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Anti-Infective Agents

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ISSN (Print): 2211-3525
ISSN (Online): 2211-3533

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Research Article

Novel Methodology for Synthesis and Computational Analysis of Zinc Complexes of Isatin Derivatives and Screening their Biological Activity

Author(s): Akriti Goel, Navidha Aggarwal* and Sandeep Jain

Volume 20, Issue 5, 2022

Published on: 19 August, 2022

Article ID: e070622205691 Pages: 10

DOI: 10.2174/2211352520666220607144207

Price: $65

Abstract

Background: Due to arising threats of microbial infectious diseases in the human population and the development of resistance against therapeutics, novel medicinal agents are required to counteract antimicrobial resistance. Heterocyclic rings, such as indole or pyrrole, have been acknowledged to possess various biological properties, like antimicrobial, anticancer, antiviral, antitubercular, etc., and metals, such as platinum, vanadium, zinc, selenium, etc., also show therapeutic actions. Thus, this work focuses on turning a heterocyclic ring compound (isatin) and metal (zinc) into a drug having antimicrobial potential.

Objective: The objective of the study was to synthesize zinc complexes of isatin Schiff bases and evaluate their antibacterial and antifungal activity.

Methods: Herein, the conventional method was used for the synthesis of isatin Schiff bases from isatin and different monosubstituted amines. Then, zinc complexes were prepared by using isatin Schiff bases and zinc acetate. Physicochemical characteristics, such as Rf value and melting point, were determined by TLC and decibel melting point apparatus, respectively. All the complexes were characterized by FT-IR and 1H NMR techniques. Further, the final zinc complexes were screened for antimicrobial potential by the serial dilution method. Some computational studies were also done with the help of MOPAC 2016.

Results: In the present work, 14 complexes of zinc were obtained in harmonious yield from isatin Schiff bases using zinc acetate. Amongst the studied complexes, Z-3, Z-4, and Z-12 depicted maximum antimicrobial activity.

Conclusion: 14 complexes of zinc were prepared by using 14 isatin Schiff bases, which were, in turn, prepared by isatin and different mono-substituted amines. Characterization of these complexes was done by using FT-IR and 1H NMR. All prepared metal complexes were obtained in appropriate yield. The synthesized complexes were screened for their antimicrobial potential.

Keywords: Isatin, substituted amines, schiff bases, zinc complexes, antimicrobial activity, metal therapeutics.

Graphical Abstract

[1]
Leekha, S.; Terrell, C.L.; Edson, R.S. General principles of antimicrobial therapy. Mayo Clin. Proc., 2011, 86(2), 156-167.
[http://dx.doi.org/10.4065/mcp.2010.0639] [PMID: 21282489]
[2]
Cheng, G.; Dai, M.; Ahmed, S.; Hao, H.; Wang, X.; Yuan, Z. Antimicrobial drugs in fighting against antimicrobial resistance. Front. Microbiol., 2016, 7, 470.
[http://dx.doi.org/10.3389/fmicb.2016.00470] [PMID: 27092125]
[3]
Ali, M.A.; Mirza, A.H.; Bakar, H.J.H.A.; Bernhardt, P.V. Preparation and structural characterization of nickel(ii), cobalt(ii), zinc(ii) and tin(iv) complexes of the isatin schiff bases of S-methyl and s-benzyldithiocarbazates. Polyhedron, 2011, 30(4), 556-564.
[http://dx.doi.org/10.1016/j.poly.2010.11.016]
[4]
Glover, V.; Halket, J.M.; Watkins, P.J.; Clow, A.; Goodwin, B.L. Isatin: Identity with the purified endogenous monoamine oxidase inhibitor tribulin. J. Neurochem., 1988, 51(2), 659-9.
[http://dx.doi.org/10.1111/j.1471-4159.1988.tb01089.x]
[5]
Pandeya, S.N.; Sriram, D.; Nath, G.; Clercq, E.D. Synthesis, antibacterial, antifungal and anti-hiv evaluation of schiff and mannich bases of isatin derivatives with 3-amino-2-methylmercapto quinazolin. Pharm. Acta Helv., 1999, 74(1), 11-17.
[6]
Pandeya, S.N.; Sriram, D.; Nath, G.; De Clercq, E. Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin mannich bases. Eur. J. Med. Chem., 2000, 35(2), 249-255.
[http://dx.doi.org/10.1016/S0223-5234(00)00125-2] [PMID: 10758286]
[7]
Matesic, L.; Locke, J.M.; Bremner, J.B.; Pyne, S.G.; Skropeta, D.; Ranson, M.; Vine, K.L. N-phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents. Bioorg. Med. Chem., 2008, 16(6), 3118-3124.
[http://dx.doi.org/10.1016/j.bmc.2007.12.026] [PMID: 18182300]
[8]
Grewal, A.S. Isatin Derivatives with Several Biological Activities. Int. J. Pharm. Res., 2014, 6, 8.
[9]
Pandeya, S.N.; 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. Eur. J. Pharm. Sci., 1999, 9(1), 25-31.
[http://dx.doi.org/10.1016/S0928-0987(99)00038-X] [PMID: 10493993]
[10]
Xie, C.; Tang, L-M.; Li, F-N.; Guan, L-P.; Pan, C-Y.; Wang, S-H. Structure-based design, synthesis, and anticonvulsant activity of isatin-1-n-phenylacetamide derivatives. Med. Chem. Res., 2014, 23, 2161-2168.
[http://dx.doi.org/10.1007/s00044-013-0811-1]
[11]
Venkateshwarlu, E.; Rao, J.V. Evaluation of anti-diabetic and hypolipidemic activity of isatin derivatives in streptozotocin-nicotinamide induced type II diabetic rats. Adv. Biol. Res., 2013, 7(6), 288-295.
[12]
Korkmaz-Icoz, S. Oral treatment with a zinc complex of acetylsalicylic acid prevents diabetic cardiomyopathy in a rat model of type-2 diabetes: Activation of the Akt pathway. Cardiovasc. Diabetol., 2016, 15, 75.
[http://dx.doi.org/10.1186/s12933-016-0383-8]
[13]
Liang, T.; Zhang, Q.; Sun, W.; Xin, Y.; Zhang, Z.; Tan, Y.; Zhou, S.; Zhang, C.; Cai, L.; Lu, X.; Cheng, M. Zinc treatment prevents type 1 diabetes-induced hepatic oxidative damage, endoplasmic reticulum stress, and cell death, and even prevents possible steatohepatitis in the OVE26 mouse model: Important role of metallothionein. Toxicol. Lett., 2015, 233(2), 114-124.
[http://dx.doi.org/10.1016/j.toxlet.2015.01.010] [PMID: 25617602]
[14]
Lin, C.-C.; Huang, Y.-L. Chromium, zinc and magnesium status in type 1 diabetes. 2015, 18(6), 5.
[http://dx.doi.org/10.1186/s12933-016-0383-8]
[15]
Saito, R.; Tamura, M.; Kawano, S.; Yoshikawa, Y.; Kato, A.; Sasaki, K.; Yasui, H. Synthesis and biological evaluation of 4-hydroxy-5-oxo-2,5- dihydro-1h-pyrrole-3-carboxamides and their zinc(ii) complexes as candidate antidiabetic agents. New J. Chem., 2017, 41, 5572-5581.
[http://dx.doi.org/10.1016/j.toxlet.2015.01.010]
[16]
Nitha, L.P.; Aswathy, R.; Mathews, N.E.; Kumari, B.S.; Mohanan, K. Synthesis, spectroscopic characterisation, DNA cleavage, superoxidase dismutase activity and antibacterial properties of some transition metal complexes of a novel bidentate Schiff base derived from isatin and 2-aminopyrimidine. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2014, 118, 154-161.
[http://dx.doi.org/10.1016/j.saa.2013.08.075] [PMID: 24051284]
[17]
Koleša-Dobravc, T.; Maejima, K.; Yoshikawa, Y.; Meden, A.; Yasui, H.; Perdih, F. Bis(Picolinato) complexes of vanadium and zinc as potential antidiabetic agents: Synthesis, structural elucidation and in vitro insulin-mimetic activity study. New J. Chem., 2018, 42(5), 3619-3632.
[http://dx.doi.org/10.1039/C7NJ04189F]
[18]
Sakurai, H.; Katoh, A.; Yoshikawa, Y. Chemistry and biochemistry of insulin-mimetic vanadium and zinc complexes trial for treatment of diabetes mellitus. Bull. Chem. Society Japan., 2006, 79(11), 1645-1664.
[19]
Muhammad, A.; Shedewo, O. Synthesis, characterization and antibacterial properties of nickel (ii) schiff base complex derived from benzoin and oamino benzoic acid. Bayero J. Pure Appl. Sci., 2015, 8(1), 33.
[20]
Zoubi, W.A.; Al-Hamdani, A.A.S.; Widiantara, I.P.; Hamoodah, R.G.; Ko, Y.G. Theoretical studies and antibacterial activity for Schiff base complexes. J. Phy. Organic Chem., 2017, 30(12), 131-142.
[21]
Arulmurugan, S.; Kavitha, H.P.; Venkatraman, B.R. Biological activities of schiff base and its complexes: A review. Inter. J. Organic Chem, 3(03), 73-95.
[http://dx.doi.org/10.4314/bajopas.v8i1.7]
[22]
Guo, Z.; Xing, R.; Liu, S.; Zhong, Z.; Ji, X.; Wang, L.; Li, P. Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. Carbohydr. Res., 2007, 342(10), 1329-1332.
[http://dx.doi.org/10.1016/j.carres.2007.04.006] [PMID: 17485075]
[23]
Jayabalakrishnan, C.; Karvembu, R.; Natarajan, K. Catalytic and antimicrobial activities of new ruthenium(ii) unsymmetrical schiff base complexes. Trans. Met. Chem., 2002, 27, 790-794.
[24]
Siraj, I.T.; Sambo, B.U. Synthesis, characterization and antimicrobial activities of schiff base derived from thiourea and anisaldehyde and Its Mn(II), Fe (II) and Co(II) complexes. Bayero J. Pure Appl. Sci., 2018, 11(1), 20-24.
[http://dx.doi.org/10.4314/bajopas.v11i1.4]
[25]
Al Zoubi, W. Biological activities of Schiff bases and their complexes: A review of recent works. Int. J. Org. Chem. (Irvine), 2013, 3, 73-95.
[http://dx.doi.org/10.4236/ijoc.2013.33A008]
[26]
Rauf, A.; Shah, A.; Khan, A.A.; Shah, A.H.; Abbasi, R.; Qureshi, I.Z.; Ali, S. Synthesis, pH dependent photometric and electrochemical investigation, redox mechanism and biological applications of novel Schiff base and its metallic derivatives. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2017, 176, 155-167.
[http://dx.doi.org/10.1016/j.saa.2017.01.018] [PMID: 28092826]
[27]
Shakir, M.; Hanif, S.; Sherwani, M.A.; Mohammad, O.; Azam, M.; Al-Resayes, S.I. Pharmacophore hybrid approach of new modulated bis-diimine Cu(II)/Zn(II) complexes based on 5-chloro Isatin Schiff base derivatives: Synthesis, spectral studies and comparative biological assessment. J. Photochem. Photobiol. B, 2016, 157, 39-56.
[http://dx.doi.org/10.1016/j.jphotobiol.2016.01.019] [PMID: 26882291]
[28]
Deep, A.; Jain, S.; Sharma, P.C.; Mittal, S.K.; Phogat, P.; Malhotra, M. Synthesis, characterization and antimicrobial evaluation of 2,5-disubstituted-4-thiazolidinone derivatives. Arab. J. Chem., 2014, 7, 287-291.
[http://dx.doi.org/10.1016/j.arabjc.2010.10.032]

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