Synthesis and Cytotoxic Activity of Platinum(II) and Platinum(IV) Complexes with 2-Hydroxymethylbenzimidazole or 5(6)-Chloro-2-hydroxymethylbenzimidazole Ligands against MCF-7 and HeLa Cell Lines

Four platinum(II) and 4 platinum(IV) complexes with the structures [PtL2Cl2], [PtL2I2], [PtL2Cl4], and [PtL2Cl2(OH)2] (L = 5(6)-non/orchloro-substituted-2-hydroxymethylbenzimidazole ligands as ``non-leaving groups''), respectively, were synthesized and characterized by their elemental analyses, and IR and 1H-NMR spectra. In vitro cytotoxic activities of the platinum(II) and platinum(IV) complexes were tested against the human MCF-7 (breast cancer) and HeLa (cervix cancer) cell lines using the cell culture method. In general, the platinum(II) complexes were more active than the corresponding platinum(IV) complexes. The complexes, which were found to be less active than cisplatin, exhibited cyctotoxicity comparable to carboplatin on the human MCF-7 and HeLa cell lines.

Synthesis and Cytotoxic Activity of Platinum(II) and Platinum(IV) Complexes with 2-Hydroxymethylbenzimidazole or 5(6)-Chloro-2-hydroxymethylbenzimidazole Ligands against MCF-7 and HeLa Cell Lines

Four platinum(II) and 4 platinum(IV) complexes with the structures [PtL2Cl2], [PtL2I2], [PtL2Cl4], and [PtL2Cl2(OH)2] (L = 5(6)-non/orchloro-substituted-2-hydroxymethylbenzimidazole ligands as ``non-leaving groups''), respectively, were synthesized and characterized by their elemental analyses, and IR and 1H-NMR spectra. In vitro cytotoxic activities of the platinum(II) and platinum(IV) complexes were tested against the human MCF-7 (breast cancer) and HeLa (cervix cancer) cell lines using the cell culture method. In general, the platinum(II) complexes were more active than the corresponding platinum(IV) complexes. The complexes, which were found to be less active than cisplatin, exhibited cyctotoxicity comparable to carboplatin on the human MCF-7 and HeLa cell lines.

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  • E.R. Jamieson and S.J. Lippard, Chem. Rev. 99, 2467-98 (1999).
  • S.M.Cohen and S.J. Lippard, Prog. Nucleic Acid Res. Mol. Biol. 67, 93-130 (2001).
  • Y. Jung and S.J. Lippard, J. Biol. Chem. 278, 52084-92 (2003).
  • V. Brabec and J. Kasparkova, Drug Resist. Updates 8, 131-46 (2005).
  • G. Chu, J. Biol. Chem. 269, 787-90 (1994).
  • D. Wang, R. Hara, G. Singh, A. Sancar and S.J. Lippard, Biochemistry 42, 6747-53 (2003).
  • G. Natile and L.G. Marzilli, Coord. Chem. Rev. 250, 1315-31 (2006).
  • V. Brabec and J. Kasparkova, Drug Resist. Updates 5, 147-61 (2002).
  • G. Tallen, C. Mock, S.B. Gangopadhyay, B. Kangarloo, B. Krebs and J.E. Wolff, Anticancer Res. 20, 445-50 (2000).
  • J. Reedijk, Chem. Commun. 7, 801-6 (1996).
  • M.D. Hall and T.W. Hambley, Coord. Chem. Rev. 232, 49-67 (2002).
  • S. Choi, C. Filotto, M. Bisanzo, S. Delaney, D. Lagasee, J.L. Whitworth, A. Jusko, C. Li, N.A. Wood, J. Willingham, A. Schwenker and K. Spaulding, Inorg. Chem. 37, 2500-4 (1998).
  • S. Zutphen and J. Reedijk, Coord. Chem. Rev. 249, 2845-53 (2005).
  • F. G¨um¨u¸s, F. ˙Izg¨u and ¨O. Alg¨ul, FABAD J. Pharm. Sci. 21, 7-15 (1996).
  • F. G¨um¨u¸s and ¨O. Alg¨ul, J. Inorg. Biochem. 68, 71-4 (1997).
  • F. G¨um¨u¸s, ˙I. Pamuk, T. ¨Ozden, S. Yıldız, N. Diril, E. ¨Oks¨uzo˘glu, S. G¨ur and A. ¨Ozkul, J. Inorg. Biochem. , 255-62 (2003).
  • F. G¨um¨u¸s, ¨O. Alg¨ul, G. Eren, H. Ero˘glu, N. Diril, S. G¨ur and A. ¨Ozkul, Eur. J. Med. Chem. 38, 473-80 (2003).
  • M. G¨ok¸ce, S. Utku, S. G¨ur, A. ¨Ozkul and F. G¨um¨u¸s, Eur. J. Med. Chem. 40, 135-41 (2005).
  • M.A. Phillips, J. Chem. Soc. 2393-99 (1928).
  • J.B. Wright, Chem. Rev. 48, 397-541 (1951).
  • G. Bernhard, H. Reile, H. Birnb¨ock, T. Spruss and H. Sch¨onenberger, J. Cancer Res. Clin. Oncol. 118, 43 (1992).
  • H. Reile, H. Birnb¨ock, G. Bernhard, T. Spruss and H. Sch¨onenberger, Anal. Biochem. 187, 262-67 (1990).
  • F. G¨um¨u¸s, A.B. Demirci, T. ¨Ozden, H. Ero˘glu and N. Diril, Die Pharmazie 58, 303-7 (2003).
  • D.J. Rabiger and M.M. Joullie, J. Org. Chem. 29, 476-82 (1964).
  • R.C. Maurya and D.D. Mishra, Syn. React. Inorg. Met. 45, 2064-78 (1990).
  • A.R. Khokhar, Y. Deng, S. Al-Baker, M. Yoshida and Z.H. Siddik, J. Inorg. Biochem. 51, 677-87 (1993).
  • C.M. Giandomenico, M.J. Abrams, B.A. Murrer, J. F. Vollano, M.I. Rheinheimer, S.B. Wyer, G.E. Bossard and J.D. Higgins, Inorg. Chem. 34, 1015-21 (1995).
  • B. Miller, J. Altman and W. Beck, Inorg. Chim. Acta 264, 101-8 (1997).
  • N. Dodoff, K. Grancharov, R. Gugova and N. Spassovska, J. Inorg. Biochem. 54, 221-33 (1994).
  • E.J. Lee, M.J. Jun and Y.S. Sohn, Bull. Korean Chem. Soc. 20, 1295-98 (1999).
  • T.W. Hambley, A.R. Battle, G.B. Deacon, E.T. Lawrenz, G.D. Fallon, B.M. Gatehouse, L.K. Webster and S. Rainone, J. Inorg. Biochem. 77, 3-12 (1999).
  • B. Lippert, Prog. Inorg. Chem. 37, 1-94 (1989).
  • C. Lottner, K.C. Bart, G. Bernhardt and H. Brunner, J. Med. Chem. 45, 2064-78 (2002).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
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