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

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, 1...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2019-05, Vol.56 (5), p.1553-1559
Main Authors: Demirbaş, Ümit, Barut, Burak, Yalçın, İzzet, Değirmencioğlu, İsmail, Yıldırmış, Sermet, Özel, Arzu
Format: Article
Language:English
Subjects:
Alzheimer's disease
Cholinesterase
Cobalt
Enzyme kinetics
Enzymes
Inhibition
Lead
Magnesium
NMR
Nuclear magnetic resonance
Structural analysis
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Summary: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, 1H‐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 μM, respectively. The enzyme kinetic study of compound (7) demonstrated noncompetitive AChE inhibition and uncompetitive BuChE inhibition. The Ki values of compound (7) against AChE and BuChE were found to 39.15 and 7.25 μM, respectively. In the tested compounds, (7) deserves further investigation for potential therapeutic candidates of Alzheimer's disease.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3530