Bacterial Photodynamic Inactivation: Eradication of Staphylococcus aureus and Escherichia coli Mediated by Pyridinium-Pyrazolyl Zinc(II) Phthalocyanines

ACS Appl Bio Mater. 2024 Nov 18;7(11):7748-7757. doi: 10.1021/acsabm.4c01368. Epub 2024 Oct 21.

Abstract

Antimicrobial resistance remains an enduring global health issue, manifested when microorganisms, such as bacteria, lack responsiveness to antimicrobial treatments. Photodynamic inactivation (PDI) of microorganisms arises as a noninvasive, nontoxic, and repeatable alternative for the inactivation of a broad range of pathogens. So, this study reports the synthesis, structural characterization, and photophysical properties of a new tetra-β-substituted pyridinium-pyrazolyl zinc(II) phthalocyanine (ZnPc 1a) that was compared with two previously described pyridinium-pyrazolyl ZnPcs 2a and 3a. The PDI efficacy of these three ZnPcs (1a-3a) against a drug-resistant Gram-positive bacterium (as Staphylococcus aureus) and a Gram-negative bacterium (as Escherichia coli) is also reported. The PDI efficacy toward these bacteria was examined with ZnPcs 1a-3a in the 5.0-10.0 μM range using a white light source with an irradiance of 150 mW/cm2. All ZnPcs displayed a significant PDI activity against S. aureus, with reductions superior to 3 Log CFU/mL. Increasing the treatment time, the E. coli was inactivated until the detection limit of the method (>6.3 Log CFU/mL) using the quaternized ZnPcs 1a-3a (10.0 μM, 120 min) being the inactivation time was reduced when added the KI for ZnPcs 1a and 3a. These findings demonstrate the effective PDI performance of pyridinium-pyrazolyl group-bearing PSs, indicating their potential use as a versatile antimicrobial agent for managing infections induced by Gram-negative and Gram-positive bacteria.

Keywords: E. coli; S. aureus; multidrug-resistant bacteria; photodynamic inactivation; phthalocyanine; singlet oxygen.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry
  • Biocompatible Materials / pharmacology
  • Escherichia coli* / drug effects
  • Indoles* / chemistry
  • Indoles* / pharmacology
  • Isoindoles*
  • Materials Testing
  • Microbial Sensitivity Tests*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology
  • Particle Size
  • Photochemotherapy
  • Photosensitizing Agents* / chemical synthesis
  • Photosensitizing Agents* / chemistry
  • Photosensitizing Agents* / pharmacology
  • Pyrazoles* / chemical synthesis
  • Pyrazoles* / chemistry
  • Pyrazoles* / pharmacology
  • Pyridinium Compounds / chemical synthesis
  • Pyridinium Compounds / chemistry
  • Pyridinium Compounds / pharmacology
  • Staphylococcus aureus* / drug effects
  • Zinc Compounds

Substances

  • Indoles
  • Photosensitizing Agents
  • Anti-Bacterial Agents
  • Isoindoles
  • Pyrazoles
  • Zn(II)-phthalocyanine
  • Biocompatible Materials
  • Organometallic Compounds
  • Pyridinium Compounds
  • Zinc Compounds