Peripheral (E)-2-[(4-hydroxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one)]-coordinated phthalocyanines with improved enzyme inhibition properties and photophysicochemical behaviors

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dc.authoridTUZUN, BURAK/0000-0002-0420-2043
dc.authoridBILGICLI, Ahmet Turgut/0000-0002-4144-7357
dc.authoridYarasir, Meryem Nilufer/0000-0002-7327-7137
dc.contributor.authorGulec, Ozcan
dc.contributor.authorBilgicli, Ahmet T.
dc.contributor.authorTuzun, Burak
dc.contributor.authorTaslimi, Parham
dc.contributor.authorGunsel, Armagan
dc.contributor.authorGulcin, Ilhami
dc.contributor.authorArslan, Mustafa
dc.date.accessioned2024-10-26T18:09:30Z
dc.date.available2024-10-26T18:09:30Z
dc.date.issued2024
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractIn this study, (E)-4-{4-[(1-oxo-3,4-dihydronaphthalen-2(1H)-ylidene)methyl]phenoxy}phthalonitrile (4) and its phthalocyanine derivatives (5-8) were synthesized for the first time. Aggregation behaviors of the novel soluble phthalocyanines in organic solvents were investigated. In addition, the efficiency of O-1(2) production of (5) and ZnPc (6) was investigated. The singlet oxygen quantum yields (Phi(Delta)) for 2HPc (5) and ZnPc (6) were found to be 0.58 and 0.83, respectively. Additionally, novel phthalocyanines (5-8) were investigated for their ability to inhibit enzymes. They exhibited a highly potent inhibition effect on human carbonic anhydrase I and II (hCA I and II) and alpha-glycosidase (alpha-Gly) enzymes. K-i values are in the range of 2.60 +/- 9.87 to 11.53 +/- 6.92 mu M, 3.35 +/- 0.53 to 15.47 +/- 1.20 mu M, and 28.60 +/- 4.82 to 40.58 +/- 7.37 nM, respectively. The calculations of the studied molecule at the B3LYP, HF, and M062X levels in the 6-31G basis sets were made using the Gaussian package program. Afterward, the interactions occurring in the docking calculation against a protein that is the crystal structure of hCA I (PDB ID: 2CAB), the crystal structure of hCA II (PDB ID: 5AML), and the crystal structure of alpha-Gly (PDB ID: 1R47), were examined. Following that, Protein-Ligand Interaction Profiler (PLIP) analysis was used to look at the interactions that occurred during the docking calculation in further detail.
dc.description.sponsorshipSakarya University [2021-9-33-118]
dc.description.sponsorshipSakarya University, Grant/Award Number: Project no: 2021-9-33-118
dc.identifier.doi10.1002/ardp.202400209
dc.identifier.issn0365-6233
dc.identifier.issn1521-4184
dc.identifier.issue9
dc.identifier.pmid38838335
dc.identifier.scopus2-s2.0-85195031462
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1002/ardp.202400209
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30152
dc.identifier.volume357
dc.identifier.wosWOS:001239566500001
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbh
dc.relation.ispartofArchiv Der Pharmazie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectDFT
dc.subjectenzyme inhibitor
dc.subjectin silico
dc.subjectphthalocyanine
dc.subjectsinglet oxygen
dc.titlePeripheral (E)-2-[(4-hydroxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one)]-coordinated phthalocyanines with improved enzyme inhibition properties and photophysicochemical behaviors
dc.typeArticle

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