Synthesis, Identification, and Biological Evaluation of Some Metal Ions Complexes Derived from Thymine-Azo Ligand

https://doi.org/10.22146/ijc.103682

Tabarak Taha Mizher(1*), Alyaa Khider Abbas(2)

(1) Department of Chemistry, College of Science, University of Baghdad, Al Jadriya Street, Baghdad 10071, Iraq
(2) Department of Chemistry, College of Science, University of Baghdad, Al Jadriya Street, Baghdad 10071, Iraq
(*) Corresponding Author

Abstract


New series of Ag(I) and Cu(II) complexes with general formulas of Ag(AAT)(H2O)]NO3·H2O and Cu(AAT)(H2O)3]Cl2·H2O from 6-((5-chloro-2-hydroxyphenyl)diazenyl)-5-methylpyrimidine-2,4(1H,3H)-dione (AAT) were synthesized. By using FTIR, UV-vis, MS, and 1H-NMR, their molecular structural and binding properties were confirmed, which indicated that the AAT ligand acts as a neutral tridentate O, N, and N, forming tetrahedral geometry with Ag-AAT and distorted octahedral with Cu-AAT. Additionally, C.H.N analysis, magnetic susceptibility, molar conductivity, and thermal analysis were used to identify the synthesized compounds' stability and molecular formula and explore their physical and chemical properties. XRD and AFM were also examined, where the ligand and Cu(II) complex exhibited nanoscale properties. The biological potential of these compounds was also investigated by testing their antioxidant activity. Furthermore, the Cu(II) complex was investigated for its effects on liver function and histological abnormalities in male albino rats. The enzymatic activities of liver markers such as glutamic-oxaloacetic transaminase, glutamic-pyruvate transaminase, and alkaline phosphatase were measured to determine the hepatoprotective properties. Histological investigations of liver tissues revealed further evidence for the biological effects of the copper compound. These results revealed the potential applications of Ag(I) and Cu(II) complexes derived from the thymine-azo ligand.

Keywords


antioxidant; histological activity; spectroscopic study; thymine azo ligand



References

[1] Lee, T.H., Kim, W.R., and Poterucha, J.J., 2012, Evaluation of elevated liver enzymes, Clin. Liver Dis., 16 (2), 183–198.

[2] Abdalah, M.E., Al-Ezzy, R.M., and Okhti, Z.A., 2018, Protective role of Viola odorata against hepatotoxicity induced by methotrexate in albino male mice, J. Pharm. Sci. Res., 10 (11), 2775–2782.

[3] Manhee, T.Q., and Alabdali, A.J.,2024 Synthesis, characterization and anticancer activity of Ni(II), Cu(II), Pd(II) and Au(III) complexes derived from novel Mannich base, Vietnam J. Chem., 62 (2), 201–210.

[4] Maliyappa, M.R., Keshavayya, J., Mahanthappa, M., Shivaraj, Y., and Basavarajappa, K.V., 2020, 6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: Synthesis, characterization, electrochemical and DFT studies, J. Mol. Struct., 1199, 126959.

[5] Matada, M.N., Jathi, K., Malingappa, P., and Pushpavathi, I., 2020, Synthesis, spectroscopic, DFT and electrochemical studies of heterocyclic azo dyes derived from 1-{[(E)-benzylideneamino](phenyl) methyl} naphthalen-2-ol, Chem. Data Collect., 25, 100314.

[6] Abdnoor, Z.M., and Alabdali, A.J., 2019, Synthesis, characterization, and anticancer activity of some azole‐heterocyclic complexes with gold(III), palladium(II), nickel(II), and copper(II) metal ions, J. Chin. Chem. Soc., 66 (11), 1474–1483.

[7] Gaber, M., Fathalla, S.K., and El‐Ghamry, H.A., 2019, 2,4‐Dihydroxy‐5‐[(5‐mercapto‐1H‐1,2,4‐triazole‐3‐yl)diazenyl]benzaldehyde acetato, chloro and nitrato Cu(II) complexes: Synthesis, structural characterization, DNA binding and anticancer and antimicrobial activity, Appl. Organomet. Chem., 33, e4707.

[8] Saad, F.A., El‐Ghamry, H.A., and Kassem, M.A., 2019, Synthesis, structural characterization and DNA binding affinity of new bioactive nano‐sized transition metal complexes with sulfathiazole azo dye for therapeutic applications, Appl. Organomet. Chem., 33 (7), e4965.

[9] El-Deen, I.M., Shoair, A.F., and El-Bindary, M.A., 2019, Synthesis, characterization and biological properties of oxovanadium(IV) complexes, J. Mol. Struct., 1180, 420–437.

[10] Khan, M.N., Parmar, D.K., and Das, D., 2021, Recent applications of azo dyes: A paradigm shift from medicinal chemistry to biomedical sciences, Mini-Rev. Med. Chem., 21 (9), 1071–1084.

[11] Abbas, A.K., 2022, Synthesis, spectroscopic, thermal and biological studies of some novel metal ions complexes, MINAR Int. J. Appl. Sci. Technol., 4 (3), 331–348.

[12] Ullah, Q., Khan, S.A., and Mohammad, A., 2021, Applications of green solvents in thin-layer chromatography (TLC)—An overview, J. Planar Chromatogr. - Mod. TLC, 34 (1), 5–29.

[13] Thilagavathi, T., Kathiravan, G., and Srinivasan, K., 2016, Antioxidant activity and synthesis of silver nanoparticles using the leaf extract of Limonia acidissima, Int. J. Pharma Bio Sci., 7, 201–205.

[14] Al-Ezzy, R.M., Hassan, Z.Y.M., and Al-Jumaili, F.T.O., 2016, Hematological toxic effect and the frequency of micronucleus formation of different doses of cyproheptadine on albino male mice blood picture, Iraqi J. Hematol., 5 (2), 149–153.

[15] Al-Ezzy, R.M., Al Anee, R.S.A., and Kathum, O.A., 2017, Hepatoprotective effects of Achillea millefolium methanolic extract on carbon tetrachloride induced hepatotoxicity on albino male mice, Int. J. Adv. Res. Biol. Sci., 4 (8), 98–109.

[16] Ibrahim, N.A., Al-Shmgani, H.S., and Ibrahim, R., 2017, Cytarabine induced reproductive histopathological changes in albino male mice, J. Biotechnol. Res. Cent., 11 (1), 6–12.

[17] Al-Ezzy, R.M., Soud, S.A., and Sadoon, Z.M., 2019, Histopathological study and oxidative stress, antioxidants parameters and liver enzymes activity determination of Cyperus methanolic extract and glucophage drug on albino male mice, Am. J. Biosci. Bioeng., 7 (1), 10–15.

[18] Salih, B.D., Dalaf, A.H., Alheety, M.A., Rashed, W.M., and Abdullah, I.Q., 2021, Biological activity and laser efficacy of new Co(II), Ni(II), Cu(II), Mn(II) and Zn(II) complexes with phthalic anhydride, Mater. Today: Proc., 43, 869–874.

[19] Mallikarjuna, N.M., Keshavayya, J., Maliyappa, M.R., Shoukat Ali, R.A., and Venkatesh, T., 2018, Synthesis, characterization, thermal and biological evaluation of Cu(II), Co(II) and Ni(II) complexes of azo dye ligand containing sulfamethaxazole moiety, J. Mol. Struct., 1165, 28–36.

[20] Abbas, A.K., and Fadhil, A.E., 2024, Preparation, structural identification, and biomedical evaluation of some new complexes, Indones. J. Chem., 24 (6), 1730–1742.

[21] Gaber, M., El-Wakiel, N., and Hemeda, O. M., 2019, Cr(III), Mn(II), Co(II), Ni(II) and Cu(II) complexes of 7-((1H-benzo[d]imidazol-2-yl)diazenyl)-5-nitroquinolin-8-ol. synthesis, thermal, spectral, electrical measurements, molecular modeling and biological activity, J. Mol. Struct., 1180, 318–329.

[22] Abbas, A.K., 2015, Lanthanide ions complexes of 2-(4-amino antipyrine)-L-tryptophane (AAT): Preparation, Identification and Antimicrobial Assay, Iraqi J. Sci., 56 (4c), 3297–3309.

[23] Noriega, P., Gortaire, G., and Osorio, E., 2022, “Mass Spectrometry and Its Importance for the Analysis and Discovery of Active Molecules in Natural Products” in Natural Drugs from Plants, Eds. El-Shemy, H., IntechOpen, Rijeka, Croatia.

[24] Hammoda, R.G., and Shaalan, N., 2024, Synthesis, spectroscopy and biological activity study of some new complexes with Schiff base derived from malonic acid dihydrazide with 2-pyridine crboxaldehyde, Baghdad Sci. J., 21 (5), 1577–1591.

[25] Hussein, K.A., Shaalan, N., Lafta, A.K., and Al Akeedi, J.M., 2024, Preparation, characterization, and biological activity of La(III), Nd(III), Er(III), Gd(III), and Dy(III) complexes with Schiff base resulted from reaction of 4-antipyrinecarboxaldehyde and 2-aminobenzothiazole, Indones. J. Chem., 24, 358–369.

[26] Prakash, S., Somiya, G., Elavarasan, N., Subashini, K., Kanaga, S., Dhandapani, R., Sivanandam, M., Kumaradhas, P., Thirunavukkarasu, C., and Sujatha, V., 2021, Synthesis and characterization of novel bioactive azo compounds fused with benzothiazole and their versatile biological applications, J. Mol. Struct., 1224, 129016.

[27] Masoud, M.S., Ali, A.E., Elasala, G.S., and Kolkaila, S.A., 2017, Spectroscopic studies and thermal analysis on cefoperazone metal complexes, J. Chem. Pharm. Res., 9 (4), 171–179.

[28] Al-Lami, N.J., 2015, New imidazo[2,1-b]naphtha[2,1-d][1,3]thiazole derivatives: Synthesis, antimicrobial and antifungal activity, Iraqi J. Sci., 56 (4c), 3274–3284.

[29] Bouhdada, M., and EL Amane, M., 2017, Synthesis, characterization and spectroscopic properties of the hydrazodye and new hydrazodye-metal complexes, J. Mol. Struct., 1150, 419–426.

[30] Patel, K.D., and Patel, H.S., 2017, Synthesis, spectroscopic characterization and thermal studies of some divalent transition metal complexes of 8-hydroxyquinoline, Arabian J. Chem., 10, S1328–S1335.

[31] Štoček, J.R., and Dračínský, M., 2020, Tautomerism of guanine analogues, Biomolecules, 10 (2), 170.

[32] Mahmoud, W.A., Ali, A.A.M., and Kareem, T.A., 2015, Preparation and spectral characterization of new azo imidazole ligand 2-[(2'-cyano phenyl) azo]-4,5-diphenyl imidazole and its complexes with Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) ions, Baghdad Sci. J., 12 (1), 96–109.

[33] Northridge, M.E., Kumar, A., and Kaur, R., 2020, Disparities in access to oral health care, Annu. Rev. Public Health, 41, 513–535.

[34] Ali, A.A., Al-Hassani, R.M., Hussain, D.H., Rheima, A.M., and Meteab, H.S., 2020, Synthesis, spectroscopic, characterization, pharmacological evaluation, and cytotoxicity assays of novel nano and micro scale of copper(II) complexes against human breast cancer cells, Drug Invent. Today, 14 (1), 31–39.

[35] Hessoon, H.M., and Abbas, H.M., 2024, Synthesis and characterization of a novel dapsone-derived bisazo ligand and its gold(III) complex, with evaluation of its antioxidant and anticancer activities, Indones. J. Chem., 24 (2), 481–491.

[36] Claridge, T.D.W., 2016, High-Resolution NMR Techniques in Organic Chemistry, 3rd Ed., Elsevier, Radarweg, Amsterdam, Netherlands.

[37] Basak, M., Rahman, M.F., Ahmed, M.F., Biswas, B., and Sharmin, N., 2022, The use of X-ray diffraction peak profile analysis to determine the structural parameters of cobalt ferrite nanoparticles using Debye-Scherrer, Williamson-Hall, Halder-Wagner and Size-strain plot: Different precipitating agent approach, J. Alloys Compd., 895, 162694.

[38] Stepanov, S., 2021, New developments including X-ray standing waves in the dynamical Bragg diffraction program of X-ray server, J. Appl. Crystallogr., 54, 1530–1534.

[39] Bhushan, B., 2017, Springer Handbook of Nanotechnology, 4th Ed., Springer, Springer-Verlag GmbH, Germany.

[40] Kosareva, E.K., Pivkina, A.N., and Muravyev, N.V., 2022, Atomic force microscopy in energetic materials research: A review, Energy Mater. Front., 3 (4), 290–302.

[41] Datta, S., Aggarwal, D., Sehrawat, N., Yadav, M., Sharma, V., Sharma, A., Zghair, A.N., Dhama, K., Sharma, A., Kumar, V., Sharma, A.K., and Wang, H., 2023, Hepatoprotective effects of natural drugs: Current trends, scope, relevance and future perspectives, Phytomedicine, 121, 155100.



DOI: https://doi.org/10.22146/ijc.103682

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