Antimicrobial activity of different substituted meso-porphyrin derivatives

Abstract

The increasing resistance against classical antibiotic treatment forces the researchers to develop novel non-toxic antimicrobial agents. The aim of this study was to determine the antimicrobial properties of seven different porphyrins having distinctive hydrophobicity/hydrophilicity: P1 meso-tetra(4-methoxy-phenyl)porphyrin, P2 Zn(II)-meso-5,10,15,20-tetrapyridylporphyrin, P3 meso-tetra(p-tolyl)porphyrin, P4 5,10,15,20-tetraphenylporphyrin; P5 (5,10,15,20-tetraphenylporphinato) dichlorophosphorus(V) chloride, P6 5,10,15,20-tetrakis-(N-methyl-4-pyridyl) porphyrin-Zn(II) tetrachloride, P7 Zn(II)-5,10,15,20-meso-tetrakis-(4-aminophenyl)porphyrin. The meso-porphyrin derivatives were screened for their antimicrobial activity against six reference strains: Streptococcus pyogenes ATCC 19615, Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 700603, Pseudomonas aeruginosa ATCC27853 and Candida albicans ATCC 10231. The antimicrobial activity of these samples was evaluated by the agar disk diffusion method and dilution method, with the determination of the minimum inhibitory concentration (MIC), the minimum bactericidal concentration (MBC) and the minimum fungicidal concentration (MFC). The most significant result is provided by the water-soluble P5 manifesting an obvious antimicrobial activity against Streptococcus pyogenes. On the other hand, P6 is a moderately active derivative against Streptococcus pyogenes and Escherichia coli and P7 presents moderate activity against Streptococcus pyogenes and Staphylococcus aureus. All the tested porphyrin bases, presenting hydrophobic character, have no antimicrobial activity under the investigated conditions. The common characteristics of the porphyrins that act as promising antimicrobial agents in the non-irradiated methods are: the cationic nature, the increased hydrophilicity and the presence of both amino functional groups grafted on the porphyrin ring and the coordination with Zn or phosphorus in the inner core.

Keywords

• meso-aryl porphyrins
• metalloporphyrins
• gram(+) and gram(-) bacteria
• antimicrobial activity