Biological properties of novel mono and double-decker hexadeca-substituted metal phthalocyanines

Farajzadeh N., Celik C., ÖZDEMİR S., GONCA S., Koçak M.

NEW JOURNAL OF CHEMISTRY, vol.46, pp.7177-7186, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 46
  • Publication Date: 2022
  • Doi Number: 10.1039/d1nj05721a
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Biotechnology Research Abstracts, Chimica, EMBASE, DIALNET
  • Page Numbers: pp.7177-7186
  • Istanbul Technical University Affiliated: Yes


This study presents the synthesis of a new phthalonitrile derivative, namely 4,5-bis(3,5-bis(trifluoro-methyl)phenoxy)-3,6-bis(hexyloxy)phthalonitrile (1), and its mono metal {Zn (2), Lu (CH3COO) (3))/double-decker lutetium (4) phthalocyanines. All the newly synthesized compounds were characterized by performing a series of spectroscopic methods encompassing H-1 NMR, FT-IR, and mass spectroscopy. In addition, compounds (2-4) exhibited good solubility in different organic solvents. The antioxidant properties of compounds (1-4) were determined by applying a DPPH radical scavenging assay and using a spectrophotometer. The highest radical scavenging activity was obtained 95.7% at 200 mg L-1 for compound 2. The DNA nuclease activity of the newly synthesized compounds was investigated by performing the agarose gel method. All of the compounds exhibited DNA cleavage ability. Moreover, the antimicrobial activity of the tested compounds was studied using the microdilution and disc diffusion methods. The newly synthesized phthalonitrile and its metal complexes displayed antimicrobial photodynamic activity against E. coli. Additionally, the biofilm inhibition of the tested compounds was investigated and the highest biofilm inhibition was obtained 93.09% against P. aeruginosa for compound 3.