Synthesis and Biological Activity Study of Co and Cr Complexes with α-(2-Salsayl)- N -phenyl Nitrone and Oxide Nanoparticles

Dhamiaa Abdul-Shaheed Issa; Hayder Baqer Abdullah; Faeza Abdulkareem Al-Mashal

doi:10.22146/ijc.77276

Synthesis and Biological Activity Study of Co and Cr Complexes with α-(2-Salsayl)-N-phenyl Nitrone and Oxide Nanoparticles

https://doi.org/10.22146/ijc.77276

Dhamiaa Abdul-Shaheed Issa⁽¹⁾, Hayder Baqer Abdullah⁽²⁾, Faeza Abdulkareem Al-Mashal^(3*)

(1) Department of Chemistry, College of Education for Pure Science, University of Basrah, 61004 Basrah, Iraq
(2) Department of Chemistry, College of Education for Pure Science, University of Basrah, 61004 Basrah, Iraq
(3) Department of Chemistry, College of Education for Pure Science, University of Basrah, 61004 Basrah, Iraq
(*) Corresponding Author

Abstract

This paper describes the synthesis of two complexes from the ligand α-(2-Salsayl)-N-phenyl nitrone with CoCl₂ and CrCl₂. The ligand was characterized by several spectroscopic techniques (ultraviolet/visible (UV/Vis), nuclear magnetic resonance (¹H-NMR and ¹³C-NMR), Fourier-transform infrared spectroscopy (FTIR), and mass spectrometry (MS). While infrared, ultraviolet-visible (UV-Vis), thermal analysis, and job method studies were used to reveal the structure of the complexes. The synthesized complexes were then synthesized by the sonochemical method, and the copper and chromium oxide nanoparticles were produced using the thermal decomposition method. Scanning electron microscopy (SEM), Energy dispersive X-ray spectroscopy (EDX), and X-ray diffraction (XRD) characterization confirmed the formation of Co₃O₄ and Cr₂O₃ nanoparticles. Antimicrobial studies of the complexes against some microorganisms, such as Staphylococcus epidermis and Escherichia coli, utilizing the disk diffusion method, revealed the antibacterial activity of the complexes.

Keywords

nitrones; complex; nanoparticles; biological activity

Full Text:

Full Text PDF Full Text PDF-Suppl. Data

References

[1] Ferraz, M.C., Mano, R.A., Oliveira, D.H., Maia, D.S.V., Silva, W.P., Savegnago, L., Lenardão, E.J., and Jacob, R.G., 2017, Synthesis, antimicrobial, and antioxidant activities of chalcogen-containing nitrone derivatives from (R)-citronellal, Medicines, 4 (2), 39.

[2] Scott, M.J., Billiar, T.R., and Stoyanovsky, D.A., 2016, N-tert-butylmethanimine N-oxide is an efficient spin-trapping probe for EPR analysis of glutathione thiyl radical, Sci. Rep., 6 (1), 38773.

[3] Pinheiro, A.C., Fazzi, R.B., Esteves, L.C., Machado, C.O., Dörr, F.A., Pinto, E., Hattori, Y., Sa, J., da Costa Ferreira, A.M., and Bastos, E.L., 2021, A bioinspired nitrone precursor to a stabilized nitroxide radical, Free Radical Biol. Med., 168, 110−116.

[4] Lo Celso, F., Barone, G., Maiuolo, L., Algieri, V., Cretu, C., and Calandra, P., 2022, Dissolution of nitrones in alkylphosphates: A structural study, J. Mol. Liq., 367, 120517.

[5] Chamorro, B., Diez-Iriepa, D., Merás-Sáiz, B., Chioua, M., García-Vieira, D., Iriepa, I., Hadjipavlou-Litina, D., López-Muñoz, F., Martínez-Murillo, R., Gonzàlez-Nieto, D., Fernández, I., Marco-Contelles, J., and Oset-Gasque, M.J., 2020, Synthesis, antioxidant properties and neuroprotection of α-phenyl-tert-butylnitrone derived HomoBisNitrones in in vitro and in vivo ischemia models, Sci. Rep., 10 (1), 14150.

[6] Towner, R.A., Saunders, D., Lerner, M., Silasi Mansat, R., Yuan, T., Barber, D., Faakye, J., Nyul-Toth, A., Csiszar, A., Greenwood-Van Meerveld, B., and Smith, N., 2021, Temporary opening of the blood-brain barrier with the nitrone compound OKN-007, Am. J. Nucl. Med. Mol. Imaging, 11 (5), 363−373.

[7] Haddad, B.S., and Al-Shawi, A.A.A., 2020, Cytotoxicity of new selenoimine, selenonitrone and nitrone derivatives against human breast cancer MDA-MB231 cells, Egypt. J. Chem., 63 (11), 4607−4613.

[8] Raspertova, I.V., Doroschuk, R.O., Khomenko, D.M., and Lampeka, R.D., 2017, Synthesis, spectroscopic, structural characterization of Cd(II) and Zn(II) complexes based on the N-methyl-C-(2-pyridyl)nitrone, J. Coord. Chem., 70 (16), 2888−2899.

[9] Sorriso, S., 1982, “Structural Chemistry” in The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives, Eds. Patai, S., John Wiley & Sons, Hoboken, New Jersey, 1–51.

[10] Hussein, K.A., and Shaalan, N., 2022, Synthesis, characterization, and antibacterial activity of lanthanide metal complexes with Schiff base ligand produced from reaction of 4,4-methylene diantipyrine with ethylenediamine, Indones. J. Chem., 22 (5), 1365−1375.

[11] Thirumalaikumar, M., Sivakolunthu, S., Muthusubramanian, S., Mohan, P., and Sivasubramanian, S., 1999, Synthesis, characterization and antimicrobial studies of metal(II) bis-chelates and mixed-ligand complexes of alpha-(2-hydroxyphenyl)-N-(1-phenyl-2-nitroethyl)nitrone, Boll. Chim. Farm., 138 (5), 207−210.

[12] Petkova, E.G., Domasevitch, K.V., Gorichko, M.V., Zub, V.Y., and Lampeka, R.D., 2001, New coordination compounds derived from nitrone ligands: Copper(II) complexes with 8-hydroxyquinoline-2-carbaldehyde- and pyridine-2-carbaldehyde-N-methylnitrones, Z. Naturforsch., B: Chem. Sci., 56 (12), 1264−1270.

[13] Subhi, H.M., Bader, A.T., and Al-Gubury, H.Y., 2022, Synthesis and characterization of ZnO nanoparticles via thermal decomposition for Zn(II) Schiff base complex, Indones. J. Chem., 22 (5), 1396−1406.

[14] Onwudiwe, D.C., 2019, Microwave-assisted synthesis of PbS nanostructures, Heliyon, 5 (3), e01413.

[15] Abdel-Monem, Y.K., Emam, S.M., and Okda, H.M.Y., 2017, Solid state thermal decomposition synthesis of CuO nanoparticles from coordinated pyrazolopyridine as novel precursors, J. Mater. Sci.: Mater. Electron., 28 (3), 2923−2934.

[16] Bekele, B., Degefa, A., Tesgera, F., Jule, L.T., Shanmugam, R., Priyanka Dwarampudi, L., Nagaprasad, N., and Ramasamy, K., 2021, Green versus chemical precipitation methods of preparing zinc oxide nanoparticles and investigation of antimicrobial properties, J. Nanomater., 2021, 9210817.

[17] Kafi-Ahmadi, L., and Shirmohammadzadeh, L., 2017, Synthesis of Co(II) and Cr(III) salicylidenic Schiff base complexes derived from thiourea as precursors for nano-sized Co₃O₄ and Cr₂O₃ and their catalytic, antibacterial properties, J. Nanostruct. Chem., 7 (2), 179–190.

[18] Chen, S., Zhao, K., and Chen, G., 2015, Synthesis and application of phenyl nitrone derivatives as acidic and microbial corrosion inhibitors, J. Chem., 2015, 201259.

[19] Lin-Vien, D., Colthup, N.B., Fateley, W.G., and Grasselli, J.G., 1991, “Double Bonds Containing Nitrogen Atoms” in The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, Academic Press, San Diego, 191–211.

[20] Kavitha, N., and Anantha Lakshmi, P.V., 2017, Synthesis, characterization and thermogravimetric analysis of Co(II), Ni(II), Cu(II) and Zn(II) complexes supported by ONNO tetradentate Schiff base ligand derived from hydrazino benzoxazine, J. Saudi Chem. Soc., 21, S457–S466.

DOI: https://doi.org/10.22146/ijc.77276