Phthalocyanine complexes with (4-isopropylbenzyl)oxy substituents: preparation and evaluation of anti-carbonic anhydrase, anticholinesterase enzymes and molecular docking studies

Güzel, Emre; Koçyiğit, Ümit M.; Taslimi, Parham; Gülçın, İlhami; Erkan, Sultan; Nebioğlu, Mehmet; Arslan, Barış Seçkin; Şişman, İlkay

doi:10.1080/07391102.2020.1818623

Cited by 24 publications

(15 citation statements)

References 45 publications

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“…The IC 50 values of these compounds ranged from 105.94 to 212.43 μM on AChE and BuChE. [ 43 ] Another study, Güzel et al reported furan‐2‐ylmethoxy‐substituted copper and manganese Pcs on cholinesterases inhibited AChE with 15.91 and 48.04 μM, respectively. [ 32 ] These results showed that our compounds had higher inhibitory effects than non‐peripherally (4‐isopropylbenzyl)oxy‐substituted and furan‐2‐ylmethoxy‐substituted Pcs compounds.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

Bıyıklıoğlu

Baş

Akkaya

et al. 2022

Applied Organom Chemis

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In this paper, we synthesized peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble metallophthalocyanines (DM‐C6‐CoQ, DM‐C6‐CuQ, DM‐C6‐MnQ) and investigated their in vitro cholinesterases inhibitory properties by using the spectrophotometric method. The results revealed that the compounds inhibited cholinesterases and had remarkable inhibitory effects when compared with galantamine (p < 0.0001). The IC50 values of the compounds ranged from 2.11 ± 0.20 to 16.40 ± 1.25 μM for AChE and BuChE. Also, the inhibitory type and inhibition constant (Ki) of the compounds were evaluated using Lineweaver–Burk and Dixon plots. These plots showed that DM‐C6‐CoQ, DM‐C6‐CuQ, and DM‐C6‐MnQ were mixed inhibitors against AChE and DM‐C6‐MnQ is the strongest binding inhibitor to the enzyme. Also, DM‐C6‐CoQ inhibited BuChE via competitive manner with 10.05 ± 0.55 μM of Ki value. These results demonstrated that the compounds might be effective agents against Alzheimer's disease.

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Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

Bıyıklıoğlu

Baş

Akkaya

et al. 2022

Applied Organom Chemis

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“…Since the difference of metal atoms in the center of the molecule affects the partial charge distribution on the molecule, it causes a change in the interaction forces as well as the differentiation of the interacted amino acids. [ 96 ] The binding interactions of Pc complexes were given in Table 7.…”

Section: Resultsmentioning

confidence: 99%

Some characteristics of new and innovative COX inhibitor derivatives: Potent hCA‐I and hCA‐II inhibitors supported by molecular docking studies

Karakılıç

Alım

Emirik

et al. 2021

Applied Organom Chemis

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In this study, two novel metallophthalocyanines (ZnPc and CoPc) were synthesized using the corresponding metal salts 4‐(4‐(4‐[4‐chlorophenyl]‐5‐methylisoxazol‐3‐yl)phenoxy)‐phthalonitrile (11), prepared from the reaction of 4‐nitrophthalonitrile and 4‐(4‐[4‐chlorophenyl]‐5‐methylisoxazol‐3‐yl)phenol (9). These metallophthalocyanines (MPcs) showed quite solubility in organic solvents such as dichloromethane (DCM), tetrahydrofuran (THF), dimethyl formamide (DMF), and dimethylsulfoxide (DMSO). The novel compounds 11a and 11b have been characterized using their UV–Vis, FT–IR, 1H NMR, 13C NMR, X‐Ray, and MALDI–TOF mass spectra. Supporting information cocerning with the study has been supplied. Photochemical, photophysical, and cyclic voltagram properties of these novel 4‐(4‐(4‐[4‐chlorophenyl]‐5‐methylisoxazol‐3‐yl)phenoxy substituted metallophthalocyanines (11a and 11b) were determined in DMF. DNA binding, metal chelating effect assay, and DPPH [2,2‐diphenyl‐1‐picrylhydrazyl hydrate] radical scavenging assay and electrochemical studies of MPcs were investigated. Further, the inhibitory effects of the COX‐inhibitor based novel metallophthalocyanines (11a and 11b) and their ligands (10 and 11) were examined on human erythrocyte carbonic anhydrase I (hCA‐I) and II (hCA‐II) isoenzymes, and the synthesized molecules exhibited very strong inhibitory effects on both isoforms. In addition, the hCA‐I and hCA‐II inhibition potential of Zn (II) and Co (II) Phthalocyanine complexes was supported by molecular docking studies. The binding interaction of metallophthalocyanines complexes 11a, 11b enzymes were analyzed in detail.

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“…The parameters showing the numerical values of the interaction between the molecule and the enzyme are Glide hbond, Glide evdw, Glide ecoul. On the other hand, Glide emodel, Glide energy, Glide einternal, and Glide posenum parameters are the numerical values of the exposure formed between the molecule and protein [65][66][67][68][69].…”

Section: Resultsmentioning

confidence: 99%

Examination of anti-oxidant properties and molecular docking parameters of some compounds in human body

Tüzün¹

2020

Turkish Computational and Theoretical Chemistry

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There are many hormones and molecules in the human body. Many of these take place in different jobs and tasks. Some of these hormones are serotonin (A1), testosterone (A2), dopamine (A3), adrenaline (A4), methylcytosine (A5) and creatine (A6). The anti-oxidant properties of these molecules in both gas and water phases of the HF/6-31++G(d,p) basis set were calculated with the Gaussian package program. After this process, molecular docking calculations were made to compare the activities of molecules against proteins with anti-oxidant properties whose name are human peroxiredoxin-5 (HP5) and bovine xanthine oxidase (BXO), were compared.

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Phthalocyanine complexes with (4-isopropylbenzyl)oxy substituents: preparation and evaluation of anti-carbonic anhydrase, anticholinesterase enzymes and molecular docking studies

Cited by 24 publications

References 45 publications

Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

Some characteristics of new and innovative COX inhibitor derivatives: Potent hCA‐I and hCA‐II inhibitors supported by molecular docking studies

Examination of anti-oxidant properties and molecular docking parameters of some compounds in human body

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