Advertisement

Chemical Papers

, Volume 73, Issue 5, pp 1199–1208 | Cite as

Synthesis of ionic liquid-based Ru(II)–phosphinite complexes and evaluation of their antioxidant, antibacterial, DNA-binding, and DNA cleavage activities

  • Nermin Meriç
  • Cezmi KayanEmail author
  • Khadichakhan Rafikova
  • Alexey Zazybin
  • Veysi Okumuş
  • Murat AydemirEmail author
  • Feyyaz Durap
Original Paper
  • 124 Downloads

Abstract

Two Ru(II) complexes were synthesized by reaction of phosphinite-functionalized imidazolium salts [(Ph2PO)C7H11N2Cl]Cl (1) and [(Cy2PO)C7H11N2Cl]Cl (2) with 1/2 equivalent of [Ru(η6-p-cymene)(µ-Cl)Cl]2 in anhydrous CH2Cl2 and under argon atmosphere. The complexes were then isolated as analytically pure substances and characterized using multinuclear NMR and infrared spectroscopies and elemental analysis. The Ru(II) compounds were used to study their biological assay. For this purpose, radical scavenging, reducing power, antibacterial activity, DNA binding, and DNA cleavage activity were fully studied. The maximum 1,1-diphenyl-2-picrylhydrazyl radicals (DPPH) scavenging (78.9%) and reducing power were obtained from compound 4 at the concentration of 200 µg/ml. The compounds were also tested against three Gram-positive and three Gram-negative bacteria, and they were found to be more effective against Gram-positive bacteria. In addition, both compounds showed excellent DNA binding and DNA cleavage activity.

Graphical abstract

Keywords

Ionic liquid Phosphinite Ruthenium Antibacterial DNA binding DNA cleavage 

Notes

Acknowledgements

Partial support from Dicle University Research Fund (Project numbers: FEN.17.023 and FEN.17.019) is gratefully acknowledged. The authors would also like to thank the Ministry of Education and Science of the Republic of Kazakhstan for the financial support (IRN: AP05132833, BR05236800 and BR05236302).

References

  1. Abdellah I, Lepetit C, Canac Y, Duhayon C, Chauvin R (2010) Imidazoliophosphines are true N-heterocyclic carbene (NHC)–phosphenium adducts. Chem Eur J 16:13095–13108.  https://doi.org/10.1002/chem.201001721 CrossRefGoogle Scholar
  2. Ağırtaş MS, Dede E, Gümüş S, Dündar A, Okumus V (2014) Metallo Phthalocyanines bearing 2-Isopropyl-6-methylpyrimidin-4-yloxy Substituents: synthesis, Characterization, Aggregation Behavior, Antioxidant and Antibacterial Activity, and Electronic Properties. Zeitschrift für anorganische und allgemeine Chemie. 640:1953–1959.  https://doi.org/10.1002/zaac.201400129 CrossRefGoogle Scholar
  3. Ağırtaş MS, Ondes MY, Ozdemir S, Okumus V (2017) DNA cleavage properties and synthesis of metallophthalocyanines with 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-oxy substituents. Synth React Inorg Met-Org Nano-Met Chem 47:1097–1102.  https://doi.org/10.1080/24701556.2017.1284086 Google Scholar
  4. Ak B, Elma D, Meriç N, Kayan C, Işık U, Aydemir M, Durap F, Baysal A (2013) New chiral ruthenium(II)–phosphinite complexes containing a ferrocenyl group in enantioselective transfer hydrogenations of aromatic ketones. Tetrahedron Asymmetry 24:1257–1264.  https://doi.org/10.1016/j.tetasy.2013.09.004 CrossRefGoogle Scholar
  5. Ak B, Aydemir M, Durap F, Meriç N, Baysal A (2015a) The first application of C 2-symmetric ferrocenyl phosphinite ligands for rhodium-catalyzed asymmetric transfer hydrogenation of various ketones. Inorg Chim Acta 438:42–51.  https://doi.org/10.1016/j.ica.2015.09.003 CrossRefGoogle Scholar
  6. Ak B, Aydemir M, Durap F, Meriç N, Elma Karakaş D, Baysal A (2015b) Highly efficient iridium catalysts based on C2-symmetric ferrocenyl phosphinite ligands for asymmetric transfer hydrogenations of aromatic ketones. Tetrahedron Asymmetry 26:1307–1313.  https://doi.org/10.1016/j.tetasy.2015.10.002 CrossRefGoogle Scholar
  7. Andrieu J, Harmand L, Picquet M (2010) Firsts lysidinyl- and lysidinium-triphosphines Pd(II) complexes. Polyhedron 29:601–605.  https://doi.org/10.1016/j.poly.2009.07.055 CrossRefGoogle Scholar
  8. Anjomshoa M, Hadadzadeh H, Fatemi SJ, Torkzadeh-Mahani M (2015) A mononuclear Ni(II) complex with 5,6-diphenyl-3-(2-pyridyl)-1,2,4- triazine: dNA- and BSA-binding and anticancer activity against human breast carcinoma cells. Spectrochim Acta A Mol Biomol Spectrosc 136:205–215.  https://doi.org/10.1016/j.saa.2014.09.016 CrossRefGoogle Scholar
  9. Appelt P, da Silva JP, Fuganti O, Aquino LEN, Sandrino B, Wohnrath K, Santos VAQ, Cunha MAA, Veiga A, Murakami FS, Back DF, de Araujo MP (2017) New heterobimetallic ruthenium (II) complexes [Ru(N-S)(bipy)(dppf)]PF6: synthesis, molecular structure, electrochemistry, DFT, antioxidant and antibacterial potential. J Organomet Chem 846:326–334.  https://doi.org/10.1016/j.jorganchem.2017.07.005 CrossRefGoogle Scholar
  10. Aydemir M, Meriç N, Baysal A, Gümgüm B, Toğrul M, Turgut Y (2010a) A modular design of ruthenium(II) catalysts with chiral C 2-symmetric phosphinite ligands for effective asymmetric transfer hydrogenation of aromatic ketones. Tetrahedron Asymmetry 21:703–710.  https://doi.org/10.1016/j.tetasy.2010.04.002 CrossRefGoogle Scholar
  11. Aydemir M, Meriç N, Durap F, Baysal A, Toğrul M (2010b) Asymmetric transfer hydrogenation of aromatic ketones with the ruthenium(II) catalyst derived from C2 symmetric N, N′-bis[(1S)-1-benzyl-2-O-(diphenylphosphinite)ethyl]ethanediamide. J Organomet Chem 695:1392–1398.  https://doi.org/10.1016/j.jorganchem.2010.02.003 CrossRefGoogle Scholar
  12. Aydemir M, Meriç N, Baysal A, Turgut Y, Kayan C, Şeker S, Toğrul M, Gümgüm B (2011) Asymmetric transfer hydrogenation of acetophenone derivatives with novel chiral phosphinite based η6-p-cymene/ruthenium(II) catalysts. J Organomet Chem 696:1541–1546.  https://doi.org/10.1016/j.jorganchem.2010.12.027 CrossRefGoogle Scholar
  13. Aydemir M, Rafikova K, Kystaubayeva N, Pasa S, Meriç N, Ocak YS, Zazybin A, Temel H, Gurbuz N, Özdemir İ (2014) Ionic liquid based Ru(II)–phosphinite compounds and their catalytic use in transfer hydrogenation: X-ray structure of an ionic compound 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol. Polyhedron 81:245–255CrossRefGoogle Scholar
  14. Aziz AAA, Elbadawy HA (2014) Spectral, electrochemical, thermal, DNA binding ability, antioxidant and antibacterial studies of novel Ru(III) Schiff base complexes. Spectrochim Acta Part A: Mol and Biomol Spec 124:404–415.  https://doi.org/10.1016/j.saa.2014.01.050 CrossRefGoogle Scholar
  15. Barthes C, Lepetit C, Canac Y, Duhayon C, Zargarian D, Chauvin R (2013) P(CH)P pincer rhodium(I) complexes: the key role of electron-poor imidazoliophosphine extremities. Inorg Chem 52:48–58.  https://doi.org/10.1021/ic3006508 CrossRefGoogle Scholar
  16. Baykara H, Ilhan S, Oztomsuk A, Seyitoglu MS, Levent A, Okumus V, Dundar A (2015) Synthesis and characterization of a new difunctional ligand and its metal complexes: an experimental, theoretical, cyclic voltammetric, and antimicrobial study. Synth React Inorg Met-Org Nano-Met Chem 45:1795–1807.  https://doi.org/10.1080/15533174.2013.872134 CrossRefGoogle Scholar
  17. Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Grätzel M (1996) Hydrophobic, highly conductive ambient-temperature molten salts. Inorg Chem 35:1168–1178.  https://doi.org/10.1021/ic951325x CrossRefGoogle Scholar
  18. Brauer DJ, Kottsieper KW, Liek C, Stelzer O, Waffenschmidt H, Wasserscheid P (2001) Phosphines with 2-imidazolium and para-phenyl-2-imidazolium moieties—synthesis and application in two-phase catalysis. J Organomet Chem 630:177–184.  https://doi.org/10.1016/S0022-328X(01)00868-3 CrossRefGoogle Scholar
  19. Canac Y, Maaliki C, Abdellah I, Chauvin R (2012) Carbeniophosphanes and their carbon → phosphorus → metal ternary complexes. New J Chem 36:17–27.  https://doi.org/10.1039/C1NJ20808J CrossRefGoogle Scholar
  20. Chen C (2010) A functionalised ionic liquid: 1-(3-chloro-2-hydroxypropyl)-3-methyl imidazolium chloride. Phy Chem Liq 48:298–306.  https://doi.org/10.1080/00319100902822745 CrossRefGoogle Scholar
  21. Chen S, Wang Y, Yao W, Zhao X, Liu Y (2013) An ionic phosphine-ligated rhodium(III) complex as the efficient and recyclable catalyst for biphasic hydroformylation of 1-octene. J Mol Catal A: Chem 378:293–298.  https://doi.org/10.1016/j.molcata.2013.07.004 CrossRefGoogle Scholar
  22. Chiappe C, Pomelli CS, Bardi U, Caporali S (2012) Interface properties of ionic liquids containing metal ions: features and potentialities. Phys Chem Chem Phys 14:5045–5051.  https://doi.org/10.1039/C2CP24012B CrossRefGoogle Scholar
  23. Deepika N, Devi CS, Kumar YP, Reddy KL, Reddy PV, Kumar DA, Singh SS, Satyanarayana S (2016) DNA-binding, cytotoxicity, cellular uptake, apoptosis and photocleavage studies of Ru(II) complexes. J Photochem Photobiol B 160:142–153.  https://doi.org/10.1016/j.jphotobiol.2016.03.061 CrossRefGoogle Scholar
  24. Devagi G, Dallemer F, Kalaivani P, Prabhakaran R (2018) Organometallic ruthenium(II) complexes containing NS donor Schiff bases: synthesis, structure, electrochemistry, DNA/BSA binding, DNA cleavage, radical scavenging and antibacterial activities. J Organomet Chem 854:1–14.  https://doi.org/10.1016/j.jorganchem.2017.10.036 CrossRefGoogle Scholar
  25. Ejidike IP, Ajibade PA (2015) Synthesis, characterization, and in vitro antioxidant and anticancer studies of ruthenium(III) complexes of symmetric and asymmetric tetradentate Schiff bases. J Coord Chem 68:2552–2564.  https://doi.org/10.1080/00958972.2015.1043127 CrossRefGoogle Scholar
  26. Elma Karakas D, Durap F, Baysal A, Ocak YS, Rafikova K, Çavuş Kaya E, Zazybin A, Temel H, Kayan C, Meriç N (2016) Aydemir M Transfer hydrogenation reaction using novel ionic liquid based Rh(I) and Ir(III)-phosphinite complexes as catalyst. J Organomet Chem 824:25–32.  https://doi.org/10.1016/j.jorganchem.2016.09.006 CrossRefGoogle Scholar
  27. Elma D, Durap F, Aydemir M, Baysal A, Meriç N, Ak B, Turgut Y, Gümgüm B (2013) Screening of C 2-symmetric chiral phosphinites as ligands for ruthenium(II)-catalyzed asymmetric transfer hydrogenation of prochiral aromatic ketones. J Organomet Chem 729:46–52.  https://doi.org/10.1016/j.jorganchem.2013.01.012 CrossRefGoogle Scholar
  28. Esquius G, Pons J, Yanez R, Ros J, Mathieu R, Donnadieu B, Lugan N (2002) Synthesis of a new potentially hemilabile ligand: 1-[2-(Diphenylphosphanyl)ethyl]-3,5-dimethylpyrazole, and comparison of its bonding properties with the related 1-[2-(Ethylamino)ethyl]-3,5-dimethylpyrazole Ligand toward RhI. Eur J Inorg Chem.  https://doi.org/10.1002/1099-0682(200211)2002:11%3c2999:AID-EJIC2999%3e3.0.CO;2-A Google Scholar
  29. Galka PW, Kraatz HB (2003) Synthesis and study of amino acid based phosphinite ligands. J Organomet Chem 674:24–31.  https://doi.org/10.1016/S0022-328X(03)00181-5 CrossRefGoogle Scholar
  30. Hallett JP, Welton T (2011) Room-temperature ionic liquids: solvents for synthesis and catalysis. Chem Rev 111:3508–3576.  https://doi.org/10.1021/cr1003248 CrossRefGoogle Scholar
  31. Hariharasarma M, Lake CH, Watkins CL, Gray GM (1999) Synthesis, reactions and X-ray crystal structures of metallacrown ethers with unsymmetrical bis(phosphinite) and bis(phosphite) ligands derived from 2-hydroxy-2′-(1,4-bisoxo-6-hexanol)-1,1′-biphenyl. J Organomet Chem 580:328–338.  https://doi.org/10.1016/S0022-328X(98)01170-X CrossRefGoogle Scholar
  32. Hauptman E, Shapiro R, Marshall W (1998) Synthesis of chiral Bis(phosphinite) ligands with a tetrahydrothiophene backbone: use in asymmetric hydrogenation. Organometallics 17:4976–4982.  https://doi.org/10.1021/om980540t CrossRefGoogle Scholar
  33. Holbrey JD, Reichert WM, Swatloski RP, Broker GA, Pitner WR, Seddon KR, Rogers RD (2002) Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions. Green Chem 4:407–413.  https://doi.org/10.1039/B204469B CrossRefGoogle Scholar
  34. Holbrey JD, Reichert WM, Tkatchenko I, Bouajila E, Walter O, Tommasi I, Rogers RD (2003a) 1,3-Dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adduct. Chem Commun.  https://doi.org/10.1039/B211519K Google Scholar
  35. Holbrey JD, Turner MB, Reichert WM, Rogers RD (2003b) New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide. Green Chem 5:731–736.  https://doi.org/10.1039/B311717K CrossRefGoogle Scholar
  36. Ilhan S, Baykara H, Oztomsuk A, Okumus V, Levent A, Seyitoglu MS, Ozdemir S (2014) Synthesis and characterization of 1,2-bis(2-(5-bromo-2-hydroxybenzilidenamino)-4-chlorophenoxy)ethane and its metal complexes: an experimental, theoretical, electrochemical, antioxidant and antibacterial study. Spectrochim Acta A Mol Biomol Spectrosc 118:632–642.  https://doi.org/10.1016/j.saa.2013.08.069 CrossRefGoogle Scholar
  37. Iranpoor N, Firouzabadi H, Azadi R (2006) A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers. Tetrahedron Lett 47:5531–5534.  https://doi.org/10.1016/j.tetlet.2006.05.145 CrossRefGoogle Scholar
  38. Iranpoor N, Firouzabadi H, Azadi R (2007) An imidazolium-based phosphinite ionic liquid (IL-OPPh2) as a reusable reaction medium and Pd(II) ligand in heck reactions of aryl halides with styrene and n-butyl acrylate. Eur J Org Chem.  https://doi.org/10.1002/ejoc.200601021 Google Scholar
  39. Iranpoor N, Firouzabadi H, Azadi R (2010) Diphenylphosphinite ionic liquid (IL-OPPh2): a solvent and ligand for palladium-catalyzed silylation and dehalogenation reaction of aryl halides with triethylsilane. J Organomet Chem 695:887–890.  https://doi.org/10.1016/j.jorganchem.2010.01.001 CrossRefGoogle Scholar
  40. Işık U, Aydemir M, Meriç N, Durap F, Kayan C, Temel H, Baysal A (2013) Tunable ferrocenyl-phosphinite ligands for the ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones. J Mol Catal A: Chem 379:225–233.  https://doi.org/10.1016/j.molcata.2013.08.005 CrossRefGoogle Scholar
  41. Keypour H, Shooshtari A, Rezaeivala M, Kup FO, Rudbari HA (2015) Synthesis of two new N2O4 macroacyclic Schiff base ligands and their mononuclear complexes: spectral, X-ray crystal structural, antibacterial and DNA cleavage activity. Polyhedron 97:75–82.  https://doi.org/10.1016/j.poly.2015.02.029 CrossRefGoogle Scholar
  42. Khan SA, Asiri AM (2012) Synthesis and in vitro antibacterial activity of novel steroidal (6R)-spiro-1,3,4-thiadiazoline derivatives. J Heterocycl Chem 49:1452–1457.  https://doi.org/10.1002/jhet.1014 CrossRefGoogle Scholar
  43. Luska KL, Moores A (2011) Improved stability and catalytic activity of palladium nanoparticle catalysts using phosphine-functionalized imidazolium ionic liquids. Adv Synth Catal 353:3167–3177.  https://doi.org/10.1002/adsc.201100551 CrossRefGoogle Scholar
  44. Luska KL, Demmans KZ, Stratton SA, Moores A (2012) Rhodium complexes stabilized by phosphine-functionalized phosphonium ionic liquids used as higher alkene hydroformylation catalysts: influence of the phosphonium headgroup on catalytic activity. Dalton Trans 41:13533–13540.  https://doi.org/10.1039/C2DT31797D CrossRefGoogle Scholar
  45. Meriç N, Aydemir M, Işık U, Ocak YS, Rafikova K, Paşa S, Kayan C, Durap F, Zazybin A, Temel H (2014a) Cross-coupling reactions in water using ionic liquid-based palladium(II)–phosphinite complexes as outstanding catalysts. Appl Organomet Chem 28:818–825.  https://doi.org/10.1002/aoc.3205 CrossRefGoogle Scholar
  46. Meriç N, Durap F, Aydemir M, Baysal A (2014b) The application of tunable tridendate P-based ligands for the Ru(II)-catalysed transfer hydrogenation of various ketones. Appl Organometal Chem 28:803–808.  https://doi.org/10.1002/aoc.3202 CrossRefGoogle Scholar
  47. Milton HL, Wheatley MV, Slawin AMZ, Woollins JD (2004) Synthesis and coordination of 2-diphenylphosphinopicolinamide. Polyhedron 23:3211–3220.  https://doi.org/10.1016/j.poly.2004.10.004 CrossRefGoogle Scholar
  48. Naveen P, Dallemer F, Butcher RJ, Prabhakaran R (2018) New Ru(II) complexes containing tris(2-pyridylmethyl)amine. Synthesis, structural, CT-DNA/albumin interaction, anti-oxidant and cytotoxicity studies. Inorg Chim Acta 471:724–734.  https://doi.org/10.1016/j.ica.2017.12.010 CrossRefGoogle Scholar
  49. Oyaizu M (1986) Studies on products of browning reaction: antioxidative activities of products of browning reaction prepared from glucosamine. Jpn J Nutr 44:307–315.  https://doi.org/10.5264/eiyogakuzashi.44.307 CrossRefGoogle Scholar
  50. Prediger P, Génisson Y, Correia CRD (2013) Ionic liquids and the heck coupling reaction: an update. Curr Org Chem 17:238–256.  https://doi.org/10.2174/1385272811317030006 CrossRefGoogle Scholar
  51. Ruhlan K, Gigler P, Herdtweck E (2008) Some phosphinite complexes of Rh and Ir, their intramolecular reactivity and DFT calculations about their application in biphenyl metathesis. J Organomet Chem 693:874–893.  https://doi.org/10.1016/j.jorganchem.2007.09.035 CrossRefGoogle Scholar
  52. Valizadeh H, Gholipour H (2010) Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as reusable catalyst and solvent for the knoevenagel condensation reaction. Synth Commun 40:1477–1485.  https://doi.org/10.1080/00397910903097310 CrossRefGoogle Scholar
  53. Valizadeh H, Khalili E (2012) Efficient synthesis of symmetrical phthalate and maleate diesters using phosphinite ionic liquids. J Iran Chem Soc 9:529–534.  https://doi.org/10.1007/s13738-011-0065-0 CrossRefGoogle Scholar
  54. Valizadeh H, Gholipour H, Mahmoudian M (2011) Phosphinite ionic liquid (IL-OPPh2) as a recyclable reagent for the efficient synthesis of coumarins under microwave irradiation conditions. J Iran Chem Soc 8:862–871.  https://doi.org/10.1007/BF03245917 CrossRefGoogle Scholar
  55. Vicente JA, Mlonka A, Gunaratne HQN, Swadzba-Kwasny M, Nockemann P (2012) Phosphine oxide functionalised imidazolium ionic liquids as tuneable ligands for lanthanide complexation. Chem Commun 48:6115–6117.  https://doi.org/10.1039/C2CC31544K CrossRefGoogle Scholar
  56. Wang X, Zhang J, Wang Y, Liu Y (2013) Amphiphilic ionic palladium complexes for aqueous–organic biphasic Sonogashira reactions under aerobic and CuI-free conditions. Catal Commun 40:23–26.  https://doi.org/10.1016/j.catcom.2013.05.005 CrossRefGoogle Scholar
  57. You H, Wang Y, Zhao X, Chen S, Liu Y (2013) Stable ionic Rh(I, II, III) complexes ligated by an imidazolium-substituted phosphine with π-acceptor character: synthesis, characterization, and application to hydroformylation. Organometallics 32:2698–2704.  https://doi.org/10.1021/om400171t CrossRefGoogle Scholar
  58. Zhang Q, Hua G, Bhattacharyya P, Slawin AMZ, Woollins JD (2003) Synthesis and coordination chemistry of aminophosphine derivatives of adenine. J Chem Soc Dalton Trans.  https://doi.org/10.1039/B303715K Google Scholar
  59. Zhang TT, Liu YJ, Yang L, Jiang JG, Zhao JW, Zhu W (2017) Extraction of antioxidant and antiproliferative ingredients from fruits of Rubus chingii Hu by active tracking guidance. Med Chem Commun 8:1673–1680.  https://doi.org/10.1039/C7MD00240H CrossRefGoogle Scholar
  60. Zhou C, Zhang J, Ðakovic M, Popovic Z, Zhao X, Liu Y (2012) Synthesis of an ionic paramagnetic ruthenium(III) complex and its application as an efficient and recyclable catalyst for the transfer hydrogenation of ketones. Eur J Inorg Chem.  https://doi.org/10.1002/ejic.201200280 Google Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceUniversity of DicleDiyarbakirTurkey
  2. 2.Institute of Chemical and Biological TechnologiesSatbayev UniversityAlmatyKazakhstan
  3. 3.School of Chemical EngineeringKazakh-British Technical UniversityAlmatyKazakhstan
  4. 4.Department of Biology, Faculty of Science and ArtUniversity of SiirtSiirtTurkey

Personalised recommendations