* Corresponding Author
Synthesis, Characterization, Antimicrobial and Time Killing Activities of New Sulfa-Derived Schiff Bases Coordinated with Cu(II)
https://doi.org/10.22146/ijc.83873 Önder İdil(1*), Hakan Şahal(2), Erdal Canpolat(3), Mustafa Özkan(4)
(1) Department of Basic Education, Faculty of Education, Amasya University, Amasya 05100, Turkey
(2) Vocational School of Tunceli, Department of Food Processing, Munzur University, Tunceli 62000, Turkey
(3) Department of Elementary Science Education, Faculty of Education, Firat University, Elazig 23200, Turkey
(4) Department of Elementary Science Education, Faculty of Education, Bursa Uludag University, Bursa 16059, Turkey
(*) Corresponding Author
Abstract
Synthesis of three Schiff bases of 5-bromo-3-nitro salicylaldehyde containing different sulfonamide group antibiotic compounds and their Cu(II) complexes was carried out. Structures of all compounds were characterized with spectroscopic methods, including Fourier transform infrared, proton nuclear magnetic resonance, and elemental analysis. The in vitro antimicrobial activity of ligands and complexes against Gram-negative and Gram-positive bacteria and the yeast Candida albicans was evaluated. It was determined that the ligand and complexes showed outstanding antimicrobial activity against almost all of the microorganisms tested. It has been observed that the newly synthesized complexes have more antimicrobial effects than the corresponding ligands. It has been determined that the newly synthesized complexes have more antimicrobial effects than the others (E. coli, L. monocytogenes, and C. albicans), especially on Staphylococcus aureus and Pseudomonas aeruginosa.
Keywords
References
[1] Garai, M., Das, A., Joshi, M., Paul, S., Shit, M., Choudhury, A.R., and Biswas, B., 2018, Synthesis and spectroscopic characterization of a photo-stable tetrazinc(II)–Schiff base cluster: A rare case of ligand centric phenoxazinone synthase activity, Polyhedron, 156, 223–230.
[2] Pal, C.K., Mahato, S., Joshi, M., Paul, S., Choudhury, A.R., and Biswas, B., 2020, Transesterification activity by a zinc(II)-Schiff base complex with theoretical interpretation, Inorg. Chim. Acta., 506, 119541.
[3] Yousif, E., Hasan, A., and El-Hiti, G.A., 2016, Spectroscopic, physical and topography of photochemical process of PVC films in the presence of Schiff base metal complexes, Polymers, 8, 204.
[4] Ibrahim, F.M., and Abdalhadi, S.M., 2021, Performance of Schiff bases metal complexes and their ligand in biological activity: A review, Al-Nahrain J. Sci., 24 (1), 1–10.
[5] Tigineh, G.T., and Liu, L.K., 2017, Solvatochromic photoluminescence investigation of functional Schiff-bases: A systematic study of substituent effects, J. Photochem. Photobiol., A, 338, 161–170.
[6] Chouhan, S., Sharma, K., and Guleria, S., 2017, Antimicrobial activity of some essential oils—Present status and future perspectives, Medicines, 4 (3), 58.
[7] Ahmed, M., Qadir, M.A., Ahmad, S., Ul-Haq, I., Hussain, R., Habib, T., Ikram, R., and Muddassar, M., 2020, Studies on the synthesis of benzene sulfonamides, evaluation of their antimicrobial activities, and molecular docking, Lat. Am. J. Pharm., 39, 38–46.
[8] Apaydın, S., and Török, M., 2019, Sulfonamide derivatives as multi-target agents for complex diseases, Bioorg. Med. Chem. Lett., 29 (16), 2042–2050.
[9] Krátký, M., Vinšová, J., Volková, M., Buchta, V., Trejtnar, F., and Stolaříková, J., 2012, Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold, Eur. J. Med. Chem., 50, 433–440.
[10] Gaffer, H.E., 2019, Antimicrobial sulphonamide azo dyes, Color. Technol.,135 (6), 484–500.
[11] Pervaiz, M., Riaz, A., Munir, A., Saeed, Z., Hussain, S., Rashid, A., Younas, U., and Adnan, A., 2020, Synthesis and characterization of sulfonamide metal complexes as antimicrobial agents, J. Mol. Struct., 1202, 127284.
[12] El-Ghamry, H.A., Alharbi, B.K., Takroni, K.M., and Khedr, A.M., 2023, A series of nanosized Cu(II) complexes based on sulfonamide azo dye ligands: An insight into complexes molecular structures, antimicrobial, antitumor and catalytic performance for oxidative dimerization of 2-aminophenol, Appl. Organomet. Chem., 37 (2), e6978.
[13] Althagafi, I., Elghalban, M.G., and El-Metwaly, N.M., 2019, Novel synthesized benzesulfonamide nanosized complexes; Spectral characterization, molecular docking, molecular modeling and analytical application, J. Inorg. Organomet. Polym. Mater., 29 (3), 876–892.
[14] Ghomashi, R., Ghomashi, S., Aghaei, H., and Massah, A.R., 2023, Recent advances in biological active sulfonamide based hybrid compounds Part A: Two-component sulfonamide hybrids, Curr. Med. Chem., 30 (4), 407–480.
[15] Ogden, R.C., and Flexner, C.W., 2001, Protease Inhibitors in AIDS Therapy, Marcel Dekker, Inc., New York, US.
[16] Mahapatra, M., Mohapatra, P., Sahoo, S.K., Bishoyi, S.K., Padhy, R.N., and Paidesetty, S.K., 2023, Design, synthesis, and in-silico study of chromen-sulfonamide congeners as potent anti-cancer and antimicrobial agents, J. Mol. Struct., 1283, 135190.
[17] Abdul Qadir, M., Ahmed, M., Aslam, H., Waseem, S., and Shafiq, M.I., 2015, Amidine sulfonamides and benzene sulfonamides: Synthesis and their biological evaluation, J. Chem., 2015, 524056.
[18] Alghuwainem, Y.A.A., Abd El-Lateef, H.M., Khalaf, M.M., Abdelhamid, A.A., Alfarsi, A., Gouda, M., Abdelbaset, M., and Abdou, A., 2023, Synthesis, structural, DFT, antibacterial, antifungal, anti-inflammatory, and molecular docking analysis of new VO(II), Fe(III), Mn(II), Zn(II), and Ag(I) complexes based on 4-((2-hydroxy-1-naphthyl)azo) benzenesulfonamide, J. Mol. Liq., 369, 120936.
[19] Feng, G., Zou, W., Zhong, Y., 2022, Sulfonamides repress cell division in the root apical meristem by inhibiting folates synthesis, J. Hazard. Mater. Adv., 5, 100045.
[20] Cheong, M.S., Seo, K.H., Chohra, H., Yoon, Y.E., Choe, H., Kantharaj, V., and Lee, Y.B., 2020, Influence of sulfonamide contamination derived from veterinary antibiotics on plant growth and development, Antibiotics, 9 (8), 456.
[21] Al-Dosari, M.S., Ghorab, M.M., Al-Said, M.S., and Nissan, Y.M., 2013, Discovering some novel 7-chloroquinolines carrying a biologically active benzenesulfonamide moiety as a new class of anti-cancer agents, Chem. Pharm. Bull., 61 (1), 50–58.
[22] Jawad, W.A., Balakit, A.A., and Al-Jibouri, M.N.A., 2021, Synthesis, characterization and antibacterial activity study of cobalt(II), nickel(II), copper(II), palladium(II), cadmium(II) and platinum(IV) complexes with 4-amino-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thione, Indones. J. Chem., 21 (6), 1514–1525.
[23] Lewis, A., and Keevil, C.W., 2004, Antibacterial Properties of Alloys and Its Alloys in HVAC&R Systems, International Copper Association, New York, US.
[24] Dayan, S., Ozpozan, N.K., Özdemir, N., and Dayan, O., 2014, Synthesis of some ruthenium(II)–Schiff base complexes bearing sulfonamide fragment: New catalysts for transfer hydrogenation of ketones, J. Organomet. Chem., 770, 21–28.
[25] Maurya, M.R., Chaudhary, N., Avecilla, F., and Correia, I., 2015, Mimicking peroxidase activity by a polymer-supported oxidovanadium(IV) Schiff base complex derived from salicylaldehyde and 1,3-diamino-2-hydroxypropane, J. Inorg. Biochem., 147, 181–192.
[26] Canpolat, E., Şahal, H., Kaya, M., and Gür, S., 2014, Synthesis, characterization, antibacterial and antifungal activities studies of copper(II), cobalt(II) and zinc(II) complexes of the Schiff base ligand derived from 4,4-diaminodiphenylether, J. Chem. Soc. Pak., 36 (1), 106–112.
[27] Fellah, M.F., Bakirdere, E.G., Canpolat, E., and Kaya, M., 2014, A density functional theory study of [(4-aminophenyl)imino]methyl-6-methoxy4-nitrophenol complexes with Co, Ni, Cu and Zn metals, J. Indian Chem. Soc., 91, 1321–1326.
[28] Şahal, H., Fellah, M.F., Gur, S., Kaya, M., Turkoglu, S., and Canpolat, E., 2017, Studies of novel sulfapyridine derivatives containing Schiff bases and Co(II), Ni(II) and Zn(II) complexes: Synthesis, experimental and theoretical (DFT) approach for characterization and biological efficacy, J. Chem. Soc. Pak., 39 (4), 650–660.
[29] Şahal, H., Pişkin, M., Organ, G.A., Öztürk, Ö.F., Kaya, M., and Canpolat, E., 2018, Zinc(II) phthalocyanine containing Schiff base containing sulfonamide: Synthesis, characterization, photophysical, and photochemical properties, J. Coord. Chem., 71 (22), 3763–3775.
[30] Pişkin, M., Canpolat, E., and Öztürk, Ö.F., 2020, The new zinc phthalocyanine having high singlet oxygen quantum yield substituted with new benzenesulfonamide derivative groups containing Schiff base, J. Mol. Struct., 1202, 127181.
[31] Hundur, Ö.D., İdil, Ö., Kandemir, N., Gül, M., and Konar, V., 2018, Phytochemical screening and in-vitro antioxidant, antimicrobial activity and DNA interaction of Leucojum aestivum, Fresenius Environ. Bull., 27 (10), 6704–6710.
[32] Gul, M., Ozturk, C.I., Cansaran, A., Idil, O., Kulu, I., and Celikoglu, U., 2017, Evaluation of phytochemical content, antioxidant, antimicrobial activity and DNA cleavage effect of endemic Linaria corifolia Desf. (Plantaginaceae), Cogent Chem., 3 (1), 1337293.
[33] Vural, H., and Idil, O., 2019, Synthesis, spectroscopic investigation and biological activities of copper(II) complex of 2-(2,4-difluorophenyl)pyridine: A combined theoretical and experimental study, J. Mol. Struct., 1177, 242–248.
[34] Evecen, M., Kara, M., Idil, O., and Tanak, H., 2017, Investigation of antimicrobial activities, DNA interaction, structural and spectroscopic properties of 2-chloro-6-(trifluoromethyl)pyridine, J. Mol. Struct., 1137, 206–215.
[35] Gul, M., Turk Celikoglu, E., Idil, O., Tas, G., and Pelit, E., 2023, Synthesis, antimicrobial activity and molecular docking studies of spiroquinoline-indoline-dione and spiropyrazolo-indoline-dione derivatives, Sci. Rep., 13 (1), 1676.
[36] Zülfikaroğlu, A., Taş, M., Vural, H., Çelikoğlu, E., and İdil, Ö., 2021, Synthesis, structural characterization, DNA cleavage studies, antimicrobial activities, and time-killing kinetics of tetranuclear Cu(II) with partial cubane Cu4O4 cores and mononuclear Co(II) and Ni(II) complexes of a new acylhydrazone ligand, Appl. Organomet. Chem., 35 (6), e6218.
[37] Isik, K., and Özdemir-Kocak, F., 2009, Antimicrobial activity screening of some sulfonamide derivatives on some Nocardia species and isolates, Microbiol. Res., 164, (1), 49–58.
[38] Heiran, R., Jarrahpour, A., Riazimontazer, E., Gholami, A., Troudi, A., Digiorgio, C., Brunel, J.M., and Turos, E., 2021, Sulfonamide-β-lactam hybrids incorporating the piperazine moiety as potential antiinflammatory agent with promising antibacterial activity, ChemistrySelect, 6 (21), 5313–5319.
[39] Verma, S.K., Verma, R., Xue, F., Thakur, P.K., Girish, Y.R., and Rakesh, K.P., 2020, Antibacterial activities of sulfonyl or sulfonamide containing heterocyclic derivatives and its structure-activity relationships (SAR) studies: A critical review, Bioorg. Chem., 105, 104400.
[40] Konieczny, J., and Rdzawski, Z., 2012, Antibacterial properties of copper and its alloys, Arch. Mater. Sci. Eng., 56 (2), 53–60.
DOI: https://doi.org/10.22146/ijc.83873
Article Metrics
Abstract views : 2065
| 
views : 955
| views : 465
Copyright (c) 2023 Indonesian Journal of Chemistry
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.