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A platinum–quinacridine hybrid as a G-quadruplex ligand

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Abstract

A novel platinum–quinacridine hybrid, comprising a monofunctional Pt moiety and a G-quadruplex ligand (mono-para-quinacridine or MPQ), has been synthesized and shown to interact with quadruplex DNA via a dual noncovalent/covalent binding mode. Denaturing gel electrophoresis was used to separate the various platination products of 22AG (an oligonucleotide that mimics the human telomeric repeat) by Pt-MPQ, and it was shown that two platinated adducts are highly stable quadruplex structures. Dimethylsulfate/piperidine treatment and 3′-exonuclease digestion of the isolated adducts allowed us to precisely determine the platination pattern of 22AG by Pt-MPQ, which displays three main sites G2, G10 and G22. Data presented herein support the hypothesis that Pt-MPQ traps preferentially the antiparallel structure of the 22AG quadruplex. Finally, the kinetics of Pt-MPQ platination using a construct containing both quadruplex DNA and a duplex DNA parts provide the first insights into the Pt-MPQ preference for quadruplex DNA over duplex DNA.

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References

  1. Balasubramanian S, Neidle S (eds) (2006) Quadruplex nucleic acids. Royal Society of Chemistry, Cambridge

  2. Hurley LH (2002) Nat Rev Cancer 2:188–200

    Article  PubMed  Google Scholar 

  3. Neidle S, Parkinson G (2002) Nat Rev Drug Discov 1:383–393

    Article  PubMed  Google Scholar 

  4. Rezler EM, Bearss DJ, Hurley MH (2003) Annu Rev Pharmacol Toxicol 43:359–379

    Article  PubMed  Google Scholar 

  5. Neidle S, Thurston DE (2005) Nat Rev Cancer 5:285–296

    Article  PubMed  Google Scholar 

  6. Gomez D, Aouali N, Londono-Vallejo A, Lacroix L, Mégnin-Chanet F, Lemarteleur T, Douarre C, Shin-ya K, Mailliet P, Trentesaux C, Morjani H, Mergny J-L, Riou J-F (2003) J Biol Chem 278:50554–50562

    Article  PubMed  Google Scholar 

  7. Burger AM, Dai F, Schultes CM, Reszka AP, Moore MJB, Double JA, Neidle S (2005) Cancer Res 65:1489–1496

    Article  PubMed  Google Scholar 

  8. Pennarun G, Granotier C, Gauthier LR, Gomez D, Hoffschir F, Mandine E, Riou J-F, Mergny J-L, Mailliet P, Boussin F (2005) Oncogene 24:2917–2928

    Article  PubMed  Google Scholar 

  9. Douarre C, Gomez D, Morjani H, Zahm J-M, O’Donohue M-F, Eddabra L, Mailliet P, Riou J-F, Trentesaux C. (2005) Nucleic Acids Res 33:2192–2203

    Article  PubMed  Google Scholar 

  10. Gomez D, O’Donohue M-F, Wenner T, Douarre C, Macadre J, Koebel P, Giraud-Panis MJ, Kaplan H, Kolkes A, Shin-ya K, Riou J-F (2006) Cancer Res 66:6908–6912

    Article  PubMed  Google Scholar 

  11. Gomez D, Wenner T, Brassart B, Douarre C, O’Donohue M-F, El Khoury V, Shin-ya K, Morjani H, Trentesaux C, Riou J-F (2006) J Biol Chem 281:38721–38729

    Article  PubMed  Google Scholar 

  12. Fedoroff OY, Salazar M, Han H, Chemeris VV, Kerwin SM, Hurley LH (1998) Biochemistry 37:12367–12374

    Article  PubMed  Google Scholar 

  13. Read MA, Neidle S (2000) Biochemistry 39:13422–13432

    Article  PubMed  Google Scholar 

  14. Duan W, Rangan A, Vankayalapati H, Kim M-Y, Zeng Q, Sun D, Han H, Fedoroff OY, Nishioka D, Rha SY, Izbicka E, Von Hoff DD, Hurley LH (2001) Mol Cancer Ther 1:103–120

    PubMed  Google Scholar 

  15. Gavathiotis E, Heald RA, Stevens MFG, Searle MS (2001) Angew Chem Int Ed Engl 40:4749–4751

    Article  PubMed  Google Scholar 

  16. Gavathiotis E, Heald RA, Stevens MFG, Searle MS (2003) J Mol Biol 334:25–36

    Article  PubMed  Google Scholar 

  17. Cocco MJ, Hanakahi LA, Huber MD, Maizels N (2003) Nucleic Acids Res 31:2944–2951

    Article  PubMed  Google Scholar 

  18. Phan AT, Kuryavyi V, Gaw HY, Patel D (2005) Nat Chem Biol 1:167–173

    Article  PubMed  Google Scholar 

  19. Cookson JC, Heald RA, Stevens MFG (2005) J Med Chem 48:7198–7207

    Article  PubMed  Google Scholar 

  20. Seenisamy J, Bashyam S, Gokhale V, Vankayalapati H, Sun D, Siddiqui-Jain A, Steiner N, Shin-ya K, White E, Wislon WD, Hurley LH (2005) J Am Chem Soc 127:2944–2959

    Article  PubMed  Google Scholar 

  21. Gonçalves DPN, Rodriguez R, Balasubramanian S, Sanders JKM (2006) Chem Commun 4685–4687

  22. Gonçalves DPN, Ladame S, Balasubramanian S, Sanders JKM (2006) Org Biomol Chem 4:3337–3342

    Article  PubMed  Google Scholar 

  23. Wang P, Ren L, He H, Liang F, Zhou X, Tan Z (2006) Chembiochem 7:1155–1159

    Article  PubMed  Google Scholar 

  24. Dixon IM, Lopez F, Tejera AM, Estève J-P, Blasco MA, Pratviel G, Meunier B (2007) J Am Chem Soc 129:1502–1504

    Article  PubMed  Google Scholar 

  25. De Cian A, DeLemos E, Mergny J-L, Teulade-Fichou M-P, Monchaud D (2007) J Am Chem Soc 129:1856–1857

    Article  PubMed  Google Scholar 

  26. Moore MJB, Schultes CM, Cuesta J, Cuenca F, Gunaratnam M, Tanious FA, Wilson WD, Neidle S (2006) J Med Chem 49:582–599

    Article  PubMed  Google Scholar 

  27. Mazzitelli CL, Brodbelt JS, Kern JT, Rodriguez M, Kerwin SM (2006) J Am Soc Mass Spectrom 17:593–604

    Article  PubMed  Google Scholar 

  28. Reed JE, Arnal AA, Neidle S, Vilar R (2006) J Am Chem Soc 128:5992–5993

    Article  PubMed  Google Scholar 

  29. Jantos K, Rodriguez R, Ladame S, Shirude PS, Balasubramanian S (2006) J Am Chem Soc 128:13662–13664

    Article  PubMed  Google Scholar 

  30. Ou T-M, Lu Y-J, Zhang C, Huang Z-H, Wang X-D, Tan J-H, Chen Y, Ma D-L, Wong K-Y, Tang JC-O, Chan AS-C, Gu L-Q (2007) J Med Chem 50:1465–1474

    Article  PubMed  Google Scholar 

  31. Hounsou C, Guittat L, Monchaud D, Jourdan M, Saettel N, Mergny J-L, Teulade-Fichou M-P (2007) ChemMedChem 2:655–666

    Article  PubMed  Google Scholar 

  32. Shin-ya K, Wierzba K, Matsuo K-I, Ohtani T, Yamada Y, Furihata K, Hayakawa Y, Seto H (2001) J Am Chem Soc 123:1262–1263

    Article  PubMed  Google Scholar 

  33. Kim MY, Vankayalapati H, Shin-Ya K, Wierzba K, Hurley LH (2002) J Am Chem Soc 124:2098–2099

    Article  PubMed  Google Scholar 

  34. Tahara H, Shin-ya K, Seimiya H, Yamada H, Tsuruo T, Ide T (2006) Oncogene 25:1955–1966

    Article  PubMed  Google Scholar 

  35. Redon S, Bombard S, Elizondo-Riojas M-A, Chottard J-C (2003) Nucleic Acids Res 31:1605–1613

    Article  PubMed  Google Scholar 

  36. Ourliac-Garnier I, Elizondo-Riojas M-A, Redon S, Farrell NP, Bombard S (2005) Biochemistry 44:10620–10634

    Article  PubMed  Google Scholar 

  37. van Zutphen S, Reedijk J (2005) Coord Chem Rev 249:2845–2853

    Article  Google Scholar 

  38. Brabec V, Kasparkova J (2005) Drug Resist Updat 8:131–146

    Article  PubMed  Google Scholar 

  39. Bowler BE, Hollis LS, Lippard SJ (1984) J Am Chem Soc 106:6102–6104

    Article  Google Scholar 

  40. Martins ET, Baruah H, Kramarczyk J, Saluta G, Day CS, Kucera GL, Bierbach U (2001) J Med Chem 44:4492–4496

    Article  PubMed  Google Scholar 

  41. Ackley MC, Barry CG, Mounce AM, Farmer MC, Springer B-E, Day CS, Wright MW, Berners-Price SJ, Hess SM, Bierbach U (2004) J Biol Inorg Chem 9:453–461

    Article  PubMed  Google Scholar 

  42. Baruah H, Wright MW, Bierbach U (2005) Biochemistry 44:6059–6070

    Article  PubMed  Google Scholar 

  43. Guddneppanavar R, Saluta G, Kucera GL, Bierbach U (2006) J Med Chem 49:3204–3214

    Article  PubMed  Google Scholar 

  44. Burge S, Parkinson GN, Hazel P, Todd AK, Neidle S (2006) Nucleic Acid Res 34:5402–5415

    Article  PubMed  Google Scholar 

  45. Phan AT, Kuryavyi V, Patel DJ (2006) Curr Opin Struct Biol 16:288–298

    Article  PubMed  Google Scholar 

  46. Davis JT (2004) Angew Chem Int Ed Engl 43:668–698

    Article  PubMed  Google Scholar 

  47. Mergny J-L, Lacroix L, Teulade-Fichou M-P, Hounsou C, Guittat L, Hoarau M, Arimondo PB, Vigneron J-P, Lehn J-M, Riou J-F, Garestier T, Hélène C (2001) Proc Natl Acad Sci USA 98:3062–3067

    Article  PubMed  Google Scholar 

  48. Teulade-Fichou M-P, Carrasco C, Guittat L, Bailly C, Alberti P, Mergny J-L, David A, Lehn J-M, Wilson WD (2003) J Am Chem Soc 125:4732–4740

    Article  PubMed  Google Scholar 

  49. Allain C, Monchaud D, Teulade-Fichou M-P (2006) J Am Chem Soc 128:11890–11893

    Article  PubMed  Google Scholar 

  50. Wang Y, Patel DJ (1993) Structure 1:263–282

    Article  PubMed  Google Scholar 

  51. Parkinson GN, Lee MPH, Neidle S (2002) Nature 417:876–880

    Article  PubMed  Google Scholar 

  52. Ambrus A, Chen D, Dai J, Bialis T, Jones RA, Yang D (2006) Nucleic Acids Res 34:2723–2735

    Article  PubMed  Google Scholar 

  53. Xu Y, Noguchi Y, Sugiyama H (2006) Bioorg Med Chem 14:5584–5591

    Article  PubMed  Google Scholar 

  54. Lartia R, Bertrand H, Teulade-Fichou M-P (2006) Synlett 4:610–614

    Google Scholar 

  55. Heetebrij RJ, Talman EG, Velzen MAv, Gijlswijk RPMv, Snoeijers SS, Schalk M, Wiegant J, Rijke Fvd, Kerkhoven RM, Raap AK, Tanke HJ, Reedijk J, Houthoff H-J (2003) Chembiochem 4:573–583

    Article  PubMed  Google Scholar 

  56. Houthoff H-J, Reedijk J, Jelsma T, van Es RM, van den Berg FM, Lempers ELM, Bloemink MJ (1996) PCT WO 96/35696

  57. Ourliac Garnier I, Bombard S (2007) J Inorg Biochem 101:514–524

    Article  PubMed  Google Scholar 

  58. Baik M-H, Friesner RA, Lippard SJ (2003) J Am Chem Soc 125:14082–14092

    Article  PubMed  Google Scholar 

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Acknowledgements

This work was supported by the Centre National de la Recherche Scientifique, the Commissariat à l’Energie Atomique (H.B.) and the Association pour la Recherche contre le Cancer [grant 3482 (M.-P.T.-F. and S.B.)]. We would like to thank C. Chopard for her expert help in platinum chemistry.

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Authors and Affiliations

  1. Institut Curie, Section Recherche, CNRS UMR176, Centre Universitaire Paris XI, Bat. 110, 91405, Orsay, France

    Hélène Bertrand, David Monchaud & Marie-Paule Teulade-Fichou

  2. Laboratoire de Chimie et Biochimie Pharmacologiques et toxicologiques, CNRS UMR8601, Université Paris Descartes, 45, rue des Saints-Pères, 75006, Paris, France

    Sophie Bombard

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  1. Hélène Bertrand
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  2. Sophie Bombard
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Correspondence to Sophie Bombard or Marie-Paule Teulade-Fichou.

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Bertrand, H., Bombard, S., Monchaud, D. et al. A platinum–quinacridine hybrid as a G-quadruplex ligand. J Biol Inorg Chem 12, 1003–1014 (2007). https://doi.org/10.1007/s00775-007-0273-3

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  • DOI: https://doi.org/10.1007/s00775-007-0273-3

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