Menthol modified zinc(II) phthalocyanine regioisomers and their photoinduced antimicrobial activity against Staphylococcus aureus

Our study is the first to investigate the antimicrobial activity of the single regioisomers rather than the mixture of isomeric phthalocyanines - regioisomers with symmetry C4, C1 and C2, functionalized with L-menthol in the periphery were obtained. The single Zn(II) phthalocyanine regioisomers were...

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Published inDyes and pigments Vol. 193; p. 109410
Main Authors Szymczak, Joanna, Sobotta, Lukasz, Dlugaszewska, Jolanta, Kryjewski, Michal, Mielcarek, Jadwiga
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.09.2021
Subjects
Liposome
Menthol
Photodynamic antimicrobial chemotherapy
Phthalocyanine
Regioisomer
Liposome
Phthalocyanine
Menthol
Photodynamic antimicrobial chemotherapy
Regioisomer
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Abstract Our study is the first to investigate the antimicrobial activity of the single regioisomers rather than the mixture of isomeric phthalocyanines - regioisomers with symmetry C4, C1 and C2, functionalized with L-menthol in the periphery were obtained. The single Zn(II) phthalocyanine regioisomers were synthesized by remetallation reaction from the metal-free phthalocyanines. The obtained compounds were characterised using NMR, UV–Vis, IR spectroscopy and mass spectrometry. The analysed macrocycles generate singlet oxygen with the quantum yield up to 0.78. Menthol substituted three regioisomers of zinc(II) phthalocyanine were loaded into liposomes and subjected to biological activity study. The investigated compounds present low – C4 and moderate – C1 and C2 activity against Staphylococcus aureus. The highest bacterial growth inhibition (2.48 log) showed regioisomer C2 at the concentration of 10 μM. [Display omitted] •Three regiosomers of 2H and Zn(II) phthalocyanine bearing menthol moieties isolated.•Spectrophotometry, spectrofluorimetry and singlet oxygen generation studied.•Photodynamic activity against Staphylococcus aureus up to 2.48 log.
AbstractList Our study is the first to investigate the antimicrobial activity of the single regioisomers rather than the mixture of isomeric phthalocyanines - regioisomers with symmetry C4, C1 and C2, functionalized with L-menthol in the periphery were obtained. The single Zn(II) phthalocyanine regioisomers were synthesized by remetallation reaction from the metal-free phthalocyanines. The obtained compounds were characterised using NMR, UV–Vis, IR spectroscopy and mass spectrometry. The analysed macrocycles generate singlet oxygen with the quantum yield up to 0.78. Menthol substituted three regioisomers of zinc(II) phthalocyanine were loaded into liposomes and subjected to biological activity study. The investigated compounds present low – C4 and moderate – C1 and C2 activity against Staphylococcus aureus. The highest bacterial growth inhibition (2.48 log) showed regioisomer C2 at the concentration of 10 μM. [Display omitted] •Three regiosomers of 2H and Zn(II) phthalocyanine bearing menthol moieties isolated.•Spectrophotometry, spectrofluorimetry and singlet oxygen generation studied.•Photodynamic activity against Staphylococcus aureus up to 2.48 log.
ArticleNumber 109410
Author Dlugaszewska, Jolanta
Kryjewski, Michal
Sobotta, Lukasz
Mielcarek, Jadwiga
Szymczak, Joanna
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  surname: Szymczak
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  organization: Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780, Poznan, Poland
– sequence: 2
  givenname: Lukasz
  surname: Sobotta
  fullname: Sobotta, Lukasz
  organization: Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780, Poznan, Poland
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  givenname: Jolanta
  surname: Dlugaszewska
  fullname: Dlugaszewska, Jolanta
  organization: Chair and Department of Genetics and Pharmaceutical Microbiology, Poznan University of Medical Sciences, Swiecickiego 4, 60-781, Poznan, Poland
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  givenname: Michal
  orcidid: 0000-0002-6737-4854
  surname: Kryjewski
  fullname: Kryjewski, Michal
  email: mkryjewski@ump.edu.pl
  organization: Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780, Poznan, Poland
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  givenname: Jadwiga
  surname: Mielcarek
  fullname: Mielcarek, Jadwiga
  organization: Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780, Poznan, Poland
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Keywords Liposome
Phthalocyanine
Menthol
Photodynamic antimicrobial chemotherapy
Regioisomer
Language English
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Snippet Our study is the first to investigate the antimicrobial activity of the single regioisomers rather than the mixture of isomeric phthalocyanines - regioisomers...
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StartPage 109410
SubjectTerms Liposome
Menthol
Photodynamic antimicrobial chemotherapy
Phthalocyanine
Regioisomer
Title Menthol modified zinc(II) phthalocyanine regioisomers and their photoinduced antimicrobial activity against Staphylococcus aureus
URI https://dx.doi.org/10.1016/j.dyepig.2021.109410
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