Self-Assembled Binaphthyl-Bridged Amphiphilic AABB Phthalocyanines: Nanostructures for Efficient Antimicrobial Photodynamic Therapy

Miguel Ángel Revuelta-Maza, Elena de las Heras, Montserrat Agut, Santi Nonell, Tomás Torres, Gema de la Torre

Research output: Indexed journal article Articlepeer-review

13 Citations (Scopus)

Abstract

Herein, the photodynamic activity of phthalocyanine (pc)-assembled nanoparticles against bacterial strains is demonstrated. The photosensitizers (PS) studied in this work are two chiral ZnIIPcs (PS-1 and PS-2), with an AABB geometry (where A and B refer to differently substituted isoindole constituents). They contain 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 aqueous media and have proved efficient in the photo-inactivation of Staphylococcus aureus and Escherichia coli, selected as models of Gram-positive and Gram-negative bacteria. The average size of the nanoparticles was determined by substitution at the binaphthyl core and, in turn, influences the toxicity of the PS. Thus, PS-1, presenting a nonsubstituted binaphthyl core, forms larger nanoparticles with a larger cationic surface than the octyl-functionalized PS-2. Although both PSs present similar structure and photophysical features, the self-assembled nanostructures of PS-1 are more effective at killing both types of strain, showing an outstanding photo-inactivation capacity with the Gram-negative E. coli.

Original languageEnglish
Pages (from-to)4955-4963
Number of pages9
JournalChemistry - A European Journal
Volume27
Issue number15
DOIs
Publication statusPublished - 12 Mar 2021

Keywords

  • amphiphiles
  • nanostructures
  • photodynamic therapy
  • phthalocyanines
  • self-assembly

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