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Original Article

Synthesis, characterization, cytotoxicity, and DNA binding of some new platinum(II) and platinum(IV) complexes with benzimidazole ligands

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Pages 502-508 | Received 07 May 2009, Accepted 25 Aug 2009, Published online: 16 Mar 2010

References

  • Jung Y, Lipard SJ. Direct cellular responses to platinum-induced DNA damage. Chem Rev 2007;107:1387–407.
  • Rabik CA, Dolan ME. Molecular mechanisms of resistance and toxicity associated with platinating agents. Cancer Treat Rev 2007;33:9–23.
  • Jamieson ER, Lippard SJ. Structure, recognition, and processing of cisplatin-DNA adducts. Chem Rev 1999;99:2467–98.
  • ChválováK, Brabec V, KaśpárkováJ. Mechanism of the formation of DNA-protein cross-links by antitumor cisplatin. Nucleic Acids Res 2007;35:1812–21.
  • Fichtinger-Schepman AMJ, Van der Veer JL, den Hartog JHJ, Lohman PHM, Reedijk J. Adducts of the antitumor drug cis-diamminedichloroplatinum(II) with DNA: formation, identification, and quantitation. Biochemistry 1985;24:707–13.
  • Fuertes MA, Alonso C, Perez JM. Biochemical modulation of cisplatin mechanisms of action: enhancement of antitumor activity and circumvention of drug resistance. Chem Rev 2003;103:645–62.
  • Brabec V, Kasparkova J. Modfication of DNA by platinum complexes. Relation to resistance of tumors to platinum antitumor drugs. Drug Resist Update 2005;8:131–46.
  • Reedijk J. Improved understanding in platinium antitumour chemistry. Chem Commun 1996;7:801–6.
  • Wong E, Giandomenico CM. Current status of platinum-based antitumor drugs. Chem Rev 1999;99:2451–66.
  • NovákováO, Vrána O, Kıseleva VI, Brabec V. DNA interactions of antitumor platinum(IV)complexes. Eur J Biochem 1995;228:616–24.
  • Ellis LT, Er HM, Hambley TW. The influence of the axial ligands of a series of platinum(IV) anti-cancer complexes on their reduction to platinum(II) and reaction with DNA. Aust J Chem 1995;48:793–806.
  • Hall MD, Hambley TW. Platinum(IV) antitumour compounds: their bioinorganic chemistry. Coord Chem Rev 2002;232:49–67.
  • Choi S, Filotto C, Bisanzo M, Delaney S, Lagasee D, Whitworth JL, et al. Reduction and anticancer activity of platinum(IV) complexes. Inorg Chem 1998;37:2500–4.
  • Hall MD, Mellor HR, Callaghan R, Hambley TW. Basis for design and development of platinum(IV) anticancer complexes. J Med Chem 2007;26:3403–11.
  • Abu-Surrah AS, Kettunen M. Platinum group antitumor chemistry: design and development of new anticancer drugs complementary to cisplatin. Curr Med Chem 2006;13:1337–57.
  • Kerr C. Satraplatin for hormone-refractory prostate cancer. Lancet Oncol 2007;8:290.
  • GümüşF, İzgüF, Algül Ö. Synthesis and structural characterization of some 5(6)-substituted-2-hydroxymethylbenzimidazole derivatives and their platinum(II) complexes and determination of their in vitro antitumor activities by “Rec-Assay” test. FABAD J Pharm Sci 1996;21:7–15.
  • GümüşF, Algül Ö. DNA binding studies with cis-dichlorobis(5(6)-non/chlorosubstituted-2-hydroxymethyl-benzimidazole)platinum(II) complexes. J Inorg Biochem 1997;68:71–4.
  • Gümüş F, Pamuk İ, Özden, T, Yıldız S, Diril N, Öksüzoğlu E, et al. Synthesis, characterization and in vitro cytotoxic, mutagenic and antimicrobial activity of platinum(II) complexes with substituted benzimidazole ligands. J Inorg Biochem 2003;94:255–62.
  • GümüşF, Algül ÖEren, G, Eroğlu H, Diril N, Gür S, et al. Synthesis, cytotoxic activity on MCF-7 cell line and mutagenic activity of platinum(II) complexes with 2-substituted benzimidazole ligands. Eur J Med Chem 2003;38:473–80.
  • Gökçe M, Utku S, Gür S, Özkul A, GümüşF. Synthesis, in vitro cytotoxic and antiviral activity of cis-[Pt(R(-) and S(+)-2-α-hydroxybenzylbenzimidazole)2Cl2] complexes. Eur J Med Chem 2005;40:135–41.
  • Utku S, GümüşF, Gür S, Özkul A. Synthesis and cytotoxic activity of platinum(II) and platinum(IV) complexes with 2-hydroxymethylbenzimidazole or 5(6)-choloro-2-hydroxymethylbenzimidazole ligands against MCF-7 and HeLa cell lines. Turk J Chem 2007;31:503–14.
  • Utku S, GümüşF, Karaoğlu T, Özkul A. Cytotoxic activity of platinum(II) and platinum(IV) complexes bearing 5(6)-non/chlorosubstituted-2-hydroxymethylbenzimidazole ligands against Hep-2 cell line. Ankara Ecz Fak Derg 2007;36:21–30.
  • GümüşF, Eren G, Açık L, Çelebi A, Öztürk F, Yılmaz Ş, et al. Synthesis, cytotoxic, and DNA interactions of new cisplatin analogues containing substituted benzimidazole ligands. J Med Chem 2009;52:1345–57.
  • Preston PN. Synthesis, reactions, and spectroscopic properties of benzimidazoles. Chem Rev 1974;74:279–314.
  • Rabıger DJ, Joullie MM. The ionization constant, ultraviolet and infrared spectra of some substituted benzimidazoles. J Org Chem 1964;29:476–82.
  • Bernhard G, Reile H, Birnböck H, Spruss T, Schönenberger H. Standardized kinetic microassay to quantify differential chemosensitivity on the basis of proliferative activity. J Cancer Res Clin Oncol 1992;118:35–43.
  • Reile H, Birnböck H, Bernhard G, Spruss T, Schönenberger H. Computerized determination of growth kinetic curves and doubling times from cells in microculture. Anal Biochem 1990;187:262–7.
  • Stellwagen N. Nucleic Acid Electrophoresis. Berlin: Springer, 1998.
  • Maurya RC, Mishra DD. Studies on some novel mixed-ligand cyanonitrosyl hetero complexes of chromium(I) with potentially bi- and tri-dentate benzimidazole derivatives. Syn React Inorg Met Org Chem 1990;20:1013–24.
  • TunalıNK, Özkar S. Anorganik Tepkime Mekanizmaları. Anorganik Kimya. Ankara: Gazi Publishing, 1999:373–402.
  • Mylonas S, Valavanidis A; Voukouvalidis V, Polyssiou M. Platinum(II)and palladium(II) complexes with amino acid derivatives. Synthesis, interpretation of IR and 1H NMR spectra and conformational implications. Inorg Chim Acta 1981;55:125–8.
  • Dodoff N, Grancharov K, Gugova R, Spassovska N. Platinum(II) complexes of benzoic- and 3-methoxybenzoic acid hydrazides. Synthesis, characterization, and cytotoxic effect. J Inorg Biochem 1994;54:221–33.
  • Giandomenico CM, Abrams MJ, Murrer BA, Vollano JF, Rheinheimer MI, Wyer SB, et al. Carboxylation of kinetically inert platinum(IV) hydroxy complexes. An entree into orally active platinum(IV) antitumor agents. Inorg Chem 1995;34:1015–21.
  • Miller B, Altman J, Beck W. Platinum(IV) complexes of vicinal-1,2-diamines, and bis(vicinal-1,2-diamines) with an acylamimo function. Evidence for a platinum hydroperoxide intermediate upon oxidation. Inorg Chim Acta 1997;264:101–8.
  • Khokhar AR, Deng Y, Al-Baker S, Yoshida M, Siddik ZH. Synthesis and antitumor activity of ammine/amine platinum(II) and (IV) complexes. J Inorg Biochem 1993;51:677–87.
  • Lee EJ, Jun MJ, Sohn YS. Synthesis and properties of novel platinum(IV) complexes involving asymmetric chiral diamines as carrier ligands. Bull Korean Chem Soc 1999;20:1295–8.
  • Hambley TW, Battle AR, Deacon GB. Lawrenz ET, Fallon GD, Gatehouse BM, et al. Modifying the properties of platinum(IV) complexes in order to increase biological effectiveness. Inorg Biochem 1999;77:3–12.
  • Lippert B. Platinum nucleobase chemistry. Prog Inorg Chem 1989;37:1–97.
  • Sawicka M, Kalinowska M, Skierska J, Lewandowski W. A review of selected anti-tumour therapeutic agents and reasons for multidrug resistance occurrence. J Pharm Pharmacol 2004;56:1067–81.
  • Kushev D, Grünert R, Spassovska N, Golovinsky E, Bednarski PJ. Unusual reactivity of cytotoxic cis-dihydrazide Pt(II) complexes in aqueous solution. J Inorg Biochem 2003;96:469–77.
  • Reedijk J. The relevance of hydrogen bonding in the mechanism of action of platinum antitumor compounds. Inorg Chim Acta 1992;198–200:873–81.
  • Whittaker J, McFadyen WD, Wickham G, Wakelin LPG, Murray V. The interaction of DNA-targeted platinum phenanthridinium complexes with DNA. Nucleic Acids Res 1998;26:3933–9.
  • Ushay HM, Tullius TD, Lippard SJ. Inhibition of the BamHI cleavage and unwinding of pBR322 deoxyribonucleic acid by the antitumor drug cis-dichlorodiammineplatinum(II). Biochemistry 1981;20:3744–8.
  • Cheng H, Huq F, Beale P, Fisher K. Synthesis, characterization, activities, cell uptake and DNA binding of trinuclear complex: [{trans-PtCl(NH3)}2µ-{trans-Pd(NH3)(2-hydroxypyridine)-(H2N(CH2)6NH2)2]Cl4. Eur J Chem 2006;41:896–903.
  • Keck MV, Lippard SJ. Unwinding of supercoiled DNA by platinum-ethidium and related complexes. J Am Chem Soc 1992;114:3386–90.
  • Bowler BE, Hollis LS, Lippard SJ. Synthesis and DNA binding and phonicking properties of acridine orange linked by a polymethylene tether to (1,2-diaminoethane)dichloroplatinum(II). J Am Chem Soc 1984;106:6102–4.
  • Perez JM, Camazon M, Alvarez-Valdes A, Quiroga AG, Kelland LR, Alonso C, et al. Synthesis, characterization and DNA modification induced by a novel Pt(IV)-bis(monoglutarate) complex which induced apoptosis in glioma cells. Chem-Biol Interact 1999;117:99–115.
  • Neplechova K, Kasparkova J, Vrana O, Novakova O, Habtemariam A, Watchman B, et al. DNA interactions of new antitumor aminophosphine platinum(II) complexes. Mol Pharmacol 1999;56:20–30.

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