Transition metal-promoted bioorthogonal transformations in biological media

Abstract

This PhD thesis describes the reactivity of Au, Pd and Ru organometallic complexes in biological media. In particualar, the reactivity of Au(I) complexes was studied for the hydroarylation reaction of fluorogenic coumarins in aqueous mixture, together with its bioorthogonality and translation to living cells. Moreover, homogenous and heterogenous Pd(0) complexes were used for the allyloxycarbonyl, propargyloxycarbonyl, propargyl groups removal in aqueous media in the presence or inside living cells. The reactivity of heterogenous palladium systems was also tested towards much more challening Suzuki-Miyaura reaction in aqueous media and under biologically relevant conditions. Finally, Ru(II) complexes were used for the annulation between azide and thioalkyne in aqueous mixture, demonstrating the robustness of the reaction in the presence of biologically relevant molecules and in the presence of living bacteria. Moreover, new phoactivable Ru(II) complexes were also active for this transformation and it was possible to use them for the modification of biomolecules like DNA and small peptides.