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Porphyrins Conjugated with Peripheral Thiolato Gold(I) Complexes for Enhanced Photodynamic Therapy
Author(s) -
Longevial JeanFrançois,
El Cheikh Khaled,
Aggad Dina,
Lebrun Aurélien,
van der Lee Arie,
Tielens Frederik,
Clément Sébastien,
Morère Alain,
Garcia Marcel,
GaryBobo Magali,
Richeter Sébastien
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702975
Subject(s) - photodynamic therapy , moiety , singlet oxygen , chemistry , carbene , photochemistry , porphyrin , conjugated system , chloride , photosensitizer , combinatorial chemistry , singlet state , stereochemistry , oxygen , organic chemistry , catalysis , excited state , polymer , physics , nuclear physics
Porphyrins fused to imidazolium salts across two neighboring β‐pyrrolic positions were used as N‐heterocyclic carbene (NHC) precursors to anchor Au I ‐Cl complexes at their periphery. Synthesis of several thiolato‐Au I 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‐Au I 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.