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

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dc.contributor.authorGuzel, Emre
dc.contributor.authorKocyigit, Umit M.
dc.contributor.authorArslan, Baris S.
dc.contributor.authorAtas, Mehmet
dc.contributor.authorTaslimi, Parham
dc.contributor.authorGokalp, Faik
dc.contributor.authorGulcin, Ilhami
dc.date.accessioned2020-06-25T18:34:20Z
dc.date.available2020-06-25T18:34:20Z
dc.date.issued2019
dc.departmentKırıkkale Üniversitesi
dc.descriptionGULCIN, Ilhami/0000-0001-5993-1668; Guzel, Emre/0000-0002-1142-3936; gokalp, faik/0000-0003-4363-3839; Sisman, Ilkay/0000-0002-0943-2817
dc.description.abstractThe 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.description.sponsorshipSakarya UniversitySakarya University [2012-02-04-036]en_US
dc.description.sponsorshipSakarya University, Grant number: 2012-02-04-036en_US
dc.identifier.citationclosedAccessen_US
dc.identifier.doi10.1002/ardp.201800292
dc.identifier.issn0365-6233
dc.identifier.issn1521-4184
dc.identifier.issue2en_US
dc.identifier.pmid30600535
dc.identifier.scopus2-s2.0-85059305253
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1002/ardp.201800292
dc.identifier.urihttps://hdl.handle.net/20.500.12587/7873
dc.identifier.volume352en_US
dc.identifier.wosWOS:000457586700007
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofArchiv Der Pharmazie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectacetylcholinesteraseen_US
dc.subjectanticholinergicen_US
dc.subjectantidiabeticen_US
dc.subjectantimicrobialen_US
dc.subjectaminopyrazoleen_US
dc.subjectcarbonic anhydraseen_US
dc.subjectphthalocyanineen_US
dc.titleAminopyrazole-substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition propertiesen_US
dc.typeArticle

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