Photodynamic Activity of Tribenzoporphyrazines with Bulky Periphery against Wound Bacteria

Int J Mol Sci. 2020 Aug 26;21(17):6145. doi: 10.3390/ijms21176145.

Abstract

Magnesium(II) tribenzoporphyrazines with phenoxybutylsulfanyl substituents were evaluated as photosensitizers in terms of their optical properties against wound bacteria. In the UV-vis spectra of analyzed tribenzoporphyrazines, typical absorption ranges were found. However, the emission properties were very weak, with fluorescence quantum yields in the range of only 0.002-0.051. What is important, they revealed moderate abilities to form singlet oxygen with the quantum yields up to 0.27. Under irradiation, the macrocycles decomposed via photobleaching mechanism with the quantum yields up to 8.64 × 10-5. The photokilling potential of tribenzoporphyrazines was assessed against Streptococcus pyogenes, Staphylococcus epidermidis, as well as various strains of Staphylococcus aureus, including methicillin-sensitive and-resistant bacteria. Both evaluated photosensitizers revealed high photodynamic potential against studied bacteria (>3 logs). S.aureus growth was reduced by over 5.9 log, methicillin-resistant S. aureus by 5.1 log, S.epidermidis by over 5.7 log, and S. pyogenes by over 4.7 log.

Keywords: photodynamic antimicrobial therapy; porphyrazins; singlet oxygen; wound.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Humans
  • Macrocyclic Compounds / chemical synthesis*
  • Macrocyclic Compounds / chemistry
  • Macrocyclic Compounds / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Photobleaching
  • Photosensitizing Agents / chemical synthesis*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology
  • Porphyrins / chemistry*
  • Quantum Dots
  • Singlet Oxygen / metabolism
  • Staphylococcus aureus / drug effects
  • Staphylococcus epidermidis / drug effects
  • Streptococcus pyogenes / drug effects
  • Wound Infection / prevention & control

Substances

  • Anti-Bacterial Agents
  • Macrocyclic Compounds
  • Photosensitizing Agents
  • Porphyrins
  • Singlet Oxygen