Synthesis, characterization, in vitro, in silico and in vivo investigations and biological assessment of Knoevenagel condensate β-diketone Schiff base transition metal complexes

Reference

• Aazam, E. S., & Zaki, M. (2020). Synthesis and characterization of Ni (II)/Zn (II) metal complexes derived from Schiff base and ortho‐phenylenediamine: in vitro DNA binding, molecular modeling and RBC hemolysis. ChemistrySelect, 5(2), 610–618. https://doi.org/10.1002/slct.201903583
   Web of Science ®Google Scholar
• Abbas, A., Murtaza, S., Tahir, M. N., Shamim, S., Sirajuddin, M., Rana, U. A., Naseem, K., & Rafique, H. (2016). Synthesis, antioxidant, enzyme inhibition and DNA binding studies of novel N-benzylated derivatives of sulfonamide. Journal of Molecular Structure, 1117, 269–275. https://doi.org/10.1016/j.molstruc.2016.03.066
   Web of Science ®Google Scholar
• Adnan, S., Ranjha, N. M., Hanif, M., & Asghar, S. (2020). O-Carboxymethylated chitosan; A promising tool with in-vivo anti-inflammatory and analgesic properties in albino rats. International Journal of Biological Macromolecules, 156, 531–536. https://doi.org/10.1016/j.ijbiomac.2020.04.038
   PubMed Web of Science ®Google Scholar
• Aghav, B. D., Patil, S. K., & Lokhande, R. S. (2015). Synthesis, characterization and antibacterial properties of the ternary complexes of cerium with Schiff base derived from 4-aminoantipyrine and some amino acids. Advances in Applied Science Research, 6(12), 37–43.
   Google Scholar
• Alaghaz, A. N. M. (2014). Synthesis, spectroscopic characterization, molecular modeling and potentiometric studies of Co (II), Ni (II), Cu (II) and Zn (II) complexes with 1, 1-diaminobutane-Schiff base. Journal of Molecular Structure, 1072, 103–113. https://doi.org/10.1016/j.molstruc.2014.04.079
   Web of Science ®Google Scholar
• Alaghaz, A. N. M., & Aldulmani, S. A. (2019). Preparation, Structural characterization and DNA binding/cleavage affinity of new bioactive nano‐sized metal (II/IV) complexes with oxazon‐Schiff’s base ligand. Applied Organometallic Chemistry, 33(10), e5135. https://doi.org/10.1016/j.molstruc.2012.11.030
   Web of Science ®Google Scholar
• Alaghaz, A. N. M., Ammar, Y. A., Bayoumi, H. A., & Aldhlmani, S. A. (2014). Synthesis, spectral characterization, thermal analysis, molecular modeling and antimicrobial activity of new potentially N2O2 azo-dye Schiff base complexes. Journal of Molecular Structure, 1074, 359–375. https://doi.org/10.1016/j.molstruc.2014.05.078
   Web of Science ®Google Scholar
• Alaghaz, A. N. M., Bayoumi, H. A., Ammar, Y. A., & Aldhlmani, S. A. (2013). Synthesis, characterization, and antipathogenic studies of some transition metal complexes with N, O-chelating Schiff’s base ligand incorporating azo and sulfonamide Moieties. Journal of Molecular Structure, 1035, 383–399. https://doi.org/10.1016/j.molstruc.2012.11.030
   Web of Science ®Google Scholar
• Al-Hamdani, A. A. S., Balkhi, A. M., Falah, A., & Shaker, S. A. (2016). Synthesis and investigation of thermal properties of vanadyl complexes with azo-containing Schiff-base dyes. Journal of Saudi Chemical Society, 20(5), 487–501. https://doi.org/10.1016/j.jscs.2012.08.001
   Web of Science ®Google Scholar
• Ali, A. M., Al-Noor, T. H., Abdalrazaq, E., & Jbarah, A. A. Q. (2021). Synthesis and DFT study of the complexation of Schiff Base derived curcumin and L-tyrosine with Al (III), Ag (I), and Pb (II) metal ions. Indonesian Journal of Chemistry, 21(3), 708. https://doi.org/10.22146/ijc.62188
   Web of Science ®Google Scholar
• Al-Janabi, A. S., Elzupir, A. O., & Yousef, T. A. (2021). Synthesis, anti-bacterial evaluation, DFT study and molecular docking as a potential 3-chymotrypsin-like protease (3CLpro) of SARS-CoV-2 inhibitors of a novel Schiff bases. Journal of Molecular Structure, 1228, 129454.https://doi.org/10.1016/j.molstru.2020.128596.
   PubMed Web of Science ®Google Scholar
• Almarhoon, Z. M., Al-OnazW, A. I., Alothman, A. A., Al-Mohaimeed, A. M.,& Al-Farraj, E. S. (2019). Synthesis, DNA Binding, and Molecular Docking Studies of Dimethylaminobenzaldehyde-Based Bioactive Schiff Bases. Journal of chemistry. https://doi.org/10.1155/2019/8152721.
   Google Scholar
• Bennie, J. J., Duffy, J. P., Inger, R., & Gaston, K. J. (2014). Bio geography of time partitioning in mammals. Proceedings of the National Academy of Sciences, 111(38), 13727–13732. https://doi.org/10.1073/pnas.1216063110
   Google Scholar
• Bhaskar, R. S., Ladole, C. A., Salunkhe, N. G., Barabde, J. M., & Aswar, A. S. (2020). Synthesis, characterization and antimicrobial studies of novel ONO donor hydrazone Schiff base complexes with some divalent metal (II) ions. Arabian Journal of Chemistry, 13(8), 6559–6567. https://doi.org/10.1016/j.arabjc.2020.06.012
   Web of Science ®Google Scholar
• Bora, P., & Yadav, H. S. (2015). Synthesis and characterization of tertadentate schiff base oxovanadium (IV) complexes. e-Jst, (1), 8. https://doi.org/10.18780/ejst.v8i1.817
   Google Scholar
• Cai, L., Du, H., Wang, D., Lyu, H., & Wang, D. (2021). Synthesis and photophysical properties of ditrifluoroacetoxyboron complexes with curcumin analogues. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 249, 119297. https://doi.org/10.1016/j.saa.2020.119297
   PubMed Web of Science ®Google Scholar
• Chatterjee, S., Singh, P., Fiedler, J., Baková, R., Záliš, S., Kaim, W., & Goswami, S. (2009). Effect of metal exchange (Os vs. Ru) and co-ligand variation (Cl − vs. acac−) on the oxidation state distribution in complexes of an o-phenylenediamido (2−)/o-quinonediimine redox system. Dalton Transactions, (37), 7778–7785. https://doi.org/10.1039/b906913e
   Google Scholar
• Chaurasia, M., Tomar, D., & Chandra, S. (2019). Synthesis, spectral characterization, and DNA binding studies of Co (II), Ni (II), Cu (II) and Zn (II) complexes of Schiff base 2-((1H-1, 2, 4-triazol-3-ylimino) methyl)-5-methoxyphenol. Journal of Molecular Structure, 1179, 431–442. https://doi.org/10.1016/j.molstruc.2018.11.027
   Web of Science ®Google Scholar
• Dhanaraj, C. J., & Raj, S. S. (2020). Synthesis, characterization and biological studies of Schiff base metal complexes derived from 4-aminoantipyrine, acetamide and p-phenylenediamine. Inorganic Chemistry Communications, 119, 108087. https://doi.org/10.1016/j.inoche.2020.108087
   Web of Science ®Google Scholar
• Gogoi, N. G., & Handique, J. G. (2019). Novel protocol for synthesis of 1, 4 diiminocurcumin stabilized silver nanoparticles and application as heterogenous recyclable catalyst and antibacterial agent. Journal of Chemical Sciences, 131(8), 1–11. https://doi.org/10.1007/s12039-019-1654-1
   Web of Science ®Google Scholar
• Jeyaraman, P., Samuel, M., Johnson, A., & Raman, N. (2021). Synthesis, characterization, ADMET, in vitro and in vivo studies of mixed ligand metal complexes from a curcumin Schiff base and lawsone. Nucleosides, Nucleotides & Nucleic Acids, 40(3), 242–263. https://doi.org/10.1080/15257770.2020.1867865
   PubMed Web of Science ®Google Scholar
• Johnson, J., & Dhanaraj, C. J. (2021). Biological and molecular modeling studies on some transition metal (II) complexes of a quinoxaline based ONO donor bishydrazone ligand. Journal of Biomolecular Structure and Dynamics, 39(12), 4385–4313. https://doi.org/10.1080/07391102.2020.1776637
   PubMed Web of Science ®Google Scholar
• Joseph, J., & Janaki, G. B. (2014). Synthesis, structural characterization and biological studies of copper complexes with 2-aminobenzothiazole derivatives. Journal of Molecular Structure, 1063, 160–169. https://doi.org/10.1016/j.molstruc.2014.01.028
   Web of Science ®Google Scholar
• Kar, N. K., Singh, M. K., & Lal, R. A. (2017). Synthesis and spectral studies on monometallic ruthenium (III) complexes of N-(2-hydroxysalicyliden-1-yl) methylenebenzoylhydrazide. Arabian Journal of Chemistry, 10, S76–S80. https://doi.org/10.1016/j.arabjc.2012.05.007
   Web of Science ®Google Scholar
• Kargar, H., Ardakani, A. A., Tahir, M. N., Ashfaq, M., & Munawar, K. S. (2021). Synthesis, spectral characterization, crystal structure determination and antimicrobial activity of Ni (II), Cu (II) and Zn (II) complexes with the Schiff base ligand derived from 3, 5-dibromosalicylaldehyde. Journal of Molecular Structure, 1229, 129842. https://doi.org/10.1016/j.molstruc.2020.129842
   Web of Science ®Google Scholar
• Lokhande, M. V., & Farooq, M. G. (2014). Spectral studies of some transition metal ion complexes with 4-[(E)-(ferrocene-1-methylidene) amino] pyridin-2-ol. J. app. Chem, 6, 36–42.
   Google Scholar
• Mahalakshmi, N., & Rajavel, R. (2014). Synthesis, spectroscopic, DNA cleavage and antibacterial activity of binuclear Schiff base complexes. Arabian Journal of Chemistry, 7(4), 509–517. https://doi.org/10.1016/j.arabjc.2010.11.010
   Web of Science ®Google Scholar
• Medigue, N. E. H., Bouakouk-Chitti, Z., Bechohra, L. L., & Kellou-Taïri, S. (2021). Theoretical study of the impact of metal complexation on the reactivity properties of Curcumin and its diacetylated derivative as antioxidant agents. Journal of Molecular Modeling, 27(6), 1–13. https://doi.org/10.1007/s00894-021-04768-3
   Web of Science ®Google Scholar
• Mishra, K., Ojha, H., & Chaudhury, N. K. (2012). Estimation of antiradical properties of antioxidants using DPPH assay: A critical review and results. Food Chemistry, 130(4), 1036–1043. https://doi.org/10.1016/j.foodchem.2011.07.127
   Web of Science ®Google Scholar
• Murtaza, S., Shamim, S., Kousar, N., Tahir, M. N., Sirajuddin, M., & Rana, U. A. (2016). Synthesis, biological investigation, calf thymus DNA binding and docking studies of the sulfonyl hydrazides and their derivatives. Journal of Molecular Structure, 1107, 99–108. https://doi.org/10.1016/j.molstruc.2015.11.046
   Web of Science ®Google Scholar
• Ojha, H., Mishra, K., Hassan, M. I., & Chaudhury, N. K. (2012). Spectroscopic and isothermal titration calorimetry studies of binding interaction of ferulic acid with bovine serum albumin. Thermochimica Acta, 548, 56–64. https://doi.org/10.1016/j.tca.2012.08.016
   Web of Science ®Google Scholar
• Omidi, S., & Kakanejadifard, A. (2020). A review on biological activities of Schiff base, hydrazone, and oxime derivatives of curcumin. RSC Advances, 10(50), 30186–30202. https://doi.org/10.1039/D0RA05720G
   PubMed Web of Science ®Google Scholar
• Pathak, M., Mishra, R., Agarwala, P. K., Ojha, H., Singh, B., Singh, A., & Kukreti, S. (2016). Binding of ethyl pyruvate to bovine serum albumin: Calorimetric, spectroscopic and molecular docking studies. Thermochimica Acta, 633, 140–148. https://doi.org/10.1016/j.tca.2016.04.006
   Web of Science ®Google Scholar
• Paul, A., Anbu, S., Sharma, G., Kuznetsov, M. L., Koch, B., da Silva, M. F. C. G., & Pombeiro, A. J. (2015). Synthesis, DNA binding, cellular DNA lesion and cytotoxicity of a series of new benzimidazole-based Schiff base copper(II) complexes. Dalton Transactions (Cambridge, England : 2003), 44(46), 19983–19996. https://doi.org/10.1039/c5dt02880a
   PubMed Web of Science ®Google Scholar
• Porkodi, J., & Raman, N. (2018). Synthesis, characterization and biological screening studies of mixed ligand complexes using flavonoids as precursors. Applied Organometallic Chemistry, 32(2), e4030. https://doi.org/10.1002/aoc.4030
   Web of Science ®Google Scholar
• Priyadharshini, N., Pillai, I. S., Joel, C., Bennie, R. B., Subramanian, S., & Venkatesh, P. (2015). Synthesis, characterization and biological activities of cu (ii), ni (ii) and zn (ii) complexes with curcumin and methyl salicylaldehyde. Indo American Journal of Pharmaceutical Sciences, 2(11), 1491–1505.
   Google Scholar
• Rahman, A. J., Kaur, L., Pathak, M., Singh, A., Verma, P., Singhal, R., Kumar, V., & Ojha, H. (2021). Spectroscopic studies of binding interactions of 2-chloroethylphenyl sulphide with bovine serum albumin. Journal of Molecular Liquids, 340, 117144. https://doi.org/10.1016/j.molliq.2021.117144
   Web of Science ®Google Scholar
• Raman, N., Raja, J. D., & Sakthivel, A. (2007). Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies. Journal of Chemical Sciences, 119(4), 303–310. https://doi.org/10.1007/s12039-007-0041-5
   Web of Science ®Google Scholar
• Raman, N., Utthra, P. P., & Chellapandi, T. (2020). Insight into the in vitro anticancer screening, molecular docking and biological efficiency of pyridine-based transition metal (II) complexes. Journal of Coordination Chemistry, 73(1), 103–119. https://doi.org/10.1080/00958972.2020.1716218
   Web of Science ®Google Scholar
• Raman, N., Kulandaisamy, A., & Jeyasubramanian, K. (2002). Synthesis, spectral, redox and biological studies of some Schiff base copper (II), nickel (II), cobalt (II), manganese (II), zinc (II) and oxovanadium (II) complexes derived from 1-phenyl-2, 3-dimethyl-4 (4-iminopentan-2-one) pyrazol-5-one and 2-aminophenol/2-aminothiophenol. NISCAIR-CSIR. http://nopr.niscair.res.in/handle/123456789/18269
   Google Scholar
• Şahin, S., & Dege, N. (2021). Synthesis, characterization, X-Ray, HOMO-LUMO, MEP, FT-IR, NLO, Hirshfeld surface, ADMET, boiled-egg model properties and molecular docking studies with human cyclophilin D (CypD) of a Schiff base compound:(E)-1-(5-nitro-2-(piperidin-1-yl) phenyl)-N-(3-nitrophenyl) methanimine. Polyhedron, 205, 115320. https://doi.org/10.1016/j.poly.2021.115320
   Web of Science ®Google Scholar
• Salib, K. A., Stefan, S. L., Abu El-Wafa, S. M., & El-Shafiy, H. F. (2001). Metal complexes of novel symmetrical schiff base ligands. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 31(5), 895–915. https://doi.org/10.1081/SIM-100104858
   Web of Science ®Google Scholar
• Samuel, M., & Raman, N. (2021). Comprehensive biological evaluation (DNA-binding, cleavage, and antimicrobial activity) of β-diketimine Schiff base ligands and their Cu (II) and Zn (II) complexes. Journal of Coordination Chemistry, 74(12), 2069–2023. https://doi.org/10.1080/00958972.2021.1931848
   Web of Science ®Google Scholar
• Sanatkar, T. H., Khorshidi, A., & Janczak, J. (2020). Dinuclear Zn (II) and tetranuclear Co (II) complexes of a tetradentate N2O2 Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation. Applied Organometallic Chemistry, 34(4), e5493. https://doi.org/10.1002/aoc.5493
   Web of Science ®Google Scholar
• Saritha, T. J., & Metilda, P. (2021). Synthesis, spectroscopic characterization and biological applications of some novel Schiff base transition metal (II) complexes derived from Curcumin moiety. Journal of Saudi Chemical Society, 25(6), 101245. https://doi.org/10.1016/j.jscs.2021.101245
   Web of Science ®Google Scholar
• Shah, A., Khuhawar, M. Y., & Shah, A. A. (2014). Preparation and characterization of poly metal complexes derived from 5, 5'-methylenebis (2-hydroxy benzaldehyde) and 6, 6'-methylenebis (2-hydroxy naphthaldehyde) with hydrazine and 4-amino phenyl ether. Asian Journal of Chemistry, 26(18), 6055–6060. https://doi.org/10.14233/ajchem.2014.16652
   Google Scholar
• Sharma, D., Ojha, H., Pathak, M., Singh, B., Sharma, N., Singh, A., Kakkar, R., & Sharma, R. (2016). Spectroscopic and molecular modelling studies of binding mechanism of metformin with bovine serum albumin. Journal of Molecular Structure, 1118, 267–274. https://doi.org/10.1016/j.molstruc.2016.04.030
   Web of Science ®Google Scholar
• Sharma, D., Singh, A., Pathak, M., Kaur, L., Kumar, V., Roy, B. G., & Ojha, H. (2020). DNA binding and antiradical potential of ethyl pyruvate: key to the DNA radioprotection. Chemico-Biological Interactions, 332, 109313. https://doi.org/10.1016/j.cbi.2020.109313
   PubMed Web of Science ®Google Scholar
• Sirajuddin, M., Ali, S., McKee, V., Wadood, A., & Ghufran, M. (2019). Exploration of organotin (IV) derivatives for medicinal applications: synthesis, spectroscopic characterization, structural elucidation and molecular docking study. Journal of Molecular Structure, 1181, 93–108. https://doi.org/10.1016/j.molstruc.2018.12.041
   Web of Science ®Google Scholar
• Sirajuddin, M., Ali, S., Shah, F. A., Ahmad, M., & Tahir, M. N. (2014). Potential bioactive Vanillin–Schiff base di-and tri-organotin (IV) complexes of 4-((3, 5-dimethylphenylimino) methyl)-2-methoxyphenol: synthesis, characterization and biological screenings. Journal of the Iranian Chemical Society, 11(2), 297–313. https://doi.org/10.1007/s13738-013-0301-x
   Web of Science ®Google Scholar
• Sirajuddin, M., Uddin, N., Ali, S., & Tahir, M. N. (2013). Potential bioactive Schiff base compounds: synthesis, characterization, X-ray structures, biological screenings and interaction with Salmon sperm DNA. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 116, 111–121. https://doi.org/10.1016/j.saa.2013.06.096
   PubMed Web of Science ®Google Scholar
• Susmitha, K., Bhargavi, M., Sumalatha, D., & Joseph, A. J. (2020). Synthesis, structural characterization, molecular docking of thiophene derived Schiff base from 4-amino indane and antibacterial, dna  binding activities of its nickel and cobalt complexes. Oriental Journal of Chemistry, 36(4), 613-620. https://doi.org/10.13005/ojc/360404
   Google Scholar
• Tahir, M., Sirajuddin, M., Zubair, M., Haider, A., Nadman, A., Ali, S., Perveen, F., Tanveer, H. B., & Tahir, M. N. (2021). Designing, spectroscopic and structural characterization and evaluation of biological potential as well as molecular docking studies of Zn (II)-based metallo-pharmaceuticals. Journal of the Iranian Chemical Society, 18(7), 1689–1702. https://doi.org/10.1007/s13738-020-02142-3
   Web of Science ®Google Scholar
• Tariq, M., Khan, R., Hussain, A., Batool, A., Rasool, F., Yar, M., Ayub, K., Sirajuddin, M., Ullah, F., Ali, S., Akhtar, A., Kausar, S., & Altaf, A. A. (2021). Synthesis, characterization, antimicrobial, cytotoxic, DNA-interaction, molecular docking and DFT studies of novel di-and tri-organotin (IV) carboxylates using 3-(3-nitrophenyl) 2-methylpropenoic acid. Journal of Coordination Chemistry, 74(14), 2407–2426. https://doi.org/10.1080/00958972.2021.1964019
   Web of Science ®Google Scholar
• Tiwari, A. D., Mishra, A. K., Mishra, S. B., Mamba, B. B., Maji, B., & Bhattacharya, S. (2011). Synthesis and DNA binding studies of Ni(II), Co(II), Cu(II) and Zn(II) metal complexes of N1,N5-bis[pyridine-2-methylene]-thiocarbohydrazone Schiff-base ligand. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 79(5), 1050–1056. https://doi.org/10.1016/j.saa.2011.04.018
   PubMed Web of Science ®Google Scholar
• Uddin, M. N., Amin, M. S., Rahman, M. S., Khandaker, S., Shumi, W., Rahman, M. A., & Rahman, S. M. (2021). Titanium (IV) complexes of some tetra‐dentate symmetrical bis‐Schiff bases of 1, 6‐hexanediamine: Synthesis, characterization, and in silico prediction of potential inhibitor against coronavirus (SARS‐CoV‐2). Applied Organometallic Chemistry, 35(1), e6067. https://doi.org/10.1002/aoc.6067
   PubMed Web of Science ®Google Scholar
• Vamsikrishna, N., Kumar, M. P., Ramesh, G., Ganji, N., & Daravath, S. (2017). DNA interactions and biocidal activity of metal complexes of benzothiazole Schiff bases: Synthesis, characterization and validation. Journal of Chemical Sciences, 129(5), 609–622. https://doi.org/10.1007/s12039-017-1273-7
   Web of Science ®Google Scholar
• Warad, I., Suboh, H., Al-Zaqri, N., Alsalme, A., Alharthi, F. A., Aljohani, M. M., & Zarrouk, A. (2020). Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N 3 S 2 Schiff base ligand and its [CuN 3 S 2] 2+ complexes. RSC Advances, 10(37), 21806–21821. https://doi.org/10.1039/D0RA04323K
   PubMed Web of Science ®Google Scholar
• Wei, X., Liu, Y., Luo, Y., Shen, Z., Wang, S., Li, M., & Zhang, L. (2021). Effect of organosolv extraction on the structure and antioxidant activity of eucalyptus kraft lignin. International Journal of Biological Macromolecules, 187, 462–470. https://doi.org/10.1016/j.ijbiomac.2021.07.082
   PubMed Web of Science ®Google Scholar
• Yadava, A. K., Yadav, H. S., Singh, S., Yadav, U. S., & Rao, D. P. (2013). Synthesis and characterization of some novel Schiff base complexes of oxovanadium (IV) cation. Journal of Chemistry, 2013, 1–5. https://doi.org/10.1155/2013/689518
   Google Scholar
• Zafar, R., Zubair, M., Ali, S., Shahid, K., Waseem, W., Naureen, H., Haider, A., Jan, M. S., Ullah, F., Sirajuddin, M., & Sadiq, A. (2021). Zinc metal carboxylates as potential anti-Alzheimer's candidate: in vitro anticholinesterase, antioxidant and molecular docking studies. Journal of Biomolecular Structure & Dynamics, 39(3), 1044–1054. https://doi.org/10.1080/07391102.2020.1724569
   PubMed Web of Science ®Google Scholar