Porphyrins Conjugated with Peripheral Thiolato Gold(I) Complexes for Enhanced Photodynamic Therapy

Abstract : Porphyrins fused to imidazolium salts across two neighboring beta-pyrrolic positions were used as N-heterocycliccarbene (NHC) precursors to anchor AuI-Cl complexes at their periphery. Synthesis of several thiolato-AuI complexes was then achieved by substituting chloride for thiolates. Photodynamic properties of these complexes were investigated: the data obtained show that the Au@S bonds could be cleaved upon irradiation. The proposed mechanism to explain the release of thiolate moiety involves the S atom oxidation by singlet oxygen generated in the course of irradiation. In view of photodynamic therapy (PDT) applications, these porphyrins fused to NHC-AuI complexes were tested as photosensitizers to kill MCF-7 breast cancer cells. Results show the important role played by the ancillary ligands (chloride versus thiolates) on the photodynamic effect.
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Submitted on : Monday, October 9, 2017 - 10:44:16 AM
Last modification on : Saturday, November 24, 2018 - 1:39:37 AM

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Jean-François Longevial, Khaled El cheikh, Dina Aggad, Aurélien Lebrun, Arie Van der lee, et al.. Porphyrins Conjugated with Peripheral Thiolato Gold(I) Complexes for Enhanced Photodynamic Therapy. Chemistry - A European Journal, Wiley-VCH Verlag, 2017, 23, pp.14017-14026. ⟨10.1002/chem.201702975⟩. ⟨hal-01613027⟩

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