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Bromoacyl Analogs of Pyrene–Containing Phosphatidylcholine as New Fluorescent Lipid Probes with Intramolecular Quenching

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Abstract

Two new derivatives of phosphatidylcholine with an intramolecularly quenched fluorescence, namely, 1–ω–bromoundecanoyl–2–[4–(pyren–1–yl)butyroyl]–sn–glycero–3–phosphocholine (BPPhC) and 1–(9,10–dibromostearoyl)–2–[4–(pyren–1–yl)butyroyl]–sn–glycero–3–phosphocholine (DBPPhC), have been obtained by replacing acyl chains by residual pyrenebutyric and bromine–labeled fatty acids. Their structure has been verified by the 1H–NMR method and the spectral properties have been characterized in media of different polarity with the aid of absorption and fluorescent spectroscopy. It has been established that when BPPhC and DBPPhC are included in liposomes, the intensity of their fluorescence changes markedly as a function of the physical state of the bilayer, which makes it possible to use the compounds obtained as lipid probes for investigating the properties of biological and artificial membranes.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 5/2 Academician Kuprevich Str., Minsk, 220141, Belarus

    S. V. Babitskaya, P. A. Kiselev & M. A. Kisel'

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  1. S. V. Babitskaya
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  2. P. A. Kiselev
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  3. M. A. Kisel'
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Babitskaya, S.V., Kiselev, P.A. & Kisel', M.A. Bromoacyl Analogs of Pyrene–Containing Phosphatidylcholine as New Fluorescent Lipid Probes with Intramolecular Quenching. Journal of Applied Spectroscopy 68, 609–615 (2001). https://doi.org/10.1023/A:1012522105937

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