Synthesis and Characterization of a Novel Dapsone-Derived Bisazo Ligand and Its Gold(III) Complex, with Evaluation of Its Antioxidant and Anticancer Activities

https://doi.org/10.22146/ijc.89115

Haider Muhammad Hessoon(1), Hussam Muhammad Abbas(2*)

(1) Department of Chemistry, College of Science, University of Al-Qadisiyah, Al-Diwaniyah 58002, Iraq
(2) Department of Chemistry, College of Science, University of Al-Qadisiyah, Al-Diwaniyah 58002, Iraq
(*) Corresponding Author

Abstract


In this study, we successfully synthesized a novel bisazo ligand derived from dapsone and explored its potential as a versatile coordination compound. Furthermore, we formed an Au(III) complex with this bisazo ligand and extensively characterized it using a range of analytical techniques, including UV-visible, FTIR, NMR spectroscopy, mass spectrometry, X-ray diffraction, and thermal analysis (TGA). The Au(III) complex exhibited significant inhibitory effects on liver cancer cells (HEPG2), achieving a maximum inhibition rate of 56.45% at a concentration of 400 µg mL−1. Interestingly, the complex showed comparatively milder effects on normal cells (HDFn). Both the ligand and the gold complex demonstrated antioxidant properties, with ascorbic acid serving as a reference for comparison. These findings underscore the promising potential of the synthesized bisazo ligand and its Au(III) complex in medicinal chemistry, particularly for cancer treatment and antioxidant applications. Additionally, these compounds exhibit nanoscale characteristics, further enhancing their relevance in various scientific and technological fields.

Keywords


dapsone; gold; liver cancer cells; anticancer; antioxidant



References

[1] Gupta, P., Drexler, H.J., Wingad, R., Wass, D., Baráth, E., Beweries, T., and Hering-Junghans, C., 2023, P,N-type phosphaalkene-based Ir(I) complexes: Synthesis, coordination chemistry, and catalytic applications, Inorg. Chem. Front., 10 (8), 2285–2293.

[2] Shanmugaraju, S., 2022, Supramolecular Coordination Complexes: Design, Synthesis, and Applications, Elsevier, Amsterdam, Netherlands.

[3] Reddy, K.H., 1999, Coordination compounds in biology, Resonance, 4 (6), 67–77.

[4] Adeyemi, J.O., and Onwudiwe, D.C., 2020, The mechanisms of action involving dithiocarbamate complexes in biological systems, Inorg. Chim. Acta, 511, 119809.

[5] Mortadza, N.A., Ngaini, Z., and Arif, M.A.M., 2021, Synthesis of silver(I) coordination of aspirinate azo ligands as potential antibacterial agents, Defect Diffus. Forum, 411, 17–24.

[6] Sahoo, J., and Paidesetty, S.K., 2016, Medicinal interest of azo-based organic compounds: A review, Asian J. Pharm. Clin. Res., 9 (7), 33–39.

[7] Shikhaliyev, N.Q., Kuznetsov, M.L., Maharramov, A.M., Gurbanov, A.V, Ahmadova, N.E., Nenajdenko, V.G., Mahmudov, K.T., and Pombeiro, A.J.L., 2019, Noncovalent interactions in the design of bis-azo dyes, CrystEngComm, 21 (34), 5032–5038.

[8] Léonard, E., and Fayeulle, A., 2021, Azo-dyes-grafted oligosaccharides—From synthesis to applications, Molecules, 26 (11), 3063.

[9] Bafana, A., Devi, S.S., and Chakrabarti, T., 2011, Azo dyes: Past, present and the future, Environ. Rev., 19, 350–371.

[10] Zollinger, H., 2003, Color Chemistry: Syntheses, Properties and Applications of Organic Dyes and Pigments, Wiley-VCH, Weinheim, Germany.

[11] Ali, Y., Abd Hamid, S., and Rashid, U., 2018, Biomedical applications of aromatic azo compounds, Mini-Rev. Med. Chem., 18 (18), 1548–1558.

[12] Karjigi, S., Murthy, S.C., Kallappa, H., Kusuma, M.R., Aruna, B., and Reddy, Y.N., 2016, Dapsone: An update, Indian J. Lepr, 87 (4), 233–239.

[13] Wozel, G., and Blasum, C., 2014, Dapsone in dermatology and beyond, Arch. Dermatol. Res., 306 (2), 103–124.

[14] Oliveira, F.R., Pessoa, M.C., Albuquerque, R.F.V., Schalcher, T.R., and Monteiro, M.C., 2014, Clinical applications and methemoglobinemia induced by dapsone, J. Braz. Chem. Soc., 25 (10), 1770–1779.

[15] Ghaoui, N., Hanna, E., Abbas, O., Kibbi, A.G., and Kurban, M., 2020, Update on the use of dapsone in dermatology, Int. J. Dermatol., 59 (7), 787–795.

[16] Hughes, W.T., 1998, Use of dapsone in the prevention and treatment of Pneumocystis carinii pneumonia: A review, Clin. Infect. Dis., 27 (1), 191–204.

[17] Kyhoiesh, H.A.K., and Al-Adilee, K.J., 2023, Pt(IV) and Au(III) complexes with tridentate-benzothiazole based ligand: Synthesis, characterization, biological applications (antibacterial, antifungal, antioxidant, anticancer and molecular docking) and DFT calculation, Inorg. Chim. Acta, 555, 121598.

[18] Kumar Bhaumik, P., Ghosh, K., and Chattopadhyay, S., 2021, Synthetic strategies, crystal structures and biological activities of metal complexes with the members of azole family: A review, Polyhedron, 200, 115093.

[19] Manju, M., Joshi, P., and Kumar, D., 2014, Metal complexes of biological active 2-aminothiazole derived ligands, Russ. J. Coord. Chem., 40 (7), 445–459.

[20] Gassim, F.A.Z.G., and Makkawi, A.J.J., 2023, Anticancer activity of synthesized ZnO and ZnO/AgCl nanocomposites against five human cancer cells, Indones. J. Chem., 23 (2), 333–340.

[21] Irfandi, R., Raya, I., Ahmad, A., Fudholi, A., Natsir, H., Kartina, D., Karim, H., Santi, S., and Salnus, S., 2022, Review on anticancer activity of essential metal dithiocarbamate complexes, Indones. J. Chem., 22 (6), 1722–1736.

[22] Yasir, A.F., and Jamel, H.O., 2023, Synthesis of a new DPTYEAP ligand and its complexes with their assessments on physical properties, antioxidant, and biological potential to treat breast cancer, Indones. J. Chem., 23 (3), 796–808.

[23] Gęgotek, A., and Skrzydlewska, E., 2023, Ascorbic acid as antioxidant, Vitam. Horm., 121, 247–270.

[24] Rahman, M.M., Islam, M.B., Biswas, M., and Khurshid Alam, A.H.M., 2015, In vitro antioxidant and free radical scavenging activity of different parts of Tabebuia pallida growing in Bangladesh, BMC Res. Notes, 8 (1), 621.

[25] Celiz, G., Renfige, M., and Finetti, M., 2020, Spectral analysis allows using the DPPH* UV–Vis assay to estimate antioxidant activity of colored compounds, Chem. Pap., 74 (9), 3101–3109.

[26] Rubab, M., Chelliah, R., and Oh, D.H., 2022, Screening for Antioxidant Activity: Diphenylpicrylhydrazine (DPPH) Assay, in Methods in Actinobacteriology, Eds. Dharumadurai, D., Springer US, New York, US, 453–454.

[27] Senthilraja, P., and Kathiresan, K., 2015, In vitro cytotoxicity MTT assay in Vero, HepG2 and MCF-7 cell lines study of marine yeast, J. Appl. Pharm. Sci., 5 (3), 80–84.

[28] Ibrahim, A.A., Kareem, M.M., Al-Noor, T.H., Al-Muhimeed, T., AlObaid, A.A., Albukhaty, S., Sulaiman, G.M., Jabir, M., Taqi, Z.J., and Sahib, U.I., 2021, Pt(II)-thiocarbohydrazone complex as cytotoxic agent and apoptosis inducer in Caov-3 and HT-29 cells through the P53 and Caspase-8 pathways, Pharmaceuticals, 14 (6), 509.

[29] Ali, I.H., Jabir, M.S., Al-Shmgani, H.S.A., Sulaiman, G.M., and Sadoon, A.H., 2018, Pathological and immunological study on infection with Escherichia coli in ale BALB/c mice, J. Phys.: Conf. Ser., 1003 (1), 012009.

[30] Jabir, M.S., Rashid, T.M., Nayef, U.M., Albukhaty, S., AlMalki, F.A., Albaqami, J., AlYamani, A.A., Taqi, Z.J., and Sulaiman, G.M., 2022, Inhibition of Staphylococcus aureus α-hemolysin production using nanocurcumin capped Au@ZnO nanocomposite, Bioinorg. Chem. Appl., 2022, 2663812.

[31] Pérez-Arantegui, J., and Laborda, F., 2019, Inorganic mass spectrometry, Phys. Sci. Rev., 4 (3), 20180003.

[32] Ferranti, P., and Picariello, G., 2016, “Mass Spectrometry: Applications” in Encyclopedia of Food and Health, Eds., Caballero, B., Finglas, P.M., and Toldrá, F., Academic Press, Oxford, UK, 654–660.

[33] Muddiman, D.C., 2018, Jürgen H. Gross: Mass spectrometry: A textbook, 3rd ed., Anal. Bioanal. Chem., 410 (8), 2051–2052.

[34] Drew, M.G.B., Murphy, B.P., Nelson, J., and Nelson, S.M., 1987, Dicopper(II) complexes of a 28-membered N8 macrocycle. Evidence for proton transfer from co-ordinated secondary amine to thiocyanate, leading to formation of an Isothiocyanic acid complex, J. Chem. Soc., Dalton Trans., (4), 873–879.

[35] Bahjat, H.H., Ismail, R.A., Sulaiman, G.M., and Jabir, M.S., 2021, Magnetic field-assisted laser ablation of titanium dioxide nanoparticles in water for anti-bacterial applications, J. Inorg. Organomet. Polym. Mater., 31 (9), 3649–3656.

[36] Jihad, M.A., Noori, F.T.M., Jabir, M.S., Albukhaty, S., AlMalki, F.A., and Alyamani, A.A., 2021, Polyethylene glycol functionalized graphene oxide nanoparticles loaded with Nigella sativa extract: A smart antibacterial therapeutic drug delivery system, Molecules, 26 (11), 3067.

[37] Tran, N.H., Kucharský, Š., Waring, T.M., Atmaca, S., and Beheim, B.A., 2021, Limited scope for group coordination in stylistic variations of kolam art, Front Psychol., 12, 742577.

[38] Lecoutre, M., Rohart, F., Huet, T.R., and Maki, A.G., 2000, Photoacoustic detection of new bands of HCN between 11 390 and 13 020 cm−1, J. Mol. Spectrosc., 203 (1), 158–164.

[39] Jabir, M.S., Nayef, U.M., Abdulkadhim, W.K., Taqi, Z.J., Sulaiman, G.M., Sahib, U.I., Al-Shammari, A.M., Wu, Y.J., El-Shazly, M., and Su, C.C., 2021, Fe3O4 Nanoparticles capped with PEG induce apoptosis in breast cancer AMJ13 cells via mitochondrial damage and reduction of NF-κB translocation, J. Inorg. Organomet. Polym. Mater., 31 (3), 1241–1259.

[40] Khashan, K.S., Abdulameer, F.A., Jabir, M.S., Hadi, A.A., and Sulaiman, G.M., 2020, Anticancer activity and toxicity of carbon nanoparticles produced by pulsed laser ablation of graphite in water, Adv. Nat. Sci: Nanosci. Nanotechnol., 11 (3), 035010.

[41] Mikheev, Y.A., and Ershov, Y.A., 2018, Assignment of the π → π* and n → π* transitions to the spectral bands of azobenzene and dimethylaminoazobenzene, Russ. J. Phys. Chem. A, 92 (8), 1499–1507.

[42] Grebenkin, S.Y., Syutkin, V.M., and Baranov, D.S., 2017, Mutual orientation of the n → π* and π → π* transition dipole moments in azo compounds: Determination by light-induced optical anisotropy, J. Photochem. Photobiol., A, 344 (1), 1–7.

[43] Mohammed, M.K.A., Mohammad, M.R., Jabir, M.S., and Ahmed, D.S., 2020, Functionalization, characterization, and antibacterial activity of single wall and multi wall carbon nanotubes, IOP Conf. Ser.: Mater. Sci. Eng., 757 (1), 012028.

[44] Khashan, K.S., Jabir, M.S., and Abdulameer, F.A., 2018, Preparation and characterization of copper oxide nanoparticles decorated carbon nanoparticles using laser ablation in liquid, J. Phys.: Conf. Ser., 1003 (1), 012100.

[45] Muniz, F.T.L., Miranda, M.A.R., Morilla dos Santos, C., and Sasaki, J.M., 2016, The Scherrer equation and the dynamical theory of X-ray diffraction, Acta Crystallogr., Sect. A: Found. Crystallogr., 72 (3), 385–390.

[46] Akbari, B., Tavandashti, M.P., and Zandrahimi, M., 2011, Particle size characterization of nanoparticles – A practical approach, Iran. J. Mater. Sci. Eng., 8 (2), 48–56.

[47] Jaillet, L., Artemova, S., and Redon, S., 2017, IM-UFF: Extending the universal force field for interactive molecular modeling, J. Mol. Graphics Modell., 77, 350–362.

[48] Fnfoon, D.Y., and Al-Adilee, K.J., 2023, Synthesis and spectral characterization of some metal complexes with new heterocyclic azo imidazole dye ligand and study biological activity as anticancer, J. Mol. Struct., 1271, 134089.

[49] Jasim, F.N., and Mohsein, H.F., 2022, Synthesis, identification and anticancer evaluation of new heterocyclic compounds derived from 2-benzimidazolylacetonitrile, HIV Nurs., 22 (2), 1410–1415.

[50] Hashim, M., and Fry, J., 2020, Evaluation of direct and indirect antioxidant properties of selected four natural chemical compounds: quercetin, epigallocatechin-3-gallate, indole-3-carbinol and sulforaphane by DPPH radical scavenging assay, J. Biomed. Res. Environ. Sci., 1 (8), 389–392.

[51] Skroza, D., Šimat, V., Vrdoljak, L., Jolić, N., Skelin, A., Čagalj, M., Frleta, R., and Generalić Mekinić, I., 2022, Investigation of antioxidant synergisms and antagonisms among phenolic acids in the model matrices using FRAP and ORAC methods, Antioxidants, 11 (9), 1784.

[52] Sönmez, F., Gür, T., and Şahin, Z., 2023, Thiophenyl-chalcone derivatives: Synthesis, antioxidant activity, FMO energies and molecular parameters, Balıkesir Üniv. Fen Bilim. Enst. Derg., 25 (1), 293–304.



DOI: https://doi.org/10.22146/ijc.89115

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