Photodynamic therapy (PDT) represents a less invasive and localizable, cancer treatment option. PDT uses light, preferably in the range that most deeply penetrates tissue (650-800 nm), to sensitize singlet oxygen which induces cell death. The development of new photochemotherapeutic agents is necessary, as current candidates have downsides including low singlet oxygen quantum yields, poor absorption cross-section within the therapeutic window, and relatively high inherent toxicity in the dark. Many previously studied PDT agents have been based on tetrapyrroles, including porphyrins, chlorins, bacteriochlorins, and phthalocyanines, which in addition to the limitations listed above, can be difficult to prepare or purify. With this in mind, we have developed the palladium dimethylbiladiene (Pd[DMBil1]), as a candidate for PDT. The Pd[DBMil1] architecture is easily prepared and generates singlet oxygen with high quantum yield upon irradiation with 550 nm light. We have built on the Pd[DMBil1] system by introducing a water-solubilizing PEG group. This biocompatible Pd[DMBil1]–PEG750 platform photosensitizes the formation of singlet oxygen under aqueous conditions and was shown to be a potent photoactive agent of apoptotic triple-negative breast cancer cell. We also have synthesized phenyl-alkyne substituted biladiene (Pd[DMBil2]) as well as derivatives containing para-substitution on the phenyl ring, in efforts towards red shifting the absorption. Introduction of the pendant alkynyl moieties has shifted the absorption profiles of these complexes to longer wavelengths (550 nm to 700 nm) to enable more deeply penetrating light to be used for singlet oxygen sensitization. By altering the electronic capabilities of the para-substituent, we can further control the photophysical characteristics of the Pd[DMBil2] system. Synthetic methods, and photophysical analysis for the suite of Pd[DMBil2] complexes will be presented.

Synthesis and photophysical characterization of extended conjugation containing palladium tetrapyrrole complexes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.