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Iron(III) Complexes Derived From Azo-Containing Salicylaldoxime Ligands: Synthesis, Structures and Biological Evaluations

Year 2021, Volume: 8 Issue: 3, 1184 - 1201, 30.09.2021
https://doi.org/10.31202/ecjse.905307

Abstract

Two novel mononuclear Fe(III) complexes derived from azo-containing salicylaldoxime ligands were synthesized and characterized by elemental analyses, spectroscopic data i.e. IR, 1H NMR, UV-Vis, electrospray ionization mass spectra, molar conductivity, and magnetic susceptibility measurements. Both the experimental and theoretical results strongly suggest that the ligands have a major contribution to the azo enol imine form instead of the hydrazo keto imine and azo keto amine forms in solution/solid-state. The electronic spectra of the ligands and their iron(III) complexes were calculated theoretically for the band assignments by using DFT and TD-DFT/CPCM methods. DNA binding, cleavage, and antioxidative activities of the investigated compounds were studied. It has been shown that the ligands and their iron (III) complexes tested bind to DNA via the intercalative mode. One of the most striking results among the antioxidant activity tests is that the hydroxyl radical scavenging activities of the ligands and complexes are higher than the standard antioxidant mannitol.

Supporting Institution

TUBİTAK

Project Number

112T526

References

  • [1]. Ragheb, M. A., Eldesouki, M. A., Mohamed M. S., "DNA binding, photo-induced DNA cleavage and cytotoxicity studies of lomefloxacin and its transition metal complexes", Spectrochim Acta A Mol Biomol Spectrosc., 2015, 138, 585–95. doi: 10.1016/j.saa.2014.11.046
  • [2]. Zeng, P., He, L., Ye, Z., Yang, N., Song, Y., Lu, J., "DNA interactions, antitumor activities and radical scavenging properties of oxovanadium complexes with pyrazino[2,3-f] [1,10]phenanthroline ligands", Transit. Met. Chem., 2015, 40, 779–787. doi: 10.1007/s11243-015-9939-9
  • [3]. Iglesias, B. A., Barata, J. F. B., Pereira, P. M. R., Girão, H., Fernandes, R., Tomé, J. P. C., Neves, M. G. P. M. S., Cavaleiro, J. A. S., "New platinum(II)–bipyridyl corrole complexes: Synthesis, characterization and binding studies with DNA and HSA", Journal of Inorganic Biochemistry, 2015,153, 32-41. doi:http://dx.doi.org/10.1016/j.jinorgbio.2015.08.016
  • [4]. Karia, P. S., Vekariya, P. A., Patidar, A. P., Kanthecha, D. N., Bhatt B. S., and Patel, M. N., "DNA Interaction, in vitro Antibacterial and Cytotoxic Activities of Ru(III) Heterochelates", Acta Chim. Slov., 2019, 66, 944–949. doi:10.17344/acsi.2019.5159
  • [5]. Kanthecha, D. N., Raval, D. B., Thakkar, V. R., Patel, M. N., "Biological Significance of Hetero-Scaffolds Based Gold(III) Complexes", Acta Chim. Slov., 2018, 65, 333–343. doi:10.17344/acsi.2017.4018
  • [6]. Terenzi, A., Barone, G., Silvestri, A.,et al., "The interaction of native calf thymus DNA with Fe-III-dipyrido[3,2-a:2 ',3 '-c]phenazine", J Inorg. Biochem., 2009, 103, 1–9. doi: 10.1016/j.jinorgbio.2008.08.011
  • [7]. Ghosh, K., Tyagi, N., Kumar, P., Singh, U. P., "Synthesis, structure, redox properties and DNA interaction studies on mononuclear iron(III) complexes with amidate ligand", Inorganica Chim Acta, 2014, 412, 20–26. doi: 10.1016/j.ica.2013.11.034
  • [8]. Chitrapriya, N., Mahalingam, V., Zeller, M., et al., "Synthesis, characterization, DNA binding and cleavage studies of Ru(II) complexes containing oxime ligands", J. Mol. Struct., 2010, 984, 30–38. doi: 10.1016/j.molstruc.2010.09.004
  • [9]. Kandaz, M., Yilmaz, I., Keskin, S., Koca, A., "Synthesis, spectroscopy and redox properties of a novel (E-E) vic-dioxime and its mono-, di- and trinuclear complexes bearing an 18-membered N2O2S2 macrocyle", Polyhedron, 2002, 21, 0–9. doi: 10.1016/S0277-5387(02)00860-4
  • [10]. Dilworth, J. R., Parrott, S. J., "The biomedical chemistry of technetium and rhenium", Chem. Soc. Rev., 1998, 27, 43-55. doi: 10.1039/a827043z
  • [11]. Blower, P. J., "Small coordination complexes as radiopharmaceuticals for cancer targeting ", Transit Met Chem., 1998, 23, 109–112. doi: 10.1023/A:1006926505754
  • [12]. Vallabhajosula, S., "The Chemistry of Therapeutic Radiopharmaceuticals", Nuclear Medicine Therapy, 2012, 339-368. doi: 10.1007/978-1-4614-4021-5_19
  • [13]. Ohta, K., Higashi, R., Ikejima, M., et al., "Disk-like liquid crystals of transition metal complexes - Part 21. Critical molecular structure change from columnar to lamellar liquid crystal in bis(diphenylglyoximato)nickel(II)-based complexes ", J Mater. Chem., (1998, 8, 1979–1991. doi: 10.1039/A800897C
  • [14]. Nejati, K., Rezvani, Z., Massoumi, B.,"Syntheses and investigation of thermal properties of copper complexes with azo-containing Schiff-base dyes", Dyes and Pigments, 2007, 75, 653–657. doi: 10.1016/j.dyepig.2006.07.019
  • [15]. Karci, F., Ertan, N., "Synthesis of some novel hetarylazo disperse dyes derived from 4-hydroxy-2H-1-benzopyran-2-one (4-hydroxycoumarin)as coupling component and investigation of their absorption spectra", Dyes and Pigments, 2005, 64:243–249. doi: 10.1016/j.dyepig.2004.06.010
  • [16]. Tao, T., Xu, F., Chen, X. C., et al., "Comparisons between azo dyes and Schiff bases having the same benzothiazole/phenol skeleton: Syntheses, crystal structures and spectroscopic properties", Dyes and Pigments, 2012, 92, 916–922. doi: 10.1016/j.dyepig.2011.09.008
  • [17]. EL Mekkawi, D., Abdel-Mottaleb, M. S. A.,"The interaction and photostability of some xanthenes and selected azo sensitizing dyes with TiO2 nanoparticles", Int. J. Photoenergy, 2005, 7, 95–101. doi: 10.1155/S1110662X05000140
  • [18]. Erdogan, D. A.,Özalp-Yaman, Ş.,"Novel Pt(II) complexes containing pyrrole oxime, synthesis, characterization and DNA binding studies", J Mol. Struct., 2014, 1064, 50–57. doi: 10.1016/j.molstruc.2014.02.005
  • [19]. Chen, G. J., Qiao, X., Qiao, P. Q., et al., "Synthesis, DNA binding, photo-induced DNA cleavage, cytotoxicity and apoptosis studies of copper(II) complexes", J Inorg. Biochem., 2011,105, 119–126. doi: 10.1016/j.jinorgbio.2010.11.008
  • [20]. Suh, J., Chei, W. S.,"Metal complexes as artificial proteases: toward catalytic drugs", Curr. Opin. Chem. Biol., 2008, 12, 207–13. doi: 10.1016/j.cbpa.2008.01.028
  • [21]. El-Sayed, B. A., Abo Aly, M. M., Emara, A. A. A.,Khalil, S. M. E., "Synthesis and structural study of the ligand o-OH acetophenone azine and its Cu(II), Ni(II), Co(II) and Zn(II) complexes", Vib. Spectrosc., 2002, 30, 93–100. doi: http://dx.doi.org/10.1016/S0924-2031(02)00043-7
  • [22]. Baran, T., Karaoğlu, K.,Serbest, K., et al., "Studies on synthesis, structure, and DNA cleaving of homo-dinuclear Mn(II), Cu(II), Ni(II), and Zn(II) complexes with a heterocycle-based macroacyclic Schiff base", Monatshefte für Chemie, 2013, 144, 1107–1115. doi: 10.1007/s00706-013-0926-6
  • [23]. Preti, C., Tassi, L.,Tosi, G.,et al., "Coordination Chemistry of Cycloserine Derivatives- Complexes of Iron(II), Iron(III), Manganese(II) and Palladium(II) with N4-N'4-Tereftal-Bis(Cycloserine)", J Coord. Chem., 1983, 12, 177–185. doi: Doi 10.1080/00958978308073846
  • [24]. Geary, W. J., "The use of conductivity measurements in organic solvents for the characterisation of coordination compounds", Coord. Chem. Rev., 1970, 7, 81–122. doi: http://dx.doi.org/10.1016/S0010-8545(00)80009-0
  • [25]. Wilson, W. D., Ratmeyer, L., Zhao, M., et al., " The Search for Structure-Specific Nucleic-Acid Interactive Drugs - Effects of Compound Structure on RNA Versus DNA Interaction Strength,", Biochemistry, 1993, 32, 4098–4104. doi: 10.1021/bi00066a035
  • [26]. Li, Y., Wu, Y., Zhao, J., Yang, P.," DNA-binding and cleavage studies of novel binuclear copper(II) complex with 1,1 '-dimethyl-2,2 '-biimidazole ligand ", Journal of Inorganic Biochemistry, 2007, 101, 283–290. doi:10.1016/j.jinorgbio.2006.10.004
  • [27]. He, X., Jin, L., Tan, L.,"DNA-binding, topoisomerases I and II inhibition and in vitro cytotoxicity of ruthenium(II) polypyridyl complexes: [Ru(dppz)2L]2+ (L = dppz-11-CO2Me and dppz)", Spectrochim. Acta A Mol. Biomol. Spectrosc., 2014, 135, 101–109. doi: 10.1016/j.saa.2014.06.147
  • [28]. Janovec, L.,Kožurková, M.,Sabolová, D.,et al., " Cytotoxic 3,6-bis((imidazolidinone) imino)acridines: Synthesis, DNA binding and molecular modeling,", Bioorg. Med. Chem., 2011, 19, 1790–1801. doi: 10.1016/j.bmc.2011.01.012
  • [29]. Zhu, L.-N., Kong, D.-M., Li, X.-Z., Wang, G.-Y., Wang, J., & Jin, Y.-W., " DNA cleavage activities of tetraazamacrocyclic oxamido nickel(II) complexes ", Polyhedron, 2010, 29, 574–580. doi: 10.1016/j.poly.2009.07.021
  • [30]. Arjmand, F., Jamsheera, A.," DNA binding studies of new valine derived chiral complexes of tin(IV) and zirconium(IV)", Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., 2011, 78. 45–51. doi: 10.1016/j.saa.2010.06.009
  • [31]. Li, D.-D., Tian, J.-L., Gu, W.,et al., " A novel 1,2,4-triazole-based copper(II) complex: Synthesis, characterization, magnetic property and nuclease activity ", J Inorg. Biochem., 2010, 104, 171–9. doi: 10.1016/j.jinorgbio.2009.10.020
  • [32]. Raman, N., Sobha, S., Mitu, L.," Design, synthesis, DNA binding ability, chemical nuclease activity and antimicrobial evaluation of Cu(II), Co(II), Ni(II) and Zn(II) metal complexes containing tridentate Schiff base ", J Saudi Chem. Soc., 2013, 17, 151–159. doi: 10.1016/j.jscs.2011.03.003
  • [33]. Bukhari, S. B., Memon, S., Mahroof-Tahir, M., Bhanger, M. I.," Synthesis, characterization and antioxidant activity copper-quercetin complex", Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 2009, 71, 1901–1906. doi: 10.1016/j.saa.2008.07.030
  • [34]. F. V. Botelho, J. I. Alvarez-Leite, V. S. Lemos, et al., J Inorg. Biochem., 2007, 101, 935–943. doi: 10.1016/j.jinorgbio.2007.03.007
  • [35]. Wang, Q., Yang, Z.-Y., Qi, G.-F.,Qin, D.-D.," Synthesis, crystal structure, antioxidant activities and DNA-binding studies of the Ln(III) complexes with 7-methoxychromone-3-carbaldehyde-(4 '-hydroxy) benzoyl hydrazone ", Eur. J Med. Chem., 2009, 44, 2425–33. doi: 10.1016/j.ejmech.2008.10.023
  • [36]. Çol Ayvaz, M., Turan, İ., Dural, B., Demir, S., Karaoğlu, K., Aliyazıcıoğlu, Y., Serbest, K.," Synthesis, in vitro DNA interactions, cytotoxicities, antioxidative activities, and topoisomerase inhibition potentials of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes with azo-oxime ligands ", Turkish J. Chem., 2017 41, 728–747. doi:10.3906/kim-1612-53.
  • [37]. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., et al., Gaussian 09, revision A.02 Gaussian, Inc, Wallingford, 2009.
  • [38]. Becke, A. D., " Density-functional exchange-energy approximation with correct asymptotic behavior", Phys. Rev. A 1988, 38, :3098–3100. doi: 10.1103/PhysRevA.38.3098
  • [39]. Hariharan, P. C., Pople, J. A.," The influence of polarization functions on molecular orbital hydrogenation energies,", Theor. Chim. Acta 1973, 28, 213–222. doi: 10.1007/BF00533485
  • [40]. Wadt, W. R., Hay, P. J.," Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg ", J Chem. Phys. 1985, 82, 284–298. doi: 10.1063/1.448800
  • [41]. K., Burke, Werschnik, J., Gross, E. K. U.,"Time-dependent density functional theory: Past, present, and future", J Chem. Phys. 2005, 123, 062206. Doi 10.1063/1.1904586
  • [42]. Barone, V., Cossi, M.,"Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model", J Phys. Chem. A 1998, 102, 1995–2001. doi: 10.1021/jp9716997
  • [43]. N. M. O. Boyle, A. L. Tenderholt, and K. M. Langner, " A library for package-independent computational chemistry algorithmsé", J Comput. Chem. 2008, 29, 839–845. doi: 10.1002/jcc
  • [44]. Dennington, T., Millam, R., V. GaussView. J. Semichem Inc. 2009.
  • [45]. Cabir, B., Avar, B.,Gulcan, M.,Kayraldiz, A.,Kurtoglu, M.,"Synthesis, spectroscopic characterization, and genotoxicity of a new group of azo-oxime metal chelates", Turkish J Chem. 2013, 37, 422–438. doi: 10.3906/kim-1210-57
  • [46]. Reddy, P. R., Shilpa, A., Raju, N., Raghavaiah, P.,"Synthesis, structure, DNA binding and cleavage properties of ternary amino acid Schiff base-phen/bipy Cu(II) complexes", J Inorg. Biochem. 2011, 105, 1603–1612. doi: 10.1016/j.jinorgbio.2011.08.022
  • [47]. Cheng, C.-C., Rokita, S. E., & Burrows, C. J., "Nickel(III)-Promoted DNA Cleavage with Ambient Dioxygen", Angew. Chem. Int. Ed. Engl. 1993, 32, 277–278. doi: DOI 10.1002/anie.199302771
  • [48]. Lesko, S. A.,Lorentzen, R. J., Ts'o, P. O. P.," Involvement of Polycyclic Aromatic-Hydrocarbons and Reduced Oxygen Radicals in Carcinogenesis .5. Role of Superoxide in Deoxyribonucleic-Acid Strand Scission ", Biochemistry 1980, 19, 3023–3028. doi: Doi 10.1021/Bi00554a029
  • [49]. Nilsson, R., Merkel, P. B., Kearns, D. R., "Unambiguous Evidence For The Participation Of Singlet Oxygen (1δ) In Photodynamic Oxidation Of Amino Acids", Photochem. Photobiol. 1972, 16, 117–124. doi: 10.1111/j.1751-1097.1972.tb07343.x
  • [50]. Jiang, Q., Xiao, N., Shi, P., et al., " Design of artificial metallonucleases with oxidative mechanism ", Coord. Chem. Rev. 2007, 251, 1951–1972. doi: 10.1016/j.ccr.2007.02.013
  • [51]. A. Turkoglu, M. E. Duru, N. Mercan, et al., "Antioxidant and antimicrobial activities of Laetiporus sulphureus (Bull.) Murrill", Food Chem. 2006, 101, 267–273. doi: 10.1016/j.foodchem.2006.01.025
  • [52]. Hagerman, A. E., Riedl, K. M., Alexander, J., et al., " High molecular weight plant polyphenolics (tannins) as biological antioxidants ", Food Chem. 1998, 46, 1887–1892. doi: Doi 10.1021/Jf970975b
  • [53]. Beauchamp, C., Fridovich, I., " Superoxide dismutase: Improved assays and an assay applicable to acrylamide gels", Anal. Biochem. 1971, 44, 276–287. doi: 10.1016/0003-2697(71)90370-8

Azo Grubu Içeren Salisilaldoksim Ligandlarından Türetilen Demir (III) Kompleksleri: Sentez, Karakterizasyon Ve Biyolojik Değerlendirmeler

Year 2021, Volume: 8 Issue: 3, 1184 - 1201, 30.09.2021
https://doi.org/10.31202/ecjse.905307

Abstract

Azo grubu taşıyan salisilaldoksim türevi ligandlarından türetilen iki yeni mononükleer Fe (III) kompleksi sentezlendi ve elementel analizler, spektroskopik veriler, yani IR, 1H NMR, UV-Vis, elektrosprey iyonizasyon kütle spektrumları, molar iletkenlik ve manyetik duyarlılık ölçümleriyle karakterize edildi. Hem deneysel hem de teorik sonuçlar, çözelti / katı halde ligandların hidrazo keto imin ve azo keto amin formları yerine azo enol imin formunun daha büyük bir katkısı olduğunu güçlü bir şekilde göstermektedir. Ligandlar ve bunların demir(III) komplekslerinin elektronik spektrumları deneysel spektrumlardaki bant atamaları için, DFT ve TD-DFT / CPCM yöntemleri kullanılarak teorik olarak hesaplandı. Araştırılan bileşiklerin DNA bağlanması, bölünmesi ve antioksidatif aktiviteleri incelenmiştir. Test edilen ligandların ve bunların demir(III) komplekslerinin interkalasyon yaparak DNA'ya bağlandığı gösterilmiştir. Antioksidan aktivite testleri arasında en çarpıcı sonuçlardan biri, ligandların ve komplekslerin hidroksil radikal süpürücü aktivitelerinin standart antioksidan mannitole göre daha yüksek olmasıdır.

Project Number

112T526

References

  • [1]. Ragheb, M. A., Eldesouki, M. A., Mohamed M. S., "DNA binding, photo-induced DNA cleavage and cytotoxicity studies of lomefloxacin and its transition metal complexes", Spectrochim Acta A Mol Biomol Spectrosc., 2015, 138, 585–95. doi: 10.1016/j.saa.2014.11.046
  • [2]. Zeng, P., He, L., Ye, Z., Yang, N., Song, Y., Lu, J., "DNA interactions, antitumor activities and radical scavenging properties of oxovanadium complexes with pyrazino[2,3-f] [1,10]phenanthroline ligands", Transit. Met. Chem., 2015, 40, 779–787. doi: 10.1007/s11243-015-9939-9
  • [3]. Iglesias, B. A., Barata, J. F. B., Pereira, P. M. R., Girão, H., Fernandes, R., Tomé, J. P. C., Neves, M. G. P. M. S., Cavaleiro, J. A. S., "New platinum(II)–bipyridyl corrole complexes: Synthesis, characterization and binding studies with DNA and HSA", Journal of Inorganic Biochemistry, 2015,153, 32-41. doi:http://dx.doi.org/10.1016/j.jinorgbio.2015.08.016
  • [4]. Karia, P. S., Vekariya, P. A., Patidar, A. P., Kanthecha, D. N., Bhatt B. S., and Patel, M. N., "DNA Interaction, in vitro Antibacterial and Cytotoxic Activities of Ru(III) Heterochelates", Acta Chim. Slov., 2019, 66, 944–949. doi:10.17344/acsi.2019.5159
  • [5]. Kanthecha, D. N., Raval, D. B., Thakkar, V. R., Patel, M. N., "Biological Significance of Hetero-Scaffolds Based Gold(III) Complexes", Acta Chim. Slov., 2018, 65, 333–343. doi:10.17344/acsi.2017.4018
  • [6]. Terenzi, A., Barone, G., Silvestri, A.,et al., "The interaction of native calf thymus DNA with Fe-III-dipyrido[3,2-a:2 ',3 '-c]phenazine", J Inorg. Biochem., 2009, 103, 1–9. doi: 10.1016/j.jinorgbio.2008.08.011
  • [7]. Ghosh, K., Tyagi, N., Kumar, P., Singh, U. P., "Synthesis, structure, redox properties and DNA interaction studies on mononuclear iron(III) complexes with amidate ligand", Inorganica Chim Acta, 2014, 412, 20–26. doi: 10.1016/j.ica.2013.11.034
  • [8]. Chitrapriya, N., Mahalingam, V., Zeller, M., et al., "Synthesis, characterization, DNA binding and cleavage studies of Ru(II) complexes containing oxime ligands", J. Mol. Struct., 2010, 984, 30–38. doi: 10.1016/j.molstruc.2010.09.004
  • [9]. Kandaz, M., Yilmaz, I., Keskin, S., Koca, A., "Synthesis, spectroscopy and redox properties of a novel (E-E) vic-dioxime and its mono-, di- and trinuclear complexes bearing an 18-membered N2O2S2 macrocyle", Polyhedron, 2002, 21, 0–9. doi: 10.1016/S0277-5387(02)00860-4
  • [10]. Dilworth, J. R., Parrott, S. J., "The biomedical chemistry of technetium and rhenium", Chem. Soc. Rev., 1998, 27, 43-55. doi: 10.1039/a827043z
  • [11]. Blower, P. J., "Small coordination complexes as radiopharmaceuticals for cancer targeting ", Transit Met Chem., 1998, 23, 109–112. doi: 10.1023/A:1006926505754
  • [12]. Vallabhajosula, S., "The Chemistry of Therapeutic Radiopharmaceuticals", Nuclear Medicine Therapy, 2012, 339-368. doi: 10.1007/978-1-4614-4021-5_19
  • [13]. Ohta, K., Higashi, R., Ikejima, M., et al., "Disk-like liquid crystals of transition metal complexes - Part 21. Critical molecular structure change from columnar to lamellar liquid crystal in bis(diphenylglyoximato)nickel(II)-based complexes ", J Mater. Chem., (1998, 8, 1979–1991. doi: 10.1039/A800897C
  • [14]. Nejati, K., Rezvani, Z., Massoumi, B.,"Syntheses and investigation of thermal properties of copper complexes with azo-containing Schiff-base dyes", Dyes and Pigments, 2007, 75, 653–657. doi: 10.1016/j.dyepig.2006.07.019
  • [15]. Karci, F., Ertan, N., "Synthesis of some novel hetarylazo disperse dyes derived from 4-hydroxy-2H-1-benzopyran-2-one (4-hydroxycoumarin)as coupling component and investigation of their absorption spectra", Dyes and Pigments, 2005, 64:243–249. doi: 10.1016/j.dyepig.2004.06.010
  • [16]. Tao, T., Xu, F., Chen, X. C., et al., "Comparisons between azo dyes and Schiff bases having the same benzothiazole/phenol skeleton: Syntheses, crystal structures and spectroscopic properties", Dyes and Pigments, 2012, 92, 916–922. doi: 10.1016/j.dyepig.2011.09.008
  • [17]. EL Mekkawi, D., Abdel-Mottaleb, M. S. A.,"The interaction and photostability of some xanthenes and selected azo sensitizing dyes with TiO2 nanoparticles", Int. J. Photoenergy, 2005, 7, 95–101. doi: 10.1155/S1110662X05000140
  • [18]. Erdogan, D. A.,Özalp-Yaman, Ş.,"Novel Pt(II) complexes containing pyrrole oxime, synthesis, characterization and DNA binding studies", J Mol. Struct., 2014, 1064, 50–57. doi: 10.1016/j.molstruc.2014.02.005
  • [19]. Chen, G. J., Qiao, X., Qiao, P. Q., et al., "Synthesis, DNA binding, photo-induced DNA cleavage, cytotoxicity and apoptosis studies of copper(II) complexes", J Inorg. Biochem., 2011,105, 119–126. doi: 10.1016/j.jinorgbio.2010.11.008
  • [20]. Suh, J., Chei, W. S.,"Metal complexes as artificial proteases: toward catalytic drugs", Curr. Opin. Chem. Biol., 2008, 12, 207–13. doi: 10.1016/j.cbpa.2008.01.028
  • [21]. El-Sayed, B. A., Abo Aly, M. M., Emara, A. A. A.,Khalil, S. M. E., "Synthesis and structural study of the ligand o-OH acetophenone azine and its Cu(II), Ni(II), Co(II) and Zn(II) complexes", Vib. Spectrosc., 2002, 30, 93–100. doi: http://dx.doi.org/10.1016/S0924-2031(02)00043-7
  • [22]. Baran, T., Karaoğlu, K.,Serbest, K., et al., "Studies on synthesis, structure, and DNA cleaving of homo-dinuclear Mn(II), Cu(II), Ni(II), and Zn(II) complexes with a heterocycle-based macroacyclic Schiff base", Monatshefte für Chemie, 2013, 144, 1107–1115. doi: 10.1007/s00706-013-0926-6
  • [23]. Preti, C., Tassi, L.,Tosi, G.,et al., "Coordination Chemistry of Cycloserine Derivatives- Complexes of Iron(II), Iron(III), Manganese(II) and Palladium(II) with N4-N'4-Tereftal-Bis(Cycloserine)", J Coord. Chem., 1983, 12, 177–185. doi: Doi 10.1080/00958978308073846
  • [24]. Geary, W. J., "The use of conductivity measurements in organic solvents for the characterisation of coordination compounds", Coord. Chem. Rev., 1970, 7, 81–122. doi: http://dx.doi.org/10.1016/S0010-8545(00)80009-0
  • [25]. Wilson, W. D., Ratmeyer, L., Zhao, M., et al., " The Search for Structure-Specific Nucleic-Acid Interactive Drugs - Effects of Compound Structure on RNA Versus DNA Interaction Strength,", Biochemistry, 1993, 32, 4098–4104. doi: 10.1021/bi00066a035
  • [26]. Li, Y., Wu, Y., Zhao, J., Yang, P.," DNA-binding and cleavage studies of novel binuclear copper(II) complex with 1,1 '-dimethyl-2,2 '-biimidazole ligand ", Journal of Inorganic Biochemistry, 2007, 101, 283–290. doi:10.1016/j.jinorgbio.2006.10.004
  • [27]. He, X., Jin, L., Tan, L.,"DNA-binding, topoisomerases I and II inhibition and in vitro cytotoxicity of ruthenium(II) polypyridyl complexes: [Ru(dppz)2L]2+ (L = dppz-11-CO2Me and dppz)", Spectrochim. Acta A Mol. Biomol. Spectrosc., 2014, 135, 101–109. doi: 10.1016/j.saa.2014.06.147
  • [28]. Janovec, L.,Kožurková, M.,Sabolová, D.,et al., " Cytotoxic 3,6-bis((imidazolidinone) imino)acridines: Synthesis, DNA binding and molecular modeling,", Bioorg. Med. Chem., 2011, 19, 1790–1801. doi: 10.1016/j.bmc.2011.01.012
  • [29]. Zhu, L.-N., Kong, D.-M., Li, X.-Z., Wang, G.-Y., Wang, J., & Jin, Y.-W., " DNA cleavage activities of tetraazamacrocyclic oxamido nickel(II) complexes ", Polyhedron, 2010, 29, 574–580. doi: 10.1016/j.poly.2009.07.021
  • [30]. Arjmand, F., Jamsheera, A.," DNA binding studies of new valine derived chiral complexes of tin(IV) and zirconium(IV)", Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., 2011, 78. 45–51. doi: 10.1016/j.saa.2010.06.009
  • [31]. Li, D.-D., Tian, J.-L., Gu, W.,et al., " A novel 1,2,4-triazole-based copper(II) complex: Synthesis, characterization, magnetic property and nuclease activity ", J Inorg. Biochem., 2010, 104, 171–9. doi: 10.1016/j.jinorgbio.2009.10.020
  • [32]. Raman, N., Sobha, S., Mitu, L.," Design, synthesis, DNA binding ability, chemical nuclease activity and antimicrobial evaluation of Cu(II), Co(II), Ni(II) and Zn(II) metal complexes containing tridentate Schiff base ", J Saudi Chem. Soc., 2013, 17, 151–159. doi: 10.1016/j.jscs.2011.03.003
  • [33]. Bukhari, S. B., Memon, S., Mahroof-Tahir, M., Bhanger, M. I.," Synthesis, characterization and antioxidant activity copper-quercetin complex", Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 2009, 71, 1901–1906. doi: 10.1016/j.saa.2008.07.030
  • [34]. F. V. Botelho, J. I. Alvarez-Leite, V. S. Lemos, et al., J Inorg. Biochem., 2007, 101, 935–943. doi: 10.1016/j.jinorgbio.2007.03.007
  • [35]. Wang, Q., Yang, Z.-Y., Qi, G.-F.,Qin, D.-D.," Synthesis, crystal structure, antioxidant activities and DNA-binding studies of the Ln(III) complexes with 7-methoxychromone-3-carbaldehyde-(4 '-hydroxy) benzoyl hydrazone ", Eur. J Med. Chem., 2009, 44, 2425–33. doi: 10.1016/j.ejmech.2008.10.023
  • [36]. Çol Ayvaz, M., Turan, İ., Dural, B., Demir, S., Karaoğlu, K., Aliyazıcıoğlu, Y., Serbest, K.," Synthesis, in vitro DNA interactions, cytotoxicities, antioxidative activities, and topoisomerase inhibition potentials of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes with azo-oxime ligands ", Turkish J. Chem., 2017 41, 728–747. doi:10.3906/kim-1612-53.
  • [37]. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., et al., Gaussian 09, revision A.02 Gaussian, Inc, Wallingford, 2009.
  • [38]. Becke, A. D., " Density-functional exchange-energy approximation with correct asymptotic behavior", Phys. Rev. A 1988, 38, :3098–3100. doi: 10.1103/PhysRevA.38.3098
  • [39]. Hariharan, P. C., Pople, J. A.," The influence of polarization functions on molecular orbital hydrogenation energies,", Theor. Chim. Acta 1973, 28, 213–222. doi: 10.1007/BF00533485
  • [40]. Wadt, W. R., Hay, P. J.," Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg ", J Chem. Phys. 1985, 82, 284–298. doi: 10.1063/1.448800
  • [41]. K., Burke, Werschnik, J., Gross, E. K. U.,"Time-dependent density functional theory: Past, present, and future", J Chem. Phys. 2005, 123, 062206. Doi 10.1063/1.1904586
  • [42]. Barone, V., Cossi, M.,"Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model", J Phys. Chem. A 1998, 102, 1995–2001. doi: 10.1021/jp9716997
  • [43]. N. M. O. Boyle, A. L. Tenderholt, and K. M. Langner, " A library for package-independent computational chemistry algorithmsé", J Comput. Chem. 2008, 29, 839–845. doi: 10.1002/jcc
  • [44]. Dennington, T., Millam, R., V. GaussView. J. Semichem Inc. 2009.
  • [45]. Cabir, B., Avar, B.,Gulcan, M.,Kayraldiz, A.,Kurtoglu, M.,"Synthesis, spectroscopic characterization, and genotoxicity of a new group of azo-oxime metal chelates", Turkish J Chem. 2013, 37, 422–438. doi: 10.3906/kim-1210-57
  • [46]. Reddy, P. R., Shilpa, A., Raju, N., Raghavaiah, P.,"Synthesis, structure, DNA binding and cleavage properties of ternary amino acid Schiff base-phen/bipy Cu(II) complexes", J Inorg. Biochem. 2011, 105, 1603–1612. doi: 10.1016/j.jinorgbio.2011.08.022
  • [47]. Cheng, C.-C., Rokita, S. E., & Burrows, C. J., "Nickel(III)-Promoted DNA Cleavage with Ambient Dioxygen", Angew. Chem. Int. Ed. Engl. 1993, 32, 277–278. doi: DOI 10.1002/anie.199302771
  • [48]. Lesko, S. A.,Lorentzen, R. J., Ts'o, P. O. P.," Involvement of Polycyclic Aromatic-Hydrocarbons and Reduced Oxygen Radicals in Carcinogenesis .5. Role of Superoxide in Deoxyribonucleic-Acid Strand Scission ", Biochemistry 1980, 19, 3023–3028. doi: Doi 10.1021/Bi00554a029
  • [49]. Nilsson, R., Merkel, P. B., Kearns, D. R., "Unambiguous Evidence For The Participation Of Singlet Oxygen (1δ) In Photodynamic Oxidation Of Amino Acids", Photochem. Photobiol. 1972, 16, 117–124. doi: 10.1111/j.1751-1097.1972.tb07343.x
  • [50]. Jiang, Q., Xiao, N., Shi, P., et al., " Design of artificial metallonucleases with oxidative mechanism ", Coord. Chem. Rev. 2007, 251, 1951–1972. doi: 10.1016/j.ccr.2007.02.013
  • [51]. A. Turkoglu, M. E. Duru, N. Mercan, et al., "Antioxidant and antimicrobial activities of Laetiporus sulphureus (Bull.) Murrill", Food Chem. 2006, 101, 267–273. doi: 10.1016/j.foodchem.2006.01.025
  • [52]. Hagerman, A. E., Riedl, K. M., Alexander, J., et al., " High molecular weight plant polyphenolics (tannins) as biological antioxidants ", Food Chem. 1998, 46, 1887–1892. doi: Doi 10.1021/Jf970975b
  • [53]. Beauchamp, C., Fridovich, I., " Superoxide dismutase: Improved assays and an assay applicable to acrylamide gels", Anal. Biochem. 1971, 44, 276–287. doi: 10.1016/0003-2697(71)90370-8
There are 53 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Makaleler
Authors

Kerim Serbest 0000-0002-2436-8163

Bayram Dural This is me 0000-0002-9121-4615

Melek Çol Ayvaz 0000-0001-5155-5784

Ali Zengin This is me 0000-0001-6871-4489

Mustafa Emirik 0000-0001-9489-9093

Project Number 112T526
Publication Date September 30, 2021
Submission Date March 29, 2021
Acceptance Date June 9, 2021
Published in Issue Year 2021 Volume: 8 Issue: 3

Cite

IEEE K. Serbest, B. Dural, M. Çol Ayvaz, A. Zengin, and M. Emirik, “Iron(III) Complexes Derived From Azo-Containing Salicylaldoxime Ligands: Synthesis, Structures and Biological Evaluations”, ECJSE, vol. 8, no. 3, pp. 1184–1201, 2021, doi: 10.31202/ecjse.905307.