Angiogenesis, Inflammation & Therapeutics | Impact 0.1 (CiteScore) | Online ISSN  2207-872X
RESEARCH ARTICLE   (Open Access)

Synthesis, Charecterization, Antibacterial and Cytotoxicity of Novel Metal Complexes Derived from Azomethine Ligand (Bis Azo-Schiff Base) In Vitro and In Silico

Hussein Abdulkadhim Hasan 1*, Saad M. Mahdi 1, Hanaa Addai Ali 2

+ Author Affiliations

Journal of Angiotherapy 8(3) 1-12 https://doi.org/10.25163/angiotherapy.839531

Submitted: 04 January 2024  Revised: 06 March 2024  Published: 10 March 2024 

This study demonstrated the synthesis of Schiff bases, like azo-Schiff metal complexes, showing therapeutic effects.

Abstract


Background: Schiff bases, especially Azo-Schiff bases, are significant ligands in organic chemistry due to their coordination capabilities. They find applications in various industrial sectors and biological studies. Metal complexes of Schiff bases, particularly with tetradentate ligands, have gained attention for their potential pharmacological benefits. However, there is limited information on the biological activities of certain Schiff base complexes, such as 1H-indole-3-ethylenesalicyldamine derivatives. Method: The synthesis of bis azo-Schiff base ligands and their metal complexes, including Ni(II), Co(II), Pd(II), and Pt(IV) complexes, was conducted. Various analytical techniques were employed to characterize the compounds using FTIR, NMR, UV-Vis spectroscopy, mass spectrometry, and molar conductivity. Biological activities, including antibacterial and cytotoxicity studies, were evaluated. Results: The synthesized compounds demonstrated stability and structural characteristics consistent with the intended coordination geometries. IR spectra confirmed the coordination of metal ions with the ligands. The complexes were evaluated for the antimicrobial activity against two types strains of Gram-negative Escherichia coli and Gram-positive bacteria Staphylococcus aureus and showed good significant against these bacteria. The Pd(II) complex demonstrated higher efficacy against cancer cells compared to normal cells, highlighting its potential as an anticancer agent. The cytotoxicity of the Pd (II) complex on human malignant melanoma A375 and Normal cell WRL-68 were IC50 23.83 and IC50 153.7, respectively. Molecular docking studies provide insights into the interaction of the complexes with target proteins, offering potential modes of action. Conclusion: The study successfully synthesized and characterized bis azo-Schiff base ligands and their metal complexes, demonstrating their stability and promising biological activities.

Keywords: Azo dye, Antibacterial, A375 cell line, Molecular docking, Complexes of Ni(II), Pd(II), and Pt(II), Schiff base.

References


Abbas, G. J., Mosaa, Z., Radhi, A. J., Abbas, H. K., & Najem, W. M. (2023). Synthesis, studying analytical properties and biological activity of new transition metal complexes with sulfadiazine derivative as reagent. Egyptian Journal of Chemistry, 66(1), 55-61.”

Abdullah, B. H., & Salh, Y. M. (2010). Synthesis, characterization and biological activity of N-phenyl-Ñ-(2-phenolyl) thiourea (PPTH) and its metal complexes of Mn (II), Co (II), Ni (II), Cu (II), Zn (II), Cd (II), Pd (II), Pt (II) and Hg (II). Oriental Journal of Chemistry, 26(3), 763.

‏‏Balinge, K. R., & Bhagat, P. R. (2019). A polymer-supported salen-palladium complex as a heterogeneous catalyst for the Mizoroki-Heck cross-coupling reaction. Inorganica Chimica Acta, 495, 119017.

Barnes, C. L., & Bosch, E. (2006). Synthesis and X-ray crystal structure of a complex formed by reaction of 1, 2-bis (2′-pyridylethynyl) benzene and mercury (II) chloride. Journal of Chemical Crystallography, 36, 563-566.

Bharti, N., Sharma, S., Naqvi, F., & Azam, A. (2003). New palladium (II) complexes of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones: synthesis, spectral studies and in vitro anti-amoebic activity. Bioorganic & medicinal chemistry, 11(13), 2923-2929.

Brückner, C., Rettig, S. J., & Dolphin, D. (2000). 2-Pyrrolylthiones as monoanionic bidentate N, S-chelators: synthesis and molecular structure of 2-pyrrolylthionato complexes of nickel (II), cobalt (III), and mercury (II). Inorganic Chemistry, 39(26), 6100-6106.

Buchberger, A. R., DeLaney, K., Johnson, J., & Li, L. (2018). Mass spectrometry imaging: a review of emerging advancements and future insights. Analytical chemistry, 90(1), 240..

Chandra, S., Parmar, S., & Kumar, Y. (2009). Synthesis, spectroscopic, and antimicrobial studies on bivalent zinc and mercury complexes of 2-formylpyridine thiosemicarbazone. Bioinorganic Chemistry and Applications, 2009.

Chandra, S., Shukla, D., & Gupta, L. K. (2008). Synthesis and spectroscopic studies of cobalt (II), nickel (II) and copper (II) complexes with N-donor (N4) macrocyclic ligand (DSLF). Journal of the Indian Chemical Society, 85(8), 800.

Choudhary, A., Sharma, R., Nagar, M., & Mohsin, M. (2011). Transition metal complexes with N, S donor ligands as synthetic antioxidants: synthesis, characterization and antioxidant activity. Journal of Enzyme Inhibition and Medicinal Chemistry, 26(3), 394-403.

Elding, L. I., & Olsson, L. F. (1978). Electronic absorption spectra of square-planar chloro-aqua and bromo-aqua complexes of palladium (II) and platinum (II). The Journal of Physical Chemistry, 82(1), 69-74.

El-Saied, F. (2001). Synthesis and characterization of iron (III), cobalt (II), nickel (II) and copper (II) complexes of 4-formylazohydrazoaniline antipyrine. Polish Journal of Chemistry, 75(6), 773-783.

Geary, W. J. (1971). The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews, 7(1), 81-122.

Ghosh, S., Malik, S., Jain, B., & Gupta, M. (2012). Synthesis, spectral and pharmacological studies of some transition metal complexes derived from Schiff base of Acetazolamide drug. Journal of the Indian Chemical Society, 89(4), 471.

Grela, E., Kozlowska, J., & Grabowiecka, A. (2018). Current methodology of MTT assay in bacteria–A review. Acta histochemica, 120(4), 303-311.

Hari Kumaran Nair, M. L., & Shamla, L. (2009). Synthesis, spectral and thermal studies of copper (II) complexes of azodyes derived from 2, 3-dimethyl-1-phenyl-4-amino-5-pyrazolone. Journal of the Indian Chemical Society, 86(2), 133-138.

Hashemi, M., Solati, Z., Ghodsi, A., & Ahmadian, S. (2015). Azo-substituted Schiff base complex of Pt (II): Synthesis, characterization, DFT and TD-DFT study. Synthetic Metals, 210, 398-403.

HUSSEIN, A. A., ALBARAZANCHI, S. I., & AL-SHANON, A. F. (2020). Evaluation of anticancer potential for L-glutaminase purified from Bacillus subtilis. International Journal of Pharmaceutical Research (09752366), 12(1).

Jailani, A. K., Gowthaman, N. S. K., & Kesavan, M. P. (2020). Synthesis, Characterisation and biological evaluation of tyramine derived Schiff base ligand and its transition metal (II) complexes. Karbala International Journal of Modern Science, 6(2), 15.

Jain, S., Jain, N. K., & Pitre, K. S. (2002). Electrochemical analysis of sparfloxacin in pharmaceutical formulation and biochemical screening of its Co (II) complex. Journal of pharmaceutical and biomedical analysis, 29(5), 795-801.

K. Shankar, R. Roshni, K. Saravankumar, P. M. Reddy, and Y. Peng, (2009)  “Synthesis of tetraaza macrocyclic PdII complexes; antibacterial and catalytic studies,” Journal of the Indian Chemical Society, vol. 86, no. 2, pp. 153–161,

Malhotra, E., Kaushik, N. K., & Malhotra, H. S. (2006). Synthesis and studies of ionic chelates of hafnocene with guanine.

Malik, S., Ghosh, S., & Mitu, L. (2011). Complexes of some 3d-metals with a Schiff base derived from 5-acetamido-1, 3, 4-thiadiazole-2-sulphonamide and their biological activity. Journal of the Serbian Chemical Society, 76(10), 1387-1394.

Mason III, W. R., & Gray, H. B. (1968). Electronic structures of square-planar complexes. Journal of the American Chemical Society, 90(21), 5721-5729.

Mihsen, H. H., & Shareef, N. K. (2018, May). Synthesis, characterization of mixed-ligand complexes containing 2, 2-Bipyridine and 3-aminopropyltriethoxysilane. In Journal of Physics: Conference Series (Vol. 1032, No. 1, p. 012066). IOP Publishing.

Mostafa MH, K., Eman H, I., Gehad G, M., Ehab M, Z., & Ahmed, B. (2012). Synthesis and characterization of a novel schiff base metal complexes and their application in determination of iron in different types of natural water. Open Journal of Inorganic Chemistry, 2012.

Muresan, V., Sbirna, L. S., Sbirna, S., Lepadatu, C. I., & Muresan, N. (2001). Transition metal complexes with a new thioamide of the dibenzofuran series. Acta Chimica Slovenica, 48(3), 439-444.

OBAID, E. K., HASANI, N. J., SALMAN, F. W., SHAHEED, H. A., & RADHI, A. J. (2019). Synthesis, characterization and study biological activity of new Iron (III) complex with sulfadiazine derivative. International Journal of Pharmaceutical Research (09752366), 11(2).

Prakash, D., Kumar, C., Prakash, S., Gupta, A. K., & Singh, K. R. R. P. (2009). Synthesis, spectral characterization and antimicrobial studies of some new binuclear complexes of CuII and NiII Schiff base. Journal of the Indian Chemical Society, 86(12), 1257-1261.

Prashanthi, Y., & Kiranmai, K. (2012). Spectroscopic characterization and biological activity of mixed ligand complexes of Ni (II) with 1, 10-phenanthroline and heterocyclic schiff bases. Bioinorganic chemistry and applications, 2012.

Przybylski, P., Huczynski, A. W., Pyta, K. K., Brzezinski, B., & Bartl, F. (2009). Biological properties of Schiff bases and azo derivatives of phenols. Current Organic Chemistry, 13.

Radhi, A. J., Zimam, E. H., & Jafer, E. A. (2021). New barbiturate derivatives as potent in vitro α-glucosidase inhibitors. Egyptian Journal of Chemistry, 64(1), 117-123.

Raman, N., Esthar, S., & Thangaraja, C. (2004). A new Mannich base and its transition metal (II) complexes—synthesis, structural characterization and electrochemical study. Journal of Chemical Sciences, 116, 209-213.

Raman, N., Johnson Raja, S., Joseph, J., Sakthivel, A., & Dhaveethu Raja, J. (2008). Designing, synthesis, spectral characterization of antimicrobial and DNA active tridentate Schiff base ligands and their complexes. Journal of the Chilean Chemical Society, 53(3), 1599-1604.

Raman, N., Muthuraj, V., Ravichandran, S., & Kulandaisamy, A. (2003). Synthesis, characterisation and electrochemical behaviour of Cu (II), Co (II), Ni (II) and Zn (II) complexes derived from acetylacetone and p-anisidine and their antimicrobial activity. Journal of Chemical sciences, 115, 161-167.

Revanasiddappa, M., Basavaraja, C., Suresh, T., & Angadi, S. D. (2009). Synthetic, spectral and antimicrobial activity studies of first row transition metal complexes derived from lansoprazole drug.

Shabani, F., Saghatforoush, L. A., & Ghammamy, S. (2010). Synthesis, characterization and anti-tumour activity of Iron (III) Schiff base complexes with unsymmetric tetradentate ligands. Bulletin of the Chemical society of Ethiopia, 24(2).

Supuran, C. T. (1996). Complexes with biologically active ligands. Part 1. Synthesis of coordination compounds of diazoxide with transition-and main-group cations. Metal-Based Drugs, 3, 25-30.

Tatar, L., Ülkü, D., & Atakol, O. R. H. A. N. (1999). Zinc (II) complexes of bidentate Schiff base ligands containing methoxyphenyl and nitrophenyl groups. Acta Crystallographica Section C: Crystal Structure Communications, 55(4), 508-510.

V. Reddy, N. Patil, and B. R. Patel, “Synthesis and characterization of Co(II), Ni(II), and Cu(II) complexes with O,N and S donar ligands,” Journal of Indian Council of Chemists, vol. 23, no. 2, pp. 1–3, 2006.

Full Text
Export Citation

View Dimensions


View Plumx



View Altmetric



0
Save
0
Citation
374
View
0
Share