Antimicrobial and antioxidant properties of novel octa-substituted phthalocyanines bearing (trifluoromethoxy)phenoxy groups on peripheral positions

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Farajzadeh N., Pekbelgin Karaoğlu H. R., Akin M., ŞAKİ N., Koçak M.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, vol.23, pp.91-102, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 23
  • Publication Date: 2019
  • Doi Number: 10.1142/s1088424619500068
  • Journal Name: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.91-102
  • Keywords: phthalocyanine, (trifluoromethoxy)phenoxy, aggregation behavior, antimicrobial and antioxidant activity, TLC-direct bioautography, TETRASUBSTITUTED METAL-FREE, THIN-LAYER-CHROMATOGRAPHY, PHOTOPHYSICAL PROPERTIES, AGGREGATION BEHAVIOR, ANTIBACTERIAL PROPERTIES, GALLIUM PHTHALOCYANINES, DIRECT BIOAUTOGRAPHY, II PHTHALOCYANINES, FLUORESCENCE, ZINC(II)
  • Kocaeli University Affiliated: Yes

Abstract

This study presents a novel phthalonitrile derivative (2) bearing (trifluoromethoxy)phenoxy groups in 4,5 positions. Cyclotetramerization of (2) in N,N-dimethylaminoethanol (DMAE) gave a series of peripherally octa-substituted metallophthalocyanines (3-Zn, 3-Co and 3-Cu). The newly synthesized phthalocyanines have been characterized by a combination of various spectroscopic techniques. Effects of solvent nature on aggregation behavior of 3-Zn were studied using different solvents such as acetone, CHCl3 and dichloromethane (DCM). In addition, the aggregation behavior of the phthalocyanine complex 3-Zn was examined in DCM at different concentrations ranging from 4 x 10(-6)-14 x 10(-6)M. Antimicrobial activities of synthesized compounds were tested by using the thin layer chromotography (TLC)-direct bioautography and disk diffusion methods. In both assays, the molecules showed activity on the tested Gram (+) bacteria. Antioxidant activities of the molecules, on the other hand, were determined by using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging method and a reducing power assay. The highest activity was obtained with 3-ZnPc for both methods.