Jump to main content
Jump to site search


Design, synthesis, characterization of peripherally tetra-pyridine-triazole-substituted phthalocyanines and their inhibitory effects on cholinesterases (AChE/BChE) and carbonic anhydrases (hCA I, II and IX)

Author affiliations

Abstract

In this study, phthalocyanine precursors (5 and 9) and 1,2,3-triazole-substituted metal-free and metallo phthalocyanines (9a–c) were designed and synthesized for the first time and evaluated in vitro for key molecular targets. The structures of the novel compounds were characterized via FT-IR, 1H/13C NMR, UV-Vis, and mass spectroscopy. The inhibitory activities of the compounds were tested against human carbonic anhydrase isoforms hCA I, II (cytosolic, ubiquitous isozymes), and IX (transmembrane, cancer-associated isozyme) and cholinesterases (AChE and BChE, which are associated with Alzheimer's disease). Among the three phthalocyanines and starting compounds, 9b showed the most interesting profile as a nanomolar selective inhibitor of hCA I (Ki = 37.2 nM) and 9c showed the most effective inhibitory effect on hCA II, IX, AChE and BChE (Ki = 41.9, 27.4, 5.8 and 45.8 nM, respectively). This study is also the first example of cancer-associated isozyme hCA IX inhibition by phthalocyanines.

Graphical abstract: Design, synthesis, characterization of peripherally tetra-pyridine-triazole-substituted phthalocyanines and their inhibitory effects on cholinesterases (AChE/BChE) and carbonic anhydrases (hCA I, II and IX)

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Oct 2019, accepted on 15 Nov 2019 and first published on 18 Nov 2019


Article type: Paper
DOI: 10.1039/C9DT03897C
Dalton Trans., 2020, Advance Article

  •   Request permissions

    Design, synthesis, characterization of peripherally tetra-pyridine-triazole-substituted phthalocyanines and their inhibitory effects on cholinesterases (AChE/BChE) and carbonic anhydrases (hCA I, II and IX)

    T. Arslan, M. Buğrahan Ceylan, H. Baş, Z. Biyiklioglu and M. Senturk, Dalton Trans., 2020, Advance Article , DOI: 10.1039/C9DT03897C

Search articles by author

Spotlight

Advertisements