Tylosin is a well-established antibiotic that has been widely employed in human and veterinary medicines. It can act as a potential ligand binding metal ions due to various donor atoms in the structure. Our study on the complexation of various metal ions with tylosin ligand revealed that they preferably coordinate with mycaminose fragment to establish Novel trends complexes. Tylosin ligand (TYS) behaves as bidentate for complexation with different metal ions such as Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II). Various essential metal complexes of tylosin were synthesized and characterized by techniques such as UV, IR, Elemental analysis, magnetic susceptibility and ESR spectra of Cu(II) complex. These techniques are used to know their geometries and mode of bonding, with stoichiometry, 2:2 (M:L). Thermal analysis (TGA and DTA) of ligands and their metal complexes were carried out to distinguish between the coordinate and hydrate solvents and to estimate the stability ranges, peak temperatures. The thermodynamic parameters, such as activation energy ( Δ E * ), the enthalpy of activation ( Δ H * ), entropy of activation ( Δ S * ) and Gibbs free energy ( Δ G * ) are calculated and discussed. Some tylosin complexes show higher activity than tylosin for some bacterial and fungal strains. Low concentration value of minimum inhibitory concentration (MIC) results is 15.625 μg/ml for both complexes [Zn 2 (TYS) 2 Cl 2 (H 2 O) 4 ] · 25H 2 O and [Cu 2 (TYS) 2 Cl 2 (H 2 O) 4 ] · 25H 2 O with B. cereus genus maybe a valuable data used to produce novel therapeutic agent. This study constitutes several essential aspects for future research on tylosin metal complexes as antibacterial assessment and as potential medicinal agents.
Khaliq, S., Akhtar, K., AfzalGhauri, M., et al. (2009) Change in Colony Morphology and Kinetics of Tylosin Production after UV and Gamma Irradiation Mutagenesis of Streptomyces fradiae NRRL-2702. Microbiological Research, 164, 469-477. https://doi.org/10.1016/j.micres.2007.02.005
Baltz, R.H. and Seno, E.T. (1988) Genetics of Streptomyces fradiae and Tylosin Biosynthesis. Annual Review of Microbiology, 42, 547-574. https://doi.org/10.1146/annurev.mi.42.100188.002555
Loftin, K.A., Adams, C.D., Meyer, M.T. and Surampalli, R. (2008) Effects of Ionic Strength, Temperature, and pH on Degradation of Selected Antibiotics. Journal of Environmental Quality, 37, 378-386. https://doi.org/10.2134/jeq2007.0230
Fish, S.A. and Cundliffe, E. (1996) Structure-Activity Studies of Tylosin-Related Macrolides. The Journal of Antibiotics, 49, 1044-1048. https://doi.org/10.7164/antibiotics.49.1044
Huang, G., Okabe, M., Kahar, P., Tsunekawa, H. and Park, Y. (2001) Optimization of Tylosin Feeding Rate Profile in Production of Acetyl-Isovaleryl Tylosin (AIV) from Tylosin by Streptomyces thermotolerans YN554. Journal of Bioscience and Bioengineering, 91, 504-508. https://doi.org/10.1016/S1389-1723(01)80281-4
Vladimirova, E.V., Dunaeva, A.A., Shipulo, E.V., et al. (2011) Studies of Complex Formation between Macrolide Antibiotics and Alkali and Alkali—Earth Metals by the Voltammetry at the Interface of Two Immiscible Electrolyte Solutions. Russian Journal of Electrochemistry, 47, 361-368. https://doi.org/10.1134/S1023193510121031
Lan, C., Yin, D., Yang, Z., Zhao, W., Chen, Y., Zhang, W. and Zhang, S. (2019) Determination of Six Macrolide Antibiotics in Chicken Sample by Liquid Chromatography-Tandem Mass Spectrometry Based on Solid Phase Extraction. Journal of Analytical Methods in Chemistry, 2019, Article ID: 6849457. https://doi.org/10.1155/2019/6849457
Prats, C., Francesch, R., Arboix, M. and Perez, B. (2002) Determination of Tylosin Residues in Different Animal Tissues by High Performance Liquid Chromatography. Journal of Chromatography B, Analytical Technologies in the Biomedical and Life Sciences, 766, 57-65. https://doi.org/10.1016/S0021-9673(01)01325-5
Yaneva, Z., Georgieva, N., Koinarski, V. and Petrova, D. (2015) Rapid RP HPLC Method with PDA Detection for Tylosin Determination in Liquid Samples. Trakia Journal of Sciences, 13, 309-314. https://doi.org/10.15547/tjs.2015.s.02.066
Przenioslo-Siwczyńska, M., Grelik, A. and Kwiatek, K. (2020) Identification and Quantification of Tylosin in Animal Feed by Liquid Chromatography Combined with Electrospray Ionisation Mass Spectrometry. Veterinary Research, 64, 299-304. https://doi.org/10.2478/jvetres-2020-0031
Keskar, M.R. and Jugade, R.M. (2015) Spectrophotometric Investigations of Macrolide Antibiotics: A Brief Review. Analytical Chemistry Insights, 10, 29-37. https://doi.org/10.4137/ACI.S31857
Sarmah, A.K., Meyer, M.T. and Boxall, A.B. (2006) A Global Perspective on the Use, Sales, Exposure Pathways, Occurrence, Fate and Effects of Veterinary Antibiotics (VAs) in the Environment. Chemosphere, 65, 725-759. https://doi.org/10.1016/j.chemosphere.2006.03.026
Caldwell, J.R. and Moyer, H.V. (1935) Determination of Chloride: A Modification of the Volhard Method. Industrial & Engineering Chemistry Analytical, 7, 38-39. https://doi.org/10.1021/ac50093a018
Bradley, K.B. and Potts, W.J. (1958) The Internally Standardized Nujol Mull as a Method of Quantitative Infrared Spectroscopy. Applied Spectroscopy, 12, 77-80. https://doi.org/10.1366/000370258774615465
Fouad, D., Bayoumi, A., ElGahami, M., Ibrahim, S. and Hammam, A. (2010) Synthesis and Thermal Studies of Mixed Ligand Complexes of Cu(II), Co(II), Ni(II) and Cd(II) with Mercaptotriazoles and Dehydroacetic Acid. Natural Science, 2, 817-827. https://doi.org/10.4236/ns.2010.28103
Clinical and Laboratory Standards Institute (CLSI) (2017) Performance Standards for Antimicrobial Susceptibility Testing. M100, 27th Edition, Replaces M100-S26.
Khalifa, R.A., Nasser, M.S., Gomaa, A.A., Osman, N.M. and Salem, H.M. (2013) Resazurin Microtiter Assay Plate Method for Detection of Susceptibility of Multidrug Resistant Mycobacterium tuberculosis to Second-Line Anti-Tuberculous Drugs. Egyptian Journal of Chest Diseases and Tuberculosis, 62, 241-247. https://doi.org/10.1016/j.ejcdt.2013.05.008
Sarker, S.D., Nahar, L. and Kumarasamy, Y. (2007) Microtitre Plate-Based Antibacterial Assay Incorporating Resazurin as an Indicator of Cell Growth, and Its Application in the in Vitro Antibacterial Screening of Phytochemicals. Methods, 42, 321-324. https://doi.org/10.1016/j.ymeth.2007.01.006
De Freitas, A.G.M., Minho, L.A.C., de Magalhaes, B.E.A., Dos Santos, W.N.L., Santos, L.S. and Fernandes, S.A.D. (2021) Infrared Spectroscopy Combined with Random Forest to Determine Tylosin Residues in Powdered Milk. Food Chemistry, 365, Article ID: 130477. https://doi.org/10.1016/j.foodchem.2021.130477
De Freitas, A.G., de Magalhaes, B.E., Minho, L.A., Leao, D.J., Santos, L.S. and Augusto de Albuquerque Fernandes, S. (2021) FTIR Spectroscopy with Chemometrics for Determination of Tylosin Residues in Milk. Journal of the Science of Food and Agriculture, 101, 1854-1860. https://doi.org/10.1002/jsfa.10799
Yin, Y.Y., Guo, X.T. and Peng, D. (2018) Iron and Manganese Oxides Modified Maize Straw to Remove Tylosin from Aqueous Solutions. Chemosphere, 205, 156-165. https://doi.org/10.1016/j.chemosphere.2018.04.108
Martin, L.Y., Sperati, C.R. and Busch, D.H. (1977) The Spectrochemical Properties of Tetragonal Complexes of High Spin Nickel(II) Containing Macrocyclic Ligands. Journal of the American Chemical Society, 99, 2968-2981. https://doi.org/10.1021/ja00451a020
Ranjan, R., Rani, R., Suman Singh, S., Singh, A.K. and Sharma, S. (2010) Tetragonal Distortion Parameter of Some Nickel(II) Complexes. Asian Journal of Chemistry, 22, 7580-7584.
Kumar, D., Singh, A.K., Kumar, A., Prasad, D., Kumar, V. and Sharma, S. (2020) Synthesis, Spectral Characterization and Biological Activity of Metal(II) Complexes of 2,4,5-Trimethoxybenzaldehyde-S-Benzyldithiocarbazone. Asian Journal of Chemistry, 32, 209-214. https://doi.org/10.14233/ajchem.2020.22476
Chandra, S. and Pipil, P. (2014) Synthesis, Spectral Characterization and Biological Evaluation of Chromium(III) Complexes of Schiff Base. Open Journal of Inorganic Chemistry, 4, 30-40. https://doi.org/10.4236/ojic.2014.42005
Choi, J.-H., Oh, I.-G., Lee, S.H. and Park, Y.C. (2003) Electronic Spectroscopy and Ligand Field Analysis of trans-[CrX2([15]aneN4)]+ (X = F, CI). Journal of the Korean Chemical Society, 47, 109-114. https://doi.org/10.5012/jkcs.2003.47.2.109
Chakradhar, R.P., Sreekanth, Ramesh, K.P., Rao, J.L. and Ramakrishna, J. (2003) Mixed Alkali Effect in Borate Glasses—Electron Paramagnetic Resonance and Optical Absorption Studies in Cu2+ Doped xNa2O-(30-x)K2O-70B2O3 Glasses. Journal of Physics: Condensed Matter, 15, 1469-1486.
Halcrow, M.A. (2013) Jahn-Teller Distortions in Transition Metal Compounds, and Their Importance in Functional Molecular and Inorganic Materials. Chemical Society Reviews, 42, 1784-1795. https://doi.org/10.1039/C2CS35253B
Reinen, D., Atanasov, M., Kohler, P. and Babel, D. (2010) Jahn-Teller Coupling and the Influence of Strain in Tg and Eg Ground and Excited States—A Ligand Field and DFT Study on Halide MIIIX6 Model Complexes [M = TiIII-CuIII; X = F-, Cl-]. Coordination Chemistry Reviews, 254, 2703-2754. https://doi.org/10.1016/j.ccr.2010.04.015
Birendra, K., Kumar, B., Kumar, S., Kumar, D. and Sharma, S. (2017) Synthesis and Characterization of Manganese, Copper and Zinc Complexes Derived from Schiff-Base Ligand. Oriental Journal of Chemistry, 33, 2643-2646. https://doi.org/10.13005/ojc/330563
Navneetsinha, R., Singh, V.P., Kumar, D. and Sharma, S. (2021) Spectroscopic Elucidation of Some Complexes of Vanillin Semicarbazone. Oriental Journal of Chemistry, 37, 826-832. https://doi.org/10.13005/ojc/370409
El-Boraey, H.A. and Serag El-Din, A.A. (2014) Transition Metal Complexes of a New 15-membered[N5]penta-azamacrocyclic Ligand with Their Spectral and Anticancer Studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 132, 663-671. https://doi.org/10.1016/j.saa.2014.05.018
Rosu, T., Negoiu, M., Pasculescu, S., Pahontu, E., Poirier, D. and Gulea, A. (2010) Metal-Based Biologically Active Agents: Synthesis, Characterization, Antibacterial and Antileukemia Activity Evaluation of Cu(II), V(IV) and Ni(II) Complexes with Antipyrine-Derived Compounds. European Journal of Medicinal Chemistry, 45, 774-781. https://doi.org/10.1016/j.ejmech.2009.10.034
Kozlevcar, B. and Segedin, P. (2008) Structural Analysis of a Series of Copper(II) Coordination Compounds and Correlation with Their Magnetic Properties. Croatica Chemica Acta, 81, 369-379.
Hassan, F.S.M., Kuran, W.S., Ibrahim, A.A. and Adam, F.A. (2020) Synthesis, Characterization and Biological Activity of Sodium Barbitone-GroupVIII Metals (viz. Ni(II), Pd(II) and Pt(II)) Complexes. Open Journal of Inorganic Nonmetallic Materials, 10, 1-14. https://doi.org/10.4236/ojinm.2020.101001
Arouri, A., Dridi, R., Kefi, R. and Zid, M.F. (2021) Structural Study, Vibrational, Optical, Thermal Properties and Hirshfeld Surface Analysis of a New Iron(III) Complex: FeCl4(C5N2H6)(C5N2H5). Crystal Structure Theory and Applications, 10, 14-26. https://doi.org/10.4236/csta.2021.101002
El-Sherbiny, G.M., Moghannem, S.A. and Sharaf, M.H. (2017) Antimicrobial Activities and Cytotoxicity of Sisymbriumirio L Extract against Multi-Drug Resistant Bacteria (MDRB) and Candida albicans. International Journal of Current Microbiology and Applied Sciences, 6, 1-13. https://doi.org/10.20546/ijcmas.2017.604.001
Naranda, A., Suskovic, B., Kelneric, Z. and Djokic, S. (1994) Structureactivity Relationship among Polyhydro Derivatives of Tylosin. The Journal of Antibiotics, 47, 581-587. https://doi.org/10.7164/antibiotics.47.581
Karim, A., Rani, R., Ranjan, R., Kumar, U., Kumar, V. and Sharma, S. (2017) Synthesis, Characterization and Biocidal Properties of Oxovanadium Complexes. Asian Journal of Chemistry, 29, 626-630. https://doi.org/10.14233/ajchem.2017.20286
Bollela, V., Sato, D. and Fonseca, B. (1999) McFarland Nephelometer as a Simple Method to Estimate the Sensitivity of the Polymerase Chain Reaction Using Mycobacterium tuberculosis as a Research Tool. Brazilian Journal of Medical and Biological Research, 32, 1073-1076. https://doi.org/10.1590/S0100-879X1999000900003