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Synthesis and Fluorescence Properties of Novel Transmembrane Probes and Determination of Their Orientation within Vesicles
Author(s) -
Quesada Ernesto,
Ardhammar Malin,
Nordén Bengt,
Miesch Michel,
Duportail Guy,
BonziCoulibaly Yvonne,
Nakatani Yoichí,
Ourisson Guy
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000906)83:9<2464::aid-hlca2464>3.0.co;2-t
Subject(s) - chemistry , vesicle , fluorescence , acceptor , bilayer , absorption (acoustics) , absorption spectroscopy , tryptophan , linear dichroism , circular dichroism , photochemistry , crystallography , membrane , analytical chemistry (journal) , organic chemistry , optics , biochemistry , physics , amino acid , condensed matter physics
Two novel transmembrane fluorescent diester probes D and E bearing an anthracenediyl moiety in the middle of the molecule have been synthesized. Their absorption and fluorescence spectra in CHCl 3 solution as well as their fluorescence characteristics in dimyristoylphosphatidylcholine (DMPC) large unilamellar vesicles were determined. Although their absorption spectra (first transition, S 0 →S 1 ) present a good overlap with the fluorescence spectrum of tryptophan, only probe E could be a good acceptor for the energy‐transfer experiments, since a strong overlap exists between the absorption spectrum of tryptophan and the second transition (S 0 →S 2 ) of the absorption spectrum of probe D . The Förster critical distance R 0 for energy transfer between tryptophan (donor) and probe E (acceptor) is found to be 23 – 24 Å. Finally, linear‐dichroism studies on shear‐deformed DMPC vesicles show the incorporated probe E to lie essentially perpendicular to the bilayer plane. These results establish that probe E could be useful in the study of membrane‐bound protein topography by the fluorescence‐energy‐transfer method.