$Nickel(II)-PPh_3$ complexes with ONS and ONN chelating thiosemicarbazones: synthesis and inhibition potential on influenza A viruses

$Nickel(II)-PPh_3$ complexes with ONS and ONN chelating thiosemicarbazones: synthesis and inhibition potential on influenza A viruses

Tetra-coordinated nickel(II) complexes of two ONS (1, 2) and seven ONN (3a–3g) chelating 2-hydroxy3-methoxy-benzaldehyde thiosemicarbazones were synthesized. The dibasic ligands and complexes bearing PPh 3 as a coligand were characterized by means of analytical and spectroscopic data. Cytotoxic activities of the ligands and nickel(II) complexes were determined using the MTT assay in vitro against MDCK cells, and then all the compounds were tested on influenza virus replication by plaque assays. The compounds showed $GI_{50}$ values varying from concentrations of 15.9 up to 161.8 µ g/mL for MDCK cells. The plaque assays indicated that one ONS (1) and two ONN (3c and 3d) chelate structures have considerable antiviral effects on influenza A viruses at lower concentrations than the $GI_{50}$ values for MDCK cells. The ligands and other complexes did not show any inhibitory effects on influenza virus plaque formation. The effects of the compounds on the influenza virus and structure–antiviral activity relationships were discussed based on the donor atoms and S-alkyl substituents.

___

  • 1. Oxford, J. S. Rev. Med. Virol. 2000, 10, 119-133.
  • 2. Yoon, S. W.; Webby, R. J.; Webster, R. G. Curr. Top. Microbiol. Immunol. 2014, 385, 359-375.
  • 3. Eagles, D.; Siregar, E. S.; Dung, D. H.; Weaver, J.; Wong, F.; Daniels, P. Rev. Sci. Tech. 2009, 28, 341-348.
  • 4. Gilbert, M.; Xiao, X.; Pfeiffer, D. U.; Epprecht, M.; Boles, S.; Czarnecki, C.; Chaitaweesub, P.; Kalpravidh, W.; Minh, P. Q.; Otte, M. J. et al. P. Natl. Acad. Sci. USA 2008, 105, 4769-4774.
  • 5. Jimenez-Alberto, A.; Alvarado-Facundo, E.; Ribas-Aparicio, R. M.; Castelan-Vega, J. A. PLoS One 2013, 8, e70005.
  • 6. Laver, W. G. Microbiol. Sci. 1984, 1, 37-43.
  • 7. Govorkova, E. A.; Gambaryan, A. S.; Claas, E. C.; Smirnov, Y. A. Acta Virol. 2000, 44, 241-248.
  • 8. Intharathep, P.; Laohpongspaisan, C.; Rungrotmongkol, T.; Loisruangsin, A.; Malaisree, M.; Decha, P.; Aruksakunwong, O.; Chuenpennit, K.; Kaiyawet, N.; Sompornpisut, P. et al. J. Mol. Graph. Model. 2008, 27, 342-348.
  • 9. De Clercq, E. J. Clin. Virol. 2004, 30, 115-133.
  • 10. Hussain, M; Galvin, H. D.; Haw, T. Y.; Nutsford, A. N.; Husain, M. Infect. Drug Resist. 2017, 20, 121-134.
  • 11. Gamblin, S. J.; Skehel, J. J. J. Biol. Chem. 2010, 285, 28403-28409.
  • 12. Tong, S.; Zhu, X.; Li, Y.; Shi, M.; Zhang, J. et al. PLoS Pathog. 2013, 9, e1003657.
  • 13. Takemoto, D. K.; Skehel, J. J.; Wiley, D. C. Virology 1996, 217, 452-458.
  • 14. Hidari, K. I; Yamaguchi, M.; Ueno, F.; Abe, T.; Yoshida, K.; Suzuki, T. Biochem. Biophys. Res. Commun. 2013, 436, 394-399.
  • 15. Palese, P.; Tobita, K.; Ueda, M.; Compans, R. W. Virology 1974, 61, 397-410.
  • 16. Liu, C.; Eichelberger, M. C.; Compans, R. W.; Air, G. M. J. Virol. 1995, 69, 1099-1106.
  • 17. Cohen, M.; Zhang, X. Q.; Senaati, H. P.; Chen, H. W.; Varki, N. M.; Schooley, R. T.; Gagneux, P. Virol. J. 2013, 10, 321.
  • 18. Shinya, K.; Fujii, Y.; Ito, H.; Ito, T.; Kawaoka, Y. J. Virol. 2004, 78, 3083-3088.
  • 19. Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang. L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y. et al. J. Am. Chem. Soc. 1997, 119, 681-690.
  • 20. Michiels, B.; Van Puyenbroeck, K.; Verhoeven, V.; Vermeire, E.; Coenen, S. PLoS One 2013, 8, e60348.
  • 21. Takashita, E.; Fujisaki, S.; Kishida, N.; Xu, H.; Imai, M.; Tashiro, M.; Odagiri, T.; Influenza Virus Surveillance Group of Japan. Influenza Other Resp. 2013, 7, 1390-1399.
  • 22. Monto, A. S.; McKimm-Breschkin, J. L.; Macken, C.; Hampson, A. W.; Hay, A.; Klimov, A.; Tashiro, M.; Webster, R. G.; Aymard, M.; Hayden, F. G. et al. Antimicrob. Agents Chemother. 2006, 50, 2395-2402.
  • 23. Atabey, H.; Sarı, H. Turk. J. Chem. 2014, 38, 806-814.
  • 24. Kurebayashi, Y.; Takahashi, T.; Tamoto, C.; Sahara, K.; Otsubo, T.; Yokozawa, T.; Shibahara, N.; Wada, H.; Minami, A; Ikeda, K. et al. PLoS One 2016, 11, e0156400.
  • 25. L’Huillier, A. G.; Abed, Y.; Petty, T. J.; Cordey, S.; Thomas, Y.; Bouhy, X.; Schibler, M.; Simon, A.; Chalandon, Y.; van Delden, C. et al. J. Infect. Dis. 2015, 212, 1721-1734.
  • 26. Yamgar, R.; Kamat, P.; Khandekar, D.; Sawant, S. J. Chem. Pharm. Res. 2011, 3, 188-198.
  • 27. Kurt, Y. D.; Ulkuseven, B. J. Coord. Chem. 2010, 63, 828-836.
  • 28. Rogolino, D.; Bacchi, A.; De Luca, L.; Rispoli, G.; Sechi, M.; Stevaert, A.; Naesens, L.; Carcelli, M. J. Biol. Inorg. Chem. 2015, 20, 1109-1121.
  • 29. Atasever, B.; Ulkuseven, B.; Bal-Demirci, T.; Erdem-Kuruca, S.; Solakoglu, Z. Invest. New Drugs 2010, 28, 421- 432.
  • 30. Bal, T.; Atasever, B.; Solakoglu, Z.; Erdem-Kuruca, S.; Ulkuseven, B. Eur. J. Med. Chem. 2007, 42, 161-167.
  • 31. Rodriguez-Arguelles, M. C.; Touron-Touceda, P.; Cao, R.; Garcia-Deibe, A. M.; Pelagatti, P.; Pelizzi, C.; Zani, F. J. Inorg. Biochem. 2009, 103, 35-42.
  • 32. Abou-Melha, K. S. J. Enzyme Inhib. Med. Chem. 2008, 23, 493-503.
  • 33. Glisoni, R. J.; Cuestas, M. L.; Mathet, V. L.; Oubina, J. R.; Moglioni, A. G.; Sosnik, A. Eur. J. Pharm. Sci. 2012, 47, 596-603.
  • 34. Domagk, G.; Behnisch, R.; Mietzsh, F.; Schmidt, H. Naturwissenshaften 1946, 33, 315-319.
  • 35. Bauer, D. J. Br. J. Exp. Pathol. 1955, 36, 105-114.
  • 36. Selvam, P.; Murugesh, N.; Chandramohan, M.; Sidwell, R. W.; Wandersee, M. K.; Smee, D. F. Antivir. Chem. Chemother. 2006, 17, 269-274.
  • 37. Bauer, D. J.; Sadler, P. W. Br. J. Pharmacol. Chemother. 1960, 15, 101-110.
  • 38. Guveli, S.; Ulkuseven, B. Polyhedron 2011, 30, 1385-1388.
  • 39. Kalaivani, P.; Saranya, S.; Poornima, P.; Prabhakaran, R.; Dallemer, F.; Vijaya Padma, V.; Natarajan, K. Eur. J. Med. Chem. 2014, 82, 584-599.
  • 40. Takjoo, R.; Akbari, A.; Ahmadi, M.; Rudbari, H. A.; Bruno, G. Polyhedron 2013, 55, 225-232.
  • 41. Kumar, S. M.; Dhahagani, K.; Rajesh, J.; Nehru, K., Annaraj, J.; Chakkaravarthi, G.; Rajagopal, G.; Rajagopal, G. Polyhedron 2013, 59, 58-68.
  • 42. Güveli, S¸.; Bal-Demirci T.; Ulk¨useven, B.; ¨ Ozdemir, N. ¨ Polyhedron 2016, 110, 188-196.
  • 43. Ulkuseven, B.; Bal-Demirci, T.; Akkurt, M.; Yalcin, S. P.; Buyukgungor, O. Polyhedron 2008, 27, 3646-3652.
  • 44. Guveli, S.; Cinar-Agopcan, S.; Karahan, O.; Aviyente, V.; Ulkuseven, B. Eur. J. Inorg. Chem. 2016, 2016, 538-544.
  • 45. Yamazaki, C. Can. J. Chem. 1975, 53, 610-615.
  • 46. Prabhakaran, R.; Karvembu, R.; Hashimoto, T.; Shimizu, K.; Natarajan, K. Inorg. Chim. Acta 2005, 358, 2093- 2096.
  • 47. Madin, S. H.; Darby, N. B. Jr. In Hatt, H. O., Ed. American Type Culture Collection Catalogue of Strains, Vol. 2 ; Library of Congress: Rockville, MD, USA, 1975, p. 47.
  • 48. Oberleithner, H.; Vogel, U.; Kersting, U.; Steigner, W. Pflugers Arch. 1990, 416, 533-539.
  • 49. Turan, K.; Nagata, K.; Kuru, A. Biochem. Biophys. Res. Commun. 1996, 225, 22-26.
  • 50. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63.