ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis, antioxidant, DNA cleavage and antimicrobial properties of phthalocyanine complexes bearing the poly-hydroxyl groups

Mehmet Salih Ağırtaş, Beyza Cabir, Ümit Yıldıko, Sadin Özdemir, and Serpil Gonca

Department of Chemistry, Faculty of Science, Van Yüzüncü Yıl University, Van, Turkey

E-mail: salihagirtas@hotmail.com

Received: 14 May 2020  Accepted: 13 November 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

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01432-7

Chemical Papers 75 (4) 1749–1760 (2021)