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Synthesis and characterization of iminophosphineplatinum(II) complexes of the type (κ2-P,N-2-Ph2PC6H4C(H)=NC6H4X)PtCl2 (X = OMe, F)

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Abstract

A series of iminophosphineplatinum(II) complexes have been prepared from pro-ligands derived from aniline derivatives containing electron-donating methoxy groups or electron-withdrawing fluorides and [PtCl2(η 2 − coe)]2 (coe = cis-cyclooctene). All new pro-ligands and metal complexes have been fully characterized, including an X-ray diffraction study for compound 11 (derived from para-methoxyaniline). Additionally, the molecular structure of a di-iminophosphineplatinum dication 11a has been determined. The platinum compounds showed no appreciable cytotoxic properties against two glioma cell lines using the MTT method.

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References

  1. Hannon MJ (2007) Pure Appl Chem 79:2243

    Article  CAS  Google Scholar 

  2. Barry NPE, Sadler PJ (2013) ACS Nano 7:5654

    Article  CAS  Google Scholar 

  3. de Biasi AR, Villena-Vargas J, Adusumilli PS (2014) Clin Cancer Res 20:5384

    Article  Google Scholar 

  4. Medici S, Peana M, Nurchi VM, Lachowicz JI, Crisponi G, Zoroddu MA (2015) Coord Chem Rev 284:329

    Article  CAS  Google Scholar 

  5. Nogales V, Reinhold WC, Varma S, Martinez-Cardus A, Moutinho C, Moran S, Heyn H, Sebio A, Barnadas A, Pommier Y, Esteller M (2016) Oncotarget 7:3084

    Article  Google Scholar 

  6. Doucette KA, Hassell KN, Crans DC (2016) J Inorg Biochem 165:56

    Article  CAS  Google Scholar 

  7. Johnstone TC, Suntharalingam K, Lippard SJ (2016) Chem Rev 116:3436

    Article  CAS  Google Scholar 

  8. Dasari S, Tchounwou PB (2014) Eur J Pharmacol 740:364

    Article  CAS  Google Scholar 

  9. Siddik ZH (2003) Oncogene 22:7265

    Article  CAS  Google Scholar 

  10. Wheate NJ, Walker S, Craig GE, Oun R (2010) Dalton Trans 39:8113

    Article  CAS  Google Scholar 

  11. Posadas I, Alonso-Moreno C, Bravo I, Carrillo-Hermosilla F, Garzón A, Villaseca N, López-Solera I, Albaladejo J, Ceña V (2017) J Inorg Biochem 168:46

    Article  CAS  Google Scholar 

  12. Altoum AOS, Alhoshani A, Alhosaini K, Altaf M, Ahmad S, Popoola SA, Al-Saadi AA, Sulaiman AA, Isab AA (2017) J Coord Chem 70:1020

    Article  CAS  Google Scholar 

  13. Hamilton G, Olszewski U (2013) Expert Opin Drug Metab Toxicol 9:1381

    Article  CAS  Google Scholar 

  14. St-Coeur P-D, Kinley S, Vogels CM, Decken A, Morin P Jr, Westcott SA (2017) Can J Chem 95:207

    Article  CAS  Google Scholar 

  15. Chiririwa H, Moss JR, Hendricks D, Smith GS, Meijboom R (2013) Polyhedron 49:29

    Article  CAS  Google Scholar 

  16. Chiririwa H, Moss JR, Hendricks D, Meijboom R, Muller A (2013) Transit Met Chem 38:165

    Article  CAS  Google Scholar 

  17. Shaver MP, Vogels CM, Wallbank AI, Hennigar TL, Biradha K, Zaworotko MJ, Westcott SA (2000) Can J Chem 78:568

    Article  CAS  Google Scholar 

  18. Chen X, Femia FJ, Babich JW, Zubieta J (2001) Inorg Chim Acta 315:147

    Article  CAS  Google Scholar 

  19. Crochet P, Gimeno J, Borge J, García-Granda S (2003) New J Chem 27:414

    Article  CAS  Google Scholar 

  20. Antonaroli S, Crociani B (1998) J Organomet Chem 560:137

    Article  CAS  Google Scholar 

  21. Scrivanti A, Matteoli U, Beghetto V, Antonaroli S, Crociani B (2002) Tetrahedron 58:6881

    Article  CAS  Google Scholar 

  22. Bruker (2008) APEX2 version 2008.5. Bruker AXS, Inc., Madison

    Google Scholar 

  23. Sheldrick GM (2008) Acta Cryst A 64:112

    Article  CAS  Google Scholar 

  24. Farrugia LJ (1997) J Appl Cryst 30:565

    Article  CAS  Google Scholar 

  25. Ishii N, Maier D, Merlo A, Tada M, Sawamura Y, Diserens AC, Van Meir EG (1999) Brain Pathol 9:469

    Article  CAS  Google Scholar 

  26. Margiotta N, Denora N, Ostuni R, Laquintana V, Anderson A, Johnson SW, Trapani G, Natile G (2010) J Med Chem 53:5144

    Article  CAS  Google Scholar 

  27. Charest G, Paquette B, Fortin D, Mathieu D, Sanche L (2010) J Neurooncol 97:187

    Article  CAS  Google Scholar 

  28. Gwak H-S, Shingu T, Chumbalkar V, Hwang Y-H, DeJournett R, Latha K, Koul D, Yung WKA, Powis G, Farrell NP, Bögler O (2011) Int J Cancer 128:787

    Article  CAS  Google Scholar 

  29. Maksimović-Ivanić D, Mijatović S, Mirkov I, Stošić-Grujičić S, Miljković D, Sabo TJ, Trajković V, Kaluđerović GN (2012) Metallomics 4:1155

    Article  Google Scholar 

  30. Mihajlović LE, Savić A, Poljarević J, Vučković I, Mojić M, Bulatović M, Maksimović-Ivanić D, Mijatović S, Kaluđerović GN, Stošić-Grujičić S, Milijković D, Grgurić-Šipka S, Sabo TJ (2012) J Inorg Biochem 109:40

    Article  Google Scholar 

  31. Soares MA, Mattos JL, Pujatti PB, Leal AS, dos Santos WG, dos Santos RGJ (2012) Radioanal Nucl Chem 292:61

    Article  CAS  Google Scholar 

  32. Yildirim H, Köçkar F, Nakīboğlu C (2012) Afr J Biotech 11:12422

    CAS  Google Scholar 

  33. Ahn M-J, D’Cruz A, Vermorken JB, Chen J-P, Chitapanarux I, Dang HQT, Guminski A, Kannarunimit D, Lin T-Y, Ng WT, Park K-U, Chan ATC (2016) Oral Oncol 53:10

    Article  Google Scholar 

  34. Mogorosi MM, Mahamo T, Moss JR, Mapolie SF, Slootweg JC, Lammertsma K, Smith GS (2011) J Organomet Chem 696:3585

    Article  CAS  Google Scholar 

  35. Antonels NC, Therrien B, Moss JR, Smith GS (2009) Inorg Chem Commun 12:716

    Article  CAS  Google Scholar 

  36. Doherty S, Knight JG, Scanlan TH, Elsegood MRJ, Clegg W (2002) J Organomet Chem 650:231

    Article  CAS  Google Scholar 

  37. Chiririwa H, Ntuli F, Muzenda E, Muller A (2013) Transit Met Chem 38:393

    Article  CAS  Google Scholar 

  38. Motswainyana WM, Onani MO, Madiehe AM, Saibu M, Thovhogi N, Lalancette RA (2013) J Inorg Biochem 129:112

    Article  CAS  Google Scholar 

  39. Blacker AJ, Clarke ML, Loft MS, Mahon MF, Williams JMJ (1999) Organometallics 18:2867

    Article  CAS  Google Scholar 

  40. Burger S, Therrien B, Süss-Fink G (2003) Eur J Inorg Chem 3099

  41. Hedden D, Roundhill DM, Fultz WC, Rheingold AL (1986) Organometallics 5:336

    Article  CAS  Google Scholar 

  42. Swanson RA, Haywood RS, Gibbons JB, Cordova KE, Patrick BO, Moore C, Rheingold AL, Daley CJA (2011) Inorg Chim Acta 368:74

    Article  CAS  Google Scholar 

  43. Hii KK, Perera SD, Shaw BL, Thornton-Pett M (1994) J Chem Soc. Dalton Trans 1:103

    Article  Google Scholar 

  44. Wong W-K, Sun C, Wong W-T (1997) J Chem Soc. Dalton Trans 18:3387

    Article  Google Scholar 

  45. Pascu SI, Coleman KS, Cowley AR, Green MLH, Rees NH (2005) New J Chem 29:385

    Article  CAS  Google Scholar 

  46. Margraf G, Pattacini R, Messaoudi A, Braunstein P (2006) Chem Commun 29:3098

    Article  Google Scholar 

  47. Durran SE, Elsegood MRJ, Hammond SR, Smith MB (2007) Inorg Chem 46:2755

    Article  CAS  Google Scholar 

  48. Crochet P, Gimeno J, García-Granda S, Borge J (2001) Organometallics 20:4369

    Article  CAS  Google Scholar 

  49. Ramírez P, Contreras R, Valderrama M, Carmona D, Lahoz FJ, Balana AI (2008) J Organomet Chem 693:349

    Article  Google Scholar 

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Acknowledgements

Thanks are gratefully extended to Mount Allison University, Saint Mary’s University, Université de Moncton, the Natural Science and Engineering Research Council of Canada (SAW, JM, PJM) and the Canada Research Chair Programme (SAW) for financial support. We also thank Deman Durant (Mount Allison University) for his expert technical assistance, and anonymous reviewers are thanked for their very helpful comments.

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Correspondence to Stephen A. Westcott.

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St-Coeur, PD., Adams, M.E., Kenny, B.J. et al. Synthesis and characterization of iminophosphineplatinum(II) complexes of the type (κ2-P,N-2-Ph2PC6H4C(H)=NC6H4X)PtCl2 (X = OMe, F). Transit Met Chem 42, 693–701 (2017). https://doi.org/10.1007/s11243-017-0176-2

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  • DOI: https://doi.org/10.1007/s11243-017-0176-2

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