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    Dimethoxyindoles based thiosemicarbazones as multi-target agents; synthesis, crystal interactions, biological activity and molecular modeling
    (Academic Press Inc Elsevier Science, 2022) Yıldız, Minhal; Bingül, Murat; Zorlu, Yunus; Sağlam, Mehmet F.; Boğa, Mehmet; Temel, Mutesir; Şengül, İbrahim F.; Kandemir, Hakan
    Alzheimer's disease (AD) is known as one of the most devastating neurodegenerative disease diagnosed for the old-aged people and cholinesterase inhibitors (ChEI) can be used as an effective palliative treatment for AD. A range of novel monomeric and dimeric indole based thiosemicarbazone derivatives 17-28 was synthesized in order to target cholinesterases (ChE). Biological importance of the targeted compounds 17-28 was investigated by employing the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes along with three different antioxidant property determination assays, namely DPPH free radical scavenging, ABTS cationic radical decolarization, and CUPRAC cupric reducing antioxidant capacity. The compounds 18 and 19 displayed the best inhibitor activity against BChE with IC50 values of 7.42 and 1.95 mu M, respectively. The antioxidant potentials were found to be moderate for DPPH and ABTS assays and the compounds 28 and 18 were the most potent candidates for both antioxidant assays. Cupric reducing capacity was the most promising assay and the compounds 25, 26 and 28 provided better inhibition values than all the standards. Further binding mode and affinity studies performed by molecular docking and molecular dynamics simulations. Accordingly, the compound 19 is the most plausible candidate that can compete with galantamine (GNT), a common pharmaceutics targeting both cholinesterase enzymes.
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    Experimental and theoretical studies of carbazole-based Schiff base as a fluorescent Fe3+ probe
    (Scientific Technical Research Council Turkey-Tubitak, 2018) Kandemir, Hakan; Koçak, Abdulkadir; Tumay, Süreyya Oguz; Cosut, Bunyemin; Zorlu, Yunus; Şengül, İbrahim Fazıl
    Synthesis of a new (E)-N1-((9-ethyl-9H-carbazol-3-yl)methylene)-5-nitrobenzene-1,2-diamine as a fluorescent chemosensor for selective detection of Fe3+ ion over a number of other metal ions is described. The method for the synthesis of the carbazole Schiff base was based on the condensation of carbazole-3-carbaldehyde with 4-nitro-o-phenyldiamine in dimethylformamide in a moderate yield. The structure of the final compound was characterized by H-1 NMR, (13) C NMR, IR, mass spectrometry, and single crystal X-ray diffraction. The final compound exhibited exceptional selective and sensitive turn-on fluorescence response to the Fe3+ cation. The fluorescent intensity of the final compound was increased 20-fold and the stoichiometry ratio of the final compound to Fe3+ was 1:1. The association constant and detection limit for Fe3+ ion were predicted from fluorescence titrations as (1.36 +/- 0.09).10(4) M-1 and 1.0 to 6.0 mu M, respectively. The photophysical behavior of the compound was further explored by DFT methods. The predicted UV-Vis spectrum by TDDFT calculations was compared to the observed absorption spectrum of the targeted compound.
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    Synthesis, characterization, UV-Vis absorption and cholinesterase inhibition properties of bis-indolyl imine ligand systems
    (Elsevier, 2020) Sağlam, Mehmet Turgut; Bingül, Murat; Şenkuytu, Elif; Boğa, Mehmet; Zorlu, Yunus; Kandemir, Hakan; Şengül, İbrahim Fazıl
    A number of bis-indolyl imine helical structures has successfully been synthesized employing Schiff base reaction conditions starting from 4,6-dimethoxy-2,3-diphenylindole with different o-phenyl diamines as pi-spacer bridged. The structures of targeted compounds were identified by FT-IR, mass, H-1 and C-13 NMR spectroscopy along with single crystal X-ray diffraction techniques. The ground state absorption properties of the bis-indolyl compounds were also investigated utilizing UV-Vis absorption spectroscopy. As the biological aspect of the synthesized compounds, the anticholinesterase potency was investigated towards the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. The highest inhibition was determined in the presence of compound 9 with the values of 89.21 and 96.06, better than standard Galantamine, for AChE and BChE, respectively. (C) 2020 Elsevier B.V. All rights reserved.