Synthesis, Characterization, and Investigation of Cholinesterase Inhibitory Properties of Novel Phthalocyanines


DEMİRBAŞ Ü., Barut B., Yalcin I., DEĞİRMENCİOĞLU İ., YILDIRMIŞ S., ÖZEL A.

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.56, no.5, pp.1553-1559, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 56 Issue: 5
  • Publication Date: 2019
  • Doi Number: 10.1002/jhet.3530
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1553-1559
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this study, 4-{2-(2-thienyl)ethoxy}phthalonitrile (3) and its tetra substituted peripherally metal-free (4), lead (II) (5), magnesium (II) (6), and cobalt (II) (7) phthalocyanines were synthesized. The structural characterization of the obtained compounds was performed by a combination of FTIR, H-1-NMR, UV-vis, and MALDI-TOF techniques. The inhibitory properties of these compounds were determined using Ingkaninan's methods against cholinesterase enzymes. Compound (7) had the highest enzyme inhibitory effect toward AChE and BuChE enzymes with IC50 values of 23.71 +/- 0.39 and 27.29 +/- 0.22 mu M, respectively. The enzyme kinetic study of compound (7) demonstrated noncompetitive AChE inhibition and uncompetitive BuChE inhibition. The K-i values of compound (7) against AChE and BuChE were found to 39.15 and 7.25 mu M, respectively. In the tested compounds, (7) deserves further investigation for potential therapeutic candidates of Alzheimer's disease.