyes dynamics in ground and excited states. Biochim Biophys Acta 1798(9):1724–1734CrossRef Barucha-Kraszewska J, Kraszewski S, Jurkiewicz P, Ramseyer C, Hof M (2010) Numerical studies of the membrane fluorescent dyes dynamics in ground and excited states. Biochim Biophys Acta 1798(9):1724–1734CrossRef
17.
go back to reference Klymchenko AS, Duportail G, Demchenko AP, Mely Y (2004) Bimodal distribution and fluorescence response of environment-sensitive probes in lipid bilayers. Biophys J 86(5):2929–2941CrossRef Klymchenko AS, Duportail G, Demchenko AP, Mely Y (2004) Bimodal distribution and fluorescence response of environment-sensitive probes in lipid bilayers. Biophys J 86(5):2929–2941CrossRef
18.
go back to reference Bagatolli LA (2006) To see or not to see: lateral organization of biological membranes and fluorescence microscopy. Biochim Biophys Acta 1758(10):1541CrossRef Bagatolli LA (2006) To see or not to see: lateral organization of biological membranes and fluorescence microscopy. Biochim Biophys Acta 1758(10):1541CrossRef
19.
go back to reference Bondar OP, Pivovarenko VG, Rowe ES (1998) Flavonols–new fluorescent membrane probes for studying the interdigitation of lipid bilayers. Biochim Biophys Acta 1369(1):119–130CrossRef Bondar OP, Pivovarenko VG, Rowe ES (1998) Flavonols–new fluorescent membrane probes for studying the interdigitation of lipid bilayers. Biochim Biophys Acta 1369(1):119–130CrossRef
20.
go back to reference Alakoskela JMI, Kinnunen PKJ (2001) Probing phospholipid main phase transition by fluorescence spectroscopy and a surface redox reaction. J Phys Chem B 105(45):11294CrossRef Alakoskela JMI, Kinnunen PKJ (2001) Probing phospholipid main phase transition by fluorescence spectroscopy and a surface redox reaction. J Phys Chem B 105(45):11294CrossRef
21.
go back to reference Demchenko AP, Shcherbatska NV (1985) Nanosecond dynamics of charged fluorescent probes at the polar interface of a membrane phospholipid bilayer. Biophys Chem 22(3):131–143CrossRef Demchenko AP, Shcherbatska NV (1985) Nanosecond dynamics of charged fluorescent probes at the polar interface of a membrane phospholipid bilayer. Biophys Chem 22(3):131–143CrossRef
22.
go back to reference Zwaal RFA, Schroit AJ (1997) Pathophysiologic implications of membrane phospholipid asymmetry in blood cells. Blood 89(4):1121 Zwaal RFA, Schroit AJ (1997) Pathophysiologic implications of membrane phospholipid asymmetry in blood cells. Blood 89(4):1121
23.
go back to reference Kucherak OA, Oncul S, Darwich Z, Yushchenko DA, Arntz Y, Didier P, Mely Y, Klymchenko AS (2010) Switchable Nile red-based probe for cholesterol and lipid order at the outer leaflet of biomembranes. J Am Chem Soc 132(13):4907CrossRef Kucherak OA, Oncul S, Darwich Z, Yushchenko DA, Arntz Y, Didier P, Mely Y, Klymchenko AS (2010) Switchable Nile red-based probe for cholesterol and lipid order at the outer leaflet of biomembranes. J Am Chem Soc 132(13):4907CrossRef
24.
go back to reference Shynkar VV, Klymchenko AS, Kunzelmann C, Duportail G, Muller CD, Demchenko AP, Freyssinet JM, Mely Y (2007) Fluorescent biomembrane probe for ratiometric detection of apoptosis. J Am Chem Soc 129(7):2187–2193CrossRef Shynkar VV, Klymchenko AS, Kunzelmann C, Duportail G, Muller CD, Demchenko AP, Freyssinet JM, Mely Y (2007) Fluorescent biomembrane probe for ratiometric detection of apoptosis. J Am Chem Soc 129(7):2187–2193CrossRef
25.
go back to reference Loura LM, Ramalho JP (2007) Location and dynamics of acyl chain NBD-labeled phosphatidylcholine (NBD-PC) in DPPC bilayers. A molecular dynamics and time-resolved fluorescence anisotropy study. Biochim Biophys Acta 1768(3):467–478CrossRef Loura LM, Ramalho JP (2007) Location and dynamics of acyl chain NBD-labeled phosphatidylcholine (NBD-PC) in DPPC bilayers. A molecular dynamics and time-resolved fluorescence anisotropy study. Biochim Biophys Acta 1768(3):467–478CrossRef
26.
go back to reference Huster D, Muller P, Arnold K, Herrmann A (2001) Dynamics of membrane penetration of the fluorescent 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD) group attached to an acyl chain of phosphatidylcholine. Biophys J 80(2):822–831CrossRef Huster D, Muller P, Arnold K, Herrmann A (2001) Dynamics of membrane penetration of the fluorescent 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD) group attached to an acyl chain of phosphatidylcholine. Biophys J 80(2):822–831CrossRef
27.
go back to reference Klymchenko AS, Duportail G, Ozturk T, Pivovarenko VG, Mely Y, Demchenko AP (2002) Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes. Chem Biol 9(11):1199–1208CrossRef Klymchenko AS, Duportail G, Ozturk T, Pivovarenko VG, Mely Y, Demchenko AP (2002) Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes. Chem Biol 9(11):1199–1208CrossRef
28.
go back to reference Lakowicz JR, Bevan DR, Maliwal BP, Cherek H, Balter A (1983) Synthesis and characterization of a fluorescence probe of the phase transition and dynamic properties of membranes. Biochemistry 22(25):5714–5722CrossRef Lakowicz JR, Bevan DR, Maliwal BP, Cherek H, Balter A (1983) Synthesis and characterization of a fluorescence probe of the phase transition and dynamic properties of membranes. Biochemistry 22(25):5714–5722CrossRef
29.
go back to reference Jurkiewicz P, Sykora J, Olzynska A, Humpolickova J, Hof M (2005) Solvent relaxation in phospholipid bilayers: principles and recent applications. J Fluoresc 15(6):883CrossRef Jurkiewicz P, Sykora J, Olzynska A, Humpolickova J, Hof M (2005) Solvent relaxation in phospholipid bilayers: principles and recent applications. J Fluoresc 15(6):883CrossRef
30.
go back to reference Kim HM, Choo HJ, Jung SY, Ko YG, Park WH, Jeon SJ, Kim CH, Joo T, Cho BR (2007) A two-photon fluorescent probe for lipid raft imaging: C-laurdan. Chembiochem 8(5):553CrossRef Kim HM, Choo HJ, Jung SY, Ko YG, Park WH, Jeon SJ, Kim CH, Joo T, Cho BR (2007) A two-photon fluorescent probe for lipid raft imaging: C-laurdan. Chembiochem 8(5):553CrossRef
31.
go back to reference Jin L, Millard AC, Wuskell JP, Dong X, Wu D, Clark HA, Loew LM (2006) Characterization and application of a new optical probe for membrane lipid domains. Biophys J 90(7):2563CrossRef Jin L, Millard AC, Wuskell JP, Dong X, Wu D, Clark HA, Loew LM (2006) Characterization and application of a new optical probe for membrane lipid domains. Biophys J 90(7):2563CrossRef
32.
go back to reference Millard AC, Jin L, Wei MD, Wuskell JP, Lewis A, Loew LM (2004) Sensitivity of second harmonic generation from styryl dyes to transmembrane potential. Biophys J 86(2):1169CrossRef Millard AC, Jin L, Wei MD, Wuskell JP, Lewis A, Loew LM (2004) Sensitivity of second harmonic generation from styryl dyes to transmembrane potential. Biophys J 86(2):1169CrossRef
33.
go back to reference Wuskell JP, Boudreau D, Wei MD, Jin L, Engl R, Chebolu R, Bullen A, Hoffacker KD, Kerimo J, Cohen LB, Zochowski MR, Loew LM (2006) Synthesis, spectra, delivery and potentiometric responses of new styryl dyes with extended spectral ranges. J Neurosci Methods 151(2):200CrossRef Wuskell JP, Boudreau D, Wei MD, Jin L, Engl R, Chebolu R, Bullen A, Hoffacker KD, Kerimo J, Cohen LB, Zochowski MR, Loew LM (2006) Synthesis, spectra, delivery and potentiometric responses of new styryl dyes with extended spectral ranges. J Neurosci Methods 151(2):200CrossRef
34.
go back to reference Wiener MC, White SH (1992) Structure of a fluid dioleoylphosphatidylcholine bilayer determined by joint refinement of x-ray and neutron diffraction data: III. Complete structure. Biophys J 61(2I):434–447CrossRef Wiener MC, White SH (1992) Structure of a fluid dioleoylphosphatidylcholine bilayer determined by joint refinement of x-ray and neutron diffraction data: III. Complete structure. Biophys J 61(2I):434–447CrossRef
35.
go back to reference Kułakowska A, Jurkiewicz P, Sýkora J, Benda A, Mely Y, Hof M (2010) Fluorescence lifetime tuning-a novel approach to study flip-flop kinetics in supported phospholipid bilayers. J Fluoresc 20(2):563–569CrossRef Kułakowska A, Jurkiewicz P, Sýkora J, Benda A, Mely Y, Hof M (2010) Fluorescence lifetime tuning-a novel approach to study flip-flop kinetics in supported phospholipid bilayers. J Fluoresc 20(2):563–569CrossRef
36.
go back to reference Clarke RJ, Kane DJ (1997) Optical detection of membrane dipole potential: avoidance of fluidity and dye-induced effects. Biochim Biophys Acta 1323(2):223CrossRef Clarke RJ, Kane DJ (1997) Optical detection of membrane dipole potential: avoidance of fluidity and dye-induced effects. Biochim Biophys Acta 1323(2):223CrossRef
37.
go back to reference Vitha MF, Clarke RJ (2007) Comparison of excitation and emission ratiometric fluorescence methods for quantifying the membrane dipole potential. Biochim Biophys Acta 1768(1):107–114CrossRef Vitha MF, Clarke RJ (2007) Comparison of excitation and emission ratiometric fluorescence methods for quantifying the membrane dipole potential. Biochim Biophys Acta 1768(1):107–114CrossRef
38.
go back to reference Ho C, Slater SJ, Stubbs CD (1995) Hydration and order in lipid bilayers. Biochemistry 34(18):6188CrossRef Ho C, Slater SJ, Stubbs CD (1995) Hydration and order in lipid bilayers. Biochemistry 34(18):6188CrossRef
39.
go back to reference Formosinho SJ, Arnaut LG (1993) Excited-state proton transfer reactions II. Intramolecular reactions. J Photochem Photobiol A 75(1):21–48CrossRef Formosinho SJ, Arnaut LG (1993) Excited-state proton transfer reactions II. Intramolecular reactions. J Photochem Photobiol A 75(1):21–48CrossRef
40.
go back to reference Klymchenko AS, Demchenko AP (2003) Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer. Phys Chem Chem Phys 5:461–468CrossRef Klymchenko AS, Demchenko AP (2003) Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer. Phys Chem Chem Phys 5:461–468CrossRef
41.
go back to reference Yesylevskyy SO, Klymchenko AS, Demchenko AP (2005) Semi-empirical study of two-color fluorescent dyes based on 3-hydroxychromone. J Mol Struct 755(1–3):229 Yesylevskyy SO, Klymchenko AS, Demchenko AP (2005) Semi-empirical study of two-color fluorescent dyes based on 3-hydroxychromone. J Mol Struct 755(1–3):229
42.
go back to reference Weber G, Farris FJ (1979) Synthesis and spectral properties of a hydrophobic fluorescent probe: 6-propionyl-2-(dimethylamino)naphthalene. Biochemistry 18(14):3075–3078CrossRef Weber G, Farris FJ (1979) Synthesis and spectral properties of a hydrophobic fluorescent probe: 6-propionyl-2-(dimethylamino)naphthalene. Biochemistry 18(14):3075–3078CrossRef
43.
go back to reference Shynkar V, Mely Y, Duportail G, Piemont E, Klymchenko A, Demchenko A (2003) Picosecond time-resolved fluorescence studies are consistent with reversible excited-state intramolecular proton transfer in 4′-(dialkylamino)-3-hydroxyflavones. J Phys Chem A 107(45):9522–9529CrossRef Shynkar V, Mely Y, Duportail G, Piemont E, Klymchenko A, Demchenko A (2003) Picosecond time-resolved fluorescence studies are consistent with reversible excited-state intramolecular proton transfer in 4′-(dialkylamino)-3-hydroxyflavones. J Phys Chem A 107(45):9522–9529CrossRef
44.
go back to reference Klymchenko AS, Demchenko AP (2002) Electrochromic modulation of excited-state intramolecular proton transfer: the new principle in design of fluorescence sensors. J Am Chem Soc 124(41):12372CrossRef Klymchenko AS, Demchenko AP (2002) Electrochromic modulation of excited-state intramolecular proton transfer: the new principle in design of fluorescence sensors. J Am Chem Soc 124(41):12372CrossRef
45.
go back to reference Klymchenko AS, Mely Y, Demchenko AP, Duportail G (2004) Simultaneous probing of hydration and polarity of lipid bilayers with 3-hydroxyflavone fluorescent dyes. Biochim Biophys Acta 1665(1–2):6–19 Klymchenko AS, Mely Y, Demchenko AP, Duportail G (2004) Simultaneous probing of hydration and polarity of lipid bilayers with 3-hydroxyflavone fluorescent dyes. Biochim Biophys Acta 1665(1–2):6–19
46.
go back to reference Das R, Klymchenko AS, Duportail G, Mely Y (2008) Excited state proton transfer and solvent relaxation of a 3-hydroxyflavone probe in lipid bilayers. J Phys Chem B 112(38):11929–11935CrossRef Das R, Klymchenko AS, Duportail G, Mely Y (2008) Excited state proton transfer and solvent relaxation of a 3-hydroxyflavone probe in lipid bilayers. J Phys Chem B 112(38):11929–11935CrossRef
47.
go back to reference Parasassi T, Di Stefano M, Loiero M, Ravagnan G, Gratton E (1994) Cholesterol modifies water concentration and dynamics in phospholipid bilayers: a fluorescence study using laurdan probe. Biophys J 66(3):763CrossRef Parasassi T, Di Stefano M, Loiero M, Ravagnan G, Gratton E (1994) Cholesterol modifies water concentration and dynamics in phospholipid bilayers: a fluorescence study using laurdan probe. Biophys J 66(3):763CrossRef
48.
go back to reference Parasassi T, Krasnowska EK, Bagatolli L, Gratton E (1998) Laurdan and prodan as polarity-sensitive fluorescent membrane probes. J Fluoresc 8(4):365CrossRef Parasassi T, Krasnowska EK, Bagatolli L, Gratton E (1998) Laurdan and prodan as polarity-sensitive fluorescent membrane probes. J Fluoresc 8(4):365CrossRef
49.
go back to reference Sykora J, Slavicek P, Jungwirth P, Barucha J, Hof M (2007) Time-dependent stokes shifts of fluorescent dyes in the hydrophobic backbone region of a phospholipid bilayer: combination of fluorescence spectroscopy and ab initio calculations. J Phys Chem B 111(21):5869CrossRef Sykora J, Slavicek P, Jungwirth P, Barucha J, Hof M (2007) Time-dependent stokes shifts of fluorescent dyes in the hydrophobic backbone region of a phospholipid bilayer: combination of fluorescence spectroscopy and ab initio calculations. J Phys Chem B 111(21):5869CrossRef
50.
go back to reference Shynkar VV, Klymchenko AS, Duportail G, Demchenko AP, Mely Y (2005) Two-color fluorescent probes for imaging the dipole potential of cell plasma membranes. Biochim Biophys Acta 1712(2):128–136CrossRef Shynkar VV, Klymchenko AS, Duportail G, Demchenko AP, Mely Y (2005) Two-color fluorescent probes for imaging the dipole potential of cell plasma membranes. Biochim Biophys Acta 1712(2):128–136CrossRef
51.
go back to reference Montana V, Farkas DL, Loew LM (1989) Dual-wavelength ratiometric fluorescence measurements of membrane potential. Biochemistry 28(11):4536CrossRef Montana V, Farkas DL, Loew LM (1989) Dual-wavelength ratiometric fluorescence measurements of membrane potential. Biochemistry 28(11):4536CrossRef
52.
go back to reference Klymchenko AS, Duportail G, Mely Y, Demchenko AP (2003) Ultrasensitive two-color fluorescence probes for dipole potential in phospholipid membranes. Proc Natl Acad Sci USA 100(20):11219–11224CrossRef Klymchenko AS, Duportail G, Mely Y, Demchenko AP (2003) Ultrasensitive two-color fluorescence probes for dipole potential in phospholipid membranes. Proc Natl Acad Sci USA 100(20):11219–11224CrossRef
53.
go back to reference M’Baye G, Shynkar VV, Klymchenko AS, Mely Y, Duportail G (2006) Membrane dipole potential as measured by ratiometric 3-hydroxyflavone fluorescence probes: accounting for hydration effects. J Fluoresc 16(1):35CrossRef M’Baye G, Shynkar VV, Klymchenko AS, Mely Y, Duportail G (2006) Membrane dipole potential as measured by ratiometric 3-hydroxyflavone fluorescence probes: accounting for hydration effects. J Fluoresc 16(1):35CrossRef
54.
go back to reference Klymchenko AS, Stoeckel H, Takeda K, Mely Y (2006) Fluorescent probe based on intramolecular proton transfer for fast ratiometric measurement of cellular transmembrane potential. J Phys Chem B 110(27):13624–13632CrossRef Klymchenko AS, Stoeckel H, Takeda K, Mely Y (2006) Fluorescent probe based on intramolecular proton transfer for fast ratiometric measurement of cellular transmembrane potential. J Phys Chem B 110(27):13624–13632CrossRef
55.
go back to reference Klymchenko A, Ozturk T, Pivovarenko VG, Demchenko A (2002) Synthesis of furanochromones: a new step in improvement of fluorescence properties. Tetrahedron Lett 43:7079–7082CrossRef Klymchenko A, Ozturk T, Pivovarenko VG, Demchenko A (2002) Synthesis of furanochromones: a new step in improvement of fluorescence properties. Tetrahedron Lett 43:7079–7082CrossRef
56.
go back to reference Klymchenko AS, Pivovarenko VG, Ozturk T, Demchenko AP (2003) Modulation of the solvent-dependent dual emission in 3-hydroxychromones by substituents. New J Chem 27:1336–1343CrossRef Klymchenko AS, Pivovarenko VG, Ozturk T, Demchenko AP (2003) Modulation of the solvent-dependent dual emission in 3-hydroxychromones by substituents. New J Chem 27:1336–1343CrossRef
57.
go back to reference Fromherz P, Hubener G, Kuhn B, Hinner MJ (2008) Annine-6plus, a voltage-sensitive dye with good solubility, strong membrane binding and high sensitivity. Eur Biophys J 37(4):509CrossRef Fromherz P, Hubener G, Kuhn B, Hinner MJ (2008) Annine-6plus, a voltage-sensitive dye with good solubility, strong membrane binding and high sensitivity. Eur Biophys J 37(4):509CrossRef
58.
go back to reference Simons K, Ikonen E (1997) Functional rafts in cell membranes. Nature 387(6633):569CrossRef Simons K, Ikonen E (1997) Functional rafts in cell membranes. Nature 387(6633):569CrossRef
59.
go back to reference Dietrich C, Bagatolli LA, Volovyk ZN, Thompson NL, Levi M, Jacobson K, Gratton E (2001) Lipid rafts reconstituted in model membranes. Biophys J 80(3):1417CrossRef Dietrich C, Bagatolli LA, Volovyk ZN, Thompson NL, Levi M, Jacobson K, Gratton E (2001) Lipid rafts reconstituted in model membranes. Biophys J 80(3):1417CrossRef
60.
go back to reference Scherfeld D, Kahya N, Schwille P (2003) Lipid dynamics and domain formation in model membranes composed of ternary mixtures of unsaturated and saturated phosphatidylcholines and cholesterol. Biophys J 85(6):3758–3768CrossRef Scherfeld D, Kahya N, Schwille P (2003) Lipid dynamics and domain formation in model membranes composed of ternary mixtures of unsaturated and saturated phosphatidylcholines and cholesterol. Biophys J 85(6):3758–3768CrossRef
61.
go back to reference Brown DA, London E (2000) Structure and function of sphingolipid- and cholesterol-rich membrane rafts. J Biol Chem 275(23):17221CrossRef Brown DA, London E (2000) Structure and function of sphingolipid- and cholesterol-rich membrane rafts. J Biol Chem 275(23):17221CrossRef
62.
go back to reference Owen DM, Rentero C, Magenau A, Abu-Siniyeh A, Gaus K (2012) Quantitative imaging of membrane lipid order in cells and organisms. Nat Protoc 7(1):24–35CrossRef Owen DM, Rentero C, Magenau A, Abu-Siniyeh A, Gaus K (2012) Quantitative imaging of membrane lipid order in cells and organisms. Nat Protoc 7(1):24–35CrossRef
63.
go back to reference Kuhry JG, Fonteneau P, Duportail G, Maechling C, Laustriat G (1983) TMA-DPH: a suitable fluorescence polarization probe for specific plasma membrane fluidity studies in intact living cells. Cell Biophys 5(2):129–140 Kuhry JG, Fonteneau P, Duportail G, Maechling C, Laustriat G (1983) TMA-DPH: a suitable fluorescence polarization probe for specific plasma membrane fluidity studies in intact living cells. Cell Biophys 5(2):129–140
64.
go back to reference Lentz BR (1989) Membrane ‘fluidity’ as detected by diphenylhexatriene probes. Chem Phys Lipids 50(3–4):171CrossRef Lentz BR (1989) Membrane ‘fluidity’ as detected by diphenylhexatriene probes. Chem Phys Lipids 50(3–4):171CrossRef
65.
go back to reference Klymchenko AS, Oncul S, Didier P, Schaub E, Bagatolli L, Duportail G, Mely Y (2008) Visualization of lipid domains in giant unilamellar vesicles using an environment-sensitive membrane probe based on 3-hydroxyflavone. Biochim Biophys Acta 1788:495–499 Klymchenko AS, Oncul S, Didier P, Schaub E, Bagatolli L, Duportail G, Mely Y (2008) Visualization of lipid domains in giant unilamellar vesicles using an environment-sensitive membrane probe based on 3-hydroxyflavone. Biochim Biophys Acta 1788:495–499
66.
go back to reference Oncul S, Klymchenko AS, Kucherak OA, Demchenko AP, Martin S, Dontenwill M, Arntz Y, Didier P, Duportail G, Mely Y (2010) Liquid ordered phase in cell membranes evidenced by a hydration-sensitive probe: effects of cholesterol depletion and apoptosis. Biochim Biophys Acta 1798:1436–1443CrossRef Oncul S, Klymchenko AS, Kucherak OA, Demchenko AP, Martin S, Dontenwill M, Arntz Y, Didier P, Duportail G, Mely Y (2010) Liquid ordered phase in cell membranes evidenced by a hydration-sensitive probe: effects of cholesterol depletion and apoptosis. Biochim Biophys Acta 1798:1436–1443CrossRef
67.
go back to reference Vermes I, Haanen C, Steffens-Nakken H, Reutelingsperger C (1995) A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V. J Immunol Methods 184(1):39CrossRef Vermes I, Haanen C, Steffens-Nakken H, Reutelingsperger C (1995) A novel assay for apoptosis. Flow cytometric detection of phosphatidylserine expression on early apoptotic cells using fluorescein labelled annexin V. J Immunol Methods 184(1):39CrossRef
68.
go back to reference Duportail G, Klymchenko A, Mely Y, Demchenko A (2001) Neutral fluorescence probe with strong ratiometric response to surface charge of phospholipid membranes. FEBS Lett 508(2):196–200CrossRef Duportail G, Klymchenko A, Mely Y, Demchenko A (2001) Neutral fluorescence probe with strong ratiometric response to surface charge of phospholipid membranes. FEBS Lett 508(2):196–200CrossRef
Metadata
Title
3-Hydroxychromone Probes Precisely Located and Oriented in Lipid Bilayers: A Toolkit for Biomembrane Research
Authors
Andrey S. Klymchenko
Guy Duportail
Yves Mély
Copyright Year
2013
Publisher
Springer Berlin Heidelberg
DOI
https://doi.org/10.1007/4243_2012_44

Premium Partners