Synthesis of two-photon sensitive pro-fluorescent photoremovable protecting groups

Abstract : Photoremovable Protecting Groups (PPG) have been widely used in organic synthesis and in various biological applications. Among the wide diversity of these groups, o-nitrobenzyl groups are the mostly used chromophores. In particular, they have been extensively used for the design of caged compounds. Those latter type of compounds are able to release a biological effector together with an uncaging side-product leading to the spatiotemporal control of various biological processes. In order to acutely monitor the uncaging event for example in cells, we developed new PPGs, based on o-nitrobenzylderivatives, able to release a fluorescent side product. Based on the photolytical mechanism of two-photon sensitive o-nitrobenzyl PPGs, we were able to design new non-fluorescent PPGs able to release fluorophores as side products. We were also able to tune the fluorescent properties of the photo-released by product using molecular engineering. Finally, those pro-fluorescent PPGs have been used in order to follow the uncaging events by fluorescent microscopy on cell cultures.
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Elie Abou Nakad. Synthesis of two-photon sensitive pro-fluorescent photoremovable protecting groups. Organic chemistry. Université de Strasbourg, 2018. English. ⟨NNT : 2018STRAF039⟩. ⟨tel-02160511⟩

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