Synthesis of two new phospholipidic fluorescent probes for membrane studies

Starck, Jean-Philippe; Nakatani, Yôichi; Ourisson, Guy

doi:10.1016/0040-4020(95)00011-v

Cited by 22 publications

(21 citation statements)

References 28 publications

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“…Absolute quantum yields and fluorescence-decay parameters are reported in Table 1. Both quantum yields and average decay times are found to be higher than in CHCl 3 solution; these fluorescence characteristics do not appear to be very sensitive to the phase transition of DMPC vesicles, which is consistent with the hypothesis of a transmembrane topography of such diesters, as was previously shown with the fluorene probe C [9].…”

supporting

confidence: 72%

“…All reagents were commercial products purchased from Aldrich, Fluka, Lancaster, Acros, or other suppliers. 2,6-Dibromoanthracene (2), methyl undec-10-ynoate (3), and 2,6-dibromoanthraquinone (4) were prepared according to recently published procedures [8] [10]. All org.…”

Section: Experimental Partmentioning

confidence: 99%

“…It is also highly regioselective for targets lying near the center of the membrane. We had extended the same principle to fluorescence studies with the novel membrane probes B and C of similar overall length [8] (Fig. 1).…”

mentioning

confidence: 99%

“…1). It was surprising to find that not only the diphospholipidic fluorene probe B, but also the fluorene diester C, carrying distal ester groups, are apparently, as judged by their fluorescence properties, well oriented perpendicularly to the bilayer [9].…”

mentioning

confidence: 99%

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Synthesis and Fluorescence Properties of Novel Transmembrane Probes and Determination of Their Orientation within Vesicles

Quesada¹,

Ardhammar²,

Nordén³

et al. 2000

HCA

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Ein kontinuierlicher Wechsel zwischen magnetischen High‐Spin‐ und Low‐Spin‐Zuständen wird durch Einstrahlen von rotem bzw. grünem Laserlicht erreicht. In der Zuschrift auf berichten S. R. Batten et al. über ein Metallosupramolekül, bei dem durch Temperaturwechsel oder durch Einstrahlen von Licht ein Spin‐Crossover(SCO)‐Schalten möglich ist. Das SCO‐Verhalten hängt zudem von der Gegenwart und der Art eingeschlossener Lösungsmittelmoleküle in der porösen Kristallstruktur ab.

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supporting

confidence: 72%

Section: Experimental Partmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis and Fluorescence Properties of Novel Transmembrane Probes and Determination of Their Orientation within Vesicles

Quesada¹,

Ardhammar²,

Nordén³

et al. 2000

HCA

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“…28 Thiol 1 was thus isolated in pure form as a white powder in amounts in the range of hundreds of milligrams and with fair overall yield (36%). 29 Alcohol 3 could be also obtained, albeit with lower overall yield (50%), from the carboxylic acid 4, after trityl protection of the terminal mercapto group and esterification/reduction of the carboxylic acid group, 30,31 following methods previously used for the incorporation of protected mercapto groups to lipid molecules. 32 Thiol 1 is stable in solid form, provided it is stored at low temperature under an inert atmosphere, and the freshly prepared samples are free of disulfide derivatives, as determined by Ellman titration 33 and 1 H NMR spectroscopy.…”

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confidence: 97%

Synthesis of 16-mercaptohexadecylphosphocholine, a miltefosine analog with leishmanicidal activity

Hornillos

Saugar

Torre

et al. 2006

Bioorganic & Medicinal Chemistry Letters

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New Transmembrane Polyene Bolaamphiphiles as Fluorescent Probes in Lipid Bilayers

Quesada¹,

Acuña²,

Amat‐Guerri³

2001

Angew. Chem.

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The former view of the cell lipid membrane as a somewhat random and disordered distribution of lipids and proteins has given way to one characterized by a complex lateral organization, with nm-sized domains in which specific lipids and proteins are assembled to carry out a particular process. [1] The study of the morphology, composition, regulation, and persistence time of these structures is an experimental challenge that has been taken up by fluorescence probe methods. In the case of lipid ± lipid and lipid ± protein interactions, the dependence of the resonant transfer of electronic excitation on the proximity of donor and acceptor probe molecules can provide very useful information in the 10-nm range. [2] We have previously developed a series of fluorescent fatty acids that contain five conjugated double bonds at the end of a flexible linear chain. [3] These probes accurately report the changes in order and dynamics of the lipid environment in artificial and natural membranes. Furthermore, the large spectral overlap of the polyene absorption with the tryptophan fluorescence from membrane proteins and peptides is very convenient for energy-transfer experiments. However, the mobility of the energy-accepting polyene group in fluid bilayers may introduce some uncertainty into the distance evaluation. This would also be the case in other possible applications of the probes, such as the detection of oxidizing radicals by fluorescence quenching. To restrict the mobility of the chromophore, a linear structure with two polar terminal groups, that is, a bolaform amphiphile similar to the membrane lipids of Archaebacteria [4] would be ideal, with the additional advantage of precisely locating the sensing group of the probe in the bilayer. Bolaamphiphiles can be constructed with the appropriate length to reach both external membrane surfaces with the distal polar groups, and with a sensitive group in the lipophilic central part of the molecule. [5] Some transmembrane bolaamphiphiles have been produced previously for altering specific membrane properties: for example, compounds with p-benzoquinone or anthraquinone groups to change the redox behavior, [6] or conjugated polyenes derived from the natural product bixine to modify the charge-transfer rate across the bilayer. [7] Furthermore, bolaamphiphiles that contain photochemically reactive benzophenone [8] or diazirine [9] groups, or emitting fluorene [10] or anthracene groups, [11] have been also synthesized. A different but interesting fluorescent bolaform structure was also produced by linking two rhodamine 101 dye molecules with a C 32 linear chain. [12] Herein we describe the synthesis of symmetrical bolaamphiphiles with four, five, or six conjugated double bonds in the center of the molecule, with terminal methyl ester (4) or carboxylic acid (5) groups (Scheme 1), and with the appropriate length for spanning the lipid bilayer (Figure 1). The intermediates in the synthesis of the former compounds are conjugated polyenediyne diesters 3 that might also be useful t...

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Synthesis of two new phospholipidic fluorescent probes for membrane studies

Cited by 22 publications

References 28 publications

Synthesis and Fluorescence Properties of Novel Transmembrane Probes and Determination of Their Orientation within Vesicles

Synthesis and Fluorescence Properties of Novel Transmembrane Probes and Determination of Their Orientation within Vesicles

Synthesis of 16-mercaptohexadecylphosphocholine, a miltefosine analog with leishmanicidal activity

New Transmembrane Polyene Bolaamphiphiles as Fluorescent Probes in Lipid Bilayers

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