Aminopyrazole‐substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition properties

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dc.contributor.author Güzel, Emre
dc.contributor.author Koçyiğit, Ümit M.
dc.contributor.author Arslan, Barış S.
dc.contributor.author Ataş, Mehmet
dc.contributor.author Taslimi, Parham
dc.contributor.author Gökalp, Faik
dc.contributor.author Nebioğlu, Mehmet
dc.contributor.author Şişman, İlkay
dc.contributor.author Gulçin, İlhami
dc.date.accessioned 2019-04-29T08:28:24Z
dc.date.available 2019-04-29T08:28:24Z
dc.date.issued 2019-02
dc.identifier.uri http://hdl.handle.net/11772/1128
dc.description.abstract 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. en_US
dc.language.iso eng en_US
dc.publisher Wiley en_US
dc.relation.isversionof 10.1002/ardp.201800292 en_US
dc.rights info:eu-repo/semantics/restrictedAccess en_US
dc.subject phthalocyanine en_US
dc.subject Acetylcholinesterase en_US
dc.subject Anticholinergics en_US
dc.subject Antidiabetic en_US
dc.subject Antimicrobial en_US
dc.subject Aminopyrazole en_US
dc.subject Carbonic anhydrase en_US
dc.subject Phthalocyanine en_US
dc.title Aminopyrazole‐substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition properties en_US
dc.type article en_US
dc.relation.journal Archiv der Pharmazie en_US
dc.contributor.department Bartın Üniversitesi, Fen Fakültesi, Biyoteknoloji Bölümü en_US
dc.identifier.volume 352 en_US
dc.identifier.startpage e1800292 en_US

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