Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057, Zurich, Switzerland.
ChemMedChem. 2021 Feb 17;16(4):694-701. doi: 10.1002/cmdc.202000702. Epub 2020 Nov 24.
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.
我们报告了首例顺铂-BODIPY 缀合物的合成，用于光动力疗法 (PDT)。含有两个碘原子的二芳基乙烯 BODIPY 被设计为在红光区吸收，容易发生系间窜跃以高效生成单线态氧，并另外提供与单活化顺铂配位的可能性。我们能够证明，BODIPY 与单活化顺铂的配位显著增加了光敏剂的光毒性指数，产生了高光毒性的二芳基乙烯 BODIPY 衍生物，其中一种对任何细胞系的光毒性指数均为有报道以来最高。此外，通过实验和时间依赖的密度泛函理论研究了经历分子内电荷转移的二芳基乙烯 BODIPY 中单线态氧生成的光物理机制。
