Photodynamic therapy characteristics of phthalocyanines in the presence of boron doped detonation nanodiamonds: Effect of symmetry and charge

The synthesis, photophysicochemical and photodynamic therapy (PDT) activities of benzothiazole substituted zinc phthalocyanine (Pc): 1 (asymmetrically substituted and composed of no charges), 2 (asymmetrically substituted and composed of three positive charges), and 3 (symmetrically substituted and composed of four positive charges), are presented. The triplet and singlet oxygen quantum yields were highest for complex 2 showing the importance of asymmetry and charge. The complexes are covalently and non-covalently linked to B doped detonation nanodiamonds (B@DNDs) to yield nanohybrids (B@DNDs-1, B@DNDs-2, B@DNDs-3). The presence of B@DNDs, asymmetry and positive charge resulted in improved PDT with the lowest cell viability being observed for B@DNDs-2 at 5%. The cell viability ranged from 5% to 7% for the nanohybrids compared to 19-26% for Pcs alone.

Automated summary

The synthesis, photophysicochemical properties, and photodynamic therapy activities of benzothiazole substituted zinc phthalocyanine compounds were investigated. The importance of asymmetry and positive charge for high triplet and singlet oxygen yields was demonstrated. Nanohybrids formed by linking the compounds to B doped detonation nanodiamonds showed improved photodynamic therapy activity.