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    Advanced-designed Ru(II) complexes containing phosphinite ligands derived from chiral amino alcohols: Electrochemical behavior, DFT calculations, and biological activity
    (Elsevier Science Sa, 2025) Meric, Nermin; Isik, Ugur; Dauletbakov, Anuar; Zolotareva, Darya; Zazybin, Alexey; Sever, Mehmet Serif; Okumus, Veysi
    We report two phosphinite ligands derived from chiral amino alcohols, and their complexes with ruthenium(II). These compounds were characterized by spectroscopic methods. Then, antimicrobial, antioxidant, and DNA binding activities of the chiral Ru(II)-phosphinite complexes were tested. Complex (1R)-2-{benzyl[(1S)-1(naphthalen-1-yl)ethyl]amino}-1-phenylethyl diphenylphos- phinito[dichloro(eta 6-p-cymene)ruthenium(II)], 7 showed both the highest radical scavenging activity (90.93 +/- 0.98 %) and the highest metal chelating activity (65.45 +/- 1.46 %) at 200.0 mg l-1 concentration. In addition, all of complexes had different rates of binding activity to calf thymus DNA (CT-DNA). Moreover, extensive theoretical and experimental investigations were conducted to gain a more profound understanding of the chemical descriptors and the diverse electronic transitions taking place within the ruthenium complexes, as well as their electrochemical characteristics.
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    Application of Half-Sandwich Metal-Phosphinite Compounds to Biological Activities: Determine the energies of the HOMO and LUMO levels
    (Wiley-V C H Verlag Gmbh, 2023) Meric, Nermin; Rafikova, Khadichakhan; Zazybin, Alexey; Guzel, Remziye; Kayan, Cezmi; Karakas, Duygu Elma; Dundar, Abdurrahman
    Mononuclear transition metal complexes 1-(furan-2-yl)ethyldiphenyl[dichloro(eta(6)-p-cymene)ruthenium(II)]phosphinite, (2), 1-(furan-2-yl)ethyldiphenyl[dichloro(eta(6)-benzene) ruthenium(II)] phosphinite (3), 1-(furan-2-yl)ethyldipheny[chloro(eta(4)-1,5-cyclooctadiene)rhodium(I)]phosphinite (4), 1-(furan-2-yl)ethyldiphenyl[dichloro (eta(5)pentamethylcyclopentadienyl)iridium (III)] phosphinite (5) were synthesized and characterized by microanalysis, infrared, MS, and NMR spectroscopy. The biological activities of the complexes were also tested. Compounds 2 and 5 were the best complexes at DPPH radical scavenging and reducing power activity at 73.27 % and 0.41 at 200 mu g/mL, respectively. The highest antimicrobial activity exhibited by complex 3 as 14 mm inhibition zone against S. aureus. All of the complexes have cleaved the DNA from the double-strand and exhibited three bands on gel electrophoresis. Moreover, cyclic voltammetry studies of the phosphinite complexes were carried out to determine the energies of the HOMO and LUMO levels as well as to estimate their electrochemical and some electronic properties.
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    Biological assays and theoretical density functional theory calculations of Rh(I), Ir(III), and Ru(II) complexes of chiral phosphinite ligand
    (Wiley, 2020) Rafikova, Khadichakhan; Binbay, Nil Ertekin; Meric, Nermin; Kerimkulova, Aygul; Zazybin, Alexey; Binbay, Veysel; Okumus, Veysi
    Four metal complexes, IL-OPPh2-Ru-p-cymene (3), IL-OPPh2-Ru-benzene (4), IL-OPPh2-Ir-Cp* (5), IL-OPPh2-Rh-COD (6), have been evaluated for in vitro antioxidant activity such as 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging and reducing power activity. Maximum scavenging activity (71.43%) was obtained with IL-OPPh2-Ru-p-cymene, whereas IL-OPPh2-Rh-COD showed the highest reducing power ability. The complexes were also studied for their antimicrobial activity against three Gram-positive and three Gram-negative bacteria. In addition, DNA binding of the complexes was evaluated using calf thymus DNA. Both Ru(II) complexes exhibited good DNA-binding activity while the other complexes did not have any activity. Furthermore, ab initio quantum calculations of four complexes were also carried out using density functional theory to better understand their chemical behaviors.
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    Ketone transfer hydrogenation reactions catalyzed by catalysts based on a phosphinite ligand
    (Taylor & Francis Ltd, 2022) Rafikova, Khadichakhan; Baysal, Akin; Meric, Nermin; Zazybin, Alexey; Kayan, Cezmi; Isik, Ugur; Saparbaykyzy, Islam Sholpan
    Reaction of (+/-)-1-(2-furyl) ethanol with an equivalent Ph2PCl in the presence of Et3N proceeds in dry toluene under an argon atmosphere to give 1-(furan-2-yl)ethyl diphenylphosphinite (1) in good yield. Mononuclear complexes [dichloro(eta(6)-p-cymene)(1-furan-2-ylethyl diphenylphosphinite)ruthenium(II)] (2), [dichloro(eta(6)-benzene)(1-furan-2-ylethyl diphenylphosphinite)ruthenium(II)] (3), [chloro(eta(4)-1,5-cyclooctadiene)(1-furan-2-ylethyl diphenylphosphinite)rhodium(I)] (4) and [dichloro(eta(5)-pentamethylcyclopentadienyl)(1-furan-2-ylethyl diphenylphosphinite)iridium(III)] (5) were synthesized and characterized by microanalysis, infrared, MS, and NMR spectroscopies. The complexes are employed as catalysts in transfer hydrogenation of aromatic ketones. The complexes catalyzed reduction of a variety of aromatic ketone substrates bearing electron-withdrawing or donating substituents with very high conversion rates (up to 99%); 5 was the most efficient catalyst for the transfer hydrogenation of ketones.
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    Synthesis of ionic liquid-based Ru(II)-phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA-binding, and DNA cleavage activities
    (Springer International Publishing Ag, 2019) Meric, Nermin; Kayan, Cezmi; Rafikova, Khadichakhan; Zazybin, Alexey; Okumus, Veysi; Aydemir, Murat; Durap, Feyyaz
    Two Ru(II) complexes were synthesized by reaction of phosphinite-functionalized imidazolium salts [(Ph2PO)C7H11N2Cl]Cl (1) and [(Cy2PO)C7H11N2Cl]Cl (2) with 1/2 equivalent of [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2) in anhydrous CH2Cl2 and under argon atmosphere. The complexes were then isolated as analytically pure substances and characterized using multinuclear NMR and infrared spectroscopies and elemental analysis. The Ru(II) compounds were used to study their biological assay. For this purpose, radical scavenging, reducing power, antibacterial activity, DNA binding, and DNA cleavage activity were fully studied. The maximum 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH) scavenging (78.9%) and reducing power were obtained from compound 4 at the concentration of 200 mu g/ml. The compounds were also tested against three Gram-positive and three Gram-negative bacteria, and they were found to be more effective against Gram-positive bacteria. In addition, both compounds showed excellent DNA binding and DNA cleavage activity.
  • Küçük Resim
    Öğe
    Synthesis of ionic liquid‑based Ru(II)–phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA‑binding, and DNA cleavage activities
    (Chemical Papers, 2019) Meriç, Nermin; Kayan, Cezmi; Rafikova, Khadichakhan; Zazybin, Alexey; Okumuş, Veysi; Aydemir, Murat; Durap, Feyyaz
    Two Ru(II) complexes were synthesized by reaction of phosphinite-functionalized imidazolium salts [(Ph2PO)C7H11N2Cl] Cl (1) and [(Cy2PO)C7H11N2Cl]Cl (2) with 1/2 equivalent of [Ru(η6-p-cymene)(μ-Cl)Cl]2 in anhydrous CH2Cl2 and under argon atmosphere. The complexes were then isolated as analytically pure substances and characterized using multinuclear NMR and infrared spectroscopies and elemental analysis. The Ru(II) compounds were used to study their biological assay. For this purpose, radical scavenging, reducing power, antibacterial activity, DNA binding, and DNA cleavage activity were fully studied. The maximum 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH) scavenging (78.9%) and reducing power were obtained from compound 4 at the concentration of 200 μg/ml. The compounds were also tested against three Gram-positive and three Gram-negative bacteria, and they were found to be more effective against Gram-positive bacteria. In addition, both compounds showed excellent DNA binding and DNA cleavage activity.
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    Transfer hydrogenation reaction using novel ionic liquid based Rh(I) and Ir(III)-phosphinite complexes as catalyst
    (Elsevier Science Sa, 2016) Karakas, Duygu Elma; Durap, Feyyaz; Baysal, Akin; Ocak, Yusuf Selim; Rafikova, Khadichakhan; Kaya, Eda Cavus; Zazybin, Alexey
    Hydrogen transfer reduction methods are attracting increasing interest from synthetic chemists in view of their operational simplicity. Thus, interaction of [Rh(mu-Cl)(cod)](2) and Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) with phosphinite ligand [(Ph2PO)-C7H11N2Cl]Cl, 1 gave new monodendate (1-chloro-3-(3-methylimidazolidin1-yl)propan-2-yl diphenylphosphinite chloride) (chloro eta(4)-1,5-cyclooctadiene rhodium(I))], 2 and (1chloro-3-(3-methylimidazolidin-1-yl)propan-2-yl diphenylphosphinite chloride) (dichloro n.5-pentamethylcyclopentadienyl iridium(III))1, 3 complexes, which were characterized by a combination of multinuclear NMR spectroscopy, IR spectroscopy, and elemental analysis. H-1-{P-31}NMR, H-1-C-13 HETCOR or H-1-H-1 COSY correlation experiments were used to confirm the spectral assignments. The novel catalysts were applied to transfer hydrogenation of acetophenone derivatives using 2-propanol as a hydrogen source. The results showed that the corresponding alcohols could be obtained with high activity (up to 99%) under mild conditions. Notably, (1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-y1 diphenylphosphinite chloride) (chloro eta(4)-1,5-cyclooctadiene rhodium(I))], 2 complex is much more active than the other analogous complex, 3 in the transfer hydrogenation. Furthermore, compound, 2 acts as excellent catalysts, giving the corresponding alcohols in 97-99% conversions in 5 min (TOF <= 1176 h(-1)). (C) 2016 Elsevier B.V. All rights reserved.