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Synthesis, characterization, antimicrobial and antitubercular evaluation of nickel (II) complexes of ON donor quinoline-hydrazide core

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Abstract

In the current work, non-toxic and safe Ni(II) complexes of unsymmetrical Schiff base ligand derived from Quinoline hybrid and isoniazid, viz. [NiII(Quibal-INH)2] (1), [NiII(Quibal-INH)(cat)] (2) and [NiII(Quibal-INH)(bha)] (3), were synthesized. The complexes were characterized by elemental analysis and ATR-IR spectroscopy. These novel complexes were further preliminary evaluated for their solution stability in varied pH conditions. Furthermore, the interactions between Ni (II) complexes with human serum albumin (HSA) have been explored by using UV–visible spectroscopy. It was inferred that the complexes could quench the intrinsic fluorescence of HSA in a steady quenching process. The compounds were tested for their therapeutic potentials, viz. antibacterial, antifungal and anti-TB potential. In preliminary screening, nickel complexes (1) and (3) were active against Candida albicans with excellent growth inhibition. Nickel complex (1) was established as active and was assigned for further validation. For complexes 1 and 3, a toxicity test was performed on human embryonic kidney cells, and a hemolytic test was conducted on human red blood cells. Both complexes (1 and 3) were found to be non-toxic and safe. Nickel Complex (2) exhibited excellent anti-TB activity against the MTB H37Rv strain, which was comparable to the standard TB drugs.

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References

  • Ahmed AH, Gumaa HA, Mohamed BH, Eraky AM (2016) Nickel(II)-oxaloyldihydrazone complexes: characterization, indirect band gap energy and antimicrobial evaluation. Cogent Chem 2:1142820

    Article  Google Scholar 

  • Bottari B, Maccari R, Monforte F, Ottanà R, Rotondo E, Vigorita MG (2000) Isoniazid-related copper(II) and nickel(II) complexes with antimycobacterial in vitro activity. Part 9. Bioorg Med Chem Lett 10:657–660

    Article  CAS  PubMed  Google Scholar 

  • Cascioferro S, Barbara P, Daniela C, Domenico S, Elisa G, Girolamo C, Patrizia D (2020) Thiazoles, their benzofused systems, and thiazolidinone derivatives: versatile and promising tools to combat antibiotic resistance. J Med Chem 63:7923–7956

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Correia I, Adao P, Roy S, Wahba M, Matos C, Maurya MR et al (2014) Hydroxyquinoline derived vanadium (IV and V) and copper (II) complexes as potential anti-tuberculosis and anti-tumor agents. J Inorg Biochem 141:83–93

    Article  CAS  PubMed  Google Scholar 

  • Das K, Sanwlani S, Rawat K, Haughn CR, Doty MF, Bohidar H (2016) Spectroscopic profile of surfactant functionalized CdSe quantum dots and their interaction with globular plasma protein BSA. Coll Surf A Physicochem Eng Asp 506:495–506

    Article  CAS  Google Scholar 

  • de Kraker ME, Stewardson AJ, Harbarth S (2016) Will 10 million people die a year due to antimicrobial resistance by 2050. PLoS Med 13:e1002184

    Article  PubMed  PubMed Central  Google Scholar 

  • Dinakaran M, Senthilkumar P, Yogeeswari P, China A, Nagaraja V, Sriram D (2008) Antimycobacterial activities of novel 2-(sub)-3-fluoro/nitro-5,12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid. Bioorg Med Chem 16:3408–3418

    Article  CAS  PubMed  Google Scholar 

  • Fleck M, Layek M, Saha R, Bandyopadhyay D (2013) Synthetic aspects, crystal structures and antibacterial activities of manganese(III) and cobalt(III) complexes containing a tetradentate Schiff base. Transit Metal Chem 38:715–724

    Article  CAS  Google Scholar 

  • Gerlier D, Thomasset N (1986) Use of MTT colorimetric assay to measure cell activation. J Imm Methods 94:57–63

    Article  CAS  Google Scholar 

  • Hegde GS, Bhat SS, Netalkar SP, Hegde PL, Kotian A, Butcher RJ, Revankar VK (2021) The Co(II), Ni(II), Cu(II) and Zn(II) complexes of aroylhydrazone of quinolone core: syntheses, characterization and evaluation of antimicrobial and antitubercular activity. Inorg Chim Acta 522:120352

    Article  CAS  Google Scholar 

  • Islam MR, Islam SM, Noman AS, Khanam JA, Ali SM, Alam S, Lee MW (2007) Biological screening of a novel nickel (II) tyrosine complex. Mycobiology 35:25–29

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Jash C, Kumar GS (2014) Binding of alkaloids berberine, palmatine and coralyne to lysozyme: a combined structural and thermodynamic study. RSC Adv 4:12514–12525

    Article  CAS  Google Scholar 

  • Jayaprakash S, Iso Y, Wan B, Franzblau SG, Kozikowski AP (2006) Design, synthesis, and SAR studies of mefloquine-based ligands as potential antituberculosis agents. Chem Med Chem 1:593–597

    Article  CAS  PubMed  Google Scholar 

  • Kongot M, Dohare N, Singh V, Reddy DS, Singhal NK, Patel R, Kumar A (2018) A novel biocompatible Ni II tethered moiety as a glucose uptake agent and a hit against methicillin-resistant Staphylococcus aureus. Eur J Pharm Sc 123:335–349

    Article  CAS  Google Scholar 

  • Kongot M, Reddy D, Singh V, Patel R, Singhal NK, Kumar A (2019a) Potent drug candidature of an ONS donor tethered copper (II) complex: anticancer activity, cytotoxicity and spectroscopically approached BSA binding studies. Spectrochim Acta A Mol Biomol Spectrosc 212:330–342

    Article  CAS  PubMed  Google Scholar 

  • Kongot M, Dohare N, Reddy DS, Pereira N, Patel R, Subramanian M, Kumar A (2019b) In vitro apoptosis-induction, antiproliferative and BSA binding studies of a oxidovanadium (V) complex. J Trace Elem Med Bio 51:176–190

    Article  CAS  Google Scholar 

  • Lilienkampf A, Mao J, Wan B, Wang Y, Franzblau SG, Kozikowski AP (2009) Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis. J Med Chem 52:2109–2118

    Article  CAS  PubMed  Google Scholar 

  • Liu Z-C, Wang B-D, Yang Z-Y, Li Y, Qin D-D, Li T-R (2009) Synthesis, crystal structure, DNA interaction and antioxidant activities of two novel water-soluble Cu2+ complexes derivated from 2-oxo-quinoline-3-carbaldehyde Schiff-bases. Eur J Med Chem 44:4477–4484

    Article  CAS  PubMed  Google Scholar 

  • Lourenco MC, de Souza MV, Pinheiro AC, Ferreira MDL, Gonçalves RS, Nogueira TCM, Peralta MA (2007) Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues. ARKIVOC 15:181–191

    Article  Google Scholar 

  • Mandewale MC, Patil UC, Shedge SV, Dappadwad UR, Yamgar RS (2017) A review on quinnline hydrazone derivatives as a new class of potent antitubercular and anticancer agents. Beni-Suef Univ J Basic Appl Sci 6:354–361

    Google Scholar 

  • Mandewale MC, Thorat B, Nivid Y, Jadhav R, Nagarsekar A, Yamgar R (2018) Synthesis, structural studies and antituberculosis evaluation of new hydrazone derivatives of quinoline and their Zn(II) complexes. J Saudi Chem Soc 22:218–228

    Article  CAS  Google Scholar 

  • Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J (2006) Antifungal properties of new series of quinoline derivatives. Bioorg Med Chem 14:3592–3598

    Article  CAS  PubMed  Google Scholar 

  • Nayyar A, Monga V, Malde A, Coutinho E, Jain R (2007) Synthesis, anti-tuberculosis activity, and 3D-QSAR study of 4-(adamantan-1-yl)-2-substituted quinolines. Bioorg Med Chem 15:626–640

    Article  CAS  PubMed  Google Scholar 

  • Pan X, Liu R, Qin P, Wang L, Zhao X (2010) Spectroscopic studies on the interaction of acid yellow with bovine serum albumin. J Lumin 130:611–617

    Article  CAS  Google Scholar 

  • Raj P, Singh A, Singh A, Singh N (2017) Syntheses and photophysical properties of schiff base Ni(II) complexes: application for sustainable antibacterial activity and cytotoxicity. ACS Sustain Chem Eng 5:6070–6080

    Article  CAS  Google Scholar 

  • Reddy DS, Kongot M, Netalkar SP, Kurjogi MM, Kumar R, Avecilla F, Kumar A (2018) Synthesis and evaluation of novel coumarin-oxime ethers as potential anti-tubercular agents: their DNA cleavage ability and BSA interaction study. Eur J Med Chem 150:864–875

    Article  CAS  PubMed  Google Scholar 

  • Reddy DS, Kongot M, Singh V, Maurya N, Patel R, Singhal NK, Avecilla F, Kumar A (2019) Coumarin tethered cyclic imides as efficacious glucose uptake agents and investigation of hit candidate to probe its binding mechanism with human serum albumin. Bioorg Chem 92:103212

    Article  CAS  PubMed  Google Scholar 

  • Reddy DS, Kongot M, Kumar A (2021a) Coumarin hybrid derivatives as promising leads to treat tuberculosis: recent developments and critical aspects of structural design to exhibit anti-tubercular activity. Tuberculosis 127:102050

    Article  CAS  PubMed  Google Scholar 

  • Reddy DS, Kongot M, Singh V, Siddiquee MA, Patel R, Singhal NK, Avecilla F, Kumar A (2021b) Biscoumarin-pyrimidine conjugates as potent anticancer agents and binding mechanism of hit candidate with human serum albumin. Arch Pharm (weinheim) 354:e2000181

    Article  PubMed  Google Scholar 

  • Reddy DS, Sinha A, Kumar A, Saini VK (2022) Drug re-engineering and repurposing: a significant and rapid approach to tuberculosis drug discovery. Arch Pharm 355:2200214

    Article  CAS  Google Scholar 

  • Regiel-Futyra A, Dąbrowski JM, Mazuryk O, Śpiewak K, Kyzioł A, Pucelik B, Brindell M, Stochel G (2017) Bioinorganic antimicrobial strategies in the resistance era. C Chem Rev 351:76–117

    Article  CAS  Google Scholar 

  • Sain S, Saha R, Mostafa G, Fleck M, Bandyopadhyay D (2012) Synthesis and crystal structure of three new copper (II) complexes with a tridentate amine and its Schiff bases. Polyhedron 31:82–88

    Article  CAS  Google Scholar 

  • Savini L, Chiasserini L, Gaeta A, Pellerano C (2002) Synthesis and anti-tubercular evaluation of 4-quinolylhydrazones. Bioorg Med Chem 10:2193–2198

    Article  CAS  PubMed  Google Scholar 

  • Singh K, Kumar Y, Puri P, Sharma C, Aneja KR (2017) Antimicrobial, spectral and thermal studies of divalent cobalt, nickel, copper and zinc complexes with triazole Schiff bases. Arab J Chem 10:978–987

    Article  Google Scholar 

  • Sinha A, Chaudhary R, Reddy DS, Kongot M, Kurjogi MM, Kumar A (2022) ON donor tethered copper (II) and vanadium (V) complexes as efficacious anti-TB and anti-fungal agents with spectroscopic approached HSA interactions. Heliyon 8:e10125

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Sridhar G, Bilal IM, Easwaramoorthy D, Rani SK, Kumar BS, Sai MC (2017) Synthesis, characterization and antimicrobial activities of copper, nickel, cobalt, chromium complexes derived from (Z)-4-Fluoro-N-(2,7-dimethylhept-6-enylidene) benzenamine. J Braz Chem Soc 28:756–767

    Google Scholar 

  • Tabong CD, Yufanyi DM, Paboudam AG, Nono KN, Eni DB, Agwara MO (2016) Synthesis, crystal structure, and antimicrobial properties of [diaquabis (hexamethylenetetramine) diisothiocyanato-κN] nickel (II) complex. Adv Chem 2016:1–8

    Article  Google Scholar 

  • Udwadia ZF, Vora A, Tripathi AR, Malu KN, Lange C, Raju RS (2020) COVID-19-Tuberculosis interactions: when dark forces collide. Ind J Tuberc 67:S155–S162

    Article  Google Scholar 

  • Yano S, Inoue S, Nouchi R, Mogami K, Shinohara Y, Yasuda Y, Kato M, Tanase T, Kakuchi T, Mikata Y, Suzuki T, Yamamoto Y (1998) Antifungal nickel(II) complexes derived from amino sugars against pathogenic yeast. Candida AlbicansJ Inorg Biochem 69:15–23

    Article  CAS  Google Scholar 

  • World Health Organization, Antimicrobial resistance. https://www.who.int/news-room/fact-sheets/detail/antimicrobial-resistance Accessed Oct (2022).

  • B Erickson (2020) Extent of antibiotic resistance unknown. C & EN. Vol 98, https://cen.acs.org/pharmaceuticals/antibiotics/Extent-antibiotic-resistance-unknown-report/98/i18

  • MTT Cell proliferation assay instruction guide ATCC, VA, USA (www.atcc.org) Accessed Nov 2022

  • World Health Organization, Global Tuberculosis Report (2019) https://www.who.int/tb/global-report-2019Accessed Jan 2023.

  • The potential impact of the COVID-19 response on Tuberclosis in high-burden countries: a modelling analysis https://stoptb.org/assets/documents/news/Modeling%20Report_1%20May%202020_FINAL.pdf Accessed Dec 2022.

  • K Todar (2011) Bacterial mechanisms of antibiotic resistance. Todar’s online textbook of bacteriology, Scientific Research, http://textbookofbacteriology.net/resantimicrobial_3.html

Download references

Acknowledgements

CNMS, Jain University, Bangalore, India, provided funding to Prof. Amit Kumar and Dr. Dinesh Reddy to carry out this research work, with reference numbers JU/MRP/CNMS/2/2022 and JU/MRP/CNMS/8/2022 respectively.

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Authors and Affiliations

  1. Centre for Nano and Material Sciences, Jain (Deemed-to-be-University), Jain Global Campus, Bengaluru, Karnataka, 562112, India

    Riya Chaudhary, Dinesh S. Reddy, Anamika Sinha & Amit Kumar

  2. Department of Chemistry, Manipal Institute of Technology Bengaluru, Manipal Academy of Higher Education, Manipal, Udupi, 576104, India

    Manasa Kongot

  3. Multi-Disciplinary Research Unit, Karnataka Institute of Medical Sciences, Hubli, India

    Mahantesh M. Kurjogi

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  1. Manasa Kongot
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  6. Amit Kumar
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Contributions

MK contributed to conceptualization, data curation, investigation, methodology, resources, validation, visualization, writing—original draft, writing—review and editing. RC contributed to methodology, validation, visualization, resources, and writing—review and editing. DSR contributed to methodology, validation, visualization, resources, writing—review and editing. Anamika Sinha contributed to validation, visualization, resources, writing—review and editing. MMK contributed to validation, resources, writing—review and editing. AK contributed to project administration, funding acquisition, investigation, resources, visualization, and writing—review and editing.

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Correspondence to Dinesh S. Reddy or Amit Kumar.

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Kongot, M., Chaudhary, R., Reddy, D.S. et al. Synthesis, characterization, antimicrobial and antitubercular evaluation of nickel (II) complexes of ON donor quinoline-hydrazide core. Chem. Pap. 78, 3223–3232 (2024). https://doi.org/10.1007/s11696-024-03307-7

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