Synthesis, Characterization, Anticancer, and Molecular Docking Investigations of Benzothiazole Metal Complexes
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Keywords:
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Schiff Base, Metal Complexes, Spectral Characterization, Anticancer, Molecular Docking
Abstract
The synthesized 2-aminobenzothiazoles based ligand reacted with various transition metal salts were smoothly converted to square planner complexes. The synthesized transition metal complexes are analyzed by using various characterization techniques. Anticancer activity of Schiff base ligand and synthesized metal complexes are examined against human prostate cancer cell line (DU145) MTTassay at different concentration (1, 2, 4, 8, 16, 32, 64, 128, 256, and 512 ug/mL). The IC50 values of metal complexes and free ligand were 16.21 (SBI-Co), 75.98 (SBI-Ni), 25.53 (SBI-Cu), 81.71 (SBI-Zn), and 29.6 (free ligand) ug/mL respectively. Cohasmorepotent against human prostate cancer cell line (DU145). In contrast, the molecular docking study shows, Cu (II) complex has significant inhibition against human 2W3L protein.
References
Abd-Elzaher, M.M., A.A. Labib, H.A. Mousa, S.A. Moustafa, M.M. Ali, and A.A. El-Rashedy (2016). Synthesis, Anticancer Activity and Molecular Docking Study of Schiff Base Complexes Containing Thiazole Moiety. Beni-Suef University Journal of Basic and Applied Sciences, 5; 85–96.
Alam, M.S., J.H. Choi, and D.U. Lee (2012). Synthesis of Novel Schiff Base Analogues of 4-Amino-1,5-Dimethyl-2-Phenylpyrazol-3-One and Their Evaluation for Antioxidant and Anti-Inflammatory Activity. Bioorganic & Medicinal Chemistry, 20; 4103–4108.
Alfonso-Herrera, L.A., D. Hernandez-Romero, J.A. Cruz-Navarro, A. Ramos-Ligonio, A. Lopez-Monteon, J.M. Rivera-Villanueva, D. Morales-Morales, and R. Colorado-Peralta (2024). Transition Metal Complexes with Tetradentate Schiff Bases (N2O2) Obtained from Salicylaldehyde: A Review of Their Possible Anticancer Properties. Coordination Chemistry Reviews, 505; 215698.
Alfonso-Herrera, L.A., S. Rosete-Luna, D. Hernández-Romero, J.M. Rivera-Villanueva, J.L. Olivares-Romero, J.A. Cruz-Navarro, A. Soto-Contreras, A. Arenaza-Corona, D. Morales-Morales, and R. Colorado-Peralta (2022). Transition Metal Complexes with Tridentate Schiff Bases (ONO and ONN) Derived from Salicylaldehyde: An Analysis of Their Potential Anticancer Activity. ChemMedChem, 17; e202200367.
Alminderej, F.M. and A. Lotfi (2021). Design, Synthesis, Characterization and Anticancer Evaluation of Novel Mixed Complexes Derived from 2-(1H-Benzimidazol-2-yl) Aniline Schiff Base and 2-Mercaptobenzimidazole or 2-Aminobenzothiazole. Egyptian Journal of Chemistry, 64; 3351–3364.
Alorini, T.A., A.N. Al-Hakimi, S.E.S. Saeed, E.H.L. Alhamzi, and A.E. Albadri (2022). Synthesis, Characterization, and Anticancer Activity of Some Metal Complexes with a New Schiff Base Ligand. Arabian Journal of Chemistry, 15; 103559.
Aslan, H.G., S. Akkoç, and Z. Kökbudak (2020). Anticancer Activities of Various New Metal Complexes Prepared from a Schiff Base on A549 Cell Line. Inorganic Chemistry Communications, 111; 107645.
Bakale, R.P., G.N. Naik, S.S. Machakanur, C.V. Mangannavar, I.S. Muchchandi, and K.B. Gudasi (2023). Synthesis, Characterization, Spectroscopic Properties and Antihypertensive Activity of 4-Chlorobenzaldehyde Hydralazine Hydrazone and Its Metal Complexes. Journal of the Iranian Chemical Society, 20(1); 147–154.
Chen, P., L.B. Horton, R.L. Mikulski, L. Deng, S. Sundriyal, T. Palzkill, and Y. Song (2012). 2-Substituted 4,5-Dihydrothiazole-4-Carboxylic Acids Are Novel Inhibitors of Metallo-β-Lactamases. Bioorganic & Medicinal Chemistry Letters, 22; 6229–6232.
Choudhary, M. (2022). Design, Synthesis and Characterization Candidates Against SARS-CoV-2 and HIV Virus. Journal of Molecular Structure, 1263; 133114.
Cordeiro, R. and M. Kachroo (2020). Synthesis and Biological Evaluation of Anti-Tubercular Activity of Schiff Bases of 2-Amino Thiazoles. Bioorganic & Medicinal Chemistry Letters, 30; 127655.
Da Silva, C.M., D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V. Martins, and A. de Fátima (2011). Schiff Bases: A Short Review of Their Antimicrobial Activities. Journal of Advanced Research, 2; 1–8.
Daravath, S., A. Rambabu, N. Vamsikrishna, N. Ganji, and S. Raj (2019). Synthesis, Structural Characterization, Antioxidant, Antimicrobial, DNA Incision Evaluation and Binding Investigation Studies on Copper (II) and Cobalt (II) Complexes of Benzothiazole Cored Schiff Bases. Journal of Coordination Chemistry, 72(12); 1973–1993.
Deswal, Y., S. Asija, D. Kumar, D.K. Jindal, G. Chandan, V. Panwar, S. Saroya, and N. Kumar (2022). Transition Metal Complexes of Triazole-Based Bioactive Ligands: Synthesis, Spectral Characterization, Antimicrobial, Anticancer and Molecular Docking Studies. Research on Chemical Intermediates; 1–27.
Devi, J., S. Sharma, S. Kumar, D.K. Jindal, P.P. Dutta, and D. Kumar (2021). Transition Metal (II) Complexes of Hydrazones Derived from Tetralone: Synthesis, Spectral Characterization, In Vitro Antimicrobial and Cytotoxic Studies. Research on Chemical Intermediates, 47; 2433–2467.
Iftikhar, B., K. Javed, M.S.U. Khan, Z. Akhter, B. Mirza, and V. Mckee (2018). Synthesis, Characterization and Biological Assay of Salicylaldehyde Schiff Base Cu (II) Complexes and Their Precursors. Journal of Molecular Structure, 1155; 337–348.
Liu, X. and J.R. Hamon (2019). Recent Developments in Penta-, Hexa- and Heptadentate Schiff Base Ligands and Their Metal Complexes. Coordination Chemistry Reviews, 389; 94–118.
Lotfi, A. (2020). Synthesis and Characterization of Novel Mixed Complexes Derived from 2-Aminomethylbenzimidazole and 2-(1H-Benzimidazol-2-yl) Aniline and Theoretical Prediction of Toxicity. Egyptian Journal of Chemistry, 63; 4757–4767.
Mishra, N., K. Kumar, H. Pandey, S.R. Anand, R. Yadav, S.P. Srivastava, and R. Pandey (2020). Synthesis, Characterization, Optical and Anti-Bacterial Properties of Benzothiazole Schiff Bases and Their Lanthanide (III) Complexes. Journal of Saudi Chemical Society, 24(12); 925–933.
Raji, S.Q. and A.T. Bader (2024). Synthesis and Characterization of Ni (II) Schiff Base Complex as a Precursor for NiO Nanoparticles and an Investigation of Their Corrosion Inhibition. Science and Technology Indonesia, 9(4); 914–928.
Rana, M.S., N.M.A. Rayhan, M.S.H. Emon, M.T. Islam, K. Rathry, M.M. Hasan, M.M.I. Mansur, B.C. Srijon, M.S. Islam, A. Ray, and M.A. Rakib (2024). Antioxidant Activity of Schiff Base Ligands Using the DPPH Scavenging Assay: An Updated Review. RSC Advances, 14; 33094–33123.
Shiju, C., D. Arish, and S. Kumaresan (2020). Novel Water Soluble Schiff Base Metal Complexes: Synthesis, Characterization, Antimicrobial-, DNA Cleavage, and Anticancer Activity. Journal of Molecular Structure, 1221; 128770.
Singh, K. and I. Bala (2023). Structural Investigations, DFT, Anti-Oxidant and α-Amylase Inhibitory Activity of Metal Complexes of Benzothiazole Based Hydrazone. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 103(7); 301–316.
Supuran, C.T., M. Barboiu, C. Luca, E. Pop, M.E. Brewster, and A. Dinculescu (1996). Synthesis of Mono and Bis Pyridinium Salt Derivatives of 2-Amino-5-(2-Aminoethyl)- and 2-Amino-5-(3-Aminopropyl)-1,3,4-Thiadiazole and Their Interaction with Isozyme II. European Journal of Medicinal Chemistry, 31; 597–606.
Turan-Zitouni, G., M.D. Altıntop, A. Özdemir, Z.A. Kaplancıklı, G.A. Çiftçi, and H.E. Temel (2016). Synthesis and Evaluation of Bis-Thiazole Derivatives as New Anticancer Agents. European Journal of Medicinal Chemistry, 107; 288–294.
Vamsikrishna, N., M.P. Kumar, G. Ramesh, N. Ganji, S. Daravath, and Shivaraj (2017). DNA Interactions and Biocidal Activity of Metal Complexes of Benzothiazole Schiff Bases: Synthesis, Characterization and Validation. Journal of Chemical Sciences, 129; 609–622.
Venkatraman, R., M.A. Hossain, and F.R. Fronczek (2010). {4-Phenyl-1-[1-(1,3-Thiazol-2-yl) Ethylidene] Thiosemicarbazidato}{4-Phenyl-1-[1-(1,3-Thiazol-2-yl) Ethylidene] Thiosemicarbazide} Nickel (II) Chloride Monohydrate. Structure Reports, 66; m541–m542.
Vigato, P.A. and S. Tamburini (2004). The Challenge of Cyclic and Acyclic Schiff Bases and Related Derivatives. Coordination Chemistry Reviews, 248; 1717–2128.
Yenilmez, H.Y., A.M. Sevim, and Z.A. Bayır (2013). Synthesis and Photophysics of New Metallo Phthalocyanine Complexes with Thiazole Groups and Their Fluorescence Quenching Studies with Benzoquinone. Synthetic Metals, 176; 11–17.
Yin, L., S. Zhang, T. Zhou, H. Zhen’guang, and S. Zhang (2023). Synthesis, Characterization, and Anticancer Activity of Mononuclear Schiff-Base Metal Complexes. Journal of Molecular Structure, 1275; 134683.
Zheng, Y., J. Li, W. Wu, C. Qi, and H. Jiang (2024). Oxygen, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect. Organic Process Research & Development, 28; 2988–3025.
Alam, M.S., J.H. Choi, and D.U. Lee (2012). Synthesis of Novel Schiff Base Analogues of 4-Amino-1,5-Dimethyl-2-Phenylpyrazol-3-One and Their Evaluation for Antioxidant and Anti-Inflammatory Activity. Bioorganic & Medicinal Chemistry, 20; 4103–4108.
Alfonso-Herrera, L.A., D. Hernandez-Romero, J.A. Cruz-Navarro, A. Ramos-Ligonio, A. Lopez-Monteon, J.M. Rivera-Villanueva, D. Morales-Morales, and R. Colorado-Peralta (2024). Transition Metal Complexes with Tetradentate Schiff Bases (N2O2) Obtained from Salicylaldehyde: A Review of Their Possible Anticancer Properties. Coordination Chemistry Reviews, 505; 215698.
Alfonso-Herrera, L.A., S. Rosete-Luna, D. Hernández-Romero, J.M. Rivera-Villanueva, J.L. Olivares-Romero, J.A. Cruz-Navarro, A. Soto-Contreras, A. Arenaza-Corona, D. Morales-Morales, and R. Colorado-Peralta (2022). Transition Metal Complexes with Tridentate Schiff Bases (ONO and ONN) Derived from Salicylaldehyde: An Analysis of Their Potential Anticancer Activity. ChemMedChem, 17; e202200367.
Alminderej, F.M. and A. Lotfi (2021). Design, Synthesis, Characterization and Anticancer Evaluation of Novel Mixed Complexes Derived from 2-(1H-Benzimidazol-2-yl) Aniline Schiff Base and 2-Mercaptobenzimidazole or 2-Aminobenzothiazole. Egyptian Journal of Chemistry, 64; 3351–3364.
Alorini, T.A., A.N. Al-Hakimi, S.E.S. Saeed, E.H.L. Alhamzi, and A.E. Albadri (2022). Synthesis, Characterization, and Anticancer Activity of Some Metal Complexes with a New Schiff Base Ligand. Arabian Journal of Chemistry, 15; 103559.
Aslan, H.G., S. Akkoç, and Z. Kökbudak (2020). Anticancer Activities of Various New Metal Complexes Prepared from a Schiff Base on A549 Cell Line. Inorganic Chemistry Communications, 111; 107645.
Bakale, R.P., G.N. Naik, S.S. Machakanur, C.V. Mangannavar, I.S. Muchchandi, and K.B. Gudasi (2023). Synthesis, Characterization, Spectroscopic Properties and Antihypertensive Activity of 4-Chlorobenzaldehyde Hydralazine Hydrazone and Its Metal Complexes. Journal of the Iranian Chemical Society, 20(1); 147–154.
Chen, P., L.B. Horton, R.L. Mikulski, L. Deng, S. Sundriyal, T. Palzkill, and Y. Song (2012). 2-Substituted 4,5-Dihydrothiazole-4-Carboxylic Acids Are Novel Inhibitors of Metallo-β-Lactamases. Bioorganic & Medicinal Chemistry Letters, 22; 6229–6232.
Choudhary, M. (2022). Design, Synthesis and Characterization Candidates Against SARS-CoV-2 and HIV Virus. Journal of Molecular Structure, 1263; 133114.
Cordeiro, R. and M. Kachroo (2020). Synthesis and Biological Evaluation of Anti-Tubercular Activity of Schiff Bases of 2-Amino Thiazoles. Bioorganic & Medicinal Chemistry Letters, 30; 127655.
Da Silva, C.M., D.L. da Silva, L.V. Modolo, R.B. Alves, M.A. de Resende, C.V. Martins, and A. de Fátima (2011). Schiff Bases: A Short Review of Their Antimicrobial Activities. Journal of Advanced Research, 2; 1–8.
Daravath, S., A. Rambabu, N. Vamsikrishna, N. Ganji, and S. Raj (2019). Synthesis, Structural Characterization, Antioxidant, Antimicrobial, DNA Incision Evaluation and Binding Investigation Studies on Copper (II) and Cobalt (II) Complexes of Benzothiazole Cored Schiff Bases. Journal of Coordination Chemistry, 72(12); 1973–1993.
Deswal, Y., S. Asija, D. Kumar, D.K. Jindal, G. Chandan, V. Panwar, S. Saroya, and N. Kumar (2022). Transition Metal Complexes of Triazole-Based Bioactive Ligands: Synthesis, Spectral Characterization, Antimicrobial, Anticancer and Molecular Docking Studies. Research on Chemical Intermediates; 1–27.
Devi, J., S. Sharma, S. Kumar, D.K. Jindal, P.P. Dutta, and D. Kumar (2021). Transition Metal (II) Complexes of Hydrazones Derived from Tetralone: Synthesis, Spectral Characterization, In Vitro Antimicrobial and Cytotoxic Studies. Research on Chemical Intermediates, 47; 2433–2467.
Iftikhar, B., K. Javed, M.S.U. Khan, Z. Akhter, B. Mirza, and V. Mckee (2018). Synthesis, Characterization and Biological Assay of Salicylaldehyde Schiff Base Cu (II) Complexes and Their Precursors. Journal of Molecular Structure, 1155; 337–348.
Liu, X. and J.R. Hamon (2019). Recent Developments in Penta-, Hexa- and Heptadentate Schiff Base Ligands and Their Metal Complexes. Coordination Chemistry Reviews, 389; 94–118.
Lotfi, A. (2020). Synthesis and Characterization of Novel Mixed Complexes Derived from 2-Aminomethylbenzimidazole and 2-(1H-Benzimidazol-2-yl) Aniline and Theoretical Prediction of Toxicity. Egyptian Journal of Chemistry, 63; 4757–4767.
Mishra, N., K. Kumar, H. Pandey, S.R. Anand, R. Yadav, S.P. Srivastava, and R. Pandey (2020). Synthesis, Characterization, Optical and Anti-Bacterial Properties of Benzothiazole Schiff Bases and Their Lanthanide (III) Complexes. Journal of Saudi Chemical Society, 24(12); 925–933.
Raji, S.Q. and A.T. Bader (2024). Synthesis and Characterization of Ni (II) Schiff Base Complex as a Precursor for NiO Nanoparticles and an Investigation of Their Corrosion Inhibition. Science and Technology Indonesia, 9(4); 914–928.
Rana, M.S., N.M.A. Rayhan, M.S.H. Emon, M.T. Islam, K. Rathry, M.M. Hasan, M.M.I. Mansur, B.C. Srijon, M.S. Islam, A. Ray, and M.A. Rakib (2024). Antioxidant Activity of Schiff Base Ligands Using the DPPH Scavenging Assay: An Updated Review. RSC Advances, 14; 33094–33123.
Shiju, C., D. Arish, and S. Kumaresan (2020). Novel Water Soluble Schiff Base Metal Complexes: Synthesis, Characterization, Antimicrobial-, DNA Cleavage, and Anticancer Activity. Journal of Molecular Structure, 1221; 128770.
Singh, K. and I. Bala (2023). Structural Investigations, DFT, Anti-Oxidant and α-Amylase Inhibitory Activity of Metal Complexes of Benzothiazole Based Hydrazone. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 103(7); 301–316.
Supuran, C.T., M. Barboiu, C. Luca, E. Pop, M.E. Brewster, and A. Dinculescu (1996). Synthesis of Mono and Bis Pyridinium Salt Derivatives of 2-Amino-5-(2-Aminoethyl)- and 2-Amino-5-(3-Aminopropyl)-1,3,4-Thiadiazole and Their Interaction with Isozyme II. European Journal of Medicinal Chemistry, 31; 597–606.
Turan-Zitouni, G., M.D. Altıntop, A. Özdemir, Z.A. Kaplancıklı, G.A. Çiftçi, and H.E. Temel (2016). Synthesis and Evaluation of Bis-Thiazole Derivatives as New Anticancer Agents. European Journal of Medicinal Chemistry, 107; 288–294.
Vamsikrishna, N., M.P. Kumar, G. Ramesh, N. Ganji, S. Daravath, and Shivaraj (2017). DNA Interactions and Biocidal Activity of Metal Complexes of Benzothiazole Schiff Bases: Synthesis, Characterization and Validation. Journal of Chemical Sciences, 129; 609–622.
Venkatraman, R., M.A. Hossain, and F.R. Fronczek (2010). {4-Phenyl-1-[1-(1,3-Thiazol-2-yl) Ethylidene] Thiosemicarbazidato}{4-Phenyl-1-[1-(1,3-Thiazol-2-yl) Ethylidene] Thiosemicarbazide} Nickel (II) Chloride Monohydrate. Structure Reports, 66; m541–m542.
Vigato, P.A. and S. Tamburini (2004). The Challenge of Cyclic and Acyclic Schiff Bases and Related Derivatives. Coordination Chemistry Reviews, 248; 1717–2128.
Yenilmez, H.Y., A.M. Sevim, and Z.A. Bayır (2013). Synthesis and Photophysics of New Metallo Phthalocyanine Complexes with Thiazole Groups and Their Fluorescence Quenching Studies with Benzoquinone. Synthetic Metals, 176; 11–17.
Yin, L., S. Zhang, T. Zhou, H. Zhen’guang, and S. Zhang (2023). Synthesis, Characterization, and Anticancer Activity of Mononuclear Schiff-Base Metal Complexes. Journal of Molecular Structure, 1275; 134683.
Zheng, Y., J. Li, W. Wu, C. Qi, and H. Jiang (2024). Oxygen, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect. Organic Process Research & Development, 28; 2988–3025.
Authors
Periyasamy, K., & Nainamalai, V. (2025). Synthesis, Characterization, Anticancer, and Molecular Docking Investigations of Benzothiazole Metal Complexes. Science and Technology Indonesia, 10(4), 1120–1129. https://doi.org/10.26554/sti.2025.10.4.1120-1129
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