Journal
DYES AND PIGMENTS
Volume 160, Issue -, Pages 292-300Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2018.08.004
Keywords
Chlorins; Singlet oxygen; PACT; Enterococcus faecalis; Staphylococcus aureus
Funding
- Polish National Centre of Sciences [2013/11/N/ST5/02040]
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Two chlorin derivatives bearing (trifluoromethyl)phenyl substituents at meso positions were synthesized via 1,3-dipolar cycloaddition. These pyrrolidine-fused chlorins are characterized by H-1, C-13 NMR spectroscopy, mass spectrometry, UV-Vis absorption and fluorescence spectroscopy. The obtained compounds revealed UV-Vis spectra typical of chlorins. Fluorescence quantum yields were calculated to be ca. 0.2 and ca. 0.3 in DMF and DMSO, respectively, for both compounds. The chlorin bearing 3,5-bis(trifluoro-methyl)phenyl substituent in mesa positions (0.69 in DMF, 0.57 in DMSO) revealed a stronger singlet oxygen formation ability than that with 4-(trifluoromethyl)phenyl moieties (0.50 in DMF, 0.45 in DMSO). Both compounds were found to be stable under irradiation in DMF. Nevertheless, irradiation of both compounds in DMSO solution caused their photo-transformation. As the studied compounds are insoluble in aqueous media, they were incorporated in lipid vesicles. Photodynamic bacteria inactivation experiments showed log reduction of bacterial growth for Enterococcus faecalis at 4.84; Staphylococcus aureus at 4.09; Escherichia coli at 2.23. No activity of both macrocycles was noticed against Pseudomonas aeruginosa and fungi: Candida albicans and Trichophyton mentagrophytes.
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