Abstract
Novel three nickel(II) complexes of type [Ni(metf)(o-phen)2]Cl2 (1), [Ni(metf)(opda)2]Cl2 (2), [Ni(metf)(2–2'bipy)2]Cl2 (3), (Metf = metformin, o-phen = ortho-phenanthroline, opda = ortho-phenylenediamine, 2–2' bipy = 2–2′ bipyridyl) were synthesized and characterized by various analytical and spectral techniques. Based on these studies, octahedral geometry is assigned to these complexes. The DNA binding properties of these complexes were investigated by absorption, emission, and viscosity studies. From the spectral data, it was concluded that the complexes bind to DNA through groove mode of binding. The intrinsic binding constants (Kb) from absorption spectroscopy were 1.60 × 104, 3.57 × 104, and 5.70 × 104 M−1 for 1, 2, and 3, respectively, and Stern–Volmer quenching constants (Ksv) from emission spectroscopy were 0.11, 0.87, and 0.24, respectively. Thermal degradation pattern of the compounds was studied and Coats–Redfern method is used to determine kinetic parameters for complexes 1, 2, and 3 from thermal studies. The software Discovery Studio 2.1 was used to assess the binding affinity and interaction pattern of complexes with the B-DNA receptor protein and complex 1 has the highest dock score.
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References
Zhao P, Zhai S, Dong J, Gao L, Liu X, Wang L et al (2018) Synthesis, structure, DNA interaction, and SOD activity of three nickel(II) complexes containing L-phenylalanine Schiff base and 1,10-phenanthroline. Bioinorg Chemi Appl 2018:8478152. https://doi.org/10.1155/2018/8478152
Liu H, Li L, Guo Q, Dong J, Li J (2013) Synthesis, crystal structure, DNA- and albumin-binding properties of a chromium(III) complex with 1,10-phenanthroline and a Schiff base derived from glycine. Trans Met Chem 38:441–448. https://doi.org/10.1007/s11243-013-9709-5
Li L, Guo Q, Dong J, Xu T, Li J (2013) DNA binding, DNA cleavage and BSA interaction of a mixed-ligand copper(II) complex with taurine Schiff base and 1,10-phenanthroline. J Photochem Photobiol B 125:56–62. https://doi.org/10.1016/j.jphotobiol.2013.05.007
Tabassum S, Ahmad M, Afzal M, Zaki M, Bharadwaj PK (2014) Synthesis and structure elucidation of a copper(II) Schiff-base complex: in vitro DNA binding, pBR322 plasmid cleavage and HSA binding studies. J Photochem Photobiol B 140:321–331. https://doi.org/10.1016/j.jphotobiol.2014.08.015
Rehman SU, Sarwar T, Husain MA, Ishqi HM, Tabish M (2015) Studying non-covalent drug-DNA interactions. Arch Biochem Biophys 576:49–60. https://doi.org/10.1016/j.abb.2015.03.024
Sirajuddin M, Ali S, Badshah A (2013) Drug-DNA interactions and their study by UV-Visible, fluorescence spectroscopies and cyclic voltametry. J Photochem Photobiol B 124:1–19. https://doi.org/10.1016/j.jphotobiol.2013.03.013
Sharma SS, Ramani J, Dalwadi D, Bhalodia J, Patel N, Patel DD et al (2011) New ternary transition metal complexes of 2-{[(2-aminophenyl)imino] methyl}phenol and metformin: synthesis, characterization and antimicrobial activity. E-J Chem 8:361–367
Chen KK, Anderson RC (1947) The toxicity and general pharmacology of N1-p-chlorophenyl-N5-isopropyl biguanide. J Pharmacol Exp Ther 91:157–160
Wakeman M, Archer DT (2020) Metformin and micronutrient status in type 2 diabetes: does polypharmacy involving acid-suppressing medications affect vitamin B12 levels? Diabetes Metab Syndr Obes 13:2093–2108. https://doi.org/10.2147/DMSO.S237454
Olar R, Dogaru A, Marinescu D, Badea M (2012) New vanadyl complexes with metformin derivatives as potential insulin mimetic agents. J Therm Anal Calor 110:257–262. https://doi.org/10.1007/s10973-012-2274-x
Olar R, Badea M, Cristurean E, Parnau C, Marinescu D (2006) Thermalbehaviour of new N, N-dimethylbiguanide complexes having selective and effectiveantibacterial activity. J Therm Anal Calor 84:53–58. https://doi.org/10.1007/s10973-005-7177-7
Shahabadi N, Heidari L (2012) Binding studies of the antidiabetic drug, metformin to calf thymus DNA using multispectroscopic methods. Spectrochim Acta A Mol Biomol Spectrosc 97:406–410. https://doi.org/10.1016/j.saa.2012.06.044
Shahabadi N, Heidari L (2014) Synthesis, characterization and multi-spectroscopic DNA interaction studies of a new platinum complex containing the drug metformin. Spectrochim Acta A Mol Biomol Spectrosc 128:377–385. https://doi.org/10.1016/j.saa.2014.02.167
Can M, Armstrong FA, Ragsdale SW (2014) Structure, function, and mechanism of the nickel metalloenzymes, CO dehydrogenase, and acetyl-CoA synthase. Chem Rev 114:4149–4174. https://doi.org/10.1021/cr400461p
Balakrishnan S, Duraisamy S, Kasi M, Kandasamy S, Sarkar R, Kumarasamy A (2019) Syntheses, physicochemical characterization, antibacterial studies on potassium morpholine dithiocarbamate nickel (II), copper (II) metal complexes and their ligands. Heliyon 5:e01687. https://doi.org/10.1016/j.heliyon.2019.e01687
Abdolmaleki S, Ghadermazi M, Fattahi A, Shokraii S, Alimoradi M, Shahbazi B et al (2017) Synthesis, crystallographic and spectroscopic studies, evaluation as antimicrobial and cytotoxic agents of a novel mixed-ligand nickel(II) complex. J Coord Chem 70:1406–1423. https://doi.org/10.1080/00958972.2017.1293821
Selvakumaran N, Bhuvanesh NSP, Endo A, Karvembu R (2014) Synthesis, structure, DNA and protein binding studies, and cytotoxic activity of nickel(II) complexes containing 3,3-dialkyl/aryl-1-(2,4-dichlorobenzoyl)thiourea ligands. Polyhedron 75:95–109. https://doi.org/10.1016/j.poly.2014.03.010
Ramadan AE-MM (2012) Macrocyclic nickel(II) complexes: synthesis, characterization, superoxide scavenging activity and DNA-binding. J Mol Struct 1015:56–66. https://doi.org/10.1016/j.molstruc.2012.01.048
Vasantha PB, Kumar BS, Shekhar B, Lakshmi PVA (2018) Copper-metformin ternary complexes: thermal, photochemosensitivity and molecular docking studies. Mat Sci Eng C 90:621–633
Shekhar B, Vasantha P, Sathish Kumar B, Anantha Lakshmi PV (2018) Multispectroscopic DNA interaction and docking studies. Appl Organomet Chem 32:e4254. https://doi.org/10.1002/aoc.4254
Shekhar B, Vasantha P, Sathish Kumar B, Anantha Lakshmi PV, Ravi Kumar V, Satyanarayana S (2019) Chromium-metformin ternary complexes: Thermal, DNA interaction and docking studies. Appl Organomet Chem 33:e5086. https://doi.org/10.1002/aoc.5086
Rajeshwari K, Vasantha P, Kumar BS, Shekhar B, Lakshmi PVA (2020) Water soluble nickel – metformin ternary complexes: Thermal, DNA binding and molecular docking studies. Appl Organomet Chem 34:e5351. https://doi.org/10.1002/aoc.5351
Vasantha P, Sathish Kumar B, Shekhar B, Anantha Lakshmi PV (2018) Cobalt(II)–metformin complexes containing α-diimine/α-diamine as auxiliary ligand: DNA binding properties. Appl Organomet Chem 32:e4074. https://doi.org/10.1002/aoc.4074
Rajeshwari K, Anantha Lakshmi PV, Archana J, Sumakanth M (2021) Ternary cobalt(II), nickel(II), and copper(II) complexes containing metformin and ethylenediamine: synthesis, characterization, thermal, in vitro DNA binding, in silico molecular docking, and in vivo antihyperglycemic studies. Appl Organomet Chem 35:e6100. https://doi.org/10.1002/aoc.6100
Olar R, Badea M, Marinescu D, Chifiriuc MC, Bleotu C, Grecu MN et al (2010) N, N-dimethylbiguanide complexes displaying low cytotoxicity as potential large spectrum antimicrobial agents. Eur J Med Chem 45:3027–3034. https://doi.org/10.1016/j.ejmech.2010.03.033
Reddy PR, Rajeshwar S, Satyanarayana B (2016) Synthesis, characterization of new copper (ii) Schiff base and 1,10 phenanthroline complexes and study of their bioproperties. J Photochem Photobiol B 160:217–224. https://doi.org/10.1016/j.jphotobiol.2016.04.017
Reddy PR, Raju N, Manjula P, Reddy KV (2007) Synthesis and DNA binding/cleavage of mononuclear copper(II) phenanthroline/bipyridine proline complexes. Chem Biodivers 4:1565–1577. https://doi.org/10.1002/cbdv.200790136
González E, Rodrigue-Witchel A, Reber C (2007) Absorption spectroscopy of octahedral nickel(II) complexes: a case study of interactions between multiple electronic excited states. Coord Chem Revi 251:351–363. https://doi.org/10.1016/j.ccr.2006.08.011
Figgis BN (2000) Ligand field theory and its applications. Wiley-VCH, New York
Radha VP, Chitra S, Jonekirubavathi S, Chung I-M, Kim S-H, Prabakaran M (2020) Transition metal complexes of novel binuclear Schiff base derived from 3,3′-diaminobenzidine: synthesis, characterization, thermal behavior, DFT, antimicrobial and molecular docking studies. J Coord Chem 73:1009–1027. https://doi.org/10.1080/00958972.2020.1752372
Daravath S, Rambabu A, Ganji N, Ramesh G, Anantha Lakshmi PV, Shivaraj (2022) Spectroscopic, quantum chemical calculations, antioxidant, anticancer, antimicrobial, DNA binding and photo physical properties of bioactive Cu(II) complexes obtained from trifluoromethoxy aniline Schiff bases. J Mol Struct 1249:131601. https://doi.org/10.1016/j.molstruc.2021.131601
Kavitha N, Anantha Lakshmi PV (2019) Transition metal complexes supported by ONNN/ONNS bis-bidentate benzoxazine Schiff base: synthesis, characterization, geometry optimization and non-isothermal kinetic parameters. J Mol Struct 1176:798–814. https://doi.org/10.1016/j.molstruc.2018.09.042
Shahabadi N, Abbasi AR, Moshtkob A, Hadidi S (2020) Design, synthesis and DNA interaction studies of new fluorescent platinum complex containing anti-HIV drug didanosine. J Biomol Struct Dyn 38:2837–2848. https://doi.org/10.1080/07391102.2019.1658643
Mirzaei-Kalar Z (2018) In vitro binding interaction of atorvastatin with calf thymus DNA: multispectroscopic, gel electrophoresis and molecular docking studies. J Pharm Biomed Anal 161:101–109. https://doi.org/10.1016/j.jpba.2018.08.033
Srishailam A, Kumar YP, Venkat Reddy P, Nambigari N, Vuruputuri U, Singh SS et al (2014) Cellular uptake, cytotoxicity, apoptosis, DNA-binding, photocleavage and molecular docking studies of ruthenium(II) polypyridyl complexes. J Photochem Photobiol B 132:111–123. https://doi.org/10.1016/j.jphotobiol.2014.02.003
Reddy MR, Reddy PV, Kumar YP, Srishailam A, Nambigari N, Satyanarayana S (2014) Synthesis, characterization, DNA binding, light switch “on and off”, docking studies and cytotoxicity, of ruthenium(II) and cobalt(III) polypyridyl complexes. J Fluoresc 24:803–817. https://doi.org/10.1007/s10895-014-1355-6
Shahabadi N, Ghaffari L, Mardani Z, Shiri F (2021) Experimental and molecular docking studies on the interaction of a water-soluble Pd(II) complex containing beta-amino alcohol with calf thymus DNA. Biol Trace Elem Res. https://doi.org/10.1007/s12011-021-02803-1
Acknowledgements
The authors thank the DST-FIST program of India (SR/FST/CSI-213/2010) for providing the infrastructural and instrumental facilities in the Department of Chemistry, University College for Women, Osmania University, Koti, CFRD, Osmania University, Hyderabad and Central Instrumentation Laboratory, Hyderabad Central University.
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Rajeshwari, K., Vasantha, P., Kumar, B.S. et al. Nickel–Metformin Ternary Complexes: Geometrical, Thermal, DNA Binding, and Molecular Docking Studies. Biol Trace Elem Res 200, 5351–5364 (2022). https://doi.org/10.1007/s12011-022-03100-1
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DOI: https://doi.org/10.1007/s12011-022-03100-1