New Series of Ni(II), Cu(II), Zr(IV), Ag(I), and Cd(II) Complexes of Trimethoprim and Diamine Ligands: Synthesis, Characterization, and Biological Studies

https://doi.org/10.22146/ijc.89167

Amaal Younis Al-Assafe(1*), Rana Abdul Malik Sulaiman Al-Quaba(2)

(1) Department of Chemistry, College of Education for Pure Science, University of Mosul, Mosul 41001, Iraq
(2) Department of Chemistry, College of Science, University of Mosul, Mosul 41001, Iraq
(*) Corresponding Author

Abstract


New compounds series of [M(TMP)(en)]X·nH2O and [M(TMP)(PD)]X·nH2O, where M = Ni2+, Cu2+, Zr4+, Ag+, Cd2+, TMP = trimethoprim, en = ethylenediamine, PD = o-phenylene and X= Cl or NO3, were prepared. The compounds were characterized using techniques including melting points, conductance, elemental analysis, FTIR, NMR, and mass spectroscopy. FTIR spectra indicated TMP acted like a bi-dentate ligand, combining via the nitrogen atoms of azomethine and pyrimidine amino groups. Diamine ligands (en or o-PD) are coordinated via two nitrogen atoms. Prepared compounds showed monomeric behavior and adopted a 6-coordinate octahedral geometry based on magnetic susceptibility and UV spectra. Conductivity measurements revealed Zr(IV) compounds were 1:2 conductive, while Ag+ and Cd2+ were 1:1 conductive; Ni2+ and Cu2+ compounds were non-conductive. Antibacterial tests on compounds and ligands against Bacillus subtilis and Staphylococcus aureus demonstrated broad-spectrum antibacterial activity. The mixed metal compounds revealed an observable tendency of antibacterial activity in the order Zr > Cd = Ag > Cu, making Zr(IV) compounds the most biologically active among them against S. aureus (Gram-positive) while the same compounds showed less antibacterial activity against B. subtilis (Gram-negative) than the free ligand.


Keywords


antibacterial activity; chelating agent; diamine ligand; mixed ligands; trimethoprim



References

[1] Eugene-Osoikhia, T.T., Ojeyemi, S.A., Akong, R.A., Oyetunde, T., Onche, E.U., and Ayeni, F., 2021, Synthesis, characterisation and antimicrobial studies of metal(II) complexes of trimethoprim and 2,2'-bipyridin heterocycle, Niger. Res. J. Chem. Sci., 9 (1), 273–295.

[2] Ikpeazu, O.V., Otuokere, I.E., and Igwe, K.K., 2020, Determination of stability constant of trimethoprim-Zn(II) complex at different temperatures by continuous variation method, Int. J. Novel Res. Phys. Chem. Math., 7 (2), 1–7.

[3] Akinyele, O.F., Adejayan, S.B., Durosinmi, L.M., Ayeni, A.O., and Ajayeoba, T.A., 2020, Interactions of metal ions with trimethoprim and metformin, Int. J. ChemTech Res., 13 (2), 38–46.

[4] Lawal, A., Ayanwale, P.A., Obaleye, J.A., Rajee, A.O., Babamale, H.F., and Lawal, M., 2017, Synthesis, characterization and biological studies of mixed ligands nicotinamide-trimethoprim complexes, Int. J. Chem. Mater. Environ. Res., 4 (1), 97–101.

[5] Ahmed, F.J., AbdAlqader, B.S., Haddad, R.A., Abed, R.R., and Saleh, M.Y., 2022, Preparation and diagnosis of Zn(II), Cd(II) and Hg(II) complexes with Schiff base ligand derived from trimethoprim, Egypt. J. Chem., 65 (10), 359–366.

[6] Hassan, Z.M., Alattar, R.A., Abass, S.K., Mihsen, H.H., Abbas, Z.F., and Hussain, K.A., 2022, Synthesis, characterization and biological activity of mixed ligand (imine of benzidine and 1,10-phenanthroline) complexes with Fe(II), Co(II), Ni(II) and Cu(II), Chem. Chem. Technol., 16 (1), 15–24.

[7] Kim, H.Y., Kang, H.G., Kim, H.M., and Jeong, H.J., 2023, Antitumor activity of trimethoprim-sulfamethoxazole against melanoma skin cancer through triggering allergic reaction and promoting immunity, Int. Immunopharmacol., 123, 110742.

[8] Olagboye, S.A., and Adebawore, A.A., 2021, Synthesis, characterization, and antimicrobial studies of mixed ligand complexes of acetanilide and ampicillin with cobalt(II) and nickel(II) ions, Global Sci. J., 9 (11), 1327–1338.

[9] Bhowmick, A.C., Dev Nath, B., and Moim, M.I., 2019, Coordination complexes of transition metals and Schiff base with potent medicinal activity, Am. J. Chem., 9 (4), 109–114.

[10] Olagboye, S.A., 2022, Synthesis, characterization and antimicrobial activities of mixed ligand metals complexes with trimethoprim and potassium thiocyanate, Eur. J. Appl. Sci., 10 (1), 428–439.

[11] Albahadly, H.H., Al-Haidery, N.H., and Al-Salami., B.K., 2021, Synthesis, biological activity trimethoprim derivative and the complexes, J. Phys.: Conf. Ser., 2063 (1), 012014.

[12] Albedair, L.A., 2020, Iron(III), gold(III), platinum(IV) and palladium(II) trimethoprim drugs complexes: Synthesis, spectroscopy, morphology and anticancer assessments, Rev. Roum. Chim., 65 (12), 1145–1152.

[13] Gülcan, M., Sönmez, M., and Berber, İ., 2012, Synthesis, characterization, and antimicrobial activity of a new pyrimidine Schiff base and its Cu(II), Ni(II), Co(II), Pt(II), and Pd(II) complexes, Turk. J. Chem., 36, 189.

[14] Ahmed, E.M., Marzouk, N.A., Hessien, S.A., and Ali, A.M., 2011, Synthesis, reactions and antimicrobial activity of some new thienopyridine and thienopyrimidine derivatives, World J. Chem., 6 (1), 25–31.

[15] Mohan, C., Kumar, V., Kumari, N., Kumari, S., Yadav, J., Gandass, T., and Yadav, S., 2020, Synthesis, characterization and antibacterial activity of semicarbazide based Schiff bases and their Pb(II), Zr(IV) and U(VI) complexes, Adv. J. Chem., Sect. B, 2 (4), 187–196.

[16] Al-Mukhtar, S.E., and Aghwan, M.T., 2013, Synthesis and characterization of 3-methoxypropyldithiocarbamate complexes with iron(II), cobalt(II), nickel(II), copper(II) and zinc(II) and their adducts with nitrogen base ligands, Rafidain J. Sci., 24 (7), 50–59.

[17] Alajrawy Othman, I., Ibraheem Kaiss, R., and Hadi Huda, A., 2019, Vanadyl VO(II) with o-phenylenediamine complexes preparation and spectral characterization, Res. J. Chem. Environ., 23, 43–49.

[18] Khanmetov, A.A., Hajiyeva, K.S., Khamiyev, M.J., Alieva, R.V., Azizbeyli, H.R., and Ahmedbekova, S.F., 2018, Synthesis of zirconyl naphthenates on the basis of oil acids and their applying as complex catalytical systems in the process of oligomerization (polymerization) of ethylene, Azerb. Chem. J., 3, 91–98.

[19] Eugene-Osoikhia, T.T., Akinpelu, I.O., and Odiaka, T.I., 2019, Synthesis, characterization and antimicrobial studies of transition metal complexes of Schiff base derived from salicylaldehyde and L-tyrosine amino acid, Niger. J. Chem. Res., 24 (1), 46–56.

[20] Hammoda, R.G., and Shaalan, N., 2023, Synthesis of Zn(II) and Co(II) complexes with a Schiff base derived from malonic acid dihydrazide for photo-stabilizers of polystyrene, Indones. J. Chem., 23 (5), 1324–1340.

[21] Osowole, A.A., Wakil, S.M., and Alao, O.K., 2015, Synthesis, characterization and antimicrobial activity of some mixed trimethoprim-sulfamethoxazole metal drug complexes, World Appl. Sci. J., 33 (2), 336–342.

[22] Ishola, K.T., Olaoye, O.J., Oladipo, M.A., Odedokun, O.A., and Aboyeji, O.O., 2023, Synthesis, characterization and antimicrobial properties of mixed-ligand complexes of some metal(II) ions with barbituric acid and 1,10-phenanthroline ligands, Tanz. J. Sci., 49 (2), 491–502.

[23] Al Alsultan, F.S., and Al Quaba, R.A.S., 2021, Preparation, spectral characterization, DFT and antibacterial study of new azo ligand derived from 2-aminoanthracene-9,10-dione with antipyrine mixed ligand complexes involving 1,10-phenanthroline ligand, Egypt. J. Chem., 64 (11), 6635.

[24] Chen, Z., Lhoussain, K., Bucher, C., Jacquemin, D., Luneau, D., and Siri, O., 2020, Unconventional access to a solvatochromic nickel(II) dye featuring a coordination-induced spin crossover behavior, Dyes Pigm., 183, 108645.

[25] Numan, A.T., Atiyah, E.M., Al-Shemary, R.K., and Abd_Ulrazzaq, S.S., 2018, Composition, characterization and antibacterial activity of Mn(II), Co(II), Ni(II), Cu(II) Zn(II) and Cd(II) mixed ligand complexes Schiff base derived from trimethoprim with 8-hydroxy quinoline, J. Phys.: Conf. Ser., 1003 (10, 012016.

[26] Bhavani, S.D., Reddy, N.N., Raju, A.K., Radhika, M., Reddy, P.M., and Bhaskar, K., 2021, Synthesis and characterization of oxo zirconium(IV) complexes of polydentate ligands, AIP Conf. Proc., 2369 (1), 020044.

[27] Bormio Nunes, J.H., de Paiva, R.E.F., Cuin, A., Lustri, W.R., and Corbi, P.P., 2015, Silver complexes with sulfathiazole and sulfamethoxazole: Synthesis, spectroscopic characterization, crystal structure and antibacterial assays, Polyhedron, 85, 437–444.

[28] Hassan, M.M.A., Abbas, A.H., Abed, E.H., and Abodi, E.E., 2018, Synthesis, characterization and antimicrobial activity of V(IV), Ag(I) and Cd(II) complexes with mixed ligands derived from sulfamethoxazole and trimethoprim, Adv. Anal. Chem., 8 (2), 15–21.

[29] Alaghaz, A.N.M.A., Farag, R.S., Elnawawy, M.A., and Ekawy, A.D.A., 2016, Synthesis and spectral characterization studies of new trimethoprim-diphenyl phosphate metal complexes, Int. J. Sci. Res., 5 (1), 1220–1229.

[30] Sadeek, S.A., Abd El‐Hamid, S.M., and Zordok, W.A., 2018, Spectroscopic, DFT and antimicrobial activity of Zn(II), Zr(IV), Ce(IV) and U(VI) complexes of N,N‐ chelated 4,6‐bis(4‐chlorophenyl)‐2‐amino‐1,2‐dihydropyridine‐3‐carbinitrile, Appl. Organomet. Chem., 32 (9), e4457.

[31] Al-Alzawi, S.M., Al-Jibouri, M.N., Rasheed, A.M., and Al-Bayati, S.M., 2023, Synthesis, characterization and antimicrobial activity of complexes metal ions Ni(II), Zn(ΙΙ), Pd(II) and Pt(IV) with polydentate 1,2,4-triazole ligand, Indones. J. Chem., 23 (1), 210–218.

[32] Mahind, L.H., Waghmode, S.A., Nawale, A., Mane, V.B., and Dagade, S.P., 2015, Evaluation of antimicrobial activities of zirconium(IV) complex, IOSR J. Pharm. Biol. Sci., 5 (4), 102–105.

[33] Prakash, B.S., Raj, C.I.S., and Raj, G.A.G., 2017, Zr(IV) and Th(IV) Complexes with Schiff base ligands: Synthesis, characterization, antimicrobial studies, Int. Refereed J. Eng. Sci., 6 (10), 43–53.

[34] Abdalrazaq, E., Jbarah, A.A.Q., Al-Noor, T.H., Shinain, G.T., and Jawad, M.M., 2022, Synthesis, DFT calculations, DNA interaction, and antimicrobial studies of some mixed ligand complexes of oxalic acid and Schiff base trimethoprim with various metal ions, Indones. J. Chem., 22 (5), 1348–1364.

[35] Vitomirov, T., Čobeljić, B., Pevec, A., Radanović, D., Novaković, I., Savić, M., Anđelković, K., and Ristović, M.Š., 2023, Binuclear azide-bridged hydrazone Cu(II) complex: Synthesis, characterization and evaluation of biological activity, J. Serb. Chem. Soc., 88 (9), 877–888.

[36] Kargar, H., Ardakani, A.A., Tahir, M.N., Ashfaq, M., and Munawar, K.S., 2021, Synthesis, spectral characterization, crystal structure and antibacterial activity of nickel(II), copper(II) and zinc(II) complexes containing ONNO donor Schiff base ligands, J. Mol. Struct., 1233, 130112.

[37] Es-Sounni, B., Nakkabi, A., Bouymajane, A., Elaaraj, I., Bakhouch, M., Filali, F.R., El Yazidi, M., El Moualij, N., and Fahim, M., 2023, Synthesis, characterization, antioxidant and antibacterial activities of six metal complexes based tetradentate salen type bis-Schiff base, Biointerface Res. Appl. Chem., 13 (4), 333.



DOI: https://doi.org/10.22146/ijc.89167

Article Metrics

Abstract views : 125 | views : 21 | views : 13


Copyright (c) 2024 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.