Synthesis, Characterization and Antimicrobial Activity of Mixed-Ligand Metal Complexes of 4,4'-Bipyridine and Aniline-2,5-Disulfonic Acid

Year 2024, Volume: 7 Issue: 2, 67 - 78, 31.12.2024

Nurgün Büyükkıdan , Seher Kaya , Halil İlkimen , Aysel Gülbandılar

Abstract

In this study, we prepared mixed-ligand Co(II) complex{[Co(ADSA)(BP)]n.2H2O, 1}, Ni(II) complex {[Ni(ADSA)(BP)]n, 2}, and Zn(II) complex {[Zn(ADSA)(BP)(H2O)2]n.3H2O, 3} of 4,4'-bipyridine (BP) with aniline-2,5-disulfonic acid (H2ADSA). The 1-3 were characterized by elemental analysis, AAS, TGA, IR, UV-Vis, molar conductivity and magnetic susceptibility techniques. Furthermore, the microdilution method was used to explore the antibacterial and antifungal activities of the initial and the synthesized metal complexes against the following bacteria and yeast: Pseudomonas aeruginosa, Escherichia coli, Enterococcus faecalis, Listeria monocytogenes, Staphylococcus aureus, Bacillus subtilis and Candida albicans. Antibacterial and antifungal activity results were compared with antibiotics (Vancomycin, Levofloxacin, Cefepime, Chloramphenicol, Fluconazole and Ketoconazole). Through the examination of the conducted studies, it was noted that the recently created compounds demonstrated efficacy in combating both bacterial and yeast infections.

Keywords

4,4'-Bipyridine, Aniline-2,5-disulfonic acid, Metal complex, Antimicrobial activity

4,4'-Bipiridin ve Anilin-2,5-Disülfonik Asidin Karışık Ligandlı Metal Komplekslerinin Sentezi, Karakterizasyonu ve Antimikrobiyal Aktivitesi

Abstract

Bu çalışmada 4,4'-bipiridin (BP) ve anilin-2,5-disülfonik asit (H2ADSA) ile karışık ligandlı Co(II) {[Co(ADSA)(BP)]n.2H2O, 1}, Ni(II) {[Ni(ADSA)(BP)]n, 2} ve Zn(II)) {[Zn(ADSA)(BP)(H2O)2]n.3H2O, 3} kompleksleri hazırladı. 1-3 Element analizi, AAS, TGA, IR, UV-Vis, molar iletkenlik ve manyetik duyarlılık teknikleri ile karakterize edildi. Ayrıca mikrodilüsyon yöntemi ile başlangıç maddeleri ve sentezlenen metal komplekslerinin aşağıdaki bakteriler ve mayaya karşı antibakteriyel ve antifungal aktivitelerini araştırmak için kullanıldı: Pseudomonas aeruginosa, Escherichia coli, Enterococcus faecalis, Listeria monocytogenes, Staphylococcus aureus, Bacillus subtilis ve Candida albicans. Antibakteriyel ve antifungal aktivite sonuçları antibiyotiklerle (Vankomisin, Levofloksasin, Sefepim, Kloramfenikol, Flukonazol ve Ketokonazol) karşılaştırıldı. Yapılan çalışmalar incelendiğinde, yeni oluşturulan bileşiklerin hem bakteri hem de maya enfeksiyonlarıyla mücadelede aktivite gösterdiği gözlenmiştir.

Keywords

4,4'-Bipiridin, anilin-2,5-disülfonik asit, Metal kompleksi, Antimikrobiyal aktivite

References

• [1] T.M. Reineke, M. Eddaoudi, D. Moler, M.O’. Keeffe, O.M. Yaghi, “Large free volume in maximally interpenetrating networks:  the role of secondary building units exemplified by Tb2(ADB)3[(CH3)2SO]4·16[(CH3)2SO]1 ”. J. Am. Chem. Soc., vol. 122, pp. 4843-4844, 2000.
• [2] C.B. Liu, S.S. Tan, Z.S. Wu, H.L. Wen, “Poly[di-µ3-chloro-µ2-4,4’-bipyridine-dicopper(I)]”. Acta Cryst., vol. E62, pp. m1496-m1496, 2006.
• [3] N. Lah, I. Leban, “Polymeric monovalent and divalent copper sulfates with 4,4'-bipyridine: [Cu2(SO4)(4,4'-bipy)2.6H2O]n and [Cu(SO4)(4.4'-bipy)(H2O).0.5H2O]n”. Inorg. Chem. Commun., vol. 9, pp. 42-45, 2006.
• [4] K. Biradha, M. Fujita, “Coordination polymers containing square grids of dimension 15 × 15 Å”. J. Chem. Soc., Dalton Trans., pp. 3805-3810, 2000.
• [5] S.A. Bourne, J. Lu, B. Moulton, M. J. Zawarokto, “Coexisting covalent and noncovalent nets: parallel interpenetration of a puckered rectangular coordination polymer and aromatic noncovalent nets”. Chem. Commun., pp. 861-862, 2001.
• [6] L.J. Moitsheki, S.A. Bourne, L. R. Nassimbeni, “A coordination polymer of thallium(III) nitrate with 4,4’-bipyridine-N,N’-dioxide”. Acta Cryst., vol. E62, pp. m542-m544, 2006.
• [7] S.J. Dalgarno, M.D. Hardie, J.L. Atwood, J.E. Warren, C.L. Raston, “A complex 3D ‘wavy brick wall’ coordination polymer based on p-sulfonatocalix[8]arene”. New J. Chem., vol. 29, pp. 649-652, 2005.
• [8] D.L. Long, A.J. Blake, N.R. Champness, M. Schroder, Constructing terbium co-ordination polymers of 4,4′-bipyridine-N,N′-dioxide by means of diffusion solvent mixtures. Chem.: A Euro. J., vol. 8, no. 9, pp. 2026-2033, 2002.
• [9] Y. Chen, S. Songsheng, E. Rex, “The effect of zinc(II) on the formation of 2,2′- and 2,3′-bipyridine complexes of [Ru2II(ttha)]2-(ttha6- = triethylenetetraminehexa-acetate)”. Trans. Met. Chem., vol. 22, pp. 338-346, 1997.
• [10] D. Czakis-Sulikowska, J. Radwanska-Doczekalska, M. Markiewicz, “Synthesis and thermal decomposition of mixed 2, 4'-bipyridine-oxalato complexes with Mn(II), Co(II), Ni(II) and Cu(II)”. J. Ther. Anal. Cal., vol. 60, no. 1, pp. 145-151, 2000.
• [11] Z. Wang, R.G. Xiong, E. Naggar, B.M. Foxman, W.B. Lin, “Coordination chemistry of 2,4'-bipyridine. synthesis and structures of Co(2,4'-bipyridine)2(NO3)2(H2O) and Cd(2,4'-bipyridine)2(NO3)2(H2O)2”. Inorg. Chim. Acta, vol. 288, pp. 215-219, 1999.
• [12] R.L. LaDuca Jr, C. Brodkin, R.C. Finn, J. Zubieta, “A three dimensional organic–inorganic composite material constructed from cobalt-3,3′-bipyridyl networks linked through tetravanadate clusters: [{Co(3,3′-bpy)2}2V4O12]”. Inorg. Chem. Commun., vol. 3, no. 5, pp. 248-250, 2000.
• [13] R.L. LaDuca Jr., M. Desciak, M. Laskoski, R.S. Rarig Jr., J. Zubieta, “Hydrothermal synthesis of twodimensional organic-inorganic hybrid materials of the nickel-molybdate family: the structures of [{Ni(3,3′-bpy)2}2Mo4O14] and [Ni(3,3′-Hbpy)Mo4O13(OH)]”. J. Chem. Soc., Dalton Trans., pp. 2255-2257, 2000.
• [14] X. Cui, A.N. Khlobystov, X. Chen, D.H. Marsh, A.J. Blake, W. Lewis, N.R. Champness, C.J. Roberts and M. Schroeder, “Dynamic equilibria in solvent-mediated anion, cation and ligand exchange in transitionmetal coordination polymers: solid-state transfer or recrystallisation?” Chem. - A Euro. J., vol. 15, no. 35, pp. 8861-8873, S8861/1-S8861/32, 2009.
• [15] F.F.B.J. Janssen, L.P.J. Veraart, J.M.M, Smits, R. de Gelder, A.E. Rowan, “1. Solvent, linker, and anion effects on the formation, connectivity, and topology of Cu(I)/PPh3/N-Donor ligand coordination polymers”. Cryst. Grow. Des., vol. 11, no. 10, pp. 4313-4325, 2011.
• [16] M.L. Tong, X.M. Chen, B.H. Ye, S.W. Ng, “Helical silver(I)−2,4‘-bipyridine chains organized into 2-D networks by metal-counterion or metal-metal bonding. structures of [Ag(2,4‘-bipyridine)]X (X- = NO3- or ClO4-)”. Inorg. Chem., vol. 37, no. 20, pp. 5278-5281, 1998.
• [17] T.J.J. Kinnunen, M. Haukka, E. Pesonen, T.A. Pakkanen, “Ruthenium complexes with 2,2′, 2,4′- and 4,4′-bipyridine ligands: The role of bipyridine coordination modes and halide ligands”. J. Organomet. Chem., vol. 655, pp. 31-38, 2002, doi: 10.1016/S0022-328X(02)01408-0
• [18] X. Xiao, L. Zou, H. Pang, Q. Xu, “Synthesis of micro/nanoscaled metal-organic frameworks and their direct electrochemical applications”. Chem. Soc. Rev., vol. 49, pp. 301-331, 2020.
• [19] Y. Zhao, Y. Yuan, X. Du, X. Lin, F. Liao, “Hydrothermal assembly of various dimensional pure-inorganic copper-molybdenum frameworks”, CrystEngComm, vol. 18, pp. 521-524, 2016.
• [20] Z. Hulvey, B.C. Melot, A.K. Cheetham, “Crystal structure of catena-poly[aqua-(µ2-hexamethylenetetramine-κ2N:N′)-bis(2,6-difluorobenzoato-κ2O:O′)cadmium(II)] monohydrate, C20H22CdF4N4O6”. Inorg. Chem., vol. 49, pp. 4594-4598, 2010.
• [21] N. Moliner, J.A. Real, M.C. Muñoz, R. Martínez-Mañez, J.M.C. Juan, “Unprecedented pseudo-trigonalbipyramidal intermediate-spin iron(III) complex: synthesis, crystal structure and magnetic properties of [Fe(4,4′-bipy)2(NCS)3](CH3)2CO”. J. Chem. Soc., Dalton Trans., pp. 1375-1380, 1999.
• [22] S.M.F. Lo, S.S.Y. Chui, L.Y. Shek, Z.Y. Lin, X.X. Zhang, G.H. Wen, I.D. Williams, “Solvothermal synthesis of a stable coordination polymer with copper-I−copper-II dimer units:  [Cu4{1,4-C6H4(COO)2}3(4,4‘-bipy)2]n”. J. Am. Chem. Soc., vol. 122, pp. 6293-6294, 2000.
• [23] H. Zhao, Z.R. Qu, Q. Ye, X.S. Wang, J. Zhang, R.G. Xiong, X.Z. You, “An unusual mixed-valence Cu(I)−Cu(II) 3-D framework”. Inorg. Chem., vol. 43, pp. 1813-1815, 2004.
• [24] B. Zhao, P. Cheng, Y. Dai, C. Cheng, W. Shi, D.Z. Liao, D.Z. Liao, S.P. Yan, Jiang, Z.H. “Coordination polymers containing 1D channels as selective luminescent probes”. J. Am. Chem. Soc., vol. 126, no. 47, pp. 15394-15395, 2004.
• [25] T.J. Prior, D. Bradshaw, S.J. Teat, M.J. Rosseinsky, “Designed layer assembly: a three-dimensional framework with 74% extra-framework volume by connection of infinite two-dimensional sheets”. Chem. Commun., pp. 500-501, 2003.
• [26] J.Y. Lu, “Crystal engineering of Cu-containing metal-organic coordination polymers under hydrothermal conditions”. Coord. Chem. Rev., vol. 246, no. 1-2, pp. 327-347, 2003.
• [27] Y.Q. Zheng, J.L. Lin, A. Y. Pan, “A novel adipate bridged supramolecular layer: crystal structure of the cobalt(II) complex [(μ-C6H8O4)4/2Co(μ-H2O)2Co(H2O)4] .4 H2O”. Zeits. Anorg. Allg. Chem., vol. 626, pp. 1718-1720, 2000.
• [28] Y.Q. Zheng, Z.P. Kong, “A suberato-pillared Mn(II) coordination Polymer: Hydrothermal synthesis, crystal structure, and magnetic properties of Mn2(H2O)[O2C(CH2)6CO2]2”. J. Solid State Chem., vol. 166, no. 2, pp. 279-284, 2002, doi: 10.1006/jssc.2002.9585
• [29] P.M. Forster, A.K. Cheetham, “Open-Framework Nickel Succinate, [Ni7(C4H4O4)6(OH)2(H2O)2].2H2O: A New hybrid material with three-dimensional Ni-O-Ni connectivity”. Ang. Chem. Inter. Ed., 41, 457-459, 2002.
• [30] E.W. Lee, Y.J. Kim, D.Y. Jung, “A coordination polymer of cobalt(II)-glutarate: Two-dimensional interlocking structure by dicarboxylate ligands with two different conformations”. Inorg. Chem., vol. 41, pp. 501-506, 2002.
• [31] N. Büyükkıdan, H. İlkimen, S. Bozyel, M. Sarı, A. Gülbandılar, “The syntheses, structural and biological studies of Co(II) complexes of 1,2-bis(pyridin-4-yl)ethane with 2-aminobenzene-1,4-disulfonic acid and 2,6-pyridinedicarboxylic acid”. J. Mol. Struct., vol. 1275, 134586, 2023.
• [32] N. Büyükkıdan, H. İlkimen, S. Bozyel, M. Sarı, A. Gülbandılar, “Two new Cu(II) coordination complexes with 1,2-bis(pyridin-4-yl)ethane bridge-ligand: Synthesis, characterization and antimicrobial activity”. Polyhedron, vol. 223, 115951, 2022.
• [33] G.K.H. Shimizu, R. Vaidhyanathan, J.M. Taylor, “Phosphonate and sulfonate metal organic frameworks”. Chem. Soc. Rev., vol. 38, pp. 1430-1449, 2009.
• [34] D. Sun, R. Cao, Y. Sun, W. Bi, X. Li, Y. Wang, Q. Shi, X. Li, “Novel silver-containing supramolecular frameworks constructed by combination of coordination bonds and supramolecular interactions”. Inorg. Chem., vol. 42, pp. 7512-7518, 2003.
• [35] N. Büyükkıdan, S.B. Turgut, H. İlkimen, M. Sarı, A. Gülbandılar, “Aniline-2,5-disulfonic acid based new proton transfer salt and new Co(II) and Cu(II) coordination polymers: synthesis, structural and antimicrobial studies”. Chem. Papers, vol. 78, pp. 6405-6416, 2024.
• [36] H. İlkimen, S.G. Salün, A. Gülbandılar, M. Sarı, “The new salt of 2-amino-3-methylpyridine with dipicolinic acid and its metal complexes: Synthesis, characterization and antimicrobial activity studies”. J. Mol. Struct., vol. 1270, pp. 133961, 2022.
• [37] R. Kant, “Magnetic behavior studies on Co (II) complexes with N- And O- donor sites ligand”. Inter. J. Sci. Res. Pub., vol. 9, no. 3, pp. 728-730, 2019.
• [38] N.N. Jha, I.P. Ray, “Magnetic studies on Co(II) and Ni(II) complexes of hydroxamic acid”. Asian J. Chem., vol. 12, no. 3, pp. 703-706, 2000.
• [39] A.A. Osowole, G.A. Kolawole, O.E. Fagade, “Synthesis, physicochemical, and biological properties of nickel (II), copper (II), and zinc (II) complexes of an unsymmetrical tetradentate Schiff base and their adducts”. Synth. Reac. Inorg. Metal-Org. Nano-Metal Chem. vol. 35, no. 10, pp. 829-836, 2005.
• [40] W.J. Geary, “The use of conductivity measurements in organic solvents for the characterisation of coordination compounds”. Coord. Chem. Rev., vol. 7, no. 1, pp. 81-122, 1971