Photodynamic Activity of Tribenzoporphyrazines with Bulky Periphery against Wound Bacteria

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.

Nipagin-Functionalized Porphyrazine and Phthalocyanine—Synthesis, Physicochemical Characterization and Toxicity Study after Deposition on Titanium Dioxide Nanoparticles P25

“…According to the literature data, the presence of a sulfur atom directly linked to the Pz core results in a strong decrease of singlet oxygen formation yield [ 51 , 52 ]. Lately, we have reported sulfanyl tribenzoporphyrazines bearing isophthaloxy moiety 11 , which was found to generate singlet oxygen with a much lower yield at 0.05 in DMF [ 42 ], in comparison to Pc 3 , with Φ ∆ equal to 0.29, studied here. Measurements performed in DMSO revealed a slighter difference in the values of singlet oxygen generation at 0.13 vs. 0.08 [ 42 ] for 3 and 11 , respectively.…”

“…Lately, we have reported sulfanyl tribenzoporphyrazines bearing isophthaloxy moiety 11 , which was found to generate singlet oxygen with a much lower yield at 0.05 in DMF [ 42 ], in comparison to Pc 3 , with Φ ∆ equal to 0.29, studied here. Measurements performed in DMSO revealed a slighter difference in the values of singlet oxygen generation at 0.13 vs. 0.08 [ 42 ] for 3 and 11 , respectively. This observation could be explained by possible quenching of the excited states by π-π interactions between molecules of compound 11 .…”

“…In the emission study of macrocycles 3 and 7 , only Pc 3 presented weak emission properties, with the quantum yields (Φ FL ) equal to 0.007 and 0.002 in DMF and DMSO, respectively. The drop in Φ FL values noted for 7 , in comparison to the unsubstituted magnesium(II) phthalocyanine (33-fold in DMF and 91-fold in DMSO [ 42 , 43 ]), could be explained by a more developed aromatic periphery in case of Pcs. It has been reported by Kobayashi and co-workers that substitution of Pc at α positions (non-peripheral) impacts a fluorescence yield [ 44 ].…”

Excited State and Reactive Oxygen Species against Cancer and Pathogens: A Review on Sonodynamic and Sono‐Photodynamic Therapy

“…[3,[26][27][28][29] The inactivation of bacteria may be very effective, for instance, 2,3-bis((4-(3,5bis(hydroxymethyl))butyl)tio)tribenzoporphyrazine 2 (Figure 4) used against S. aureus represents the killing rate of over 5.9 log at a concentration of 10 μM and under low light doses. [25] The PDT and SDT might be combined with antibiotic therapy resulting in increased disinfection efficacy on bacterial pathogens compared to monotherapies alone. [5,[30][31][32] This multi-directional strategy may take advantage of a wide range of combinations of therapeutic compounds, such as bacterial cell membrane-targeting antibiotics, bacterial cell wall-targeting antibiotics, and bacterial protein synthesis-inhibiting antibiotics, bacterial nucleic acid synthesis-inhibiting antibiotics, multiantibiotic combinations, and various sensitizer molecules.…”

“…These therapies can be used against both, Gram‐positive and Gram‐negative bacteria [3,7,24] . It is very promising in the “post‐antibiotic era” as it brings an opportunity to efficiently deal with nosocomial infections related to surgical wounds etc [25] . The main bactericidal factor of PDT and SDT is the ability of the sensitizers to generate ROS that disrupt functions of organelles such as cell membrane, ribosomes, etc., and generally put bacteria into a state of oxidative stress [14] …”