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Design, Synthesis and Evaluation of Fluorescent Probes for Biological Applications

Defense Thèse de doctorat : Univ. Genève, 2012 - Sc. 4492 - 2012/11/19
Abstract We have introduced a conceptually new family of fluorophores for application in chemical biology. The concepts of planarization and polarization as it is found in natural systems like the chemistry of vision were merged. A flexible aromatic scaffold based on substituted oligothiophenes was chosen to modulate the conjugation of the probe and the insertion of an electron-donating moiety and different acceptor groups at the terminal positions introduced a permanent dipole moment in the fluorophores. The optoelectronical properties were determined and the subsequent investigations in large unilamellar vesicles (LUVs) evidenced the simultaneous ability of these fluorophores to respond to membrane fluidity and membrane potential. In parallel aromatic substrates naphthalenediimides (NDI) and perylendiimides (PDI) were functionalized with hydroxyl moieties to obtain a series of compact panchromatic probes able to cover all the visible range. These results evidenced the possibility to modulate the optoelectronic properties, to potentially employ these molecules as biological pH-probes.
Keywords OligothiophenesFluorescent probesMultistep synthesisChemical biology
URN: urn:nbn:ch:unige-245337
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FIN, Andréa. Design, Synthesis and Evaluation of Fluorescent Probes for Biological Applications. Université de Genève. Thèse, 2012. https://archive-ouverte.unige.ch/unige:24533

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Deposited on : 2012-12-13

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