Investigation of tyrosinase enzyme (from mushroom) inhibitory activities and antioxidant properties of new fluorine-containing phthalocyanines

Farajzadeh N., Sağlam Ö., Akin M., ŞAKİ N., Koçak M.

ARCHIV DER PHARMAZIE, vol.354, no.4, 2021 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 354 Issue: 4
  • Publication Date: 2021
  • Doi Number: 10.1002/ardp.202000340
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, CAB Abstracts, Chimica, EMBASE, International Pharmaceutical Abstracts, MEDLINE, Veterinary Science Database
  • Keywords: antioxidant, enzyme inhibition, nonperipherally, phthalocyanines, tyrosinase, METAL II PHTHALOCYANINES, SUBSTITUTED PHTHALOCYANINES, AGGREGATION BEHAVIOR, METALLOPHTHALOCYANINES, COPPER(II), NICKEL(II), SEPARATION, BINDING
  • Kocaeli University Affiliated: Yes

Abstract

A series of new peripherally or nonperipherally substituted phthalocyanines bearing 4-(trifluoromethoxy)thiophenyl groups was synthesized. In addition, a new metal-free phthalocyanine bearing 4-(trifluoromethoxy)phenoxy on the nonperipheral position was prepared. The resulting phthalocyanines were characterized using some spectroscopic techniques such as H-1 nuclear magnetic resonance, Fourier-transform infrared spectroscopy, and UV-Vis spectroscopy, together with elemental analysis. When the tyrosinase enzyme inhibition activities of the synthesized phthalocyanines were examined, molecules 2b and 3b showed an inhibitory activity against the enzyme with IC50 values of 176.2 +/- 0.65 and 284.4 +/- 1.03, respectively. The inhibition types of the molecules and standard inhibitor kojic acid were found as competitive for 2b, mixed for 1b and kojic acid, and uncompetitive for 3b. Antioxidant activities were also assessed by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and reducing power assays, and the molecules showed moderate antioxidant activities.