Photochemical properties and photocytotoxicities against wound bacteria of sulfanyl porphyrazines with bulky peripheral substituents

•Photochemical properties of magnesium(II) phenylalkylsulfanyl porphyrazines were evaluated.•High inactivation potential against S. pyogenes was observed.•Moderate inactivation potential against S. aureus was observed. Porphyrazine macrocycles with bulky peripheral phenylalkylsulfanyl substituents w...

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Published in:Journal of organometallic chemistry 2021-02, Vol.934, p.121669, Article 121669
Main Authors: Stolarska, Magdalena, Glowacka-Sobotta, Arleta, Ziental, Daniel, Dlugaszewska, Jolanta, Falkowski, Michal, Mielcarek, Jadwiga, Goslinski, Tomasz, Sobotta, Lukasz
Format: Article
Language:English
Subjects:
Macrocycle
Photocytotoxicity
Porphyrazine
Singlet oxygen
Wound infections
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Summary:•Photochemical properties of magnesium(II) phenylalkylsulfanyl porphyrazines were evaluated.•High inactivation potential against S. pyogenes was observed.•Moderate inactivation potential against S. aureus was observed. Porphyrazine macrocycles with bulky peripheral phenylalkylsulfanyl substituents were subjected to photochemical studies. The singlet oxygen generation potential of these macrocycles was assessed using an indirect method with DPBF and all molecules revealed low singlet oxygen generation with quantum yields up to 0.03. In the photostability study, porphyrazine derivatives underwent photobleaching processes under light irradiation with quantum yields up to 2.45 ∙ 10−5. The photocytotoxicities of sulfanyl porphyrazine derivatives were researched in liposomal nanoparticles against wound bacteria, such as Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus epidermidis, and Streptococcus pyogenes. The most active macrocycles appeared magnesium(II) porphyrazines with 5-(3,5-dibutoxycarbonylphenoxy)pentylthio- and 2-[2-(3,5-dibutoxycarbonylphenoxy)ethoxy]ethylthio-substitents. According to calculated photokilling rates obtained in the photoinactivation study, the greatest reduction of bacterial growth up to 4.7 log was noted for S. pyogenes, whereas moderate activity 2.5–2.6 log was observed against S. aureus. Low or no photocytotoxicity of studied macrocycles was noted against MRSA and S. epidermidis. [Display omitted]
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2020.121669