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Synergistic Effects in Pt II –Porphyrinoid Dyes as Candidates for a Dual‐Action Anticancer Therapy: A Theoretical Exploration
Author(s) -
Alberto Marta Erminia,
Adamo Carlo
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.201702876
Subject(s) - porphyrin , photodynamic therapy , chemistry , moiety , tetra , photosensitizer , conjugate , combinatorial chemistry , ligand (biochemistry) , chlorin , cisplatin , platinum , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , biochemistry , catalysis , chemotherapy , receptor , mathematical analysis , mathematics , medicine , surgery
The combination of a photosensitizer (PS) with a cisplatin‐like unit represents a challenging strategy to increase the effectiveness of photodynamic therapy and to afford a dual‐action anticancer treatment. Recently, new tetra‐Pt II –porphyrin conjugates have been proposed as promising multitarget agents. To reveal the effect of the Pt II center on the chemical and physical properties of the PS and to explore the effect of the PS on the activation mechanism of Pt II ligand before reaching its biological target, we carried out a first‐principle investigation on these tetra‐Pt II –porphyrin conjugates. To propose a further advance in this novel field and to gain useful insights for the design of new, more efficient Pt II –PS conjugates, we introduced structural modifications into the porphyrin dye, which involved the synthesis of the tetra‐Pt II –chlorin and tetra‐Pt II –bacteriochlorin derivatives. Results showed that the designed dyes better met the criteria to be successful in a dual‐action therapy, as they displayed improved optical properties and reduced the hydrolysis rate of the Pt II moiety, the latter being a desirable feature to avoid many side reactions of the conjugate during their transport to the biological target.