Citation: Maitri Bhattacharjee, Rekha Boruah Smriti, R. N. Dutta Purkayastha, Waldemar Maniukiewicz, Shubhamoy Chowdhury, Debasish Maiti, Tamanna Akhtar. Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007 shu

Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands

1.
Department of Chemistry, Tripura University, Suryamaninagar-799022, Tripura, India
2.
Institute of General and Ecological Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Łódz, Poland
3.
Department of Chemistry, University of Gourbanga, Mokdumpur, Malda, West Bengal-732103, India
4.
Department of Human Physiology, Tripura University, Suryamaninagar-799022, Tripura, India

Corresponding author: R. N. Dutta Purkayastha, rndp09@gmail.com; rndp@tripurauniv.ac.in
Received Date: 4 January 2024
Revised Date: 18 April 2024

Figures(8)

Three new copper(Ⅱ) complexes 1-3 of Schiff base ligands HL¹ (2-hydroxybenzaldehyde2-(2-oxo-1, 2-diphenylethylidene)hydrazone), HL² (4-hydroxybenzaldehyde2-(2-oxo-1, 2-diphenylethylidene)hydrazone) and L³ (2-methoxybenzaldehyde2-(2-oxo-1, 2-diphenylethylidene)hydrazone) were synthesized from methanolic medium. The complexes were characterized by elemental analyses, spectroscopic methods, magnetic susceptibility measurements, and density functional theory (DFT) studies. The synthesized ligands were characterized structurally by single-crystal X-ray diffraction studies. The optimized structure of the complexes was ascertained by DFT studies. The DNA binding ability of the complexes with calf thymus DNA (CT-DNA) was studied by UV-Vis absorption and fluorescence emission spectral studies. Absorption spectral studies revealed a hyperchromic effect and suggested the possible mode of interaction with CT-DNA. The competitive binding studies using ethidium bromide (EB) show that the complexes can replace DNA from DNA-EB adduct and suggests that the complexes probably bind to CT-DNA in intercalative mode. In vitro antibacterial activity of the complexes against Gram-negative bacteria Klebsiella pneumoniae (K. pneumoniae), Escherichia coli(E. coli), and Shigella boydii (S. boydii), and gram-positive bacteria Staphylococcus aureus (S. aureus) exhibited an appreciable antibacterial activity of complex 2 against K. pneumoniae and S. boydii, but complexes 1 and 3 did not show any significant antibacterial activity.
- Cu(Ⅱ) complex,
- Schiff base,
- structure,
- bio-activity,
- density functional theory
1. [1]
  Yamada S. Advancement in stereochemical aspects of Schiff base metal complexes[J]. Coord. Chem. Rev., 1999,190-192:537-555. doi: 10.1016/S0010-8545(99)00099-5
2. [2]
  Niederhoffer E C, Timmons J H, Martell A E. Thermodynamics of oxygen binding in natural and synthetic dioxygen complexes[J]. Chem. Rev., 1984,84(2):137-203. doi: 10.1021/cr00060a003
3. [3]
  Choudhury C R, Dey S K, Mondal N, Mitra S, Mahalli S O G, Abdul Malik K M. J[J]. Chem. Crystallogr., 2002,31(1):57-62.
4. [4]
  Refat M S, El-Sayed M Y, Adam A M. Cu (Ⅱ), Co (Ⅱ) and Ni (Ⅱ) complexes of new Schiff base ligand: Synthesis, thermal and spectroscopic characterizations[J]. J. Mol. Struct., 2013,1038:62-72. doi: 10.1016/j.molstruc.2013.01.059
5. [5]
  Holm R H. Studies on Ni (Ⅱ) complexes. Ⅰ. Spectra of tricyclic Schiff base complexes of Ni (Ⅱ) and Cu (Ⅱ)[J]. J. Am. Chem. Soc., 1960,82(21):5632-5636.
6. [6]
  Lyons C T, Stack T D P. Recent advances in phenoxyl radical complexes of salen-type ligands as mixed-valent galactose oxidase models[J]. Coord. Chem. Rev., 2013,257(2):528-540. doi: 10.1016/j.ccr.2012.06.003
7. [7]
  Mascharak P K. Structural and functional models of nitrile hydratase[J]. Coord. Chem. Rev., 2002,225(1/2):201-214.
8. [8]
  Aziz A A. Synthesis, spectroscopic characterization, thermal studies, catalytic epoxidation and biological activity of chromium and molybdenum hexacarbonyl bound to a novel N₂O₂ Schiff base[J]. J. Mol. Struct., 2010,979(1/2/3):77-85.
9. [9]
  Zhang W, Loebach J L, Wilson S R, Jacobsen E N. Enantioselective epoxidation of unfunctionalized olefins catalyzed by salen manganese complexes[J]. J. Am. Chem. Soc., 1990,112(7):2801-2803. doi: 10.1021/ja00163a052
10. [10]
  Tisato J, Refosco F, Bandoli F. Structural survey of technetium complexes[J]. Coord. Chem. Rev., 1994,135-136:325-397. doi: 10.1016/0010-8545(94)80072-3
11. [11]
  Kakanejadifard A, Esna-Ashari F, Hashemi P, Zabardasti A. Synthesis and characterization of an azo dibenzoic acid Schiff base and its Ni (Ⅱ), Pb (Ⅱ), Zn (Ⅱ) and Cd (Ⅱ) complexes[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2013,106:80-85. doi: 10.1016/j.saa.2012.12.044
12. [12]
  Tawfik A M, El-Ghamry M A, Abu-El-Wafa S M, Ahmed N M. A new bioactive Schiff base ligands derived from propylazo-N-pyrimidin-2-yl-benzenesulfonamides Mn (Ⅱ) and Cu (Ⅱ) complexes: Synthesis, thermal and spectroscopic characterization biological studies and 3D modeling structures[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2012,97:1172-1180. doi: 10.1016/j.saa.2012.07.102
13. [13]
  Keypour H, Shayesteh M, Rezaeivala M, Chalabian F, Elerman Y, Buyukgungor O. Synthesis, spectral characterization, structural investigation and antimicrobial studies of mononuclear Cu (Ⅱ), Ni (Ⅱ), Co (Ⅱ), Zn (Ⅱ) and Cd (Ⅱ) complexes of a new potentially hexadentate N₂O₄ Schiff base ligand derived from salicylaldehyde[J]. J. Mol. Struct., 2013,1032:62-68. doi: 10.1016/j.molstruc.2012.07.056
14. [14]
  Cheng J H, Ma X F, Zhang Y H, Liu J Y, Zhou X G, Xiang H F. Optical chemosensors based on transmetalation of salen-based Schiff base complexes[J]. Inorg. Chem., 2014,53(6):3210-3219. doi: 10.1021/ic5000815
15. [15]
  AbuDiet A M, Díaz-Torres R, Sañudo E C, Abdel-Rahman L H, Aliaga-Alcalde N. Novel sandwich triple-decker dinuclear Nd^Ⅲ-(bis-N, N'-p-bromo-salicylideneamine-1, 2-diaminobenzene) complex[J]. Polyhedron, 2013,64:203-208. doi: 10.1016/j.poly.2013.04.010
16. [16]
  Xu H, He C, Sui Y X, Ren X M, Guo L M, Zhang Y G, Nishihara S, Hosokoshi Y. Self-assembled molecular magnets from discrete dimer to onedimensional helical chain: Syntheses, crystal structures and magnetic properties[J]. Polyhedron, 2007,26(15):4463-4469. doi: 10.1016/j.poly.2007.05.047
17. [17]
  Ulusoy M, BirelÖ , Sahin O, Büyükgüngör O, Cetinkaya B. Structural, spectral, electrochemical and catalytic reactivity studies of a series of N₂O₂ chelated palladium (Ⅱ) complexes[J]. Polyhedron, 2012,38(1):141-148. doi: 10.1016/j.poly.2012.02.035
18. [18]
  Yousef T A, El-Gammal O A, Ahmed S F, Abu El-Reash G M. Synthesis, biological and comparative DFT studies on Ni (Ⅱ) complexes of NO and NOS donor ligands[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2015,135:690-703. doi: 10.1016/j.saa.2014.07.015
19. [19]
  Gupta K C, Sutar A K. Catalytic activities of Schiff base transition metal complexes[J]. Coord. Chem. Rev., 2008,252(12/13/14):1420-1450.
20. [20]
  Jacobsen E N. Catalytic asymmetric synthesis[J]. New York: VCH, 1993159.
21. [21]
  Barone G, Gambino N, Ruggirello A, Silvestri A, Terenzi A, Liveri V T. Spectroscopic study of the interaction of NiⅡ-5-triethyl ammonium methyl salicylidene ortho-phenylendiiminate with native DNA[J]. J. Inorg. Biochem., 2009,103(5):731-737. doi: 10.1016/j.jinorgbio.2009.01.006
22. [22]
  Gupta S, Mukherjee A, Nethaji M, Chakravarty , A R. An angular trinuclear copper (Ⅱ) complex as a model for the active site of multicopper oxidases[J]. Polyhedron, 2004,23(4):643-647. doi: 10.1016/j.poly.2003.11.001
23. [23]
  Wood A, Aris W, Brook D J R. Coordinated hydrazone ligands as nucleophiles: Reactions of Fe (papy)2[J]. Inorg. Chem., 2004,43(26):8355-8360. doi: 10.1021/ic0492688
24. [24]
  Concilio S, Sessa L, Petrone A M, Porta A, Diana R, Iannelli P, Piotto S. Structure modification of an active azo-compound as a route to new antimicrobial compounds[J]. Molecules, 2017,22875. doi: 10.3390/molecules22060875
25. [25]
  Ghosh K, Kumar P, Tyagi N, Singh U P, Goel N, Chakraborty A, Roy P, Baratto M C. DNA interaction, superoxide scavenging and cytotoxicity studies on new copper (Ⅱ) complexes derived from a tridentate ligand[J]. Polyhedron, 2011,30(16):2667-2677. doi: 10.1016/j.poly.2011.07.019
26. [26]
  Yusuf T L, Oladipo S D, Zamisa S, Kumalo H M, Lawal I A, Lawal M M, Mabuba N. Design of new Schiff-base copper (Ⅱ) complexes: Synthesis, crystal structures, DFT study, and binding potency toward cytochrome P450 3A4[J]. ACS Omega, 2021,6(21):13704-13718. doi: 10.1021/acsomega.1c00906
27. [27]
  Kovacic J E. The C=N stretching frequency in the infrared spectra of Schiff's base complexes-Ⅰ. Copper complexes of salicylidene anilines[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 1967,23(1):183-187.
28. [28]
  Odabaşoğlu M, AlbayrakÇ , Özkanca R, Aykan F Z, Lonecke P. Some polyhydroxy azo-azomethine derivatives of salicylaldehyde: Synthesis, characterization, spectroscopic, molecular structure and antimicrobial activity studies[J]. J. Mol. Struct., 2007,840(1/2/3):71-89.
29. [29]
  Yang C T, Vetrichelvan M, Yang X D, Moubaraki B, Murray K S, Vittal J J. Syntheses, structural properties and catecholase activity of copper (Ⅱ) complexes with reduced Schiff base N-(2-hydroxybenzyl) amino acids[J]. Dalton Trans., 2004(1):113-121. doi: 10.1039/B310262A
30. [30]
  Lever A B P. Inorganic electronic spectroscopy. 2nd ed., Amsterdam: Elsevier Science, 1984.
31. [31]
  Ebrahimi H P, Hadi J S, Abdulnabi Z A, Bolandnazar Z. Spectroscopic, thermal analysis and DFT computational studies of salen-type Schiff base complexes[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2014,117:485-492. doi: 10.1016/j.saa.2013.08.044
32. [32]
  Elmacı G, Duyar H, Aydıner B, Seferoğlu N, Naziri M A, Şahin E, Seferoğlu Z. The syntheses, molecular structure analyses and DFT studies on new benzil monohydrazone based Schiff bases[J]. J. Mol. Struct., 2018,1162:37-44. doi: 10.1016/j.molstruc.2018.02.035
33. [33]
  Elmacı G, Aktan E, Seferoğlu N, Hökelek T, Seferoğlu Z. Synthesis, molecular structure and computational study of (Z)-2-((E)-4-nitrobenzylidene) hydrazone)-1, 2-diphenylethan-1-one[J]. J. Mol. Struct., 2015,1099:83-91. doi: 10.1016/j.molstruc.2015.06.041
34. [34]
  Bouchama A, Yahiaoui M, Chiter C, Setifi Z, Simpson J. Crystal structure of (Z)-2-[(E)-2-benzyl-idene-hydrazin-1-yl-idene]-1, 2-diphenyl-ethanone[J]. Acta Crystallogr. Sect. E, 2015,E71:35-37.
35. [35]
  Barton J K, Danishefsky A T, Goldberg G M. Tris (phenanthroline) ruthenium (Ⅱ): Stereoselectivity in binding to DNA[J]. J. Am. Chem. Soc., 1984,106(7):2172-2176. doi: 10.1021/ja00319a043
36. [36]
  Fekri R, Salehi M, Asadi A, Kubicki M. DNA/BSA interaction, bioactivity, molecular docking simulation study and electrochemical properties of hydrazone Schiff base derived Cu (Ⅱ)/Ni (Ⅱ) metal complexes: Influence of the nuclearity and metal ions[J]. Polyhedron, 2017,128:175-187. doi: 10.1016/j.poly.2017.02.047
37. [37]
  Czarny A, Boykin D W, Wood A A, Nunn C M, Neidle S, Zhao M, Wilson W D. Analysis of van der Waals and electrostatic contributions in the interactions of minor groove binding benzimidazoles with DNA[J]. J. Am. Chem. Soc., 1995,117(16):4716-4717. doi: 10.1021/ja00121a034
38. [38]
  Benesi H A, Hildebrand J H. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons[J]. J. Am. Chem. Soc., 1949,71(8):2703-2707. doi: 10.1021/ja01176a030
39. [39]
  Kathiravan A, Renganathan R. Photoinduced interactions between colloidal TiO 2 nanoparticles and calf thymus-DNA[J]. Polyhedron, 2009,28(7):1374-1378. doi: 10.1016/j.poly.2009.02.040
40. [40]
  Liu Y X, Mo H W, Lv Z Y, Shen F, Zhang C L, Qi Y Y, Mao Z W, Le X Y. DNA binding, crystal structure, molecular docking studies and anticancer activity evaluation of a copper (Ⅱ) complex[J]. Transit. Met. Chem., 2018,43(3):259-271. doi: 10.1007/s11243-018-0211-y
41. [41]
  Reihardt C G, Krugh T R. A comparative study of ethidium bromide complexes with dinucleotides and DNA: Direct evidence for intercalation and nucleic acid sequence preferences[J]. Biochemistry, 1978,17(23):4845-4854. doi: 10.1021/bi00616a001
42. [42]
  Zhao G H, Lin H K, Zhu S R, Sun H W, Chen Y T. Dinuclear palladium (Ⅱ) complexes containing two monofunctional[Pd (en)(pyridine) Cl]⁺ units bridged by Se or S. Synthesis, characterization, cytotoxicity and kinetic studies of DNA-binding[J]. J. Inorg. Biochem., 1998,70(3/4):219-226.
43. [43]
  Novakova O, Chen H, Vrana O, Rodger A, Sadler P J, Brabec V. DNA interactions of monofunctional organometallic ruthenium (Ⅱ) antitumor complexes in cell-free media[J]. Biochemistry, 2003,42(39):11544-11554. doi: 10.1021/bi034933u
44. [44]
  Dimitrakopoulou A, Dendrinou-Samara C, Pantazaki A A, Alexiou M, Nordlander E, Kessissglou D P. Synthesis, structure and interactions with DNA of novel tetranuclear, [Mn₄(Ⅱ/Ⅱ/Ⅱ/Ⅳ)] mixed valence complexes[J]. J. Inorg. Biochem., 2008,102(4):618-628. doi: 10.1016/j.jinorgbio.2007.10.005
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