Anticancer Activity against Brain Cancer Using Ni (II), Cu (II), Pd (II) and Au (III) Complexes Derived from Novel Mannich Base
Main Article Content
Keywords
Mannich Base, intermolecular cyclization, Ni(II), Cu(II), Pd(II), Au(III) Complexes
Abstract
New four metal ion complexes of Ni(II), Cu(II), Pd(II) and Au(III) were derived from the tridentate ligand 3-((3-(4-hydroxyphenyl)-5-mercapto-4H-1,2,4-triazol-4-yl)amino)benzofuran-2(3H)-one (L), which synthesized using condensation reaction of formaldehyde, acetone and secondary amine (Mannich reaction). The secondary amine is a heterocyclic compound possesses two rings. The structures of the new compounds and metal ion complexes were characterized using elemental analysis (C.H.N.S), FT-IR, UV-Vis spectroscopy, thermal gravimetric analysis (TGA), flame atomic absorption, molar conductivity and magnetic susceptibility measurements. Accordingly, the probable geometries of these complexes were suggested as square planner and all complexes were found to be of electrolytic nature. Thus, chemical formula; [NiLCl] Cl.6H2O, [CuLCl]Cl.H2O, [PdLCl]Cl.2H2O and [AuLCl]Cl2.3H2O. Cytotoxic effect studding was applied onbrain cancer cell line (AMJM) at using the MMT method for complexes and L. Gold (III) complex has the highest cytotoxicity among all tested compounds.
References
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35. Jørgensen, C.K., Absorption spectra and chemical bonding in complexes. 2015: Elsevier.
36. Figgis, B.N. and I. Goodman, Introduction to ligand fields. 1966: Interscience publishers.
37. Rasheed, R.T., Synthesis of new metal complexes derived from 5-nitroso 8-hydroxy quinoline and Salicylidene P-imino acetophenone with Fe (II), Co (II), Ni (II) and Cu (II) ions. Journal of Al-Nahrain University, 2012. 15(4): p. 68-73.
38. Tiera, M.J., et al., Synthesis and characterization of phosphorylcholine-substituted chitosans soluble in physiological pH conditions. Biomacromolecules, 2006. 7(11): p. 3151-3156.
39. Abdel-Aziz, M., et al., Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: synthesis, physicochemical properties, anticancer and topoisomerase I and II inhibitory activity. European journal of medicinal chemistry, 2013. 69: p. 427-438.
40. Chen, D., et al., Inhibition of prostate cancer cellular proteasome activity by a pyrrolidine dithiocarbamate-copper complex is associated with suppression of proliferation and induction of apoptosis. Front Biosci, 2005. 10(2): p. 2932-9.
41. Sun, R.W.-Y., et al., Some uses of transition metal complexes as anti-cancer and anti-HIV agents. Dalton Transactions, 2007(43): p. 4884-4892.
42. Abdnoor, Z.M. and A.J. Alabdali, Synthesis, characterization, and anticancer activity of some azole‐heterocyclic complexes with gold (III), palladium (II), nickel (II), and copper (II) metal ions. Journal of the Chinese Chemical Society, 2019. 66(11): p. 1474-1483.
43. Tugrak, M., et al., Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2, 3-dihydroinden-1-one and evaluation of their cytotoxicities. Journal of Enzyme Inhibition and Medicinal Chemistry, 2016. 31(5): p. 818-823
2. Farrell, N., Biomedical uses and applications of inorganic chemistry. An overview. Coordination Chemistry Reviews, 2002. 232(1-2): p. 1-4.
3. Crabtree, R.H., The organometallic chemistry of the transition metals. 2009: John Wiley & Sons.
4. Lyčka, A., et al., 27Al, 15N, 13C and 1H NMR spectra and negative-ion electrospray mass spectra of the 2: 1 aluminium (III) complexes of azo dyes derived from anthranilic acid. Dyes and pigments, 2001. 50(3): p. 203-209.
5. Crichton, R. and R. Louro, Practical approaches to biological inorganic chemistry. 2019: Elsevier.
6. Kaim, W., B. Schwederski, and A. Klein, Bioinorganic Chemistry--Inorganic Elements in the Chemistry of Life: An Introduction and Guide. 2013: John Wiley & Sons.
7. Verma, C., et al., Pyridine based N-heterocyclic compounds as aqueous phase corrosion inhibitors: a review. Journal of the Taiwan Institute of Chemical Engineers, 2020. 117: p. 265-277.
8. Goni, L.K., et al., Bioinspired heterocyclic compounds as corrosion inhibitors: a comprehensive review. Chemistry–An Asian Journal, 2021. 16(11): p. 1324-1364.
9. Maeng, S.K., et al., Occurrence and fate of bulk organic matter and pharmaceutically active compounds in managed aquifer recharge: a review. Water Research, 2011. 45(10): p. 3015-3033.
10. Omar, A., REVIEW ARTICLE; ANTICANCER ACTIVITIES OF SOME FUSED HETEROCYCLIC MOIETIES CONTAINING NITROGEN AND/OR SULFUR HETEROATOMS. Al-Azhar Journal of Pharmaceutical Sciences, 2020. 62(2): p. 39-54.
11. Hossain, M. and A.K. Nanda, A review on heterocyclic: synthesis and their application in medicinal chemistry of imidazole moiety. Science, 2018. 6(5): p. 83-94.
12. Ali, K. and A.S. Alimuddin, Short review on 1, 2, 4-Triazole with various pharmacological activity. SD Int. J. Pharm. Sci, 2018. 1(1): p. 14-22.
13. Zafar, W., S.H. Sumrra, and Z.H. Chohan, A review: pharmacological aspects of metal based 1, 2, 4-triazole derived Schiff bases. European journal of medicinal chemistry, 2021. 222: p. 113602.
14. Prasanna, C.A. and A. Sharma, Pharmacological Exploration of Triazole-based Therapeutics for Alzheimer’s Disease: An Overview. Current Drug Targets, 2022. 23(9): p. 933-953.
15. Maria, K., H.-L. Dimitra, and G. Maria, Synthesis and anti-inflammatory activity of chalcones and related Mannich bases. Medicinal chemistry (Shariqah (United Arab Emirates)), 2008. 4(6): p. 586-596.
16. El-Gendy, A.A. and H.A. El-Banna, Synthesis and antihypertensive activity of certain Mannich Bases of 2-ethoxycarbonylindoles and 5 H-pyridazino [4, 5-b] indoles. Archives of Pharmacal Research, 2001. 24: p. 21-26.
17. Buravlev, E.V., et al., Novel Mannich bases of α-and γ-mangostins: synthesis and evaluation of antioxidant and membrane-protective activity. European journal of medicinal chemistry, 2018. 152: p. 10-20.
18. Abdel-Rahman, I.M., et al., Novel Mannich bases of ciprofloxacin with improved physicochemical properties, antibacterial, anticancer activities and caspase-3 mediated apoptosis. Bioorganic Chemistry, 2021. 107: p. 104629.
19. M Patel, H., K. D Patel, and H. D Patel, Facile synthesis and biological evaluation of New Mannich products as potential antibacterial, antifungal and antituberculosis agents: molecular docking study. Current Bioactive Compounds, 2017. 13(1): p. 47-58.
20. Kalaivanan, C., et al., Novel Cu (II) and Ni (II) complexes of nicotinamide based Mannich base: Synthesis, characterization, DFT calculation, DNA binding, molecular docking, antioxidant, antimicrobial activities. Journal of Molecular Liquids, 2020. 320: p. 114423.
21. Zulfareen, N., et al., Adsorption and quantum chemical studies on the inhibition potential of Mannich base for the corrosion of brass in acid medium. Arabian Journal for Science and Engineering, 2017. 42(1): p. 125-138.
22. Al-Shammari, A.M., et al., In vitro synergistic enhancement of Newcastle Disease Virus to 5-fluorouracil cytotoxicity against tumor cells. Biomedicines, 2016. 4(1): p. 3.
23. Liu, Y., et al., Synthesis of novel ferrocenyl Mannich bases and their antibacterial activities. Journal of Molecular Structure, 2018. 1157: p. 482-485.
24. Spinu, C. and A. Kriza, Co (II), Ni (II) and Cu (II) complexes of bidentate Schiff bases. Acta Chimica Slovenica, 2000. 47(2): p. 179-186.
25. Yousef, T.A., G.M. Abu El-Reash, and R.M. El Morshedy, Structural, spectral analysis and DNA studies of heterocyclic thiosemicarbazone ligand and its Cr(III), Fe(III), Co(II) Hg(II), and U(VI) complexes. Journal of Molecular Structure, 2013. 1045: p. 145-159.
26. Panchal, P., et al., Coordination Polymeric Assemblies of some d‐Block Elements with Schiff Bases and its Characterization. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 2007. 44(4): p. 373-378.
27. Shupack, S., et al., The electronic structures of square-planar metal complexes. V. Spectral properties of the maleonitriledithiolate complexes of nickel, palladium, and platinum. Journal of the American Chemical Society, 1964. 86(21): p. 4594-4602.
28. Bosnich, B., An interpretation of the circular dichroism and electronic spectra of salicylaldimine complexes of square-coplanar diamagnetic nickel (II). Journal of the American Chemical Society, 1968. 90(3): p. 627-632.
29. Jeslin Kanaga Inba, P., et al., Cu (II), Ni (II), and Zn (II) complexes of salan-type ligand containing ester groups: synthesis, characterization, electrochemical properties, and in vitro biological activities. Bioinorganic chemistry and applications, 2013. 2013. 30. Mohod, R., Synthesis, characterization and thermal studies of 1-substituted-3-formamidinothiocarbamides Complexes. 2018.
31. Lever, A.P., Inorganic electronic spectroscopy. Studies in physical and theoretical chemistry, 1984. 33.
32. Rush, R.M., D.S. Martin, and R.G. LeGrand, Polarized crystal spectra of potassium tetrachloropalladate (II) and potassium tetrabromopalladate (II). Inorganic Chemistry, 1975. 14(10): p. 2543-2550.
33. Sekhar, E.V., K. Jayaveera, and S. Srihari, Synthesis and characterization of metal complexes of 4-((furan-2-ylmethylene) amino) benzene sulfonamide. IOSR J. Appl. Chem. Ver. I., 2015. 8: p. 42-45.
34. Mostafa MH, K., et al., 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. 2012.
35. Jørgensen, C.K., Absorption spectra and chemical bonding in complexes. 2015: Elsevier.
36. Figgis, B.N. and I. Goodman, Introduction to ligand fields. 1966: Interscience publishers.
37. Rasheed, R.T., Synthesis of new metal complexes derived from 5-nitroso 8-hydroxy quinoline and Salicylidene P-imino acetophenone with Fe (II), Co (II), Ni (II) and Cu (II) ions. Journal of Al-Nahrain University, 2012. 15(4): p. 68-73.
38. Tiera, M.J., et al., Synthesis and characterization of phosphorylcholine-substituted chitosans soluble in physiological pH conditions. Biomacromolecules, 2006. 7(11): p. 3151-3156.
39. Abdel-Aziz, M., et al., Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: synthesis, physicochemical properties, anticancer and topoisomerase I and II inhibitory activity. European journal of medicinal chemistry, 2013. 69: p. 427-438.
40. Chen, D., et al., Inhibition of prostate cancer cellular proteasome activity by a pyrrolidine dithiocarbamate-copper complex is associated with suppression of proliferation and induction of apoptosis. Front Biosci, 2005. 10(2): p. 2932-9.
41. Sun, R.W.-Y., et al., Some uses of transition metal complexes as anti-cancer and anti-HIV agents. Dalton Transactions, 2007(43): p. 4884-4892.
42. Abdnoor, Z.M. and A.J. Alabdali, Synthesis, characterization, and anticancer activity of some azole‐heterocyclic complexes with gold (III), palladium (II), nickel (II), and copper (II) metal ions. Journal of the Chinese Chemical Society, 2019. 66(11): p. 1474-1483.
43. Tugrak, M., et al., Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2, 3-dihydroinden-1-one and evaluation of their cytotoxicities. Journal of Enzyme Inhibition and Medicinal Chemistry, 2016. 31(5): p. 818-823
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Apr 18, 2023
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Tamara Q. Manhee, & Ammar J. Alabdali. (2023). Anticancer Activity against Brain Cancer Using Ni (II), Cu (II), Pd (II) and Au (III) Complexes Derived from Novel Mannich Base. Journal of Population Therapeutics and Clinical Pharmacology, 30(8), 87–100. https://doi.org/10.47750/jptcp.2023.30.08.010
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