Abstract
Pyrimidine derivative Schiff base ligand (DPMC) stabilized metal nanoparticles of copper (DPMC-CuNPs) and nickel (DPMC-NiNPs) were synthesized by modified Brust-Schiffrin technique, which is a two-step phase transfer assisted synthesis. The prepared metal nanoparticles were confirmed by UV-Visible and Infrared spectroscopy. The size, surface morphology and the quality of the DPMC and its MNPs were analyzed by Scanning Electron Microscopy (SEM) and Transmission Electron Microscopy (TEM) methods respectively. Electrochemical behavior of the DPMC-CuNPs and DPMC-NiNPs was analyzed by cyclic voltammetry method. DNA binding studies of the synthesized compounds with CT-DNA were examined by four different techniques such as UV-Visible and emission spectroscopy, cyclic voltametry and viscometric measurments. Thermal denaturation and sono-chemical denaturation studies of DNA with the DPMC, DPMC-CuNPs and DPMC-NiNPs results also suggest the synthesized compounds have good DNA binding ability. Various antioxidant scavenging studies results shows that DPMC and its copper and nickel nanoparticles have significant antioxidant activity. Antimicrobial studies of the DPMC and its MNPs were studied by Agar-Agar well diffusion method. Anticancer studies of the DPMC and its MNPs show that the DPMC-CuNPs and DPMC-NiNPs have significant anticancer activity with least toxicity than the standard drug cis-platin.
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Sanvicens N, Marco MP (2008) Multifunctional nanoparticles-properties and prospects for their use in human medicine. Trends Biotechnol 26(8):425–433. https://doi.org/10.1016/j.tibtech.2008.04.005
Baptista P, Pereira P, Eaton P, Doria G, Miranda A, Gomes I, Quaresma P, Franco R (2007) Gold nanoparticles for the development of clinical diagnosis methods. Anal Bioanal Chem 391(3):943–950. https://doi.org/10.1007/s00216-007-1768-z
Huang X, Jain PK, El-Sayed IH, El-Sayed MA (2007) Gold nanoparticles: interesting optical properties and recent applications in cancer diagnostics and therapy. Nanomedicine Future 2(5):681–693. https://doi.org/10.2217/17435889.2.5.681
Hainfeld JF, Dilmanian FA, Slatkin DN, Smilowitz HM (2008) Radiotherapy enhancement with gold nanoparticles. J Pharm Pharmacol 60(8):977–985. https://doi.org/10.1211/jpp.60.8.0005
Hainfeld JF, Slatkin DN, Smilowitz HM (2004) The use of gold nanoparticles to enhance radiotherapy in mice. Phys Med Biol 49(18):N309–N315. https://doi.org/10.1088/0031-9155/49/18/n03
Han G, Ghosh P, Rotello VM (2007) Multi-functional gold nanoparticles for drug delivery. Adv Exp Med Biol 620:48–56. https://doi.org/10.1007/978-0-387-76713-0_4
Gahlawat G, Choudhury AR (2019) A review on the biosynthesis of metal and metal salt nanoparticles by microbes. RSC Adv 9(23):12944–12967. https://doi.org/10.1039/c8ra10483b
Azharuddin M, Zhu GH, Das D, Ozgur E, Uzun L, Turner APF, Patra HK (2019) A repertoire of biomedical applications of noble metal nanoparticles. Chem Commun 55(49):6964–6996. https://doi.org/10.1039/c9cc01741k
Erbs JJ, Gilbert B, Penn RL (2008) Influence of size on reductive dissolution of six-line Ferrihydrite. J Phys Chem C 112(32):12127–12133. https://doi.org/10.1021/jp801601h
Hinman JG, Eller JR, Lin W, Li J, Li J, Murphy CJ (2017) Oxidation state of capping agent affects spatial reactivity on gold nanorods. J Am Chem Soc 139(29):9851–9854. https://doi.org/10.1021/jacs.7b06391
Sedighi A, Montazer M (2016) Tunable shaped N-doped CuO nanoparticles on cotton fabric through processing conditions: synthesis, antibacterial behavior and mechanical properties. Cellulose 23(3):2229–2243. https://doi.org/10.1007/s10570-016-0892-3
Makhdoomi H, Moghadam HM, Zabihi O (2013) Effect of different conditions on the size and quality of titanium dioxide nanoparticles synthesized by a reflux process. Res Chem Intermed 41(3):1777–1788. https://doi.org/10.1007/s11164-013-1311-0
Wang P, Li C, Gong H, Jiang X, Wang H, Li K (2010) Effects of synthesis conditions on the morphology of hydroxyapatite nanoparticles produced by wet chemical process. Powder Technol 203(2):315–321. https://doi.org/10.1016/j.powtec.2010.05.023
Liu H, Zhang H, Wang J, Wei J (2017) Effect of temperature on the size of biosynthesized silver nanoparticle: deep insight into microscopic kinetics analysis. Arab J Chem. https://doi.org/10.1016/j.arabjc.2017.09.004
Lee PC, Meisel D (1982) Adsorption and surface-enhanced Raman of dyes on silver and gold sols. J Phys Chem 86(17):3391–3395. https://doi.org/10.1021/j100214a025
Longenberger L, Mills G (1995) Formation of metal particles in aqueous solutions by reactions of metal complexes with polymers. J Phys Chem 99(2):475–478. https://doi.org/10.1021/j100002a001
Bunge SD, Boyle TJ, Headley TJ (2003) Synthesis of coinage-metal nanoparticles from mesityl precursors. Nano Lett 3(7):901–905. https://doi.org/10.1021/nl034200v
Panigrahi S, Kundu S, Ghosh S, Nath S, Pal T (2004) General method of synthesis for metal nanoparticles. J Nanopart Res 6(4):411–414. https://doi.org/10.1007/s11051-004-6575-2
Brust M, Walker M, Bethell D, Schiffrin DJ, Whyman R (1994) Synthesis of Thiol-derivatised gold nanoparticles in a two-phase liquid-liquid system. J Chem Soc Chem Commun 0, 801–802. https://doi.org/10.1039/c39940000801
Rossi LM, Fiorio JL, Garcia MAS, Ferraz CP (2018) The role and fate of capping ligands in colloidally prepared metal nanoparticle catalysts. Dalton Trans 47(17):5889–5915. https://doi.org/10.1039/c7dt04728b
Newman JDS, Blanchard GJ (2006) Formation of gold nanoparticles using amine reducing agents. Langmuir 22(13):5882–5887. https://doi.org/10.1021/la060045z
Battocchio C, Meneghini C, Fratoddi I, Venditti I, Russo MV, Aquilanti G, Bondino CMF, Rossi RMM, Giovanni SM (2012) Silver nanoparticles stabilized with Thiols: a close look at the local chemistry and chemical structure. J Phys Chem C 116(36):19571–19578. https://doi.org/10.1021/jp305748a
Kretschmer F, Mansfeld U, Hoeppener S, Hager MD, Schubert US (2014) Tunable synthesis of poly(ethylene imine)–gold nanoparticle clusters. Chem Commun 50(1):88–90. https://doi.org/10.1039/c3cc45090b
Bai J, Li Y, Du J, Wang S, Zheng J, Yang Q, Chen X (2007) One-pot synthesis of polyacrylamide-gold nanocomposite. Mater Chem Phys 106(2–3):412–415. https://doi.org/10.1016/j.matchemphys.2007.06.021
Nath S, Jana S, Pradhan M, Pal T (2010) Ligand-stabilized metal nanoparticles in organic solvent. J Colloid Interface Sci 341(2):333–352. https://doi.org/10.1016/j.jcis.2009.09.049
Tauran Y, Brioude A, Coleman AW, Rhimi M, Kim B (2013) Molecular recognition by gold, silver and copper nanoparticles. World J Biol Chem 4(3):35–63. https://doi.org/10.4331/wjbc.v4.i3.35
Sankarganesh M, Adwin Jose P, Dhaveethu Raja J, Kesavan MP, Vadivel M, Rajesh J, Jeyamurugan R, Senthil Kumar R, Karthikeyan S (2017) New pyrimidine based ligand capped gold and platinum nano particles: synthesis, characterization, antimicrobial, antioxidant, DNA interaction and in vitro anticancer activities. J Photochem Photobiol B Biol 176:44–53. https://doi.org/10.1016/j.jphotobiol.2017.09.013
Adwin Jose P, Dhaveethu Raja J, Sankarganesh M, Rajesh J (2018) Evaluation of antioxidant, DNA targeting, antimicrobial and cytotoxic studies of imine capped copper and nickel nanoparticles. J Photochem Photobiol B Biol 178:143–151. https://doi.org/10.1016/j.jphotobiol.2017.11.005
Raman N, Dhaveethu Raja J, Sakthivel A (2007) Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies. J Chem Sci 119(4):303–310. https://doi.org/10.1007/s12039-007-0041-5
Rajalakshmi S, Weyhermüller T, Dinesh M, Nair BU (2012) Copper(II) complexes of terpyridine derivatives: a footstep towards development of antiproliferative agent for breast cancer. J Inorg Biochem 117:48–59. https://doi.org/10.1016/j.jinorgbio.2012.08.010
Sankarganesh M, Dhaveethu Raja J, Adwin Jose PR, Vinoth Kumar GG, Rajesh J, Rajasekaran R (2018) Spectroscopic, computational, antimicrobial, dna interaction, in vitro anticancer and molecular docking properties of biochemically active cu(II) and Zn(II) complexes of pyrimidine-ligand. J Fluoresc 28(4):975–985. https://doi.org/10.1007/s10895-018-2261-0
Serpen A, Capuano E, Fogliano V, Gokmen V (2007) A new procedure to measure the antioxidant activity of insoluble food components. J Agric Food Chem 55(19):7676–7681. https://doi.org/10.1021/jf071291z
Patel A, Patel A, Patel A, Patel N (2010) Determination of polyphenols and free radical scavenging activity of Tephrosia purpurealinn leaves (Leguminosae). Pharm Res 2(3):152–158. https://doi.org/10.4103/0974-8490.65509
Nishikimi M, Appaji Rao N, Yagi K (1972) The occurrence of superoxide anion in the reaction of reduced phenazine methosulfate and molecular oxygen. Biochem Biophys Res Commun 46(2):849–854. https://doi.org/10.1016/s0006-291x(72)80218-3
Cos P, Ying L, Calomme M, Hu JP, Cimanga K, Van Poel B, PietersL VAJ, Berghe DV (1978) Structure−activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J Nat Prod 61(1):71–76. https://doi.org/10.1021/np970237h
Sankarganesh M, Dhaveethu Raja J, Sakthikumar K, Solomon RV, Rajesh J, Athimoolam S, Vijayakumar V (2018) New bio-sensitive and biologically active single crystal of pyrimidine scaffold ligand and its gold and platinum complexes: DFT, antimicrobial, antioxidant, DNA interaction, molecular docking with DNA/BSA and anticancer studies. Bioorg Chem 81:144–156. https://doi.org/10.1016/j.bioorg.2018.08.006
Kou Y, Tian J, Li D, Gu W, Liu X, Yan S, Liao D, Chemg P (2009) Synthesis, structure, magnetic properties and DNA cleavage of binuclear cu(II) Schiff-base complexes. Dalton Trans 13:2374–2382. https://doi.org/10.1039/b819052f
Cohen G, Eisenberg H (1969) Viscosity and sedimentation study of sonicated DNA-proflavine complexes. Biopolymers 8(1):45–55. https://doi.org/10.1002/bip.1969.360080105
Sakthikumar K, Dhaveethu Raja J, Vijay Solomon R, Sankarganesh M (2018) Density functional theory molecular modelling, DNA interactions, antioxidant, antimicrobial, anticancer and biothermodynamic studies of bioactive water soluble mixed ligand complexes. J Biomol Struct Dyn 37(10):2498–2514. https://doi.org/10.1080/07391102.2018.1492970
Raman N, Sudharsan S (2011) Phase transfer synthesis of N,N′(1,2-phenylene)bis-hippuricamide tethered metal based functionalized nanoparticles: A study on some novel microbial targeting peptide-mimic nanoparticles. Appl Surf Sci 257(24):10659–10666. https://doi.org/10.1016/j.apsusc.2011.07.070
Helm I, Jalukse L, Leito I (2012) A highly accurate method for determination of dissolved oxygen: gravimetric Winkler method. Anal Chim Acta 741:21–31. https://doi.org/10.1016/j.aca.2012.06.049
Silverstein RM, Bassler GC, Morrill TC, Spectrometric identification of organic compounds, 4th, New York, NY, USA, 1981
Lu M, Yang S, Ho Y-P, Grigsby CL, Leong KW, Huang TJ (2014) Shape-Controlled Synthesis of Hybrid Nanomaterials via Three-Dimensional Hydrodynamic Focusing. ACS Nano 8(10):10026–10034
Hong SY, Popovitz-Biro R, Prior Y, Tenne R (2003) Synthesis of SnS2/SnS Fullerene-like Nanoparticles: A Superlattice with Polyhedral Shape. J Am Chem Soc 125(34):10470–10474
Sankarganesh M, Raja JD, Revathi N, Solomon RV, Kumar RS (2019) Gold(III) complex from pyrimidine and morpholine analogue Schiff base ligand: synthesis, characterization, DFT, TDDFT, catalytic, anticancer, molecular modeling with DNA and BSA and DNA binding studies. J Mol Liq 294:111655. https://doi.org/10.1016/j.molliq.2019.111655
Acknowledgements
The authors express their sincere and heartfelt thanks to Managing Board, Principal, Head and staff members, The American College, Madurai for providing the research facilities and their constant encouragements. Authors acknowledge the Research and Development Centre, Bharathiar University, Coimbatore, Tamil Nadu, India and also authors acknowledge the Managing Board, Dean, Principal, Head and staff members of Department of Chemistry, Mohamed Sathak Engineering College, Kilakarai for providing research facilities. The authors express their sincere thanks to Department of Scienceand Technology (DST)-Science and Engineering Research Board (SERB Ref. No.: SR/FT/CS-117/2011 dated 29.06.2012) Government of India, New Delhi for the financial support.
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Highlights
• Solid air stable metal nano particles of copper and nickel were prepared.
• The nano particles was stabilized by pyrimidine derivative Schiff base ligand
• Stabilized nanoparticles were readily soluble in most of the solvents.
• Synthesized metal nanoparticles have good antibacterial activity.
• Both metal nanoparticles have least toxicity than cis-platin.
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P., A., M., S., J., D. et al. Pyrimidine Derivative Schiff Base Ligand Stabilized Copper and Nickel Nanoparticles by Two Step Phase Transfer Method; in Vitro Anticancer, Antioxidant, Anti-Microbial and DNA Interactions. J Fluoresc 30, 471–482 (2020). https://doi.org/10.1007/s10895-020-02510-5
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DOI: https://doi.org/10.1007/s10895-020-02510-5