Synthesis, antioxidant, DNA cleavage and antimicrobial properties of phthalocyanine complexes bearing the poly-hydroxyl
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ORIGINAL PAPER
Synthesis, antioxidant, DNA cleavage and antimicrobial properties of phthalocyanine complexes bearing the poly‑hydroxyl groups Mehmet Salih Ağırtaş1 · Beyza Cabir1 · Ümit Yıldıko2 · Sadin Özdemir3 · Serpil Gonca4 Received: 14 May 2020 / Accepted: 13 November 2020 © Institute of Chemistry, Slovak Academy of Sciences 2020
Abstract (4-((1-((2-(bis(2-hydroxypropyl) amino) ethyl) (2-hydroxypropyl) amino) propan-2-yl) oxy) phthalonitrile) (BHHP) was synthesized from reaction N, N, N′, N′- tetrakis (2-hydroxypropyl) ethylene diamine (SM) with 4-nitro phthalonitrile. Zinc, cobalt and copper phthalocyanine complexes were achieved from the reaction of BHHP compound with metal salts. Quantum chemical studies of these phthalocyanines have been computationally supported using density functional theory methods. The antioxidant properties of phthalocyanine compounds were determined with the help of l, l-diphenyl-2-picrilhydrazyl radical scavenging ability and chelating ability to iron ions. Compound 6 showed 72.8% inhibition of DPPH free radicals at 200 mg/L concentration and compound 4 showed 71.5% ferrous metal chelating activity at 200 mg/L concentration. The antimicrobial and DNA cleavage activities of compounds were also investigated. All tested phthalocyanine compounds showed excellent nuclease activity at all concentration. Antimicrobial activities of phthalocyanine compounds were detected using broth microdilution method and all test compounds demonstrated perfect antimicrobial activities. According to in vitro studies, copper phthalocyanine compound 6 has the best activity against the P. aeruginosa with 8 µg/mL of MIC value. Keywords Phthalocyanines · Synthesis · Antioxidant · DNA cleavage · Antimicrobial
Introduction Phthalocyanines (Pcs) which are synthetic analogues of porphyrin compounds have great thermal stability and visible optical properties due to owning an 18-π aromatic macrocycle (Hepokur et al. 2017). These unrivaled specifications enable these materials to be used in many fields, such as Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01432-7) contains supplementary material, which is available to authorized users. * Mehmet Salih Ağırtaş [email protected] 1
Department of Chemistry, Faculty of Science, Van Yüzüncü Yıl University, 65080 Van, Turkey
2
Architecture and Engineering Faculty, Department of Bioengineering, Kafkas University, Kars, Turkey
3
Food Processing Programme, Technical Science Vocational School, Mersin University, Yenisehir, TR‑33343 Mersin, Turkey
4
Department of Medical Laboratory Services, Health Services Vocational School, Mersin University, Yenisehir, TR‑33343 Mersin, Turkey
Langmuir–Blodgett films (Roberts et al. 1985), photovoltaic cells (Pia Donzello et al. 2010; Li et al. 2016), fluorescence and chemical sensors (Günsel et al. 2019), semiconductor materials (Kantekin and Bıyıklıoğlu 2008), nonlinear optics (Salan et al. 2009), catalysis (Burkitt et al. 2016), data storage sys
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