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JBIC Journal of Biological Inorganic Chemistry

, Volume 15, Issue 6, pp 841–850 | Cite as

Biological activity of enantiomeric complexes [PtCl2L2] (L2 is aromatic bisphosphanes and aromatic diamines)

  • Sophie Bombard
  • Marzia Bruna Gariboldi
  • Elena Monti
  • Elisabetta Gabano
  • Luca Gaviglio
  • Mauro Ravera
  • Domenico Osella
Original Paper

Abstract

Enantiomeric complexes of formula [PtCl2L2] [L2 is (R)-(+)-BINAP and (S)-(−)-BINAP, where BINAP is 2,2′-bis(diphenylphosphane)-1,1′-binaphthyl, and (R)-(+)-DABN and (S)-(−)-DABN, where DABN is 1,1′-binaphthyl-2,2′-diamine], were tested for their cytotoxic activity against three cancer cell lines and for their ability to bind to the human telomeric sequence folded in the G-quadruplex structure. Similar experiments were carried out on prototypal complexes cisplatin and cis-[PtCl2(PPh3)2] for comparison. Platinum complexes containing phosphanes proved less cytotoxic to cancer cell lines and less likely to interact with the nucleobases of the G-quadruplex than those containing amines; in both cases the S-(−) isomer was more active than the R-(+) counterpart. More specifically, whereas all the platinum complexes were able to platinate the G-quadruplex structure from the human telomeric repeat, the extent and sites of platination depended on the nature of the ligands. Complexes containing (bulky) phosphanes interacted only with the adenines of the loops, whereas those containing the less sterically demanding amines interacted with adenines and some guanines of the G-quartet.

Keywords

Platinum complexes Phosphanes and amines DNA quadruplex Telomere Cytotoxicity 

Notes

Acknowledgments

Financial support for this work was provided by the Regione Piemonte (CIPE project-code A 370 and Ricerca Sanitaria Finalizzata 2009), ATF Association (Alessandria, Italy), CNRS, and ARC 4835 (Paris, France). The study was carried out within the framework of the European Cooperation COST D39 (Metallo-Drug Design and Action) and Consorzio Interuniversitario di Ricerca in Chimica dei Metalli nei Sistemi Biologici (CIRCMSB, Bari, Italy). We are indebted to Cristina Prandi (University of Turin, Italy) for her assistance in measuring optical rotatory power.

Supplementary material

775_2010_648_MOESM1_ESM.pdf (304 kb)
Supplementary material (PDF 303 kb)

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Copyright information

© SBIC 2010

Authors and Affiliations

  • Sophie Bombard
    • 1
    • 2
  • Marzia Bruna Gariboldi
    • 3
  • Elena Monti
    • 3
  • Elisabetta Gabano
    • 4
  • Luca Gaviglio
    • 4
  • Mauro Ravera
    • 4
  • Domenico Osella
    • 4
  1. 1.Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR8601Université Paris DescartesParisFrance
  2. 2.Laboratoire de l’Homéostasie Cellulaire et Cancer, INSERM UMR-S1007Université Paris DescartesParisFrance
  3. 3.Dipartimento di Biologia Strutturale e FunzionaleUniversità dell’InsubriaBusto Arsizio (VA)Italy
  4. 4.Dipartimento di Scienze dell’Ambiente e della VitaUniversità del Piemonte Orientale “Amedeo Avogadro”AlessandriaItaly

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