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Highly Phototoxic Transplatin‐Modified Distyryl‐BODIPY Photosensitizers for Photodynamic Therapy
Author(s) -
Padrutt Roxane,
Babu Vipin,
Klingler Simon,
Kalt Martina,
Schumer Frank,
Anania Maria I.,
Schneider Lukas,
Spingler Bernhard
Publication year - 2021
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202000702
Subject(s) - bodipy , singlet oxygen , photodynamic therapy , phototoxicity , chemistry , intersystem crossing , photochemistry , photosensitizer , intramolecular force , combinatorial chemistry , singlet state , oxygen , fluorescence , excited state , stereochemistry , organic chemistry , biochemistry , physics , quantum mechanics , nuclear physics , in vitro
We report the synthesis of the first transplatin‐BODIPY conjugates for application in photodynamic therapy (PDT). The distyryl BODIPYs containing two iodine atoms were designed to absorb in the red region, easily undergo intersystem crossing for efficient singlet oxygen generation, and additionally offer the possibility for coordination with mono‐activated transplatin. We were able to demonstrate that coordination of the BODIPYs with a mono‐activated transplatin increases the phototoxic index of the photosensitizers significantly, giving rise to highly phototoxic distyryl BODIPY derivatives, of which one was shown to have the highest ever reported phototoxic index against any cell line. Furthermore, the photophysical mechanism of singlet oxygen generation in distyryl BODIPYs undergoing intramolecular charge transfer was studied experimentally and using time‐dependent density functional theory.