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Synthesis and biological properties of benzyl 2-(oxy)benzoate-substituted silicon phthalocyanine

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Abstract

Bis-benzyl 2-(oxy) benzoate substituted axially silicon phthalocyanine was synthesized by the reaction of silicon phthalocyanine dichloride and benzyl salicylate compounds. Characterization of the compound was done by FT-IR, 1H NMR, 13C NMR, UV-visible and Mass spectrum. Photochemical and photophysical properties of new silicon phthalocyanine (SiPc) was investigated. Biological properties of SiPc was carried out by several different parameters. The highest antioxidant ability of 73.18% was obtained at 100 mg/L concentration while the lowest antioxidant activity of 38.46% was obtained at 6.25 mg/L concentration. The antimicrobial effects of SiPc were investigated against different bacteria and microfungi. The results regarding the antimicrobial activity of this compound 3 showed that E. faecalis (ATCC 29,212) was the most sensitive microorganism to the tested compounds, while C. tropicalis was the most resistant microorganism. In addition, when the antimicrobial photodynamic treatment of SiPc was examined, a better activity was observed against all microorganisms. DNA fragmentation activity and microbial cell viability of compound 3 was investigated. SiPc showed excellent DNA nuclease activity and 99.96% inhibition of cell viability at 100 mg/L. The effect of compound 3 on antibiofilm activity fabricated by S. aureus and P. aureginosa was also measured and a good biofilm inhibition values of 86.51% and 75.24% was achieved at 50 mg/, respectively. In addition, when the antidiabetic effects of the compounds were examined, it showed an antidiabetic effect of 20.14% at 400 mg/L.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Van Yuzuncu Yıl University, Van, 65080, Turkey

    Derya Güngördü Solğun & Mehmet Salih Ağırtaş

  2. Food Processing Programme, Technical Science Vocational School, Mersin University, Yenisehir, Mersin, TR-33343, Turkey

    Sadin Özdemir

  3. Laboratory and Veterinary Health, Technical Science Vocational School, Mersin University, Yenisehir, Mersin, TR-33343, Turkey

    Gülşah Tollu

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  1. Derya Güngördü Solğun
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  2. Sadin Özdemir
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  3. Mehmet Salih Ağırtaş
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  4. Gülşah Tollu
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Contributions

M. S. A. wrote the main manuscript text. D. G. S. prepared the synthesis and Figs. 1, 2, 3, 4 and 5. S. Ö. prepared text and biological properties. G. T. prepared related biological shapes. All authors reviewed the article.

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Correspondence to Mehmet Salih Ağırtaş.

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Solğun, D.G., Özdemir, S., Ağırtaş, M.S. et al. Synthesis and biological properties of benzyl 2-(oxy)benzoate-substituted silicon phthalocyanine. J Incl Phenom Macrocycl Chem 104, 137–148 (2024). https://doi.org/10.1007/s10847-024-01226-4

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