Synthesis, Structural Characterization, in Vitro Biological Activity, and Computational Quantum Chemical Studies of New Cobalt (II), Nickel (II), and Copper (II) Complexes Based on an Azo-Azomethine Ligand

References

• F. Naderi, M. Orojloo, R. Jannesar, and S. Amani, “Synthesis and Spectroscopic Studies of an Azo-Azomethine Receptor for Naked-Eye Detection of Hydrogen Carbonate Ions in Aqueous Media,” Polycyclic Aromatic Compounds 41, no. 6 (2021): 1284–98. doi:10.1080/10406638.2019.1672201.
   Web of Science ®Google Scholar
• J. Valentová, S. Varényi, P. Herich, P. Baran, A. Bilková, J. Kožíšek, and L. Habala, “Synthesis, Structures and Biological Activity of Copper(II) and Zinc(II) Schiff Base Complexes Derived from Aminocyclohexane-1-Carboxylic Acid. New Type of Geometrical Isomerism in Polynuclear Complexes,” Inorganica Chimica Acta 480 (2018): 16–26. doi:10.1016/j.ica.2018.04.058.
   Web of Science ®Google Scholar
• C. R. Vickery, B. M. K. Wood, H. G. Morris, R. Losick, and S. Walker, “Reconstitution of Staphylococcus aureus Lipoteichoic Acid Synthase Activity Identifies Congo Red as a Selective Inhibitor,” Journal of the American Chemical Society 140, no. 3 (2018): 876–9. doi:10.1021/jacs.7b11704.
   PubMed Web of Science ®Google Scholar
• P. Raj, A. Singh, A. Singh, and N. Singh, “Syntheses and Photophysical Properties of Schiff-Base Ni (II) Complexes: Application for Sustainable Antibacterial Activity and Cytotoxicity,” ACS Sustainable Chemistry & Engineering 5, no. 7 (2017): 6070–80. doi:10.1021/acssuschemeng.7b00963.
   Web of Science ®Google Scholar
• M. Korzec, S. Senkała, R. Rzycka-Korzec, S. Kotowicz, E. Schab-Balcerzak, and J. Polański, “A Highly Selective and Sensitive Sensor with Imine and Phenyl-Ethynylphenyl Units for the Visual and Fluorescent Detection of Copper in Water,” Journal of Photochemistry and Photobiology A: Chemistry 382 (2019): 111893. doi:10.1016/j.jphotochem.2019.111893.
   Web of Science ®Google Scholar
• Y. S. Yang, S. S. Ma, Y. P. Zhang, J. X. Ru, X. Y. Liu, and H. C. Guo, “A Novel Biphenyl-Derived Salicylhydrazone Schiff Base Fluorescent Probes for Identification of Cu2+ and Application in Living Cells,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 199 (2018): 202–8. doi:10.1016/j.saa.2018.03.060.
   PubMed Web of Science ®Google Scholar
• M. L. Low, L. Maigre, P. Dorlet, R. Guillot, J. M. Pagès, K. A. Crouse, C. Policar, and N. Delsuc, “Conjugation of a New Series of Dithiocarbazate Schiff Base Copper(II) Complexes with Vectors Selected to Enhance Antibacterial Activity,” Bioconjugate Chemistry 25, no. 12 (2014): 2269–84. doi:10.1021/bc5004907.
   PubMed Web of Science ®Google Scholar
• K. Venkateswarlu, N. Ganji, S. Daravath, K. Kanneboina, and K. Rangan, Shivaraj, “Crystal Structure, DNA Interactions, Antioxidant and Antitumor Activity of Thermally Stable Cu(II), Ni(II) and Co(III) Complexes of an N,O Donor Schiff Base Ligand,” Polyhedron 171 (2019): 86–97. doi:10.1016/j.poly.2019.06.048.
   Web of Science ®Google Scholar
• H. Wen, G. Liu, and Z. H. Huang, “Recent Advances in Tridentate Iron and Cobalt Complexes for Alkene and Alkyne Hydrofunctionalizations,” Coordination Chemistry Reviews 386 (2019): 138–53. doi:10.1016/j.ccr.2019.01.024.
   Web of Science ®Google Scholar
• G. Yao, J. Lei, W. Zhang, C. Yu, Z. Sun, S. Zheng, and S. Komarneni, “Antimicrobial Activity of X Zeolite Exchanged with Cu2+ and Zn2+ on Escherichia Coli and Staphylococcus Aureus,” Environmental Science and Pollution Research International 26, no. 3 (2019): 2782–93. doi:10.1007/s11356-018-3750-z.
   PubMed Web of Science ®Google Scholar
• J. Fujita, Y. Maeda, E. Mizohata, T. Inoue, M. Kaul, A. K. Parhi, E. J. LaVoie, D. S. Pilch, and H. Matsumura, “Structural Flexibility of an Inhibitor Overcomes Drug Resistance Mutations in Staphylococcus Aureus FtsZ,” ACS Chemical Biology 12, no. 7 (2017): 1947–55. doi:10.1021/acschembio.7b00323.
   PubMed Web of Science ®Google Scholar
• S. Wang, W. Deng, L. Yang, Y. Tan, Q. Xie, and S. Yao, “Copper-Based Metal-Organic Framework Nanoparticles with Peroxidase-Like Activity for Sensitive Colorimetric Detection of Staphylococcus aureus,” ACS Applied Materials & Interfaces 9, no. 29 (2017): 24440–5. doi:10.1021/acsami.7b07307.
   PubMed Web of Science ®Google Scholar
• S. Wang, Q. Wang, X. Zeng, Q. Ye, S. Huang, H. Yu, T. Yang, and S. Qiao, “Use of the Antimicrobial Peptide Sublancin with Combined Antibacterial and Immunomodulatory Activities to Protect \against Methicillin-Resistant Staphylococcus Aureus Infection in Mice,” Journal of Agricultural and Food Chemistry 65, no. 39 (2017): 8595–605. doi:10.1021/acs.jafc.7b02592.
   PubMed Web of Science ®Google Scholar
• D. F. Zhang, X. Y. Yang, J. Zhang, X. Qin, X. Huang, Y. Cui, M. Zhou, G. Shi, N. P. French, and X. Shi, “Identification and Characterization of Two Novel Superantigens among Staphylococcus Aureus Complex,” International Journal of Medical Microbiology 308, no. 4 (2018): 438–46. doi:10.1016/j.ijmm.2018.03.002.
   PubMed Web of Science ®Google Scholar
• M. A. Farha, A. Leung, E. W. Sewell, M. A. D. Elia, S. E. Allison, L. Ejim, P. M. Pereira, M. G. Pinho, G. D. Wright, and E. D. Brown, “Inhibition of WTA Synthesis Blocks the Cooperative Action of PBPs and Sensitizes MRSA to β-Lactams,” ACS Chemical Biology 8, no. 1 (2013): 226–33.
   PubMed Web of Science ®Google Scholar
• N. S. Naik, L. A. Shastri, S. D. Joshi, S. R. Dixit, B. M. Chougala, S. Samundeeswari, M. Holiyachi, F. Shaikh, J. Madar, R. Kulkarni, et al, “3,4-Dihydropyrimidinone-Coumarin Analogues as a New Class of Selective Agent against S. Aureus: Synthesis, Biological Evaluation and Molecular Modelling Study,” Bioorganic & Medicinal Chemistry 25, no. 4 (2017): 1413–22. doi:10.1016/j.bmc.2017.01.001.
   PubMed Web of Science ®Google Scholar
• M. Lein, and G. Frenking, “Chapter 13 - the Nature of the Chemical Bond in the Light of an Energy Decomposition Analysis,” Journal of Theoretical & Computational Chemistry 9 (2005): 291–372.
   Google Scholar
• R. Arab Ahmadi, F. Hasanvand, G. Bruno, H. Amiri Rudbari, and S. Amani, “Synthesis, Spectroscopy, and Magnetic Characterization of Copper(II) and Cobalt(II) Complexes with 2-Amino-5-Bromopyridine as Ligand,” ISRN Inorganic Chemistry 2013 (2013): 1–8. doi:10.1155/2013/426712.
   Google Scholar
• D. F. Evans, “The Determination of the Paramagnetic Susceptibility of Substances in Solution by Nuclear Magnetic Resonance,” Journal of the Chemical Society (Resumed) (1959): 2003–5. doi:10.1039/jr9590002003.
   Google Scholar
• W. J. Geary, “The Use of Conductivity Measurements in Organic Solvents for the Characterization of Coordination Compounds,” Coordination Chemistry Reviews 7, no. 1 (1971): 81–122. doi:10.1016/S0010-8545(00)80009-0.
   Web of Science ®Google Scholar
• M. Orojloo, P. Zolgharnein, M. Solimannejad, and S. Amani, “Synthesis and Characterization of Cobalt (II), Nickel (II), Copper (II) and Zinc (II) Complexes Derived from Two Schiff Base Ligands: Spectroscopic, Thermal, Magnetic Moment, Electrochemical and Antimicrobial Studies,” Inorganica Chimica Acta 467 (2017): 227–37. doi:10.1016/j.ica.2017.08.016.
   Web of Science ®Google Scholar
• L. Taghizadeh, M. Montazerozohori, A. Masoudiasl, S. Joohari, and J. M. White, “New Tetrahedral Zinc Halide Schiff Base Complexes: Synthesis, Crystal Structure, Theoretical, 3D Hirshfeld Surface Analyses, Antimicrobial and Thermal Studies,” Materials Science & Engineering. C, Materials for Biological Applications 77 (2017): 229–44. doi:10.1016/j.msec.2017.03.150.
   PubMed Web of Science ®Google Scholar
• E. S. A. El-Samanody, S. A. AbouEl-Enein, and E. M. Emara, “Molecular Modeling, “Spectral Investigation and Thermal Studies of the New Asymmetric Schiff Base Ligand; (E)-N'-(1- (4-((E)-2-Hydroxybenzylideneamino) Phenyl) Ethylidene) Morpholine-4 Carbothiohydrazide and Its Metal Complexes: Evaluation of Their Antibacterial and anti Molluscicidal Activity,” Applied Organometallic Chemistry 32, no. 4 (2018): e4262. doi:10.1002/aoc.4262.
   Web of Science ®Google Scholar
• S. A. AbouEl-Enein, S. M. Emam, M. W. Polis, and E. M. Emara, “Synthesis and Characterization of Some Metal Complexes Derived from Azo Compound of 4,4`-Methylenedianiline and Antipyrine: Evaluation of Their Biological Activity on Some Land Snail Species,” Journal of Molecular Structure 1099 (2015): 567–78. doi:10.1016/j.molstruc.2015.06.072.
   Web of Science ®Google Scholar
• N. Nassirinia, N. Sadeghi, and S. Amani, “Two New Alkoxo-Bridged Dinuclear Copper (II) Complexes with 3-Aminopyrazidine-2-Carboxylic Acid as Ligands,” Journal of Coordination Chemistry 61, no. 5 (2008): 796–801. doi:10.1080/00958970701370575.
   Web of Science ®Google Scholar
• A. Rodríguez, A. Sousa-Pedrares, J. A. García-Vázquez, J. Romero, and A. Sousa, “Electrochemical Synthesis and Characterization of Zinc (II) Complexes with Pyrimidine-2-Thionato Ligands and Their Adducts with N, N Donors,” Polyhedron 28, no. 11 (2009): 2240–8. doi:10.1016/j.poly.2009.03.029.
   Web of Science ®Google Scholar
• S. Kida, Y. Nishida, and M. Sakamoto, “The near-Ultraviolet Absorption of Aqueous Solution of Copper (II) Ammine Complex with an Access of Ammonia,” Bulletin of the Chemical Society of Japan 46 (1973): 3228–9.
   Web of Science ®Google Scholar
• N. Venugopal, G. Krishnamurthy, H. S. Bhojyanaik, and P. M. Krishna, “Synthesis, Spectral Characterization and Biological Studies of Cu (II), Co (II) and Ni (II) Complexes of Azo Dye Ligand Containing 4‒Amino Antipyrine Moiety,” Journal of Molecular Structure 1183 (2019): 37–51. doi:10.1016/j.molstruc.2019.01.031.
   Web of Science ®Google Scholar
• C. A. Koch, C. A. Reed, G. A. Brewer, N. P. Rath, W. R. Scheidt, G. Gupta, and G. Lang, “Ferromagnetic Coupling via Imidazolate in an Iron (III)-Porphyrin-Dicopper (II) System,” Journal of the American Chemical Society 111, no. 19 (1989): 7645–8. doi:10.1021/ja00201a073.
   Web of Science ®Google Scholar
• S. Liu, P. Jiang, G. Song, R. Liu, and H. Zhu, “Synthesis and Optical Properties of a Series of Thermally Stable Diphenylanthrazolines,” Dyes and Pigments 81, no. 3 (2009): 218–23. doi:10.1016/j.dyepig.2008.10.010.
   Web of Science ®Google Scholar
• L. H. Abdel-Rahman, A. M. Abu-Dief, E. F. Newair, and S. K. Hamdan, “Some New Nano-Sized Cr(III), Fe(II), Co(II), and Ni(II) Incorporating 2-((E)-(Pyridine-2-Ylimino) Methyl)Napthalen-1-ol Ligand: Structural Characterization, Electrochemical, Antioxidant, Antimicrobial, Antiviral Assessment and DNA Interaction,” Journal of Photochemistry and Photobiology B: Biology 160 (2016): 18–31. doi:10.1016/j.jphotobiol.2016.03.040.
   PubMed Web of Science ®Google Scholar
• E. Ispir, M. Ikiz, A. Inan, A. B. Sünbül, S. E. Tayhan, S. Bilgin, M. Köse, and M. Elmastaş, “Synthesis, Structural Characterization, Electrochemical, Photoluminescence, Antiproliferative and Antioxidant Properties of Co(II), Cu(II) and Zn(II) Complexes Bearing the Azo-Azomethine Ligands,” Journal of Molecular Structure 1182 (2019): 63–71. doi:10.1016/j.molstruc.2019.01.029.
   Web of Science ®Google Scholar
• A. Naz, S. Arun, S. S. Narvi, M. S. Alam, A. Singh, P. Bhartiya, and P. K. Dutta, “Cu(II)-Carboxymethyl Cchitosan-silane Schiff Base Complex Grafted on Nano Silica: Structural Evolution, Antibacterial Performance and Dye Degradation Ability,” International Journal of Biological Macromolecules 110 (2018): 215–26. doi:10.1016/j.ijbiomac.2017.11.112.
   PubMed Web of Science ®Google Scholar
• H. Kargar, V. Torabi, A. Kbari, R. Behjatmanesh-Ardakani, A. Sahraei, and M. Nawaz. Tahir, “Pd(II) and Ni(II) Complexes Containing an Asymmetric Schiff Base Ligand: Synthesis, x-Ray Crystal Structure, Spectroscopic Investigations and Computational Studies,” Journal of Molecular Structure 1205 (2020): 127642. doi:10.1016/j.molstruc.2019.127642.
   Web of Science ®Google Scholar
• N. S. Abdel-Kader, A. L. El-Ansary, T. A. El-Tayeb, and M. M. F. Elnagdi, “Synthesis and Characterization of Schiff Base Complexes Derived from Cephradine: Fluorescence, Photostability and Photobiological Applications,” Journal of Photochemistry and Photobiology A: Chemistry 321 (2016): 223–37. doi:10.1016/j.jphotochem.2016.01.021.
   Web of Science ®Google Scholar
• V. S. Violet Rani, T. Dhanasekaran, M. Jayathuna, V. Narayanan, and D. Jesudurai, “Synthesis, Characterization of Cu (II) Schiff Base Complexes: Optical and Magnetic Studies,” Materials Today 5, no. 2 (2018): 8784–8. doi:10.1016/j.matpr.2017.12.306.
   Google Scholar
• M. Orojloo, and S. Amani, “A Highly Selective Chemosensor for Naked-Eye Detection of Fluoride and Aluminium(III) Ions Based on a New Schiff Base Derivative,” Australian Journal of Chemistry 69, no. 8 (2016): 911–8. doi:10.1071/CH15826.
   Web of Science ®Google Scholar
• S. M. Wilkinson, T. M. Sheedy, and E. J. New, “Synthesis and Characterization of Metal Complexes with Schiff Base Ligands,” Journal of Chemical Education 93, no. 2 (2016): 351–4. doi:10.1021/acs.jchemed.5b00555.
   Web of Science ®Google Scholar
• E. A. El-Samanody, M. W. Polis, and E. M. Emara, “Spectral Studies, Thermal Investigation and Biological Activity of Some Metal Complexes Derived from (E)-N′-(1-(4 Aminophenyl) Ethylidene) Morpholine-4- Carbothiohydrazide,” Journal of Molecular Structure 1144 (2017): 300–12. doi:10.1016/j.molstruc.2017.05.014.
   Web of Science ®Google Scholar
• E. S. A. El-Samanody, S. M. Emam, and E. M. Emara, “Synthesis, Characterization, Molecular Modeling and Biological Activity of Metal Complexes Derived from (E)-N'-(Furan-2 Ylmethylene) Morpholine-4-Carbothiohydrazide,” Journal of Molecular Structure 1146 (2017): 868–80. doi:10.1016/j.molstruc.2017.06.034.
   Web of Science ®Google Scholar
• S. M. Emam, S. A. AbouEl-Enein, and E. M. Emara, “Spectroscopic Studies and Thermal Decomposition for (Bis-((E)-2- (4-Ethylphenylimino)-1,2-Diphenylethanone) Schiff Base and Its Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) Complexes Prepared by Direct and Template Reactions,” Journal of Thermal Analysis and Calorimetry 127, no. 2 (2017): 1611–30. doi:10.1007/s10973-016-5835-6.
   Web of Science ®Google Scholar
• M. Montazerozohori, S. Zahedi, A. Naghiha, and M. M. Zohour, “Synthesis, Characterization and Thermal Behavior of Antibacterial and Antifungal Active Zinc Complexes of Bis (3(4-dimethylaminophenyl)-allylidene-1,2-diaminoethane,” Materials Science & Engineering. C, Materials for Biological Applications 35 (2014): 195–204. doi:10.1016/j.msec.2013.10.030.
   PubMed Web of Science ®Google Scholar
• H. Kaur, S. Meng Lim, K. Ramasamy, M. Vasudevan, S. A. Ali Shah, and B. Narasimhan, “Diazenyl Schiff Bases: Synthesis, Spectral Analysis, Antimicrobial Studies and Cytotoxic Activity on Human Colorectal Carcinoma Cell Line (HCT-116),” Arabian Journal of Chemistry 13, no. 1 (2020): 377–92. doi:10.1016/j.arabjc.2017.05.004.
   Web of Science ®Google Scholar
• B. Alizadeh Behbahani, F. Shahidi, F. Tabatabaei Yazdi, S. A. Mortazavi, and M. Mohebbi, “Antioxidant Activity and Antimicrobial Effect of Tarragon (Artemisia Dracunculus) Extract and Chemical Composition of Its Essential Oil,” Journal of Food Measurement and Characterization 11, no. 2 (2017): 847–63. doi:10.1007/s11694-016-9456-3.
   Web of Science ®Google Scholar
• S. H. Najafi, M. Safari, S. Amani, K. Mansouri, and M. Shahlaei, “Preparation, Characterization and Cell Cytotoxicity of Pd‐Doped CdTe Quantum Dots and Its Application as a Sensitive Fluorescent Nanoprobe,” Journal of Materials Science: Materials in Electronics 30, no. 15 (2019): 14233–42. doi:10.1007/s10854-019-01792-1.
   Web of Science ®Google Scholar
• M. Bayat, and S. Kamali, “Computational Landscape of the Formation and Nature of Bond in the “1 + 1” versus “1 + 2” Nano-Sized Complexes of Some Adducts of N-Heterocyclic Carbenes (NHC) with Heavy Elements of Group II (Ca, Sr, Ba) Metallocene’s,” Journal of Molecular Liquids 222 (2016): 953–62. doi:10.1016/j.molliq.2016.07.097.
   Web of Science ®Google Scholar
• H. Keypour, M. Mahmoudabadi, A. Shooshtari, M. Bayat, R. Karamian, M. Asadbegy, and R. W. Gable, “Synthesis, Crystal Structure, Theoretical Studies and Biological Properties of Three Novel Trigonal Prismatic Co(II), Ni(II) and Cu(II) Macrocyclic Schiff Base Complexes Incorporating Piperazine Moiety,” Inorganica Chimica Acta 478 (2018): 176–86. doi:10.1016/j.ica.2018.02.028.
   Web of Science ®Google Scholar