Preparation, Structural Identification, and Biomedical Evaluation of Some New Complexes

https://doi.org/10.22146/ijc.95759

Alyaa Khider Abbas(1*), Asmaa Edrees Fadhil(2)

(1) Department of Chemistry, College of Science, University of Baghdad, Al Jadriya Street, Baghdad 10071, Iraq
(2) College of Pharmacy, Al-Turath University, Al Mansour Street, Baghdad 10013, Iraq
(*) Corresponding Author

Abstract


A new nano azo ligand, [2-amino-6-oxo-6,7-dihydro-1H-purin-8-yl)diazenyl)nitrobenzene (AH), and its Ag(I), Cu(II), and Zn(II) complexes were successfully synthesized and characterized using elemental analyses, magnetic susceptibility, molar conductance, and spectroscopic techniques (FTIR, UV-vis, ¹H-NMR), along with thermal analysis. FTIR confirmed the ligand acts as a neutral N,N-bidentate. The metal-to-ligand ratio was determined to be 1:1 for Ag(I) and Zn(II) complexes and 1:2 for the Cu(II) complex. Stability constants and Gibbs free energy, assessed via spectrophotometry, indicated high stability for all complexes. SEM and X-ray diffraction revealed nanoscopic properties for the Ag(I) and Cu(II) complexes. The antimicrobial activity against Staphylococcus aureus, Klebsiella pneumoniae, and Candida albicans species showed good efficiency compared to reference drugs. The ligand also exhibited moderate antioxidant activity using the DPPH assay. Additionally, the Zn(II) complex demonstrated effective anti-inflammatory activity, promoting wound healing within 14 days, compared to 16 days with silver sulfadiazine and 18 days without treatment.


Keywords


hypoxanthine-azo ligand; anti-microbial activity; antioxidant; burn healing



References

[1] Crespi, S., Simeth, N.A., and König, B., 2019, Heteroaryl azo dyes as molecular photoswitches, Nat. Rev. Chem., 3 (3), 133–146.

[2] Akram, D., Elhaty, I.A., and AlNeyadi, S.S., 2020, Synthesis and antibacterial activity of rhodanine-based azo dyes and their use as spectrophotometric chemosensor for Fe3+ ions, Chemosensors, 8 (16), 16.

[3] Hussein, N.A., and Abbas, A.K., 2022, Synthesis, spectroscopic characterization and thermal study of some transition metal complexes derived from caffeine azo ligand with some of their applications, Eurasian Chem. Commun., 4 (1), 67–93.

[4] Jasim, D.J., and Abbas, A.K., 2022, Synthesis, identification, antibacterial, medical and dying performance studies for azo-sulfamethoxazole metal complexes, Eurasian Chem. Commun., 4 (1), 16–40.

[5] 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.

[6] Merino, E., 2011, Synthesis of azobenzenes: The coloured pieces of molecular materials, Chem. Soc. Rev., 40 (7), 3835–3853.

[7] Fadhil, A.E., and Abbas, A.K., 2023, Synthesis and structural views on new azo ligand and its metal complexes with some of their application, Iraqi J. Sci., 64 (12), 6119–6134.

[8] Toledo-Ibelles, P., Gutiérrez-Vidal, R., Calixto-Tlacomulco, S., Delgado-Coello, B., and Mas-Oliva, J., 2021, Hepatic accumulation of hypoxanthine: A link between hyperuricemia and nonalcoholic fatty liver disease, Arch. Med. Res., 52 (7), 692–702.

[9] Furuhashi, M., Koyama, M., Higashiura, Y., Murase, T., Nakamura, T., Matsumoto, M., Sakai, A., Ohnishi, H., Tanaka, M., Saitoh, S., Moniwa, N., Shimamoto, K., and Miura, T., 2020, Differential regulation of hypoxanthine and xanthine by obesity in a general population, J. Diabetes Invest., 11 (4), 878–887.

[10] Al-Assafe, A.Y., and Al-Quaba, R.A.M.S., 2024, 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, Indones. J. Chem., 24 (3), 812–821.

[11] Benkhaya, S., M'rabet, S., and El Harfi, A., 2020, Classifications, properties, recent synthesis and applications of azo dyes, Heliyon, 6 (1), e03271.

[12] Meyer Jr., A.S., and Ayres, G.H., 1957, The mole ratio method for spectrophotometric determination of complexes in solution, J. Am. Chem. Soc., 79 (1), 49–53.

[13] Volman, D.H., 1987, Gibbs energy and equilibrium: Dimensions in the Lewis equation, Thermochim. Acta, 111, 321–324.

[14] Khaleel, A.M.N., and Jaafar, M.I., 2017, Synthesis and characterization of boron and 2-aminophenol Schiff base ligands with their Cu(II) and Pt(IV) complexes and evaluation as antimicrobial agents, Orient. J. Chem., 33 (5), 2394–2404.

[15] Al-Daffay, R.K.H., and Al-Hamdani, A.A.S., 2023, Synthesis, characterization, and thermal analysis of a new acidicazo ligand's metal complexes, Baghdad Sci. J., 20 (1), 0121.

[16] 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.

[17] 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.

[18] 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 (2), 258–369.

[19] Abd, Z.Z., and Abbas, A.K., 2024, Metal complexes of adenine azo ligand: Synthesis, identification and study some of their applications, Iraqi J. Sci., 65 (3), 1212–1229.

[20] 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.

[21] Abbas, A.K., Kadhim, R.S., Khedher, R., and Latif, H.B., 2019, Synthesis, spectral and antibacterial studies of new 1-(4-Antipyrine azo)-2-hydroxy-3, 6-disulphonic acid sodium salt with group IIB metal ions, J. Global Pharma Technol., 11 (4), 375–382.

[22] Abbas, A.K., and Kadhim, R.S., 2017, Metal complexes of proline-azo dyes, synthesis, characterization, dying performance and antibacterial activity studies, Orient. J. Chem., 33 (1), 402–417.

[23] Hasan Mubark, H.M., Witwit, I.N., and Ali, A.A.M., 2020, Synthesis of new azo imidazole ligand and fabricating it’s chelate complexes with some metallic ions, J. Phys.: Conf. Ser., 1660 (1), 012031.

[24] Purwono, B., Anwar, C., and Hanapi, A., 2013, Syntheses of azo-imine derivatives from vanillin, Indones. J. Chem., 13 (1), 1–6.

[25] Abbas, A.K., and AL-Qaysi, W.W., 2023, Synthesis and characterization of novel nano azo compounds as a new pH sensor, Arabian J. Sci. Eng., 48 (1), 399–415.

[26] Shafeeulla, M., Krishnamurthy, G., Bhojynaik, H.S., and Manjuraj, T., 2017, Synthesis, cytotoxicity, and molecular docking study of complexes containing thiazole moiety, J. Turk. Chem. Soc., Sect. A, 4 (3), 787–810.

[27] Shaker, I.M., Salih, H.A., and Mahdi, S.M., 2016, Preparation and identification of new Azo (methyl-xanthine) ligands and their transition metal complexes, Int. J. ChemTech Res., 9 (10), 99–110.

[28] Abbas, N.F., and Abbas, A.K., 2020, Novel complexes of thiobarbituric acid-azo dye: Structural, spectroscopic, biological activity and dying, Biochem. Cell. Arch., 20 (1), 2419–2433.

[29] Mahmoud, S.S., and Khaleel, A.M.N., 2023, Synthesis, identification and biological study of new pharmaceutical model based on amino acids with some of its complexes, Iraqi J. Sci., 64 (11) 5501–5516.

[30] Al-Hamdani, A.A.S., and Abdulridha, M.Q., 2023, Synthesis, characterization of new metal complexes of Co(II), Cu(II), Cd(II) and Ru(III) from azo ligand 5-((2-(1H-indol-2-yl)ethyl) diazinyl)-2-aminophenol, thermal and antioxidant studies, Baghdad Sci. J., 20 (Suppl. 5), 1964–1975.

[31] AL-Qaysi, W.W., and Abbas, A.K., 2023, Novel nano Zn+2-compound from LA ligand as an acid-base indicator: Synthesis, characterization, pH sensor, and fluorescent study, Iraqi J. Sci., 64 (11), 5525–5540.

[32] 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.

[33] Zolnhofer, E.M., Wijeratne, G.B., Jackson, T.A., Fortier, S., Heinemann, F.W., Meyer, K., Krzystek, J., Ozarowski, A., Mindiola, D.J., and Telser, J., 2020, Electronic structure and magnetic properties of a titanium(II) coordination complex, Inorg. Chem., 59 (9), 6187–6201.

[34] Lađarević, J., Radovanović, L., Božić, B., Mašulović, A., Lunić, T., Radovanović, Ž., Rogan, J., and Mijin, D., 2023, New copper(II) complexes derived from azo pyridone dyes: Structure characterization, thermal properties, and molecular docking studies, Appl. Organomet. Chem., 37 (10), e7219.

[35] Emam, S.M., Abou EL-Enein, S.A., and Monir, E., 2017, Spectrochemical and thermal sudies for bivalent metal complexes of azodye ligand containing pyrimidine ring, Int. J. Eng. Res. Sci. Technol., 6 (9), 354–364.

[36] Kurutos, A., Kamounah, F.S., Dobrikov, G.M., Pittelkow, M., Sauer, S.P.A., and Hansen, P.E., 2021, Azo-hydrazone molecular switches: Synthesis and NMR conformational investigation, Magn. Reson. Chem., 59 (11), 1116–1125.

[37] Qazi, S.J.S., Rennie, A.R., Cockcroft, J.K., and Vickers, M., 2009, Use of wide-angle X-ray diffraction to measure shape and size of dispersed colloidal particles, J. Colloid Interface Sci., 338 (1), 105–110.

[38] Bragg, W.H., and Bragg, W.L., 1913, The reflection of X-rays by crystals, Proc. R. Soc. A, 88 (605), 428–438

[39] Humphreys, C.J., 2013, The significance of Bragg's law in electron diffraction and microscopy, and Bragg's second law, Acta Crystallogr., Sect. A: Found. Adv., 69 (1), 45–50.

[40] Greenberg, B., 1989, Bragg's law with refraction, Acta Crystallogr., Sect. A: Found. Adv., 45 (3), 238–241.

[41] Ghomrasni, N.B., Chivas-Joly, C., Devoille, L., Hochepied, J.F., and Feltin, N., 2020, Challenges in sample preparation for measuring nanoparticles size by scanning electron microscopy from suspensions, powder form and complex media, Powder Technol., 359, 226–237.

[42] Elsayed, E.H., Al-Wahaib, D., Ali, A.E.D., Abd-El-Nabey, B.A., and Elbadawy, H.A., 2023, Synthesis, characterization, DNA binding interactions, DFT calculations, and Covid-19 molecular docking of novel bioactive copper(I) complexes developed via unexpected reduction of azo-hydrazo ligands, BMC Chem., 17 (1), 159.

[43] AbdulRazzaq, A.B., Shami, A.M., and Ghaima, K.K., 2022, Detection of vanA and vanB genes among vancomycin resistant Staphylococcus aureus isolated from clinical samples in Baghdad hospitals, Iraqi J. Biotechnol., 21 (1), 19–25.

[44] Al-Hayali, O.Z., AL Marjani, M.F., and Maleki, A., 2023, Evaluation of Rosmarinus officinalis leaves essential oils activity against vancomycin intermediate Staphylococcus aureus (VISA) isolated from Baghdad hospital patients, Iraqi J. Sci., 64 (5), 2153–2167.

[45] Kumar, A., Sharma, P., and Sharma, P.K., 2017, Exploration of antioxidant activity of newly synthesized azo flavones and its correlation with electrochemical parameters along with the study of their redox behaviour, J. Anal. Chem., 72 (10), 1034–1044.

[46] Lestari, T., Syukur, S., Revilla, G., Rita, R.S., and Rustini, R., 2023, The burn wound healing process: A review, Int. J. Prog. Sci. Technol., 40 (1), 77–88.



DOI: https://doi.org/10.22146/ijc.95759

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