Chemistry in biosystem—A contemporary review of Schiff bases and their metal complexes as antioxidants and anti-fungal agents

Shallu Sachdeva, Neelu Dheer, Sunita Hooda, Neeti Misra, Bipasa Arya, Manisha Verma, Sangeeta Kaul

Article ID: 1943
Vol 6, Issue 1, 2023

VIEWS - 942 (Abstract) 187 (PDF)

Abstract


Schiff bases are a class of organic compounds which have good chelating properties. Due to this, they can form complexes with metal ions of the transition series. Schiff bases and their derivatives are bioactive and hence find widespread uses in various fields of inorganic, organic and medicinal chemistry. These are synthesised by condensation reactions and have been studied extensively as they can exhibit biological properties like anti-oxidant, anti-fungal, anti-cancer, anti-bacterial and anti-microbial, apart from finding uses in the field of material science. With the advent of nanotechnology and its increasing importance, the introduction of nanoparticles of Schiff bases can increase the effectiveness of their various biological properties. In the present article, we aim at providing an exhaustive review of the behaviour of metal complexes of Schiff bases and their various derivatives as anti-oxidant and anti-fungal agents. The most pertinent and contemporary literature has been chosen for this review article.

Keywords


Schiff Bases; Transition Metal Ions; Chelation; Bioactive; Chitosan

Full Text:

PDF


References


1. Siham S, Adeline FT, Gérald L, et al. Imidazole and azo-based Schiff bases ligands as highly active antifungal and antioxidant components. Heteroatom Chemistry 2019. doi: 10.1155/2019/6862170.

2. Muzammil K, Trivedi P, Khetani DB. Synthesis and characterization of Schiff base m-nitro aniline and their complexes. Research Journal of Chemical Sciences 2015; 5(5): 52–55.

3. Kolapwar BG. Study of Schiff base compounds and its derivatives. Anveshana’s International Journal of Research in Pharmacy and Life Sciences 2017; 2: 15–18.

4. Hameed A, Al-Rashida M, Uroos M, et al. Schiff bases in medicinal chemistry—A patent review. Expert Opinion on Therapeutic Patents 2017; 27(1): 63–79. doi: 10.1080/13543776.2017.1252752.

5. Dalia S, Afsan F, Hossai M, et al. A short review on chemistry of Schiff base metal complexes and their catalytic application. International Journal of Chemical Studies 2018; 6(3): 2859–2866. doi: 10.1016/j.inoche.2023.110451.

6. Alafeefy AM, Bakht MA, Ganie MA, et al. Synthesis, analgesic, anti-inflammatory and anti-ulcerogenic activities of certain novel Schiff’s bases as fenamate isosteres. Bioorganic & Medicinal Chemistry Letters 2015; 25(2): 179–183. doi: 10.1016/j.bmcl.2014.11.088.

7. Mou Z, Deng N, Zhang F, et al. “Half-sandwich” Schiff-base Ir(III) complexes as anticancer agents. European Journal of Medicinal Chemistry 2017; 138: 72–82. doi: 10.1016/j.ejmech.2017.06.027.

8. Thomas AB, Nanda RK, Kothapalli LB, et al. Synthesis and biological evaluation of Schiff’s bases and 2-azetidinones of isonocotinyl hydrazone as potential antidepressant and nootropic agents. Arabian Journal of Chemistry 2016; 9: S79–S90. doi: 10.1016/j.arabjc.2011.02.015.

9. Murtaza S, Akhtar MS, Kanwal F, et al. Synthesis and biological evaluation of Schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent. Journal of Saudi Chemical Society 2017; 21: S359–S372. doi: 10.1016/j.jscs.2014.04.003.

10. Zhan P, Liu X, Zhu J, et al. Synthesis and biological evaluation of imidazole thioacetanilides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorganic & Medicinal Chemistry 2009; 17(16): 5775–5781. doi: 10.1016/j.bmc.2009.07.028.

11. Gungor E, Celen S, Azaaz D, et al. Two tridentate Schiff base ligands and their mononuclear cobalt(III) complexes-synthesis, characterization, antibacterial and antifungal activities. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012; 94: 216–221. doi: 10.1016/j.saa.2012.03.034.

12. Mishra N, Poonia K, Soni SK, et al. Synthesis, characterization and antimicrobial activity of Schiff base Ce(III) complexes. Polyhedron 2016; 120: 60–68. doi: 10.1016/j.poly.2016.05.026.

13. Ziessel R, Harriman A, El-Ghayoury A, et al. First assembly of copper(I) naphthyridine-based helicates. New Journal of Chemistry 2000; 24(10): 729–732. doi: 10.1039/B003342L.

14. Young MC, Johnson AM, Gamboa AS, et al. Achiral endohedral functionality provides stereochemical control in Fe(II)-based self-assemblies. Chemical Communications 2013; 49(16): 1627–1629. doi: 10.1039/C3CC37912D.

15. Cloete J, Mapolie SF. Functionalized pyridinyl–imine complexes of palladium as catalyst precursors for ethylene polymerization. Journal of Molecular Catalysis A: Chemical 2006; 243(2): 221–225. doi: 10.1016/j.molcata.2005.08.002.

16. Kontham V, Ansari KR, Padmaja KV. Tribological properties of 10-undecenoic acid-derived Schiff base lubricant additives. Arabian Journal for Science and Engineering 2021; 46: 5593–5603. doi: 10.1007/s13369-020-05125-x.

17. Wang X, Ding G, Duan Y, et al. A novel triphenylamine-based bis-Schiff bases fluorophores with AIE-activity as the hydrazine fluorescence turn-off probes and cell imaging in live cells. Talanta 2020; 217: 121029. doi: 10.1016/j.talanta.2020.121029.

18. Shalini K, Sharma PK, Kumar N. Imidazole and its biological activities—A review. Der Chemica Sinica 2010; 1(3): 36–47. doi: 10.2174/1389557521666210521221808.

19. Matsumoto Y, Sawamura J, Murata T, et al. Amino acid Schiff base bearing benzophenone imine as a platform for highly congested unnatural α-amino acid synthesis. Journal of American Chemical Society 2020; 142(18): 8498–8505. doi: 10.1021/jacs.0c02707.

20. Satpati S, Saha SK, Suhasaria A, et al. Adsorption and anti-corrosion characteristics of vanillin Schiff bases on mild steel in 1 M HCl-experimental and theoretical study. RSC Advances 2020; 10(16): 9258–9273. doi: 10.1039/C9RA07982C.

21. Ying G, Xiong W, Wang H, et al. Preparation, water solubility and antioxidant activity of branched-chain chitosan derivatives. Carbohydrate Polymers 2011; 83(4): 1787–1796. doi: 10.1016/j.carbpol.2010.10.037.

22. Hu D, Chen L, Yang Y, et al. Syntheses, structures and antioxidant activities of two new Cu(II) complexes with a benzimidazole Schiff base ligand. Inorganic Nano-Metal Chemistry 2018; 1556. doi: 10.1080/15533174.2013.843562.

23. Mishra N, Yadav R, Kumar K, et al. Conventional vs microwave assisted SiO2/P2O5 catalyzed synthesis of Schiff bases. Journal of Physics: Conference Series 2020; 1504(1): 012002. doi: 10.1088/1742-6596/1504/1/012002.

24. Nartop D, Özkan EH, Gündem M, et al. Synthesis, antimicrobial and antimutagenic effects of novel polymeric Schiff bases including indol. Journal of Molecular Structure 2019; 1195: 877–882. doi: 10.1016/j.molstruc.2019.06.042.

25. Pervaiz M, Sadiq S, Sadiq A, et al. Azo-Schiff base derivatives of transition metal complexes as antimicrobial agents. Coordination Chemistry Reviews 2021; 447: 214128. doi: 10.1016/j.ccr.2021.214128.

26. Socea LI, Visan DC, Barbuceanu SF, et al. The antioxidant activity of some acylhydrazones with dibenzo [ad][7] annulene moiety. Revista de Chimie 2018; 69(4): 795–797. doi: 10.37358/rc.18.4.6202.

27. Chen Y, Mi Y, Li Q, et al. Synthesis of Schiff bases modified inulin derivatives for potential antifungal and antioxidant applications. International Journal of Biological Macromolecules 2020; 143: 714–723. doi: 10.1016/j.ijbiomac.2019.09.127.

28. Wei L, Tan W, Zhang J, et al. Synthesis, characterization, and antifungal activity of Schiff bases of inulin bearing pyridine ring. Polymers 2019; 11(2): 371. doi: 10.3390/polym11020371.

29. Slassi S, Fix-Tailler A, Larcher G, et al. Imidazole and azo-based Schiff bases ligands as highly active antifungal and antioxidant components. Heteroatom Chemistry 2019; 47: 1–8. doi: 10.1155/2019/6862170.

30. Wei L, Tan W, Wang G, et al. The Antioxidant and antifungal activity of chitosan derivatives bearing Schiff bases and quaternary ammonium salts. Carbohydrate Polymers 2019; 226: 115256. doi: 10.1016/j.carbpol.2019.115256.

31. Mi Y, Chen Y, Tan W, et al. The influence of bioactive glyoxylate bearing Schiff base on antifungal and antioxidant activities to chitosan quaternary ammonium salts. Carbohydrate Polymers 2022; 278: 118970. doi: 10.1016/j.carbpol.2021.118970.

32. Wei L, Zhang J, Tan W, et al. Antifungal activity of double Schiff bases of chitosan derivatives bearing active halogeno benzenes. International Journal of Biological Macromolecules 2021; 179: 292–298. doi: 10.1016/j.ijbiomac.2021.02.184.

33. Raouf O, Salim S, Muhamad H, et al. Synthesis, characterization and biological activity of Schiff bases based on chitosan and acetophenone derivatives. Advanced Journal of Chemistry-Section A 2020; 3(3): 274–282. doi: 10.33945/SAMI/AJCA.2020.3.5.

34. Kenawy El-Refaie, Ali SS, Al-Etewy M, et al. Synthesis, characterization and biomedical applications of a novel Schiff base on methyl acrylate-functionalized chitosan bearing p-nitrobenzaldehyde groups. International Journal of Biological Macromolecules 2019; 122: 833–843. doi: 10.1016/j.ijbiomac.2018.11.005.

35. Singh G, Kalra P, Singh A, et al. A quick microwave preparation of isatin hydrazone Schiff base conjugated organosilicon compounds: Exploration of their antibacterial, antifungal, and antioxidative potentials. Journal of Organometallic Chemistry 2021; 953: 122051. doi: 10.1016/j.jorganchem.2021.122051.

36. Login CC, Baldea I, Tiperciuc B, et al. A novel thiazolyl Schiff base-antibacterial and antifungal effects and in-vitro oxidative stress modulation on human endothelial cells. Oxidative Medicine and Cellular Longevity 2019; 2019: 1607903. doi: 10.1155/2019/1607903.

37. Rasheed MK, Alkreem Al-Rifaie DA. Synthesis some of thiazolidinone and tetrazole compounds derived from acriflavine and evaluation of their antimicrobial, antifungal and antioxidant activity. Systematic Reviews in Pharmacy 2020; 11(12): 1889–1895.

38. Neelofar, Ali N, Khan A, et al. Synthesis of Schiff bases derived from 2-hydroxy-1-naphthaldehyde and their tin(II) complexes for antimicrobial and antioxidant activities. Bulletin of Chemical Society Ethiopia 2017; 31(3): 445–456. doi: 10.4314/bcse.v31i3.8.

39. Ejidike IP. Cu(II) Complexes of 4-[(1E)-N-{2-[(Z)-Benzylidene-amino]ethyl}ethanimidoyl]benzene-1,3-diol Schiff base: Synthesis, spectroscopic, in-vitro antioxidant, antifungal and antibacterial studies. Molecules 2018; 23(7): 1581. doi: 10.3390/molecules23071581.

40. Wang C, Fan L, Shi L, et al. Synthesis of novel indole Schiff base compounds and their antifungal activities. Molecules 2022; 27(20): 6858. doi: 10.3390/molecules27206858.

41. Festus C, Okafor SN, Ekennia AC. Heteroleptic metal complexes of a pyrimidinyl based Schiff base ligand incorporating 2,2’-bipyridine moiety-synthesis, characterization, and biological studies. Frontiers in Chemistry, Section-Medicinal and Pharmaceutical Chemistry 2019; 7: 862. doi: 10.3389/fchem.2019.00862.

42. Gur’eva YA, Zalevskaya OA, Shevchenko G, et al. Copper(II) complexes with terpene derivatives of ethylenediamine-synthesis, and antibacterial, antifungal and antioxidant activity. RSC Advances 2022; 12(15): 8841–8851. doi: 10.1039/D2RA00223J.

43. Horozić E, Suljagić J, Husejnagić D, et al. Synthesis, characterization and in vitro biological evaluation of the Schiff base derived from benzidine and 1,3‐diphenyl‐1,3‐propanedione. Engineering Processing and Management 2019; 11(2): 112–116. doi: 10.7251/JEPM1902112H.

44. Hamed AA, Abdelhamid IA, Saad GR, et al. Synthesis, characterization and antimicrobial activity of a novel chitosan Schiff bases based on heterocyclic moieties. International Journal of Biological Macromolecules 2020; 153: 492–501. doi: 10.1016/j.ijbiomac.2020.02.302.

45. Horozić E, Suljagić J, Suljkanović M. Synthesis, characterization, antioxidant and antimicrobial activity of copper(II) complex with Schiff base derived from 2,2-dihydroxyindane-1,3-dione and tryptophan. American Journal of Organic Chemistry 2019; 9(1): 9–13. doi: 10.5923/j.ajoc.20190901.02.

46. Turan N, Buldurun K. Synthesis, characterization and antioxidant activity of Schiff base and its metal complexes with Fe(II), Mn(II), Zn(II), and Ru(II) ions: Catalytic activity of ruthenium(II) complex. European Journal of Chemistry 2018; 9(1): 22–29. doi: 10.5155/eurjchem.9.1.22-29.1671.

47. Elsayed SA, Noufal AM, El-Hendawy AM. Synthesis, structural characterization and antioxidant activity of some vanadium(IV), Mo(VI)/(IV) and Ru(II) complexes of pyridoxal Schiff base derivatives. Journal of Molecular Structure 2017; 1144: 120–128. doi: 10.1016/j.molstruc.2017.05.020.

48. Abdel Aziz AA, Seda SH. Synthesis, spectral characterization, SEM, antimicrobial, antioxidative activity evaluation, DNA binding and DNA cleavage investigation of ransition Metal(II) complexes derived from a tetradentate Schiff base bearing thiophene moiety. Journal of Fluorescence 2017; 27(3): 1051–1066. doi: 10.1007/s10895-017-2039-9.

49. Gueye MN, Dieng M, Thiam IE, et al. Lanthanide(III) complexes with tridentate Schiff base ligand, antioxidant activity and X-ray crystal structures of the Nd(III) and Sm(III) complexes. South African Journal of Chemistry 2017; 70: 8–15. doi: 10.17159/0379-4350/2017/v70a2.

50. Aboafia SA, Shadia A. Elsayed SA, et al. New transition metal complexes of 2,4-dihydroxybenzaldehyde benzoylhydrazone Schiff base (H2dhbh)-synthesis, spectroscopic characterization, DNA binding/cleavage and antioxidant activity. Journal of Molecular Structure 2018; 1158: 39–50. doi: 10.1016/j.molstruc.2018.01.008.

51. Öğütçü H, Yetim NK, Özkan EH, et al. Nanospheres caped Pt(II) and Pt(IV): Synthesis and evaluation as antimicrobial and antifungal agent. Polish Journal of Chemical Technology 2017; 19(1): 74–80. doi: 10.1515/pjct-2017-0011.

52. Bozkır E, Sarı N, Öğütcü H. Polystyrene containing carbinolamine/azomethine potentially useful as antimicrobial agent: Synthesis and biological evaluation. Journal of Inorganic and Organometallic Polymers and Materials 2012; 22: 1146–1155. doi: 10.1007/s10904-012-9697-5.




DOI: https://doi.org/10.24294/ace.v6i1.1943

Refbacks

  • There are currently no refbacks.


Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.