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Binding of Metallated Porphyrin-Imidazophenazine Conjugate to Tetramolecular Quadruplex Formed by Poly(G): a Spectroscopic Investigation

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Abstract

The binding of telomerase inhibitor ZnTMPyP3+–ImPzn, Zn(II) derivative of tricationic porphyrin–imidazophenazine conjugate, to tetramolecular quadruplex structure formed by poly(G) was studied in aqueous solutions at neutral pH and near physiological ionic strength using absorption and polarized fluorescent spectroscopy techniques. Three binding modes were determined from the dependences of the fluorescence intensity and polarization degree for the porphyrin and phenazine moieties of the conjugate on molar polymer-to-dye ratio (P/D). The first one is outside electrostatic binding of positively charged porphyrin fragments to anionic phosphate groups of the polymer which prevails only at very low P/D values and manifests itself by substantial fluorescence quenching. It is suggested that the formation of externally bound porphyrin dimers occurs. The other two binding modes observed at high P/D are embedding of the ZnTMPyP3+ moiety into the groove of poly(G) quadruplex accompanied by more than 3-fold enhancement of the conjugate emission, and simultaneous intercalation of the phenazine fragment between the guanine bases accompanied by the increase of its fluorescence polarization degree up to 0.25. Thus Zn(II) conjugate seems to be promising ligand for the stabilization of G-quadruplex structures since porphyrin binding to poly(G) is strengthened by additional intercalation of phenazine moiety.

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References

  1. Balasubramanian S, Neidle S (2009) Curr Opin Chem Biol 13(3):345–353

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  2. Collie GW, Parkinson GN (2011) Chem Soc Rev 40(12):5867–5892

    Article  CAS  PubMed  Google Scholar 

  3. Duchler M (2012) J Drug Target 20(5):389–400

    Article  CAS  PubMed  Google Scholar 

  4. Xu Y (2011) Chem Soc Rev 40(5):2719–2740

    Article  CAS  PubMed  Google Scholar 

  5. Dai J, Carver M, Yang D (2008) Biochimie 90(8):1172–1183

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  6. Burge S, Parkinson GN, Hazel P, Todd AK, Neidle S (2006) Nucleic Acids Res 34(19):5402–5415

    Article  PubMed Central  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  8. Pochon F, Michelson AM (1965) Proc Natl Acad Sci U S A 53:1425–1430

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  9. Howard FB, Frazier J, Miles HT (1977) Biopolymers 16(4):791–809

    Article  CAS  PubMed  Google Scholar 

  10. De Cian A, Lacroix L, Douarre C, Temime-Smaali N, Trentesaux C, Riou J-F, Mergny J-L (2008) Biochimie 90(1):131–155

    Article  PubMed  Google Scholar 

  11. Monchaud D, Teulade-Fichou M-P (2008) Org Biomol Chem 6(4):627–636

    Article  CAS  PubMed  Google Scholar 

  12. Dolphin D (ed) (1978) The porphyrins. Academic Press, New York

    Google Scholar 

  13. Josefsen LB, Boyle RW (2012) Theranostics 2(9):916–966

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  14. Munson BR, Fiel RJ (1992) Nucleic Acids Res 20(6):1315–1319

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  15. Sehlstedt U, Kim SK, Carter P, Goodisman J, Vollano JF, Norden B, Dabrowiak JC (1994) Biochemistry 33(2):417–426

    Article  CAS  PubMed  Google Scholar 

  16. Da Ros T, Spalluto G, Boutorine AS, Bensasson RV, Prato M (2001) Curr Pharm Des 7(17):1781–1821

    Article  PubMed  Google Scholar 

  17. O’Connor AE, Gallagher WM, Byrne AT (2009) Photochem Photobiol 85(5):1053–1074

    Article  PubMed  Google Scholar 

  18. Ormond AB, Freeman HS (2013) Materials 6(3):817–840

    Article  CAS  Google Scholar 

  19. Pitié M, Boldron C, Pratviel G (2006) Adv Inorg Chem 58:77–130

    Article  Google Scholar 

  20. Mestre B, Pratviel G, Meunier B (1995) Bioconjug Chem 6(4):466–472

    Article  CAS  PubMed  Google Scholar 

  21. Li H, Fedorova OS, Trumble RW, Flechter TR (1997) Bioconjug Chem 8(1):49–56

    Article  PubMed  Google Scholar 

  22. Dubey I, Pratviel G, Meunier B (2000) J Chem Soc Perkin Trans 1:3088–3095

    Article  Google Scholar 

  23. Mezo G, Herenyi L, Habdas J, Majer Z, Mysliwa-Kurdziel B, Toth K, Csik G (2011) Biophys Chem 155(1):36–44

    Article  CAS  PubMed  Google Scholar 

  24. Ishikawa Y, Yamashita A, Uno T (2001) Chem Pharm Bull 49(3):287–293

  25. Zhao P, Hu L-C, Huang J-W, Zheng K-C, Liu J, Yu H-C, Ji L-N (2008) Biophys Chem 134(1–2):72–83

    Article  CAS  PubMed  Google Scholar 

  26. Jia T, Jiang Z-X, Wang K, Li Z-Y (2006) Biophys Chem 119(3):295–302

    Article  CAS  PubMed  Google Scholar 

  27. Kumar D, Mishra BA, Shekar KPC, Kumar A, Akamatsu K, Kusaka E, Ito T (2013) Chem Commun 49(7):683–685

    Article  CAS  Google Scholar 

  28. Schwach G, Thamyongkit P, Reith LM, Svejda B, Knor G, Pfragner R, Schoefberger W (2012) Bioorg Chem 40:108–113

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  29. Marczak R, Sgobba V, Kutner W, Gadde S, D’Souza F, Guldi DM (2007) Langmuir 23(4):1917–1923

    Article  CAS  PubMed  Google Scholar 

  30. Dixon IM, Lopez F, Esteve J-P, Tejera AM, Blasco MA, Pratviel G, Meunier B (2005) ChemBioChem 6(1):123–132

    Article  CAS  PubMed  Google Scholar 

  31. Maraval A, Franco S, Vialas C, Pratviel G, Blasco MA, Meunier B (2003) Org Biomol Chem 1(6):921–927

  32. Zhao P, Hu L-C, Huang J-W, Fu D, Yu H-C, Ji L-N (2009) Dyes Pigm 83(1):81–87

    Article  CAS  Google Scholar 

  33. Dubey LV, Ilchenko MM, Zozulya VN, Ryazanova OA, Pogrebnoy PV, Dubey IY (2011) Int Rev Biophys Chem 2(4):147–152

    Google Scholar 

  34. Zozulya V, Yu B, Dubey I, Fedoryak D, Makitruk V, Ryazanova O, Shcherbakova A (2003) Biopolym (Biospectrosc) 72(4):264–273

    Article  CAS  Google Scholar 

  35. Ryazanova O, Dubey L, Dubey I, Zozulya V (2012) J Fluoresc 22(6):1431–1439

    Article  CAS  PubMed  Google Scholar 

  36. Negrutska VV, Dubey LV, Ilchenko MM, Dubey IY (2013) Biopolym Cell 29(3):169–176

    Article  CAS  Google Scholar 

  37. Zozulya VN, Ryazanova OA, Voloshin IM, Dubey LV, Dubey IY (2011) Int Rev Biophys Chem 2(4):112–119

    Google Scholar 

  38. Ryazanova O, Zozulya V, Voloshin I, Dubey L, Dubey I, Karachevtsev V (2015) J Fluoresc 25:1013–1021

    Article  CAS  PubMed  Google Scholar 

  39. Pasternack RF, Gibbs EJ, Villafranca JJ (1983) Biochemistry 22(10):2406–2414

    Article  CAS  PubMed  Google Scholar 

  40. Casas C, Saint-Jalmes B, Loup C, Lacey CJ, Meunier B (1993) J Org Chem 58:2913–2917

    Article  CAS  Google Scholar 

  41. Dubey I, Pratviel G, Meunier B (1998) Compt Rend Acad Sci (Paris), Ser IIC 1(4):259–267

    CAS  Google Scholar 

  42. Dubey L, Ryazanova O, Zozulya V, Fedoryak D, Dubey I (2011) Nucleosides Nucleotides Nucleic Acids 30(7–8):585–596

  43. Mergny J-L, Phan A, Lacroix L (1998) FEBS Lett 435:74–78

    Article  CAS  PubMed  Google Scholar 

  44. Zozulya VN, Ryazanova OA, Voloshin IM, Glamazda AY, Karachevtsev VA (2010) J Fluoresc 20(3):695–702

    Article  CAS  PubMed  Google Scholar 

  45. Ryazanova OA, Voloshin IM, Makitruk VL, Zozulya VN, Karachevtsev VA (2007) Spectrochimica Acta - Part A: Mol Biomol Spectroscopy 66(4–5):849–859

    Article  CAS  Google Scholar 

  46. Schwarz G, Klose S, Balthasar W (1970) Eur J Biochem 12(3):454–460

    Article  CAS  PubMed  Google Scholar 

  47. Schwarz G, Klose S, Balthasar W (1970) Eur J Biochem 12(3):461–467

    Article  CAS  PubMed  Google Scholar 

  48. Zozulya VN, Ryazanova OA, Voloshin IM, Ilchenko MM, Dubey IY, Glamazda AY, Karachevtsev VA (2014) Biophys Chem 185(1):39–46

    Article  CAS  PubMed  Google Scholar 

  49. Zozulya V, Yu B, Löber G, Voloshin I, Winter S, Makitruk V, Shalamay A (1997) Biophys Chem 65(1):55–63

    Article  CAS  PubMed  Google Scholar 

  50. Ryazanova OA, Voloshin IM, Dubey IY, Dubey LV, Zozulya VN (2008) Ann N Y Acad Sci 1130:293–299

  51. Ryazanova OA, Voloshin IM, Dubey IY, Dubey LV, Zozulya VN (2008) IFMBE Proc 20:397–400

    Article  Google Scholar 

  52. Fiel R (1989) J Biomol Struct Dyn 6:1259–1274

    Article  CAS  PubMed  Google Scholar 

  53. Kelly JM, Murphy MJ, McConnell DJ, OhUigin C (1985) Nucleic Acids Res 13(1):167–184

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  54. Monaselidze J, Gorgoshidze M, Khachidze D, Kiladze M, Bregadze V, Kiziria E, Margaryan H, Hakobyan N (2013) Am J Anal Chem 4:744–748

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Molecular Biophysics, B. Verkin Institute for Low Temperature Physics and Engineering, National Academy of Sciences of Ukraine, 47 Lenin ave, 61103, Kharkov, Ukraine

    Olga Ryazanova, Victor Zozulya, Igor Voloshin & Victor Karachevtsev

  2. Department of Synthetic Bioregulators, Institute of Molecular Biology and Genetics, National Academy of Sciences of Ukraine, 150 Zabolotnogo str, 03680, Kyiv, Ukraine

    Larysa Dubey & Igor Dubey

Authors
  1. Olga Ryazanova
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  2. Victor Zozulya
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  3. Igor Voloshin
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  4. Larysa Dubey
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  5. Igor Dubey
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  6. Victor Karachevtsev
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Correspondence to Olga Ryazanova.

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Ryazanova, O., Zozulya, V., Voloshin, I. et al. Binding of Metallated Porphyrin-Imidazophenazine Conjugate to Tetramolecular Quadruplex Formed by Poly(G): a Spectroscopic Investigation. J Fluoresc 25, 1897–1904 (2015). https://doi.org/10.1007/s10895-015-1682-2

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  • DOI: https://doi.org/10.1007/s10895-015-1682-2

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