Biologically active phthalocyanine metal complexes: Preparation, evaluation of α-glycosidase and anticholinesterase enzyme inhibition activities, and molecular docking studies
Citation
Emre Güzel1 | Ümit M.Koçyiğit2 | Parham Taslimi3 | Sultan Erkan4 | Omer S.Taskin5 1Department of fundamental sciences, Sakarya UniversityofAppliedSciences, Sakarya, Turkey 2Department of basic pharmaceutical Sciences, SivasCumhuriyetUniversity, Sivas, Turkey 3Department of biotechnology,Bartın University, Bartın, Turkey 4Department of chemistry,SivasCumhuriyet University, Sivas,Turkey 5Department of chemical oceanography, İstanbul University, İstanbul, TurkeyAbstract
In this study, preparation, as well as investigation of α-glycosidase and cholinesterase (ChE) enzyme inhibition activities of furan-2-ylmethoxy-substituted compounds 1–7, are reported. Peripherally, tetra-substituted copper and manganese phthalocyanines (5 and 6) were synthesized for the first time. The substitution of furan-2-ylmethoxy groups provides remarkable solubility to the complex and redshift of the phthalocyanines Q-band. Besides, the inhibitory effects of these compounds on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase (α-Gly) enzymes have been investigated. The AChE was inhibited by these compounds (1–7) in low micromolar levels, and K i values were recorded between 11.17 ± 1.03 and 83.28 ± 11.08 µM. Against the BChE, the compounds demonstrated K i values from 7.55 ± 0.98 to 81.35 ± 12.80 µM. Also, these compounds (1–7) effectively inhibited α-glycosidase, with K i values in the range of 744.87 ± 67.33 to 1094.38 ± 88.91 µM. For α-glycosidase, the most effective K i values of phthalocyanines 3 and 6 were with K i values of 744.87 ± 67.33 and 880.36 ± 56.77 µM, respectively. Moreover, the studied metal complexes were docked with target proteins PDB ID: 4PQE, 1P0I, and 3WY1. Pharmacokinetic parameters and secondary chemical interactions that play an active role in interaction were predicted with docking simulation results. Overall, furan-2-ylmethoxy-substituted phthalocyanines can be considered as potential agents for the treatment of Alzheimer's diseases and diabetes mellitus.
Source
J Biochem Mol ToxicolVolume
35URI
https://onlinelibrary.wiley.com/doi/full/10.1002/jbt.22765https://hdl.handle.net/20.500.12418/13046