Structural Characterization and Antibacterial, Antifungal, Antioxidant Activity of ONO Salicyl Based Schiff Base and its VO(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Pd(II) and Hg(II) Complexes

Authors

  • Dildora Pardaeva
  • Aydin Tavman Istanbul University-Cerrahpasa
  • Erol Erçag
  • Mayram Hacioglu
  • Demet Gürbüz
  • Adem Çinarli
  • A. Seher Birteksöz Tan

DOI:

https://doi.org/10.17721/fujcV12I1P92-110

Keywords:

Schiff base, salicyl, metal complexes, antimicrobial, antioxidant

Abstract

An ONO tridentate Schiff base derived from 3,5-dichlorosalicylaldehyde and 2-amino-4-methylphenol (H2L) and its complexes with VO(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Pd(II) and Hg(II) were synthesized and characterized. The structures of the complexes were confirmed by means of elemental analysis, molar conductivity, magnetic moment, UV-visible, fluorescence, FT-IR and NMR spectroscopy. The M:L ratio is 1:2 in Fe(III) and Co(II) complexes whereas 1:1 in the other complexes. It was observed that the Pd(II) complex is 1:1 ionic while the others are non-ionic according to molar conductivity measurements. H2L showed weak fluorescence at different wavelengths in neutral, acidic and basic areas and in the form of some metal complexes. The VO(II) and Cu(II) complexes increased the fluorescence effect compared to the ligand, while the Fe(III) complex completely quenched it. Antibacterial and antifungal activity of the compounds was evaluated against six bacteria and three fungi. In general, all the compounds showed moderate antimicrobial activity. It was observed that some of the complexes exhibited higher activity towards S. epidermidis and S. aureus compared to the ligand. Antioxidant activity of the compounds was investigated in terms of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•) scavenging and Cupric Reducing Antioxidant Capacity (CUPRAC) methods. It was found that Zn(II) and Pd(II) complexes showed higher antioxidant activity than the ligand and the other complexes.

References

Aboul-Fadl T, Mohammed F, Hassan E. Synthesis, antitubercular activity and pharmacokinetic studies of some schiff bases derived from 1- alkylisatin and isonicotinic acid hydrazide (INH). Archives of Pharmacal Research 2003;26(10):778-784. https://doi.org/10.1007/bf02980020

Miri R, Razzaghi-asl N, Mohammadi M. QM study and conformational analysis of an isatin Schiff base as a potential cytotoxic agent. Journal of Molecular Modeling 2012;19(2):727-735. https://doi.org/10.1007/s00894-012-1586-x

Ren S, Wang R, Komatsu K, Bonaz-Krause P, Zyrianov Y, McKenna C, Csipke C, Tokes Z, Lien E. Synthesis, Biological Evaluation, and Quantitative Structure−Activity Relationship Analysis of New Schiff Bases of Hydroxysemicarbazide as Potential Antitumor Agents. Journal of Medicinal Chemistry 2001;45(2):410-419. https://doi.org/10.1021/jm010252q

Pandeya S, Sriram D, Nath G, DeClercq E. Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl)thiazol-2-yl] thiosemicarbazide. European Journal of Pharmaceutical Sciences 1999;9(1):25-31. https://doi.org/10.1016/s0928-0987(99)00038-x

da Silva CM, da Silva DL, Modolo LV, Alves RB, de Resende MA, Martins CVB, de Fatima A. Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2011;2(1):1-8. https://doi.org/10.1016/j.jare.2010.05.004

Kajal A, Bala S, Kamboj S, Sharma N, Saini V. Schiff Bases: A Versatile Pharmacophore. Journal of Catalysts 2013;2013:1-14. https://doi.org/10.1155/2013/893512

Shi L, Ge H, Tan S, Li H, Song Y, Zhu H, Tan R. Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde. European Journal of Medicinal Chemistry 2007;42(4):558-564. https://doi.org/10.1016/j.ejmech.2006.11.010

Sahu R, Thakur D, P K. Schiff Base: An Overview of its Medicinal Chemistry Potential for New Drug Molecules. International Journal of Pharmaceutical Sciences and Nanotechnology 1970;5(3):1757-1764. https://doi.org/10.37285/ijpsn.2012.5.3.2

Cozzi P. Metal–Salen Schiff base complexes in catalysis: practical aspects. Chem. Soc. Rev. 2004;33(7):410-421. https://doi.org/10.1039/b307853c

Tarafder M, Jin K, Crouse K, Ali A, Yamin B, Fun H. Coordination chemistry and bioactivity of Ni2+, Cu2+, Cd2+ and Zn2+ complexes containing bidentate Schiff bases derived from S-benzyldithiocarbazate and the X-ray crystal structure of bis[S-benzyl-β-N-(5-methyl-2-furylmethylene)dithiocarbazato]cadmium(II). Polyhedron 2002;21(25-26):2547-2554. https://doi.org/10.1016/s0277-5387(02)01188-9

Alterhoni E, Tavman A, Gürbüz D, Hacioglu M, Çinarli A, Şahin O, Tan A. Synthesis, Characterization and Antimicrobial Activity of Schiff Bases Including Three Hydroxy Groups and Their CoCl2, PdCl2, CuCl2 and ZnCl2 Complexes. Chemistry Select 2020;5(31):9730-9735. https://doi.org/10.1002/slct.202001498

Alterhoni E, Tavman A, Hacioglu M, Şahin O, Seher Birteksöz Tan A. Synthesis, structural characterization and antimicrobial activity of Schiff bases and benzimidazole derivatives and their complexes with CoCl2, PdCl2, CuCl2 and ZnCl2. Journal of Molecular Structure 2021;1229:129498. https://doi.org/10.1016/j.molstruc.2020.129498

Fujita E, Brunschwig B, Ogata T, Yanagida S. Toward photochemical carbon dioxide activation by transition metal complexes. Coordination Chemistry Reviews 1994;132:195-200. https://doi.org/10.1016/0010-8545(94)80040-5

Opstal T, Verpoort F. Synthesis of Highly Active Ruthenium Indenylidene Complexes for Atom‐Transfer Radical Polymerization and Ring‐Opening‐Metathesis Polymerization. Angewandte Chemie International Edition 2003;42(25):2876-2879. https://doi.org/10.1002/anie.200250840

Clercq B, Lefebvre F, Verpoort F. Immobilization of multifunctional Schiff base containing ruthenium complexes on MCM-41. Applied Catalysis A: General 2003;247(2):345-364. https://doi.org/10.1016/s0926-860x(03)00126-1

Tantaru G, Dorneanu V, Stan M. Schiff bis bases: analytical reagents. II. Spectrophotometric determination of manganese from pharmaceutical forms. Journal of Pharmaceutical and Biomedical Analysis 2002;27(5):827-832. https://doi.org/10.1016/s0731-7085(01)00517-9

McAuliffe C, Parish R, Abu-El-Wafa S, Issa R. High-valent manganese complexes of tetradentate schiff base ligands. ESR-active and ESR-silent dimeric species. Inorganica Chimica Acta 1986;115(1):91-94. https://doi.org/10.1016/s0020-1693(00)87702-6

Boghaei D, Mohebi S. Non-symmetrical tetradentate vanadyl Schiff base complexes derived from 1,2-phenylene diamine and 1,3-naphthalene diamine as catalysts for the oxidation of cyclohexene. Tetrahedron 2002;58(26):5357-5366. https://doi.org/10.1016/s0040-4020(02)00481-7

Papic S, Koprivanac N, Grabaric Z, Parac-Osterman D. Metal complex dyes of nickel with schiff bases. Dyes and Pigments, 1994;25:229-240.https://doi.org/10.1016/0143-7208(94)85012-7

Nejati K, Rezvani Z, Massoumi B. Syntheses and investigation of thermal properties of copper complexes with azo-containing Schiff-base dyes. Dyes and Pigments 2007;75(3):653-657. https://doi.org/10.1016/j.dyepig.2006.07.019

Kumar S, Dhar DN, Saxena PN. Applications of metal complexes of Schiff bases-A review. Journal of Scientific and Industrial Research, 2009;68:181-187.

Chantarasiri N, Ruangpornvisuti V, Muangsin N, Detsen H, Mananunsap T, Batiya C, Chaichit N. Structure and physico-chemical properties of hexadentate Schiff base zinc complexes derived from salicylaldehydes and triethylenetetramine. Journal of Molecular Structure 2004;701(1-3):93-103. https://doi.org/10.1016/j.molstruc.2004.05.015

Abdallah S, Mohamed G, Zayed M, El-Ela M. Spectroscopic study of molecular structures of novel Schiff base derived from o-phthaldehyde and 2-aminophenol and its coordination compounds together with their biological activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2009;73(5):833-840. https://doi.org/10.1016/j.saa.2009.04.005

Nartop D, Özdemir Ö, Gürkan P. Synthesis, characterization and investigation of tautomeric, potentiometric and antimicrobial properties of a novel unsymmetric Schiff base and its Fe (III) and Ni (II) complexes. Moroccan Journal of Chemistry, 2017;5:560-572. https://doi.org/10.48317/IMIST.PRSM/morjchem-v5i4.7897

Cinarli A, Gürbüz D, Tavman A, Seher Birteksöz A. Synthesis, spectral characterizations and antimicrobial activity of some Schiff bases of 4-chloro-2-aminophenol. Bulletin of the Chemical Society of Ethiopia 2011;25(3):407-417. https://doi.org/10.4314/bcse.v25i3.68593

Cinarli A, Gürbüz D, Tavman A, Birteksöz A. Spectral Characterization and Antimicrobial Activity of Some Schiff Bases Derived from 4‐Chloro‐2‐aminophenol and Various Salicylaldehyde Derivatives. Chinese Journal of Chemistry 2012;30(2):449-459. https://doi.org/10.1002/cjoc.201180473

Gürbüz D, Cinarli A, Tavman A, Birteksöz A. Spectral Characterization and Antimicrobial Activity of Some Schiff Bases Derived from 4‐Methyl‐2‐aminophenol. Chinese Journal of Chemistry 2012;30(4):970-978. https://doi.org/10.1002/cjoc.201100237

Gürbüz D, Çinarli A, Tavman A, Tan ASB. Synthesis, characterization and antimicrobial activity of some transition metal complexes of N-(5-chloro-2-hydroxyphenyl)-3-methoxy-salicylaldimine. Bulletin of the Chemical Society of Ethiopia 2015;29(1):63. https://doi.org/10.4314/bcse.v29i1.6

Kusmariya B, Mishra A. Co(II), Ni(II), Cu(II) and Zn(II) complexes of tridentate ONO donor Schiff base ligand: Synthesis, characterization, thermal, non-isothermal kinetics and DFT calculations. Journal of Molecular Structure 2017;1130:727-738. https://doi.org/10.1016/j.molstruc.2016.11.009

Zhang Z, Zeng H, Liu Y, Kuang D, Zhang F, Tan Y, Jiang W. Synthesis, crystal structure and anticancer activity of the dibutyltin(IV)oxide complexes containing substituted salicylaldehyde-o-aminophenol Schiff base with appended donor functionality. Inorganic and Nano-Metal Chemistry 2018;48(10):486-494. https://doi.org/10.1080/24701556.2019.1571513

Afrin A, Jayaraj A, Gayathri M, P. C. An overview of Schiff base-based fluorescent turn-on probes: a potential candidate for tracking live cell imaging of biologically active metal ions. Sensors & Diagnostics 2023;2(5):988-1076. https://doi.org/10.1039/d3sd00110e

Lohar S, Pal S, Mukherjee M, Maji A, Demitri N, Chattopadhyay P. A turn-on green channel Zn2+ sensor and the resulting zinc(ii) complex as a red channel HPO42− ion sensor: a new approach. RSC Advances 2017;7(41):25528-25534. https://doi.org/10.1039/c7ra02175e

Jung J, Yun D, Lee H, Kim K, Kim C. Selective chemosensor capable of sensing both CN− and Zn2+: Its application to zebrafish. Sensors and Actuators B: Chemical 2019;297:126814. https://doi.org/10.1016/j.snb.2019.126814

Clinical and Laboratory Standards Institute (CLSI). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard-Third Edition. M27-A3, Wayne, PA, USA, (2012).

Clinical and Laboratory Standards Institute (CLSI). Performance Standards for Antimicrobial. Document M100-Ed.31., Wayne, PA, USA (2021).

Apak R, Güçlü K, Özyürek M, Karademir S. Novel Total Antioxidant Capacity Index for Dietary Polyphenols and Vitamins C and E, Using Their Cupric Ion Reducing Capability in the Presence of Neocuproine: CUPRAC Method. Journal of Agricultural and Food Chemistry 2004;52(26):7970-7981. https://doi.org/10.1021/jf048741x

Apak R, Güçlü K, Özyürek M, Esin Karademir S, Erçağ E. The cupric ion reducing antioxidant capacity and polyphenolic content of some herbal teas. International Journal of Food Sciences and Nutrition 2006;57(5-6):292-304. https://doi.org/10.1080/09637480600798132

Sánchez-Moreno C, Larrauri J, Saura-Calixto F. A procedure to measure the antiradical efficiency of polyphenols. Journal of the Science of Food and Agriculture 1998;76(2):270-276. https://doi.org/10.1002/(sici)1097-0010(199802)76:2<270::aid-jsfa945>3.0.co;2-9

Geary W. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coordination Chemistry Reviews 1971;7(1):81-122. https://doi.org/10.1016/s0010-8545(00)80009-0

Amer S, El-Wakiel N, El-Ghamry H. Synthesis, spectral, antitumor and antimicrobial studies on Cu(II) complexes of purine and triazole Schiff base derivatives. Journal of Molecular Structure 2013;1049:326-335. https://doi.org/10.1016/j.molstruc.2013.06.059

Ahmad Mantoo I, Bashir M, Yousuf I. A novel diaqua−bridged water soluble copper(II) complex acts as an efficient cytotoxic agent against lung cancer cells. Inorganic Chemistry Communications 2023;157:111384. https://doi.org/10.1016/j.inoche.2023.111384

Lomjanský D, Rajnák C, Titiš J, Moncoľ J, Smolko L, Boča R. Impact of tetrahedral and square planar geometry of Ni(II) complexes with (pseudo)halide ligands to magnetic properties. Inorganica Chimica Acta 2018;483:352-358. https://doi.org/10.1016/j.ica.2018.08.029

Starikov A, Minyaev R, Minkin V. Theoretical modeling of the square-planar to tetrahedral isomerization of bis-chelate nickel(II) complexes. Chemical Physics Letters 2008;459(1-6):27-32. https://doi.org/10.1016/j.cplett.2008.04.132

Bridgeman A. On the origin of paramagnetism in planar nickel(ii) complexes. Dalton Transactions 2008;(15):1989. https://doi.org/10.1039/b717767d

Kaya Y, Mutlu H, Irez G. Uv-vis spectra and fluorescence properties of two iminooxime ligands and their metal complexes: optical band gaps. Gazi University Journal of Science, 2010;23:13-18.

Mautner F, Fischer R, Torvisco A, Henary M, Louka F, Massoud S, Salem N. Five-Coordinated Geometries from Molecular Structures to Solutions in Copper(II) Complexes Generated from Polydentate-N-Donor Ligands and Pseudohalides. Molecules 2020;25(15):3376. https://doi.org/10.3390/molecules25153376

Khan S, Al Masum A, Islam M, Drew M, Bauzá A, Frontera A, Chattopadhyay S. Observation of π-hole interactions in the solid state structures of three new copper(II) complexes with a tetradentate N4 donor Schiff base: Exploration of their cytotoxicity against MDA-MB 468 cells. Polyhedron 2017;123:334-343. https://doi.org/10.1016/j.poly.2016.11.012

Pardaeva D, Tavman A, Gürbüz D, Hacioglu M, Yilmaz FN, Şahin O, Tan ASB, Çinarli, A. Spectral characterization and antibacterial, antifungal, antiviral activity of salicyl based new Schiff bases and their Co(II), Ni(II), Cu(II), Zn(II), and Pd(II) complexes. Revue Roumaine de Chimie, 2024;69:83-96.

Jain P, Sharma S, Kumar N, Misra N. Ni(II) and Cu(II) complexes of bidentate thiosemicarbazone ligand: Synthesis, structural, theoretical, biological studies and molecular modeling. Applied Organometallic Chemistry 2020;34(9):e5371. https://doi.org/10.1002/aoc.5736

Abu-Dief A, Abdel-Rahman L, Abdelhamid A, Marzouk A, Shehata M, Bakheet M, Almaghrabi O, Nafady A. Synthesis and characterization of new Cr(III), Fe(III) and Cu(II) complexes incorporating multi-substituted aryl imidazole ligand: Structural, DFT, DNA binding, and biological implications. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2020;228:117700. https://doi.org/10.1016/j.saa.2019.117700

Abdel-Rahman L, Abu-Dief A, Moustafa H, Abdel-Mawgoud A. Design and nonlinear optical properties (NLO) using DFT approach of new Cr(III), VO(II), and Ni(II) chelates incorporating tri-dentate imine ligand for DNA interaction, antimicrobial, anticancer activities and molecular docking studies. Arabian Journal of Chemistry 2020;13(1):649-670. https://doi.org/10.1016/j.arabjc.2017.07.007

Udhayakumari D, Inbaraj V. A Review on Schiff Base Fluorescent Chemosensors for Cell Imaging Applications. Journal of Fluorescence 2020;30(5):1203-1223. https://doi.org/10.1007/s10895-020-02570-7

Devi J, Yadav M, Kumar D, Naik L, Jindal D. Some divalent metal(II) complexes of salicylaldehyde‐derived Schiff bases: Synthesis, spectroscopic characterization, antimicrobial and in vitro anticancer studies. Applied Organometallic Chemistry 2018;33(2):e4693. https://doi.org/10.1002/aoc.4693

Abdel Aziz A, Salem A, Sayed M, Aboaly M. Synthesis, structural characterization, thermal studies, catalytic efficiency and antimicrobial activity of some M(II) complexes with ONO tridentate Schiff base N-salicylidene-o-aminophenol (saphH2). Journal of Molecular Structure 2012;1010:130-138. https://doi.org/10.1016/j.molstruc.2011.11.043

Oloyede-Akinsulere A, Olalekan Babajide J, Olonkwoh Salihu S. Synthesis, Antibacterial and Antioxidant Activities of Some Tridentate Substituted Salicylaldimines. Asian Journal of Applied Chemistry Research 2018;1(4):1-10. https://doi.org/10.9734/ajacr/2018/v1i49706

Aslam M, Anis I, Mehmood R, Iqbal L, Iqbal S, Khan I, Chishti M, Perveen S. Synthesis and biological activities of 2-aminophenol-based Schiff bases and their structure–activity relationship. Medicinal Chemistry Research 2015;25(1):109-115. https://doi.org/10.1007/s00044-015-1468-8

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2025-01-23

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