Advertisement

JBIC Journal of Biological Inorganic Chemistry

, Volume 18, Issue 7, pp 791–801 | Cite as

Study of the synthesis, antiproliferative properties, and interaction with DNA and polynucleotides of cisplatin-like Pt(II) complexes containing carcinogenic polyaromatic amines

  • Elisabetta Gabano
  • Sofia Gama
  • Filipa Mendes
  • Marzia B. Gariboldi
  • Elena Monti
  • Sophie Bombard
  • Sabrina Bianco
  • Mauro Ravera
Original Paper

Abstract

The chemical and biological features of two newly synthesized [PtCl2(L)(2-aminonaphthalene)] complexes (L is NH3 or 2-aminonaphthalene) were compared with those of two already reported enantiomeric complexes of formula [PtCl2(DABN)] [DABN is (R)-1,1′-binaphthyl-2,2′-diamine or (S)-1,1′-binaphthyl-2,2′-diamine]. Solution behavior, lipophilicity, cytotoxicity with regard to one colorectal (HCT116) and two ovarian (A2780 and A2780Cp8) human carcinoma cell lines, and in vitro DNA- and G-quadruplex-binding properties were evaluated. In particular, the cytotoxicity of [PtCl2(NH3)(2-aminonaphthalene)] was better than that of cisplatin for all cell lines, and rather resembled that of oxaliplatin. The solution behavior of the whole series of complexes and the absence of an evident relationship between lipophilicity and cytotoxicity seem to suggest that all these experimental parameters are probably smoothed out during the 3-day cytotoxicity experiments and do not strongly affect the half-maximal inhibitory concentrations. The results of electrophoretic studies indicate that different kinds of interaction with DNA can be involved in the mode of action of these complexes, with intercalation in double-stranded DNA and stacking on G-quadruplex DNA being strongly implicated in particular for [PtCl2(NH3)(2-aminonaphthalene)].

Keywords

Platinum complexes DNA interaction Cytotoxicity 

Notes

Acknowledgments

The research was conducted within the framework of the European Cooperation COST CM1105 (Functional Metal Complexes That Bind to Biomolecules) and Consorzio Interuniversitario di Ricerca in Chimica dei Metalli nei Sistemi Biologici (CIRCMSB, Bari, Italy).

Supplementary material

775_2013_1022_MOESM1_ESM.pdf (272 kb)
Supplementary material 1 (PDF 272 kb)

References

  1. 1.
    Bischoff G, Hoffmann S (1996) Curr Med Chem 9:321–348CrossRefGoogle Scholar
  2. 2.
    Brabec V (2002) Prog Nucleic Acid Res Mol Biol 71:1–68PubMedCrossRefGoogle Scholar
  3. 3.
    Erkkila KE, Odom DT, Barton JK (1999) Chem Rev 99:2777–2795PubMedCrossRefGoogle Scholar
  4. 4.
    Zeglis BM, Pierre VC, Barton JK (2007) J Chem Soc Chem Commun 4565–4579Google Scholar
  5. 5.
    Georgiades SN, Karim NHA, Suntharalingam K, Vilar R (2010) Angew Chem Int Ed 49:4020–4034CrossRefGoogle Scholar
  6. 6.
    Natile G, Cannito F (2009) In: Hadjiliadis N, Sletten E (eds) Metal complex–DNA interactions. Wiley-Blackwell, Chichester, pp 135–173Google Scholar
  7. 7.
    Rabik CA, Dolan ME (2007) Cancer Treat Rev 33:9–23PubMedCrossRefGoogle Scholar
  8. 8.
    Ourliac-Garnier I, Charif R, Bombard S (2009) In: Hadjiliadis N, Sletten E (eds) Metal complex–DNA interactions, Wiley-Blackwell, Chichester, pp 209–234Google Scholar
  9. 9.
    Palm W, de Lange T (2008) Annu Rev Genet 42:301–334PubMedCrossRefGoogle Scholar
  10. 10.
    Burge S, Parkinson GN, Hazel P, Todd AK, Neidle S (2006) Nucleic Acids Res 34:5402–5415PubMedCrossRefGoogle Scholar
  11. 11.
    Neidle S (2009) Curr Opin Struct Biol 19:239–250PubMedCrossRefGoogle Scholar
  12. 12.
    Harley CB, Futcher AB, Greider CW (1990) Nature 345:458–460PubMedCrossRefGoogle Scholar
  13. 13.
    Zahler AM, Williamson JR, Cech TR (1991) Nature 350:718–720PubMedCrossRefGoogle Scholar
  14. 14.
    Riou JF, Guittat L, Mailliet P, Laoui A, Renou E, Petitgenet O, Megnin-Chanet F, Helene C, Mergny JL (2002) Proc Natl Acad Sci USA 99:2672–2677PubMedCrossRefGoogle Scholar
  15. 15.
    Gomez D, Wenner T, Brassart B, Douarre C, O’Donohue MF, El Khoury V, Shin-Ya K, Morjani H, Trentesaux C, Riou JF (2006) J Biol Chem 281:38721–38729PubMedCrossRefGoogle Scholar
  16. 16.
    Tahara H, Shin-Ya K, Seimiya H, Yamada H, Tsuruo T, Ide T (2006) Oncogene 25:1955–1966PubMedCrossRefGoogle Scholar
  17. 17.
    Rodriguez R, Miller KM, Forment JV, Bradshaw CR, Nikan M, Britton S, Oelschlaegel T, Xhemalce B, Balasubramanian S, Jackson SP (2012) Nat Chem Biol 8:301–310PubMedCrossRefGoogle Scholar
  18. 18.
    Bombard S, Gariboldi MB, Monti E, Gabano E, Gaviglio L, Ravera M, Osella D (2010) J Biol Inorg Chem 15:841–850PubMedCrossRefGoogle Scholar
  19. 19.
    Abrams MJ, Giandomenico CM, Vollano JF, Schwartz DA (1987) Inorg Chim Acta 131:3–4CrossRefGoogle Scholar
  20. 20.
    Giandomenico CM, Abrams MJ, Murrer BA, Vollano JF, Rheinheimer MI, Wyer SB, Bossard GE, Higgins JD (1995) Inorg Chem 34:1015–1021PubMedCrossRefGoogle Scholar
  21. 21.
    Monti E, Gariboldi MB, Ravizza R, Molteni R, Sparnacci K, Laus M, Gabano E, Ravera M, Osella D (2009) Inorg Chim Acta 362:4099–4109CrossRefGoogle Scholar
  22. 22.
    Miller B, Wild S, Zorbas H, Beck W (1999) Inorg Chim Acta 290:237–246CrossRefGoogle Scholar
  23. 23.
    Platts JA, Oldfield SP, Reif MM, Palmucci A, Gabano E, Osella D (2006) J Inorg Biochem 100:1199–1207PubMedCrossRefGoogle Scholar
  24. 24.
    Heudi O, Mercier-Jobard S, Cailleux A, Allain P (1999) Biopharm Drug Dispos 20:107–116PubMedCrossRefGoogle Scholar
  25. 25.
    Papadopoulos N, Nicolaides NC, Wei YF, Ruben SM, Carter KC, Rosen CA, Haseltine WA, Fleischmann RD, Fraser CM, Adams MD, Venter JC, Hamilton SR, Peterson GM, Watson P, Lynch HT, Peltomaki P, Mecklin JP, de la Chapelle A, Kinzler KW, Vogelstein B (1994) Science 263:1625–1629PubMedCrossRefGoogle Scholar
  26. 26.
    Umar A, Boyer JC, Thomas DC, Nguyen DC, Risinger JI, Boyd J, Ionov Y, Perucho M, Kunkel TA (1994) J Biol Chem 269:14367–14370PubMedGoogle Scholar
  27. 27.
    Cvitkovic E (1998) Br J Cancer 77(Suppl 4):8–11PubMedCrossRefGoogle Scholar
  28. 28.
    Alley MC, Scudiero DA, Monks A, Hursey ML, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker RH, Boyd MR (1988) Cancer Res 48:589–601PubMedGoogle Scholar
  29. 29.
    Francisco C, Gama S, Mendes F, Marques F, Cordeiro dos Santos I, Paulo A, Santos I, Coimbra J, Gabano E, Ravera M (2011) Dalton Trans 40:5781–5792PubMedCrossRefGoogle Scholar
  30. 30.
    Redon S, Bombard S, Elizondo-Riojas MA, Chottard JC (2003) Nucleic Acids Res 31:1605–1613PubMedCrossRefGoogle Scholar
  31. 31.
    Ourliac-Garnier I, Elizondo-Riojas MA, Redon S, Farrell NP, Bombard S (2005) Biochemistry 44:10620–10634Google Scholar
  32. 32.
    Bertrand H, Bombard S, Monchaud D, Teulade-Fichou MP (2007) J Biol Inorg Chem 12:1003–1014PubMedCrossRefGoogle Scholar
  33. 33.
    Mergny JL, Phan AT, Lacroix L (1998) FEBS Lett 435:74–78PubMedCrossRefGoogle Scholar
  34. 34.
    Ghezzi AR, Aceto M, Cassino C, Gabano E, Osella D (2004) J Inorg Biochem 98:73–78PubMedCrossRefGoogle Scholar
  35. 35.
    Platts JA, Hibbs DE, Hambley TW, Hall MD (2001) J Med Chem 44:472–474PubMedCrossRefGoogle Scholar
  36. 36.
    Bloemink MJ, Pérez JM, Heetebrij RJ, Reedijk J (1999) J Biol Inorg Chem 4:554–567PubMedCrossRefGoogle Scholar
  37. 37.
    Hambley TW (1997) Coord Chem Rev 166:181–223CrossRefGoogle Scholar
  38. 38.
    Gust R, Beck W, Jaouen G, Schönenberger H (2009) Coord Chem Rev 2009:2760–2779CrossRefGoogle Scholar
  39. 39.
    Keck MV, Lippard SJ (1992) J Am Chem Soc 114:3386–3390CrossRefGoogle Scholar
  40. 40.
    Cohen G, Bauer W, Barton J, Lippard SJ (1979) Science 203:1014–1016PubMedCrossRefGoogle Scholar
  41. 41.
    Scovell WM, Collart F (1985) Nucleic Acids Res 13:2881–2895PubMedCrossRefGoogle Scholar
  42. 42.
    Bellon SF, Coleman JH, Lippard SJ (1991) Biochemistry 30:8026–8035PubMedCrossRefGoogle Scholar
  43. 43.
    Moradell S, Lorenzo J, Rovira A, Robillard MS, Avilés FX, Moreno V, de Llorens R, Martinez MA, Reedijk J, Llobet A (2003) J Inorg Biochem 96:493–502PubMedCrossRefGoogle Scholar
  44. 44.
    Bertrand H, Bombard S, Monchaud D, Talbot E, Guédin A, Mergny JL, Grünert R, Bednarski PJ, Teulade-Fichou MP (2009) Org Biomol Chem 7:2864–2871PubMedCrossRefGoogle Scholar

Copyright information

© SBIC 2013

Authors and Affiliations

  • Elisabetta Gabano
    • 1
  • Sofia Gama
    • 2
  • Filipa Mendes
    • 2
  • Marzia B. Gariboldi
    • 3
  • Elena Monti
    • 3
  • Sophie Bombard
    • 4
  • Sabrina Bianco
    • 1
  • Mauro Ravera
    • 1
  1. 1.Dipartimento di Scienze e Innovazione Tecnologica (DiSIT)Università del Piemonte Orientale “Amedeo Avogadro”AlessandriaItaly
  2. 2.Unidade de Ciências Químicas e Radiofarmacêuticas, Instituto Superior Técnico-Campus Tecnológico e NuclearBobadela LRSPortugal
  3. 3.Dipartimento di Scienze Teoriche e Applicate (DiSTA)Università dell‘InsubriaVareseItaly
  4. 4.Université Paris Descartes, INSERM UMR-S-1007ParisFrance

Personalised recommendations