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LAURDAN Fluorescence Properties in Membranes: A Journey from the Fluorometer to the Microscope

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Fluorescent Methods to Study Biological Membranes

Part of the book series: Springer Series on Fluorescence ((SS FLUOR,volume 13))

Abstract

After 32 years since its introduction, the particular fluorescence properties of 6-lauroyl-2-(dimethylamino)-naphtalene (LAURDAN) in model and biological membranes are revisited. This review includes a historical perspective about the design, synthesis and initial description of the probe’s fluorescent properties, a discussion about the proposed mechanism of LAURDAN sensitivity to membrane lateral packing, and a detailed description of the definition of the Generalized Polarization function. This article includes as well examples of the different experimental strategies involving LAURDAN in model and biological membranes, using both bulk fluorescence spectroscopy measurements and spatially resolved information from fluorescence microscopy. The value of this probe in the study of membrane structure and dynamics is reflected in more than 330 papers reported in the existing literature.

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Abbreviations

ACDAN:

6-Acethyl-2-dimethylamine-naphthalene

ACRYLODAN:

6-Acryloyl-2-dimethylaminonaphtalene

C-LAURDAN:

6-Dodecanoyl-2-[N-methyl-N-(carboxymethyl)amino]naphthalene

Cer:

(ceramide) N-acylsphingosine

Cholesterol:

(3β)-Cholest-5-en-3-ol

D2O:

Deuterium oxide

DANCA:

2′-(N,N-dimethyl)amino-6-naphtophyl-4-trans-cyclohexanoic acid

DHPC:

1,2-Di-O-hexadecyl-sn-glycero-3-phosphocholine

DLPC:

1,2-Dilauroyl-sn-glycero-3-phosphocholine

DMPC:

1,2-Dimiristoyl-sn-glycero-3-phosphocholine

DOPC:

1-Oleoyl-2-palmitoyl-sn-glycero-3-phosphocholine

DPPC:

1,2-Dipalmitoyl-sn-glycero-3-phosphocholine

Gal:

Galactose

GD1a :

NeuAc2α → 3Galβ1 → 3Gal-NAcβ1 → 4Gal (3 ← 2αNeuAc)β1 → 4Glcβ1 → 1’Cer

GalCer:

Galβ1 → 1’Cer

Glc:

Glucose

Gg3Cer:

(Asialo GM2) Gal-NAcβ1 → 4Galβ1 → 4Glcβ1 → 1’Cer

Gg4Cer:

(Asialo GM1) Galβ1 → 3Gal-NAcβ1 → 4Galβ1 → 4Glcβ1 → 1’Cer

GM3 :

NeuAc2α → 3Galβ1 → 4Glcβ1 → 1’Cer

GM2 :

Gal-NAcβ1 → 4Gal(3 ← 2αNeuAc)β1 → 4Glcβ1 → 1’Cer

GM1 :

Galβ1 → 3Gal-NAcβ1 → 4Gal(3 ← 2αNeuAc)β1 → 4Glcβ1 → 1’Cer

GP:

Generalized Polarization function

GPex :

Generalized Polarization, excitation

GPem :

Generalized Polarization, emission

GT1b :

NeuAc2α → 3Galβ1 → 3GalNAcβ1 → 4Gal(3 ← 2αNeuAc8 ← 2αNeuAc)β1 → 4Glcβ1 → 1’Cer

LAURDAN:

6-Dodecanoyl-2-dimethylamine-naphthalene

LAURISAN:

2-Diisopropylamino-6-lauroylnaphthalene

LAURMEN:

2-Methoxy-6-lauroylnapthalene

LAURNA:

2-Hydroxy-6-lauroylnapthalene

ld :

Liquid disordered phase

lo :

Liquid ordered phase

NeuAc:

Neuraminic acid

PATMAN:

6-Palmitoyl-2-[[(2-trimethylammonium)ethyl]methyl]amino] naphthalene

Phre:

(phrenosine) Galβ1 → 1’(N-[α-OH]acylsphingosine)

PRODAN:

6-Propionyl-2-dimethylamine-naphthalene

so :

Solid ordered (gel) phase

Sphingomyelin:

N-acyl-D-erythro-sphingosylphosphorylcholine

Sulf:

(Sulfatide) HSO3 → 3Galβ1 → 1’Cer

TPEFM:

Two photon excitation fluorescence microscopy

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Acknowledgments

The author is greatly indebted to the following: Jonathan Brewer, Gerardo Fidelio, Enrico Gratton, Theodore Hazlett, David Jameson, Parkson Lee-Gau Chong, Tiziana Parasassi, Susana Sanchez, Patricio Sotomayor, Roberto Stock, and Gregorio Weber for the stimulating scientific discussions concerning the 2-(dimethylamino)-6-acylnaphtalene derivatives. The author wants to thank his colleagues at the Center for Biomembrane Physics (MEMPHYS), particularly Ole Mouritsen for his support during the last 10 years in Denmark. Part of the research presented in this article was supported by the Danish Research Council (FNU and FSS) and the Danish National Research Foundation (which supports MEMPHYS).

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  1. Membrane Biophysics and Biophotonics Group/MEMPHYS-Center for Biomembrane Physics, Department of Biochemistry and Molecular Biology, University of Southern Denmark, Campusvej 55, DK-5230, Odense M, Denmark

    L. A. Bagatolli

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  1. Faculté de Pharmacie, Laboratoire de Biophotonique, Université de Strasbourg, route du Rhin 74, Illkirch, 67401, France

    Yves Mély

  2. Faculté de Pharmacie, Laboratoire de Biophotonique et, Université de Strasbourg, route du Rhin 74, Illkirch, 67401, France

    Guy Duportail

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Bagatolli, L.A. (2012). LAURDAN Fluorescence Properties in Membranes: A Journey from the Fluorometer to the Microscope. In: Mély, Y., Duportail, G. (eds) Fluorescent Methods to Study Biological Membranes. Springer Series on Fluorescence, vol 13. Springer, Berlin, Heidelberg. https://doi.org/10.1007/4243_2012_42

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