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    Aminopyrazole-substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition properties
    (WILEY-V C H VERLAG GMBH, 2019) Guzel, Emre; Kocyigit, Umit M.; Arslan, Baris S.; Atas, Mehmet; Taslimi, Parham; Gokalp, Faik; Nebioglu, Mehmet; Sisman, Ilkay; Gulcin, Ilhami
    The synthesis, characterization, aggregation behavior, theoretical studies, and investigation of antimicrobial, antidiabetic, and anticholinergic properties of 4-(2-(5-amino-4-(4-bromophenyl)-3-methyl-1H-pyrazol-1-yl)ethoxy)phthalonitrile (2) and its soluble aminopyrazole-substituted peripheral metallo (Mn, Co, and Ni)-phthalocyanine complexes (3-5) are reported for the first time. The synthesized compounds and phthalocyanine complexes were characterized spectroscopically. The new phthalonitrile derivative (2) and its peripheral metallophthalocyanine complexes (3-5) were found to be effective inhibitors of alpha-glycosidase, acetylcholinesterase (AChE), human carbonic anhydrase I and II isoforms (hCA I and II), and butyrylcholinesterase (BChE) with K-i values in the range of 1.55 +/- 0.47 to 10.85 +/- 3.43 nM for alpha-glycosidase, 8.44 +/- 0.32 to 21.31 +/- 7.91 nM for hCA I, 11.73 +/- 2.82 to 31.03 +/- 4.81 nM for hCA II, 101.62 +/- 26.58 to 326.54 +/- 89.67 nM for AChE, and 68.68 +/- 11.15 to 109.53 +/- 19.55 nM for BChE. This is the first study of peripherally substituted phthalocyanines containing an aminopyrazole group as potential carbonic anhydrase enzyme inhibitor. Also, the antimicrobial activities of the synthesized compounds were evaluated against six microorganisms (four bacteria and two Candida species) using the broth microdilution method. The gram-positive bacteria were detected to be more sensitive than gram-negative bacteria and yeasts in the synthesized compounds.
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    Evaluation of carbonic anhydrase and paraoxonase inhibition activities and molecular docking studies of highly water-soluble sulfonated phthalocyanines
    (Tubitak Scientific & Technological Research Council Turkey, 2020) Guzel, Emre; Sonmez, Fatih; Erkan, Sultan; Cikrikci, Kubra; Ergun, Adem; Gencer, Nahit; Arslan, Oktay
    The investigation of carbonic anhydrase and paraoxonase enzyme inhibition properties of water-soluble zinc and gallium phthalocyanine complexes (1 and 2) are reported for the first time. The binding of p-sulfonylphenoxy moieties to the phthalocyanine structure favors excellent solubilities in water, as well as providing an inhibition effect on carbonic anhydrase (CA) I and II isoenzymes and paraoxonase (PON I) enzyme. According to biological activity results, both complexes inhibited hCA I, hCA II, and PON1. Whereas 1 and 2 showed moderate hCA I and hCA II (off-target cytosolic isoforms) inhibitory activity (K-i values of 26.09 mu M and 43.11 mu M for hCA I and 30.95 mu M and 33.19 mu M for hCA II, respectively), they exhibited strong PON1 (associated with high-density lipoprotein [HDL]) inhibitory activity (K-i values of 0.37 mu M and 0.27 mu M, respectively). The inhibition kinetics were analyzed by Lineweaver-Burk double reciprocal plots. It revealed that 1 and 2 were noncompetitive inhibitors against PON1, hCA I, and hCA II. These complexes can be snore advantageous than other synthetic CA and PON inhibitors due to their water solubility. Docking studies were carried out to examine the interactions between hCA I, hCA II, and PON1 inhibitors and metal complexes at a molecular level and to predict binding energies.
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    Evaluation of the effects of newly synthesized metallophthalocyanines on breast cancer cell lines with photodynamic therapy (vol 51, pg 15996, 2022)
    (Royal Soc Chemistry, 2023) Bostanci, Hayrani Eren; Bilgicli, Ahmet T. T.; Guzel, Emre; Gunsel, Armagan; Hepokur, Ceylan; cimen, Behzat; Yarasir, M. Nilufer
    Correction for 'Evaluation of the effects of newly synthesized metallophthalocyanines on breast cancer cell lines with photodynamic therapy' by Hayrani Eren Bostanc et al., Dalton Trans., 2022, 51, 15996-16008, https://doi.org/10.1039/d2dt01912d.
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    Phthalocyanine complexes with (4-isopropylbenzyl)oxy substituents: preparation and evaluation of anti-carbonic anhydrase, anticholinesterase enzymes and molecular docking studies
    (Taylor & Francis Inc, 2022) Guzel, Emre; Kocyigit, Umit M.; Taslimi, Parham; Gulcin, Ilhami; Erkan, Sultan; Nebioglu, Mehmet; Arslan, Baris S.
    In this study, the preparation, aggregation behavior and investigation of carbonic anhydrase and cholinesterase enzyme inhibition features of non-peripherally (4-isopropylbenzyl)oxy-substituted phthalocyanines (4-6) are reported for the first time. The chemical structures of these new phthalocyanines were elucidated by UV-Vis (ultraviolet-visible), FT-IR (Fourier transform infrared spectrometry), NMR (nuclear magnetic resonance) and MALDI-TOF (matrix-assisted laser desorption/ionization time-of-flight) mass spectrometry. The substitution of 4-isopropylbenzyl)oxy groups benefits a remarkable solubility and redshift of the phthalocyanines Q-band. Also, these complexes were tested against some enzymes such as butyrylcholinesterase enzyme, human carbonic anhydrase I and II isoforms and acetylcholinesterase enzyme. The phthalocyanine complexes showed Ki values of in the range of 478.13 +/- 57.25-887.25 +/- 101.20 mu M against hCA I, 525.16 +/- 45.87-921.14 +/- 81.25 mu M against hCA II, 68.33 +/- 9.13-201.15 +/- 35.86 mu M against AChE and 86.25 +/- 13.65-237.54 +/- 24.7 mu M against BChE. Molecular docking studies were performed to investigate the binding modes and interaction energies of the (2-6) complexes with the hCA I (PDB ID:1BMZ), hCA II (PDB ID:2ABE), AChE (PDB ID:4EY6) and BChE (PDB ID:2PM8).
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    Synthesis of tetra-substituted metallophthalocyanines: Spectral, structural, computational studies and investigation of their photophysical and photochemical properties
    (PERGAMON-ELSEVIER SCIENCE LTD, 2019) Guzel, Emre; Gunsel, Armagan; Tuzun, Burak; Atmaca, Goknur Yasa; Bilgicli, Ahmet T.; Erdogmus, Ali; Yarasir, M. Nilufer
    This work presents the synthesis of peripherally and non-peripherally tetra-substituted metallophthalocyanines (6-14) containing the 2-(3,4-dimethoxyphenyl)ethanol group. The synthesized compounds were characterized by standard spectroscopy methods. The ligands of the metallophthalocyanines were investigated by quantum chemical calculations. The quantum chemical parameters of these ligands (1 and 2) such as the HOMO, LUMO and chemical hardness were calculated by the B3lyp, HF and M062x methods. The Delta G value of the metal complexes of the ligands were calculated with the obtained results. In addition, photophysical (fluorescence quantum yields) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of newly synthesized phthalocyanines were investigated in DMSO solutions, comparatively. (C) 2018 Elsevier Ltd. All rights reserved.