New Carboxamid ligand and its metal complexes containing sulfonamide group: Synthesis, Characterization, DNA cleavage and antimicrobial activity

Year 2021, Volume: 14 Issue: 2, 724 - 736, 31.08.2021

Semih Güler Hatice Gamze Soğukömeroğulları , Sadin Özdemir , Mustafa Serkan Yalçın , Mehmet Sönmez

https://doi.org/10.18185/erzifbed.852416

Cited By: 2

Abstract

In this work, N-(4-(N-acetylsulfamoyl)phenyl)-2-benzoyl-3-oxo-3-phenylpropanamide (HL) was synthesized by treating the appropriate dibenzoylaceticacid-N-carboxyethylamide with N-(4-aminophenyl)sulfonylacetamide and also characterized by using various analytical and spectroscopic techniques. Further, six metal complexes were synthesized from Zn(II), Ni(II), Mn(II), Cu(II), Co(II), and Pd(II) acetate and ligand in 1:2 ratio respectively. While Cu(II) and Pd(II) complexes exhibited square planar geometry, the others displayed octahedral geometry. Newly synthesized compounds were performed for antioxidant, DNA cleavage and antimicrobial activities. Tested compounds exhibited great potential antioxidant activity, especially Zn and Pd complexes. DNA cleavage results indicated that DNA could cleave with compounds through interaction. These compounds were investigated for their antimicrobial activity against seven microorganism species and showed moderate antimicrobial activity.

Keywords

N-carboxamid ligand, metal complexes, DNA cleavage, antimicrobial activity

Supporting Institution

Presidency of Scientific Research Projects of University Gaziantep

Project Number

FEF.YLT.16.06

Sülfonamid Grubu İçeren Yeni Karboksamid Ligand ve Metal Kompleksleri: Sentez, Karakterizasyon, DNA Bölünmesi ve Antimikrobiyal Aktivite

Abstract

Yeni karboksamid ligand N-(4-(N-asetilsülfamoil)fenil)-2-benzoil-3-okso-3-fenilpropanamit (HL) ve Zn(II), Ni(II), Mn(II), Cu(II), Co(II) ve Pd(II) kompleksleri sentezlenmiş ve çeşitli analitik ve spektroskopik teknikler kullanılarak karakterize edilmiştir. Cu (II) ve Pd (II) kompleksleri kare düzlem geometri sergilerken, diğerleri oktahedral geometri sergilemiştir. Yeni sentezlenen bileşiklerin, antioksidan, DNA bölünmesi ve antimikrobiyal aktiviteleri incelenmiştir. Test edilen bileşikler, özellikle Zn ve Pd kompleksleri, büyük potansiyel antioksidan aktivite sergilemiştir. DNA bölünmesi sonuçları, DNA'nın etkileşim yoluyla bileşiklerle parçalanabileceğini göstermiştir. Bu bileşikler, yedi mikroorganizma türüne karşı antimikrobiyal aktiviteleri açısından araştırılmış ve orta düzeyde antimikrobiyal aktivite gösterdiği bulunmuştur.

Keywords

N-karboksamit ligand, metal kompleksler, DNA bölünmesi, antimikrobiyal aktivite

Project Number

FEF.YLT.16.06

References

• Akkurt, M., Sarıoglu, A.O., Sönmez, M., Tahir, M.N. 2013. "Ethyl N-(2-benzoyl-3-oxo-3 phenylpropanoyl) carbamate". Acta Crystallographica Section E: Crystallographic Communications, E69, o220.
• Amjad, M., Sumrra, S.H., Akram, M.S., Chohan, Z.H. 2016. "Metal-based ethanolamine-derived compounds: a note on their synthesis, characterization and bioactivity". Journal of Enzyme Inhibition and Medicinal Chemistry, 31, 88–97.
• Bajpai, V.K., Baek, K.-H., Kang, S.C. 2017. "Antioxidant and free radical scavenging activities of taxoquinone, a diterpenoid isolated from Metasequoia glyptostroboides". The South African Journal of Botany, 111, 93–98.
• Bilgin, R., Yalcin, M.S., Yucebilgic, G., Koltas, I.S., Yazar, S. 2012. "Oxidative Stress in Vivax Malaria". The Korean Journal of Parasitology, 50, 375-377.
• Blois, M.S. 1958. "Antioxidant determinations by the use of a stable free radical". Nature, 181, 1199-1200.
• Boyd III, A.E. 1988. "Sulfonylurea receptors, ion channels, and fruit flies". Diabetes 37, 847–850.
• Çelik, A., Sogukomerogullari, H.G., Ozdemir, S., Yalcin, M.S., Sönmez, M. 2018. "Synthesis of Complexes Co, Cu, Ni and Pd Supported by “ONNO” type Schiff Base Ligand and their DNA cleavage, antioxidant effects and antimicrobial studies". International Journal of Chemical Technology, 2, 68-75.
• Demir, S., Sarıoğlu, A.O., Güler, S., Dege, N., Sönmez, M. 2016. "Synthesis, crystal structure analysis, spectral IR, NMR Uv-Vis investigations, NBO and NLO of 2-benzoyl-N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide with use of X-ray diffractions studies along with DFT calculations". Journal of Molecular Structure, 1118, 316-324.
• Drew, J., 2000. "Drug Discovery: A Historical Perspective". Science, 287, 1960–1964.
• Eze, F.U., Okoro, U.C., Ugwu, D.I., Okafor, S.N. 2019. "New carboxamides bearing benzenesulphonamides:Synthesis, molecular docking and pharmacological properties". Bioorganic Chemistry, 92, 103265.
• Fabian, W.F., Kollenz, G., Akçamur, Y., Kök, T.R., Tezcan, M., Akkurt, M., Hiller, W. 1992. "Reaktionen cyclischer Oxalylverbindungen, 34. Mitt.: Synthese von Dibenzoylacet-N-carboxyalkylamiden und semiempirische Rechnungen zur Keto-Enol Tautomerie". Monatshefte für Chemie/Chemical Monthly, 123, 265-275.
• Gali, R., Banothu, J., Gondru, R., Bavantula, R., Velivela, Y., Crooks, P.A. 2015. "One-pot multicomponent synthesis of indole incorporated thiazolylcoumarins and their antibacterial, anticancer and DNA cleavage studies". Bioorganic & Medicinal Chemistry Letters, 25, 106–112.
• German, N., Lüthje, F., Hao, X., Rensing, C. 2016. "Chapter Two - Microbial Virulence and Interactions With Metals". Progress in Molecular Biology and Translational Science, 142, 27-49.
• Gülcan, M., Sönmez, M., Berber, I. 2012. "Synthesis, characterization, and antimicrobial activity of a new pyrimidine Schiff base and its Cu(II), Ni(II), Co(II), Pt(II), and Pd(II) complexes". Turkish Journal of Chemistry, 36, 189-200.
• Hanif, M., Chohan, Z.H., Winum, J.-Y., Akhtar, J. 2014. "Metal-based carboxamide-derived compounds endowed with antibacterial and antifungal activity". Journal of Enzyme Inhibition and Medicinal Chemistry, 29, 517-526.
• Hseu, Y., Chang, W., Chen, C., Liao, L., Huang, C., Lu, F., Chia, Y., Hsu, H., Wu, J., Yang, H. 2008. "Antioxidant activities of Toona Sinensis leaves extracts using different antioxidant models". Food and Chemical Toxicology, 46, 105-114.
• Hsu, C., Chen, W., Weng, Y., Tseng, C. 2003. "Chemical composition, physical properties, and antioxidant activities of yam flours as affected by different drying methods". Food Chemistry, 83, 85–92.
• Ilhan, S., Baykara, H., Seyitoglu, M.S., Levent, A., Özdemir, S., Dündar, A., Öztomsuk, A., Cornejo, M. H. 2014. "Preparation, spectral studies, theoretical, electrochemical and antibacterial investigation of a new Schiff base and its some metal complexes". Journal of Molecular Structure, 1075, 32–42.
• Kalemba, D., Kunicka, A. 2003. "Antibacterial and antifungal properties of essential oils". Current Medicinal Chemistry, 10, 813–829.
• Lever, A.B.P. (1980). "Inorganic electronic spectroscopy", vol 4. Elsevier, London.
• Ogden, R.C., Flexner, C.W. (2001). "Recensie: Protease Inhibitors in AIDS Therapy", Basel, New York, 1468.
• Owa, T., Nagasu, T. 2000. "Novel sulphonamide derivatives for the treatment of cancer". Expert Opinion on Therapeutic Patents, 10, 1725–1740.
• Ravinder, V., Swamy, S.J., SriHari, S., Lingaiah, P. 1985. "Synthesis and spectral studies of copper(II) complexes with amide group ligands". Polyhedron, 4, 1511-1518.
• Sarioglu, A.O., Taskin-Tok, T., Akkurt, M., Tahir, M.N., Sönmez, M. 2016. "Synthesis and structural properties of N-(3,4-dichlorophenyl)-3-oxo-3-phenyl-2-(phenyl carbonyl)propanamide and its Cu(II) complex". Turkish Journal of Chemistry, 40, 76-92.
• Sharma, O.P., Bhat, T.K. 2009. "DPPH antioxidant assay revisited". Food Chemistry, 113, 1202–1205.
• Sönmez, M. 2001. "Synthesis and characterization of copper(II), nickel(II), cadmium(II), cobalt(II) and zinc(II) complexes with 2-Benzoyl-3-hydroxy-1-naphthylamino-3-phenyl-2-propen-1-on". Turkish Journal of Chemistry, 25, 181-185.
• Sönmez, M., Çelebi, M., Berber, I. 2010. "Synthesis, spectroscopic and biological studies on the new symmetric Schiff base derived from 2,6-diformyl-4-methylphenol with N-aminopyrimidine". European Journal of Medicinal Chemistry, 45, 1935-1940.
• Sönmez, M., Sogukomerogullari, H.G., Öztemel, F., Berber, İ. 2014. "Synthesis, characterization and antimicrobial studies of ONO/ONS tridentate Schiff bases derived from 5-chloro-2-hydroxyacethophenone with 1-amino-5-benzoyl-4-phenyl-1H-pyrimidine-2-one/thione and their Cu(II), Co(II), Ni(II), Pd(II) and Mn(II) complexes". Medicinal Chemistry Research, 23, 3451-3457.
• Sönmez, M., Hacıyusufoğlu, M.E., Levent, A., Zengin, H., Zengin, G. 2018. "Synthesis of pyrimidine Schiff base transition metal complexes: Characterization, spectral, electrochemical analyses and photoluminescence properties". Research on Chemical Intermediates, 44, 5531–5546.
• Supuran, C.T., Scozzafava, A. 2000. "Carbonic anhydrase inhibitors and their therapeutic potential". Expert Opinion on Therapeutic Patents, 10, 575–600.
• Supuran, C.T., Scozzafava, A. 2002. "Applications of carbonic anhydrase inhibitors and activators in therapy". Expert Opinion on Therapeutic Patents, 12, 217–242.
• Thaker, B.T., Surati, K.R., Patel, P., Parmar, S.D. 2006. "Synthesis and spectroscopic studies of mononuclear mixed ligand Schiff base complexes of Cu(II) involving conjugated heterocyclic nitrogen base and N-PhOHA or N-PhDHA". Journal of the Iranian Chemical Society, 3, 371-377.
• Thornber, C.W. 1979. "Isosterism and molecular modification in drug design". Chemical Society Reviews, 8, 563–580.
• Uçan, S.Y.,Uçan, M., Mercimek, B. 2005. "Synthesis and characterization of new Schiff bases and their cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II) and mercury(II) complexes". Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 35, 417–421.
• Yalçın, Ş.P., Ceylan, Ü., Sarıoğlu, A.O., Sönmez, M., Aygün, M. 2015. "Synthesis, molecular structure and spectroscopic studies of N-(4-nitrophenyl)-2, 2-dibenzoylacetamide (NPDBA): with experimental (X-Ray, FT-IR, 1H and 13C-NMR and UV-Vis) techniques and theoretical calculations". Journal of Molecular Structure, 1098, 400-407.