Abstract
Background: The transition metal complexes are derived from a natural biopolymer which is a very potent material in various research areas of study.
Objective: This study aims to show the preparation of ruthenium(III) complexes from chitosan Schiff base ligand for effective application in antifungal studies.
Methods: Chemical modification was carried out through a condensation reaction of chitosan with some aromatic aldehydes, which resulted in the formation of a bidentate Schiff base ligand. The Ru(III) complexes were prepared by complexation of ruthenium metal ion with bidentate ligands. The series of Ru(III) complexes were characterized by Scanning Electron Microscope with Electron dispersive X-ray (SEM-EDX) analysis, Powder XRD. The biopolymer-based transition metal complexes have potential uses for their biological activities. The synthesized metal complexes were directed for antifungal study by the disc diffusion method.
Results: The antifungal study results showed that the transition metal complexes have significant antifungal activities against some vital fungal pathogens such as Aspergillus flavus, Aspergillus niger, Fusarium oxysporum, Penicillim chryogenum and Trigoderma veride.
Conclusion: A chitosan biopolymer offers some peculiar features such as biodegradability, biocompatibility etc., which are favorable for green synthesis of transition metal complexes through complexation with bidentate ligands. These metal complexes possess good antifungal property due to their chelation effect on micro-organisms.
Keywords: Antifungal study, bidentate ligands, chitosan Schiff base ligand, chitosan, fungal pathogens, ruthenium(III) complex.
Graphical Abstract
[1]
Guo CC, Huang G, Guo DC. Preparation of nitrogenous polysaccharide-supported ironporphyrins and their catalysis for the aerobic oxidation of cyclohexane. Kinet Catal 2006; 47: 93-7.
[http://dx.doi.org/10.1134/S0023158406010149]
[http://dx.doi.org/10.1134/S0023158406010149]
[2]
Hamdine M, Heuzey MC, Bégin A. Effect of organic and inorganic acids on concentrated chitosan solutions and gels. Int J Biol Macromol 2005; 37(3): 134-42.
[http://dx.doi.org/10.1016/j.ijbiomac.2005.09.009] [PMID: 16257048]
[http://dx.doi.org/10.1016/j.ijbiomac.2005.09.009] [PMID: 16257048]
[3]
Volesky B. Detoxification of metal-bearing effluents: Biosorption for the next century. Hydrometallurgy 2001; 59: 203-16.
[http://dx.doi.org/10.1016/S0304-386X(00)00160-2]
[http://dx.doi.org/10.1016/S0304-386X(00)00160-2]
[4]
Jeon YJ, Kim SK. Continuous production of chitooligosaccharides using a dual reactor system. Process Biochem 2000; 35: 623-32.
[http://dx.doi.org/10.1016/S0032-9592(99)00118-1]
[http://dx.doi.org/10.1016/S0032-9592(99)00118-1]
[5]
Moore GK, Roberts GAF. Reactions of chitosan: 4. Preparation of organosoluble derivatives of chitosan. Int J Biol Macromol 1982; 42: 46-9.
[http://dx.doi.org/10.1016/0141-8130(82)90023-X]
[http://dx.doi.org/10.1016/0141-8130(82)90023-X]
[6]
Fattahi A, Sadrjavadi K, Golozar MA, Varshosaz J, Fathi MH, Mirmohammad-Sadeghi H. Preparation and characterization of oligochitosan-tragacanth nanoparticles as a novel gene carrier. Carbohydr Polym 2013; 97(2): 277-83.
[http://dx.doi.org/10.1016/j.carbpol.2013.04.098] [PMID: 23911446]
[http://dx.doi.org/10.1016/j.carbpol.2013.04.098] [PMID: 23911446]
[7]
Mao JS, Liu HF, Yin YJK, Yao KD. The properties of chitosan-gelatin membranes and scaffolds modified with hyaluronic acid by different methods. Biomaterials 2003; 24(9): 1621-9.
[http://dx.doi.org/10.1016/S0142-9612(02)00549-5] [PMID: 12559822]
[http://dx.doi.org/10.1016/S0142-9612(02)00549-5] [PMID: 12559822]
[8]
Croisier F, Jérôme C. Chitosan-based biomaterials for tissue engineering. Eur Polym J 2013; 49: 780-92.
[http://dx.doi.org/10.1016/j.eurpolymj.2012.12.009]
[http://dx.doi.org/10.1016/j.eurpolymj.2012.12.009]
[9]
Park H, Choi B, Hu J, Lee M. Injectable chitosan hyaluronic acid hydrogels for cartilage tissue engineering. Acta Biomater 2013; 9(1): 4779-86.
[http://dx.doi.org/10.1016/j.actbio.2012.08.033] [PMID: 22935326]
[http://dx.doi.org/10.1016/j.actbio.2012.08.033] [PMID: 22935326]
[10]
Zayed EM, Zayed MA, Hindy AMM. Thermal and spectroscopic investigation of novel Schiff base, its metal complexes, and their biological activities. J Therm Anal Calorim 2014; 116: 391-400.
[http://dx.doi.org/10.1007/s10973-013-3560-y]
[http://dx.doi.org/10.1007/s10973-013-3560-y]
[11]
Mohamed NA, Sabaa MW, El-Ghandour AH, Abdel-Aziz MM, Abdel-Gawad OF. Quaternized N-substituted carboxymethyl chitosan derivatives as antimicrobial agents. Int J Biol Macromol 2013; 60: 156-64.
[http://dx.doi.org/10.1016/j.ijbiomac.2013.05.022] [PMID: 23732327]
[http://dx.doi.org/10.1016/j.ijbiomac.2013.05.022] [PMID: 23732327]
[12]
Kumar S, Kumari M, Dutta PK, Koh J. Chitosan biopolymer schiff base: Preparation, characterization, optical, and antibacterial activity. Int J Polym Mater Polym Biomater 2014; 63: 173-7.
[http://dx.doi.org/10.1080/00914037.2013.812088]
[http://dx.doi.org/10.1080/00914037.2013.812088]
[13]
Younes I, Hajji S, Frachet V, Rinaudo M, Jellouli K, Nasri M. Chitin extraction from shrimp shell using enzymatic treatment. Antitumor, antioxidant and antimicrobial activities of chitosan. Int J Biol Macromol 2014; 69: 489-98.
[http://dx.doi.org/10.1016/j.ijbiomac.2014.06.013] [PMID: 24950313]
[http://dx.doi.org/10.1016/j.ijbiomac.2014.06.013] [PMID: 24950313]
[14]
Harris R, Lecumberri E, Mateos-Aparicio I, et al. Chitosan nanoparticles and microspheres for the encapsulation of natural antioxidants extracted from Ilex paraguariensis. Carbohydr Polym 2011; 84: 803-6.
[http://dx.doi.org/10.1016/j.carbpol.2010.07.003]
[http://dx.doi.org/10.1016/j.carbpol.2010.07.003]
[15]
Liu J, Wen XY, Lu JF, Kan J, Jin CH. Free radical mediated grafting of chitosan with caffeic and ferulic acids: Structures and antioxidant activity. Int J Biol Macromol 2014; 65: 97-106.
[http://dx.doi.org/10.1016/j.ijbiomac.2014.01.021] [PMID: 24444883]
[http://dx.doi.org/10.1016/j.ijbiomac.2014.01.021] [PMID: 24444883]
[16]
Vicente S, Goins BA, Sanchez A, Alonso MJ, Phillips WT. Biodistribution and lymph node retention of polysaccharide-based immunostimulating nanocapsules. Vaccine 2014; 32(15): 1685-92.
[http://dx.doi.org/10.1016/j.vaccine.2014.01.059] [PMID: 24508040]
[http://dx.doi.org/10.1016/j.vaccine.2014.01.059] [PMID: 24508040]
[17]
Nogueira DR, Tavano L, Mitjans M, Pérez L, Infante MR, Vinardell MP. In vitro antitumor activity of methotrexate via pH-sensitive chitosan nanoparticles. Biomaterials 2013; 34(11): 2758-72.
[http://dx.doi.org/10.1016/j.biomaterials.2013.01.005] [PMID: 23352041]
[http://dx.doi.org/10.1016/j.biomaterials.2013.01.005] [PMID: 23352041]
[18]
Karagozlu MZ, Kim JA, Karadeniz F, et al. Anti-proliferative effect of aminoderivatized chitooligosaccharides on AGS human gastric cancer cells. Process Biochem 2010; 45: 1523-8.
[http://dx.doi.org/10.1016/j.procbio.2010.05.035]
[http://dx.doi.org/10.1016/j.procbio.2010.05.035]
[19]
Guo Z, Xing R, Liu S, et al. The synthesis and antioxidant activity of the Schiff bases of chitosan and carboxymethyl chitosan. Bioorg Med Chem Lett 2005; 15(20): 4600-3.
[http://dx.doi.org/10.1016/j.bmcl.2005.06.095] [PMID: 16122924]
[http://dx.doi.org/10.1016/j.bmcl.2005.06.095] [PMID: 16122924]
[20]
Shen JM, Xu L, Lu Y, et al. Chitosan-based luminescent/magnetic hybrid nanogels for insulin delivery, cell imaging, and antidiabetic research of dietary supplements. Int J Pharm 2012; 427(2): 400-9.
[http://dx.doi.org/10.1016/j.ijpharm.2012.01.059] [PMID: 22342466]
[http://dx.doi.org/10.1016/j.ijpharm.2012.01.059] [PMID: 22342466]
[21]
Russo E, Gaglianone N, Baldassari S, et al. Preparation, characterization and in vitro antiviral activity evaluation of foscarnet-chitosan nanoparticles. Colloids Surf B Biointerfaces 2014; 118: 117-25.
[http://dx.doi.org/10.1016/j.colsurfb.2014.03.037] [PMID: 24742953]
[http://dx.doi.org/10.1016/j.colsurfb.2014.03.037] [PMID: 24742953]
[22]
Sarilmiser HK, Oner ET. Investigation of anti-cancer activity of linear and aldehyde-activated levan from Halomonas smyrnensis AAD6T. Biochem Eng J 2014; 92: 28-34.
[http://dx.doi.org/10.1016/j.bej.2014.06.020]
[http://dx.doi.org/10.1016/j.bej.2014.06.020]
[23]
Yang J, Luo K, Li D, et al. Preparation, characterization and in vitro anticoagulant activity of highly sulfated chitosan. Int J Biol Macromol 2013; 52: 25-31.
[http://dx.doi.org/10.1016/j.ijbiomac.2012.09.027] [PMID: 23041665]
[http://dx.doi.org/10.1016/j.ijbiomac.2012.09.027] [PMID: 23041665]
[24]
Baran T, Menteş A. Cu(II) and Pd(II) complexes of water soluble O-carboxymethyl chitosan Schiff bases: Synthesis, characterization. Int J Biol Macromol 2015; 79: 542-54.
[http://dx.doi.org/10.1016/j.ijbiomac.2015.05.021] [PMID: 26021275]
[http://dx.doi.org/10.1016/j.ijbiomac.2015.05.021] [PMID: 26021275]
[25]
Varma AJ, Deshpande SV, Kennedy JF. Metal complexation by chitosan and its derivatives: A review. Carbohydr Polym 2004; 55: 77-93.
[http://dx.doi.org/10.1016/j.carbpol.2003.08.005]
[http://dx.doi.org/10.1016/j.carbpol.2003.08.005]
[26]
Kurita K. Controlled functionalization of the polysaccharide chitin. Prog Polym Sci 2001; 26: 1921-71.
[http://dx.doi.org/10.1016/S0079-6700(01)00007-7]
[http://dx.doi.org/10.1016/S0079-6700(01)00007-7]
[27]
Dharmaraj N, Viswanathamurthi P, Natarajan K. Ruthenium(II) complexes containing bidentate Schiff bases and their antifungal activity. Transition Met Chem 2001; 26: 105-9.
[http://dx.doi.org/10.1023/A:1007132408648]
[http://dx.doi.org/10.1023/A:1007132408648]
[28]
Muthukumar M, Viswanathamurthi PJ. Spectral, catalytic, and antifungal studies of ruthenium(II) chalcone complexes. Coord Chem 2010; 63: 1263-72.
[http://dx.doi.org/10.1080/00958971003728304]
[http://dx.doi.org/10.1080/00958971003728304]
[29]
Ramesh R, Sivagamasundari M. Synthesis, Spectral and Antifungal Activity of Ru(II) Mixed Ligand Complexes. Synth React Inorg Met-Org Chem 2003; 33: 899-10.
[http://dx.doi.org/10.1081/SIM-120021656]
[http://dx.doi.org/10.1081/SIM-120021656]
[30]
Liu W, Qin Y, Liu S, et al. C-coordinated O-carboxymethyl chitosan metal complexes: Synthesis, characterization and antifungal efficacy. Int J Biol Macromol 2018; 106: 68-77.
[http://dx.doi.org/10.1016/j.ijbiomac.2017.07.176] [PMID: 28774807]
[http://dx.doi.org/10.1016/j.ijbiomac.2017.07.176] [PMID: 28774807]
[31]
Fatih S, Ugur B, Ahmed NK, Ersin G. Fe (III), Co(II), Ni(II), Cu(II) and Zn(II) complexes of schiff bases based on glycine and phenylalanine: Synthesis, magnetic/thermal properties and antimicrobial activity. J Mol Struct 2018; 1154: 256-60.
[http://dx.doi.org/10.1016/j.molstruc.2017.10.052]
[http://dx.doi.org/10.1016/j.molstruc.2017.10.052]
[32]
Ângelo DF. Camila de PP, Carolina Raquel DGO, Breno Germano de FO, Lucas LF, Pedro Henrique Corrêa da Silva. Schiff bases and their metal complexes as urease inhibitors - A brief Review. J Adv Res 2018; 13: 113-26.
[http://dx.doi.org/10.1016/j.jare.2018.03.007]
[http://dx.doi.org/10.1016/j.jare.2018.03.007]
[33]
Chen W, Li Y, Cui Y, Zhang X, Zhu H-L, Zeng Q. Synthesis, molecular docking and biological evaluation of Schiff base transition metal complexes as potential urease inhibitors. Eur J Med Chem 2010; 45(10): 4473-8.
[http://dx.doi.org/10.1016/j.ejmech.2010.07.007] [PMID: 20691510]
[http://dx.doi.org/10.1016/j.ejmech.2010.07.007] [PMID: 20691510]
[34]
Anan NA, Hassan SM, Saad EM, Butler IS, Mostafa SI. Preparation, characterization and pH-metric measurements of 4-hydroxysalicylidenechitosan Schiff-base complexes of Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ru(III), Rh(III), Pd(II) and Au(III). Carbohydr Res 2011; 346(6): 775-93.
[http://dx.doi.org/10.1016/j.carres.2011.01.014] [PMID: 21392736]
[http://dx.doi.org/10.1016/j.carres.2011.01.014] [PMID: 21392736]
[35]
Jiao TF, Zhou J, Zhou JX, et al. synthesis and characterization of chitosan-based schiff base compounds with aromatic substituent groups. Iran Polym J 2011; 20: 123-36.
[36]
Dash M, Chiellini F, Ottenbrite RM, Chiellini E. Chitosan-A versatile semi-synthetic polymer in biomedical applications. Prog Polym Sci 2011; 36: 981-14.
[http://dx.doi.org/10.1016/j.progpolymsci.2011.02.001]
[http://dx.doi.org/10.1016/j.progpolymsci.2011.02.001]
[37]
Burton AW, Ong K, Rea T, Chan IY. On the estimation of average crystallite size of zeolites from the Scherrer equation: A critical evaluation of its application to zeolites with one-dimensional pore systems. Microporous Mesoporous Mater 2009; 117: 75-90.
[http://dx.doi.org/10.1016/j.micromeso.2008.06.010]
[http://dx.doi.org/10.1016/j.micromeso.2008.06.010]
[38]
Motlagh MK, Noroozifar M, Shahroosvand H. A new reduction route for the synthesis of nanoscale metals and metal oxides with ascorbic acid at low temperature. J Iran Chem Soc 2010; 7: 113-22.
[http://dx.doi.org/10.1007/BF03246190]
[http://dx.doi.org/10.1007/BF03246190]
[39]
Monteiro OAC Jr, Airoldi C. Some studies of crosslinking chitosan-glutaraldehyde interaction in a homogeneous system. Int J Biol Macromol 1999; 26(2-3): 119-28.
[http://dx.doi.org/10.1016/S0141-8130(99)00068-9] [PMID: 10517518]
[http://dx.doi.org/10.1016/S0141-8130(99)00068-9] [PMID: 10517518]
[40]
Sun S, Wang A. Adsorption properties of carboxymethyl-chitosan and cross-linked carboxymethyl-chitosan resin with Cu(II) as template. Separ Purif Tech 2006; 49: 197-04.
[http://dx.doi.org/10.1016/j.seppur.2005.09.013]
[http://dx.doi.org/10.1016/j.seppur.2005.09.013]
[41]
Yuan G, Zhu C, Xuan W, Cui Y. Enantioselective recognition and separation by a homochiral porous lamellar solid based on unsymmetrical schiff base metal complexes. Chemistry 2009; 15(26): 6428-34.
[http://dx.doi.org/10.1002/chem.200900037] [PMID: 19462387]
[http://dx.doi.org/10.1002/chem.200900037] [PMID: 19462387]
[42]
Zhang Z, Yu X, Fong LK, Margerum LD. Ligand effects on the phosphoesterase activity of Co(II) schiff base complexes built on PAMAM dendrimers. Inorg Chim Acta 2001; 317: 72-80.
[http://dx.doi.org/10.1016/S0020-1693(01)00424-8]
[http://dx.doi.org/10.1016/S0020-1693(01)00424-8]
[43]
Anuradha KS, Pathak DD. Synthesis and development of Chitosan anchored copper(II) Schiff base complexes as heterogeneous catalysts for N-arylation of amines. Tetrahedron Lett 2015; 56: 4135-42.
[http://dx.doi.org/10.1016/j.tetlet.2015.05.049]
[http://dx.doi.org/10.1016/j.tetlet.2015.05.049]
[44]
Selwin Joseyphus R, Justin Dhanaraj C, Sivasankaran Nair M. Synthesis and characterization of some Schiff base transition metal complexes derived from vanillin and L(+)alanine. Transition Met Chem 2006; 31: 699-02.
[http://dx.doi.org/10.1007/s11243-006-0048-7]
[http://dx.doi.org/10.1007/s11243-006-0048-7]
[45]
Kulkarni AD, Patil SA, Badami PS. electrochemical properties of some transition metal complexes: synthesis, characterization and in-vitro antimicrobial studies of Co(II), Ni(II), Cu(II), Mn(II) and Fe(III) complexes. Int J Electrochem Sci 2009; 4: 717-29.
[46]
Rani S, Kumar S, Chandra S. Spectroscopic and biological approach in the characterization of a novel 14-membered [N4] macrocyclic ligand and its palladium(II), platinum(II), ruthenium(III) and iridium(III) complexes. Spectrochim Acta A Mol Biomol Spectrosc 2014; 118: 244-50.
[http://dx.doi.org/10.1016/j.saa.2013.08.079] [PMID: 24051297]
[http://dx.doi.org/10.1016/j.saa.2013.08.079] [PMID: 24051297]
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