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Self-assembled binaphthyl-bridged amphiphilic AABB phthalocyanines: nanostructures for efficient antimicrobial photodynamic therapy.

Herein, the photodynamic activity of phthalocyanine-assembled nanoparticles against bacterial strains is demonstrated. The photosensitizers (PS) studied in this work are two chiral Zn(II)Pcs (PS-1 and PS-2), with an AABB geometry (where A and B refer to differently substituted isoindole constituents) containing differently functionalized, chiral binaphthyloxy-linked A isoindole units, which determine the hydrophobicity of the system, and cationic methyl pyridinium moieties in the other two isoindoles to embody hydrophilicity. Both compounds have the ability to self-assemble into nanoparticles in water media and have proved efficient in the photoinactivation of S. aureus and E. coli, selected as models of Gram-positive and Gram-negative bacteria. The size average of the nanoparticles is determined by the substitution at the binaphthyl core and, in turn, it influences the toxicity of the PS. Thus, PS-1, presenting a non-substituted binaphthyl core, forms larger nanoparticles with a larger cationic surface than octyl-functionalized PS-2. Although both PS present similar structure and photophysical features, the self-assembled nanostructures of PS-1 are more effective in killing both types of strains, showing an outstanding photoinactivation capacity with the Gram-negative E. coli.