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Copolymers of pyrrole and N-(hydroxypropyl)pyrrole: properties and interaction with DNA

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Abstract

Copolymers derived from mixtures of pyrrole and N-(hydroxypropyl)pyrrole have been prepared electrochemically using various concentration ratios. Copolymers were generated on stainless electrodes by chronoamperometry and cyclic voltammetry in a LiClO4 acetonitrile solution. Relevant physical (density and doping level) and electrochemical (electroactivity and electrostability) properties of the copolymers have been examined and compared with those of the two corresponding homopolymers, which were prepared using the same electrochemical procedures. Results show that the copolymer obtained using the 25:75 N-(hydroxypropyl)pyrrole:pyrrole molar ratio presents an interesting behavior. Finally, the ability of the latter copolymer to form specific interactions with plasmid DNA has been compared with that of polypyrrole.

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References

  1. Chan HSO, Ng SC (1998) Progr Polym Sci 23:1167–1231

    Article  CAS  Google Scholar 

  2. Perepichka IF, Perepichka DF, Meng H, Wudl F (2005) Adv Mat 17:2281

    Article  CAS  Google Scholar 

  3. Yamamoto T, Hayashida N (1998) React Funct Polym 37:1

    Article  CAS  Google Scholar 

  4. Guernion NJL, Hayes W (2004) Curr Org Chem 8:637

    Article  CAS  Google Scholar 

  5. Díaz AF, Castillo J, Kanazawa KK, Logan JA (1982) J Electroanal Chem 133:233

    Article  Google Scholar 

  6. Díaz AF, Castillo J, Logan JA, Lee W-Y (1981) J Electroanal Chem 129:115

    Article  Google Scholar 

  7. Stanke D, Hallensleben ML, Toppare L (1995) Synth Met 73:267

    Article  CAS  Google Scholar 

  8. Hlavaty J, Papez V, Kavan L, Krtil P (1994) Synth Met 66:165

    Article  CAS  Google Scholar 

  9. Demanze F, Cornill J, Garnier F, Horowitz G, Valat P, Yassar A, Lazzaroni R, Bread JL (1997) J Phys Chem B 101:4553

    Article  CAS  Google Scholar 

  10. González-Tejera MJ, Sánchez de la Blanca E, Carrillo I, Redondo MI, Raso MA, Tortajada J, García MV (2005) Synth Met 151:100

    Article  CAS  Google Scholar 

  11. Ocampo C, Alemán C, Oliver R, Arnedillo ML, Ruiz O, Estrany F (2007) Polym Int 56:803

    Article  CAS  Google Scholar 

  12. Oliver R, Muñoz A, Ocampo C, Alemán C, Armelin E, Estrany F (2006) Chem Phys 328:299

    Article  CAS  Google Scholar 

  13. Benincori T, Brenna E, Sannicolo F, Zotti G, Zecchin S, Schiavon G, Gatti C, Frigerio G (2000) Chem Mat 12:1480

    Article  CAS  Google Scholar 

  14. Casanovas J, Cho LY, Ocampo C, Alemán C (2005) Synth Met 151:239

    Article  CAS  Google Scholar 

  15. Ocampo C, Casanovas J, Liesa F, Alemán C (2006) Polymer 47:3257

    Article  CAS  Google Scholar 

  16. Bidan G, Guglielmi M (1986) Synth Met 15:49

    Article  CAS  Google Scholar 

  17. Chen-Yang YW, Li JL, Wu TL, Wang WS, Hon TF (2004) Electrochim Acta 49:2031

    Article  CAS  Google Scholar 

  18. Konry T, Novoa A, Shemer-Avni Y, Hanuka N, Cosnier S, Lepellec A, Marks RS (2005) Anal Chem 77:1771

    Article  CAS  Google Scholar 

  19. Weiss Z, Mandler D, Shustak G, Domb AJ (2004) J Polym Sci Part A Polym Chem 42:1658

    Article  CAS  Google Scholar 

  20. Lee J-W, Serna F, Nickels J, Schmidt CE (2007) Biomacromolecules 7:1692

    Article  CAS  Google Scholar 

  21. Pernaut J-M, Reynolds JR (2000) J Phys Chem B 104:4080

    Article  CAS  Google Scholar 

  22. Wang X, Gu X, Yuan C, Chen S, Zhang P, Zhang T, Yao J, Chen F, Chen G (2004) J Biomed Mater Res A 68:411

    Article  CAS  Google Scholar 

  23. Jakubiec B, Marois Y, Zhang Z, Roy R, Sigot-Luizar M-F, Dugré FJ, King MW, Dao L, Laroche G, Guidoin R (1998) J Biomed Mat Res A 41:519

    Article  CAS  Google Scholar 

  24. Garner B, Hodgson AJ, Wallace GG, Underwood PA (1999) J Mat Sci Mat Med 10:19

    Article  CAS  Google Scholar 

  25. Rivers TJ, Hudson TW, Schmidt CE (2002) Adv Mater 12:33

    Article  CAS  Google Scholar 

  26. Ocampo C, Oliver R, Armelin E, Alemán C, Estrany F (20006) J Polym Res 13:193

    Article  CAS  Google Scholar 

  27. Carrasco J, Brillas E, Fernández V, Cabot PL, Garrido JA, Centellas F, Rodríguez RM (2001) J Electrochem Soc 148:E19

    Article  CAS  Google Scholar 

  28. Lallemand F, Auguste D, Amato C, Hevesi L, Delhalle J, Mekhalif Z (2007) Electrochim Acta 52:4334

    Article  CAS  Google Scholar 

  29. Wernet W, Monkenbusch M, Wegner G (1985) Mol Cryst Liq Cryst 118:193

    Article  CAS  Google Scholar 

  30. Rodríguez J, Otero TF, Grande H, Moliton JP, Moliton A, Trigaud T (1996) Synth Met 76:301

    Article  Google Scholar 

  31. Bay L, Mogensen N, Skaarup S, Sommer-Larsen P, Jorgensen M, West K (2002) Macromolecules 35:9345

    Article  CAS  Google Scholar 

  32. Meyers F, Heeger AJ, Bredas JL (1992) J Chem Phys 97:2750

    Article  CAS  Google Scholar 

  33. Ferraris JP, Hanlor TR (1989) Polymer 30:1319

    Article  CAS  Google Scholar 

  34. Burn PL, Holmes AB, Kraff A, Bardley DDC, Brown AR, Friend RH, Gymer RW (1992) Nature 356:47

    Article  CAS  Google Scholar 

  35. Burn PL, Holmes AB, Kraff A, Bardley DDC, Brown AR, Friend RH, Gymer RW (1992) J Chem Soc Chem Commun, pp 32–34

  36. Nobutoki H, Koezuka H (1996) J Phys Chem 100:6451

    Article  CAS  Google Scholar 

  37. Bakhshi AK, Ladik J, Seel M (1987) Phys Rev B35:704

    Google Scholar 

  38. Kao J, Lilly AC Jr (1987) J Am Chem Soc 109:4149

    Article  CAS  Google Scholar 

  39. Minehands S, Marx KA, Tripathy SK (1994) Macromolecules 27:777

    Article  Google Scholar 

  40. Pande R, Ruben GC, Lim JO, Tripathy SK, Marx KA (1998) Biomaterials 19:1657

    Article  CAS  Google Scholar 

  41. Gambhir A, Gerard M, Jain SK, Malhotra BD (2001) Appl Biochem Biotech 96:303

    Article  CAS  Google Scholar 

  42. Riccardi CD, Yamanaka H, Josowicz M, Kowlik J, Mizaikoff B, Kranz C (2006) Analyt Chem 78:1139

    Article  CAS  Google Scholar 

  43. Minehands S, Marx KA, Tripathy SK (2001) J Macromol Sci Pure Appl Chem 38:1245

    Article  Google Scholar 

  44. Saoudi B, Jammul N, Chehimi MM, McCarthy GP, Armes SP (1997) J Colloid Interface Sci 192:269

    Article  CAS  Google Scholar 

  45. Wellenzohn B, Loferer MJ, Trieb M, Rauch C, Winger RH, Mayer E, Liedl KR (2003) J Am Chem Soc 125:1088

    Article  CAS  Google Scholar 

  46. Ocampo C, Armelin E, Estrany F, del Valle LJ, Oliver R, Sepulcre F, Alemán C (2007) Macromol Mater Eng 292:85

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by MEC and FEDER funds with Grant MAT2006-04029. PP acknowledges the fellowship given by the Generalitat de Catalunya (DURSI). Dr. Luis J. del Valle acknowledges the pWL102 plasmid clone given by WF Doolittle (Dalhousie University, Canada).

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Correspondence to Elaine Armelin or Carlos Alemán.

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Pfeiffer, P., Armelin, E., Estrany, F. et al. Copolymers of pyrrole and N-(hydroxypropyl)pyrrole: properties and interaction with DNA. J Polym Res 15, 225–234 (2008). https://doi.org/10.1007/s10965-007-9162-2

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  • DOI: https://doi.org/10.1007/s10965-007-9162-2

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