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Spectral properties and photophysical behaviour of water soluble cationic Mg(II) and Al(III) phthalocyanines

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Central European Journal of Chemistry

Abstract

Peripherally and non-peripherally tetrasubstituted-[(N-methyl-2-pyridylthio)]phthalocyaninato magnesium (II) (5 and 6) and chloro aluminium (III) (7 and 8) tetraiodide have been synthesized and characterized. The photophysical properties of the complexes in dimethyl sulfoxide (DMSO) and aqueous medium in the presence and absence of cremophore EL have been studied. These complexes show high solubility in aqueous medium though they were aggregated. The triplet state quantum yields (FT) and the triplet lifetimes (tT) were found to be higher in DMSO with ΦT ranging from 0.32 to 0.51, while tT ranged from 282 to 622 ms in DMSO, compared to aqueous medium (pH 7.4 buffer) where ΦT ranged from 0.15 to 0.19 and tT from 26 to 35 ms. Addition of cremophore EL in aqueous solution resulted in partial disaggregation and increased photoactivity. The fluorescence lifetimes of the complexes showed strong dependence on their immediate environment. The ionic magnesium(II) and aluminium(III) phthalocyanines strongly bind to bovine serum albumin (BSA).

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References

  1. D. Jocham, in: J.G. Moser, (Ed.), Photodynamic Tumor Therapy: 2° and 3° Generation Photosensitizers (Harwood Academic Publishers, London, 1998

  2. W.S. Cahn, N. Brasseur, C. La Madeleine, R. Quellet, J.E. van Lier, Eur. J. Cancer 33, 1855 (2001)

    Google Scholar 

  3. C.M. Allen, W.M. Sharman, J.E. van Lier, J. Porphyrins Phthalocyanines 5(2), 161 (2001)

    Article  CAS  Google Scholar 

  4. T. Nyokong, Coord. Chem. Rev. 251, 1707 (2007)

    Article  CAS  Google Scholar 

  5. A.C. Tedesco, J.C.G. Rotta, C.N. Lunardi, Curr. Org. Chem. 7, 187 (2003)

    Article  CAS  Google Scholar 

  6. F. Dumoulin, M. Durmus, V. Ahsen, T. Nyokong, Coord. Chem. Rev. 254, 2792 (2010)

    Article  CAS  Google Scholar 

  7. M. Idowu, T. Nyokong, Polyhedron 28, 416 (2009)

    Article  CAS  Google Scholar 

  8. Y.C. Yang, J.R. Ward, R.P. Seiders, Inorg. Chem. 24, 1765 (1985)

    Article  CAS  Google Scholar 

  9. W.M. Sharman, S.V. Kudrevich, J.E. van Lier, Tetrahedron Lett. 37, 5831 (1996)

    Article  CAS  Google Scholar 

  10. I. Scalise, E.N. Durantini, Bioorg. Med. Chem. 13, 3037 (2005)

    Article  CAS  Google Scholar 

  11. A.P. Castano, T.N. Demidova, M.R. Hamblin, Photodiag. Photodyn. Therapy 1, 279 (2004)

    Article  CAS  Google Scholar 

  12. D.J. Ball, S. Mayhew, S.R. Wood, J. Griffiths, D.I. Vernon, S.B. Brown, Photochem. Photobiol. 69, 390 (1999)

    Article  CAS  Google Scholar 

  13. D. Wöhrle, N. Iskandar, G. Graschew, H. Sinn, E.A. Friedrich, W. Maier-Borst, J. Stern, P. Schlag, Photochem. Photobiol. 51, 351 (1990)

    Article  Google Scholar 

  14. N. Sehlotho, M. Durmus, V. Ahsen, T. Nyokong, Inorg. Chem. Commun. 11, 479 (2008)

    Article  CAS  Google Scholar 

  15. N. Saydan, M. Durmus, M.G. Dizge, H. Yaman, A.G. Gürek, E. Antunes, T. Nyokong, V. Ahsen, J. Porphyrins. Phthalocyanines 13, 681 (2009)

    Article  CAS  Google Scholar 

  16. M. Durmus, V. Ahsen, J. Inorg. Biochem. 104, 297 (2010)

    Article  CAS  Google Scholar 

  17. M. Durmus, H. Yaman, C. Gol, V. Ahsen, T. Nyokong, Dyes & Pigmt. 91, 153 (2011)

    Article  CAS  Google Scholar 

  18. V.N. Mantareva, V. Kussovski, I.P. Angelov, E. Borisova, L. Avramov, G. Schnurpfeil, D. Wöhrle, Bioorganic & Medicinal Chemistry 15, 4829 (2007)

    Article  CAS  Google Scholar 

  19. V. Mantareava, V. Kussovski., I. Angelov, D. Wöhrle, G. Schnurpfeil, I. Popova, S. Dimitrov, Photochem. Photobiol. Sci. 10, 91 (2011)

    Article  Google Scholar 

  20. V. Mantareva, I. Angelov, V. Kussovski, R. Dimitrov, L. Lapok, D. Wöhrle, European Journal of Medicinal Chemistry 46, 4430 (2011)

    Article  CAS  Google Scholar 

  21. V. Mantareva, I. Angelov, D. Wöhrle, E. Borisova, V. Kussovski, J. Porphyrins Phthalocyanines 17, 399 (2013)

    Article  CAS  Google Scholar 

  22. Y. Arslanoglu, M. Idowu, T. Nyokong, Spec. Acta: A 95, 407 (2012)

    Article  CAS  Google Scholar 

  23. G. Rajagopal, S.S. Kim, J.M. Kwak, Bull. Korean Chem. Soc. 27, 1907 (2006)

    Article  CAS  Google Scholar 

  24. V.H.C. Silva, L.T.F.M. Camargo, H.B. Napolitano, C.N. Pérez, A.J. Camargo, J. Mol. Grap. Model. 29, 206 (2010)

    Article  CAS  Google Scholar 

  25. C.M. Allen, W.M. Sharman, J.E. van Lier, J. Porphyrins Phthalocyanines 5, 161 (2001)

    Article  CAS  Google Scholar 

  26. M. Canlica, T. Nyokong, Dalton Trans. 40, 5285 (2011)

    Article  CAS  Google Scholar 

  27. M. Idowu, T. Nyokong, J. Photochem. Photobiol. A: Chem. 188, 200 (2007)

    Article  CAS  Google Scholar 

  28. Y. Arslanoglu, T. Nyokong, Polyhedron 30, 2733 (2011)

    Article  CAS  Google Scholar 

  29. T. Nyokong, E. Antunes, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Handbook of Porphyrin Science (Academic Press/World Scientific, Singapore, 2010) vol. 7,34, 247

    Article  CAS  Google Scholar 

  30. N.A. Kuznetsova, N.S. Gretsova, V.M. Derkacheva, O.L. Kaliya, E.A. Lukyanets, J. Porphyrins Phthalocyanines 7(2), 147 (2003)

    Article  CAS  Google Scholar 

  31. M. Idowu, T. Nyokong, J. Photochem. Photobiol. A: Chem. 197, 273 (2008)

    Article  CAS  Google Scholar 

  32. G. Jori, in: B.W. Henderson, T.J. Dougherty (Eds.), Photodynamic therapy: Basic principles and clinical applications (M. Dekker Inc, New York, 1992) 173

  33. A.A. Bhattacharya, S. Curry, N.P. Franks, J. Biol. Chem. 275, 38731 (2000)

    Article  CAS  Google Scholar 

  34. J.H. Weber, D.H. Busch, Inorg. Chem. 4, 469 (1965)

    Article  CAS  Google Scholar 

  35. D.D. Perrin, W.L.F. Armarego, Purification of Laboratory Chemicals, 2nd edition (Pergamon Press, Oxford, 1989)

    Google Scholar 

  36. J.R. Lakowicz, Principles of Fluorescence Spectroscopy, 2nd edition (Kluwer Academic/Plenum Publishers, New York, 1999) vol. 1, 134

    Book  Google Scholar 

  37. S.M.T. Nunes, F.S. Squilla, A.C. Tedesco, Braz. J. Med. Biol. Res. 37, 273 (2004)

    Article  CAS  Google Scholar 

  38. S. Fery-Forgues, D.J. Lavabre, J. Chem. Ed. 76, 1260 (1999)

    Article  CAS  Google Scholar 

  39. A. Ogunsipe, J.Y. Chen, T. Nyokong, New J. Chem. 7, 822 (2004)

    Article  Google Scholar 

  40. A. Harriman, M.C. Richoux, J. Chem. Soc., Faraday Trans. 2 76, 1618 (1980)

    Article  Google Scholar 

  41. T.H. Tran-Thi, C. Desforge, C. Thies, J. Phys. Chem. 93, 1226 (1989)

    Article  CAS  Google Scholar 

  42. D.M. Chipman, V. Grisaro, N. Sharon, J. Biol. Chem. 242, 4388 (1967)

    CAS  Google Scholar 

  43. J. Rose, Advanced Physico-chemical Experiments (Sir Isaac Pitman and Sons Ltd., London, 1964) 257

    Google Scholar 

  44. M. Guo, J.W. Zou, P.G. Yi, Z.C. Shang, G.X. Hu, Q.S. Yu, Anal. Sci. 20, 465 (2004)

    Article  CAS  Google Scholar 

  45. C.Q. Jiang, M.X. Gao, J.X. He, Anal. Chim. Acta 452, 185 (2002)

    Article  CAS  Google Scholar 

  46. M. Sommerauer, C. Rager, M. Hanack, J. Am. Chem. Soc. 118, 10085 (1996)

    Article  CAS  Google Scholar 

  47. H. Li, T. J. Jensen, F.R. Fronczek, M. G. H. Vicente, J. Med. Chem. 51, 502 (2008)

    Article  CAS  Google Scholar 

  48. Z. Petrasek, D. Phillips, Photochem. Photobiol. Sci. 2, 236 (2003)

    Article  CAS  Google Scholar 

  49. R.D. George, A.W. Snow, J.S. Shirk, W.R. Barger, J. Porphyrins Phthalocyanines 2, 1 (1998)

    Article  CAS  Google Scholar 

  50. A. Ogunsipe, T. Nyokong, J. Photochem. Photobiol. A: Chem. 173, 211 (2005)

    Article  CAS  Google Scholar 

  51. M.J. Stillman, T. Nyokong, in: C.C. Leznoff, A.B.P. Lever (Eds.), Phthalocyanines: Properties and Applications (VCH Publishers, New York, 1989) 133, 1

    Google Scholar 

  52. G. Chen, X. Peng, G. Hao, V.O. Kennedy, I.N. Ivanov, K. Knappenberger, J.J. Hill, M.A.J. Rodgers, M.E. Kenney, J. Phys. Chem., A 107, 3503 (2003)

    Article  Google Scholar 

  53. J. Mark, M.J. Stillman, J. Am. Chem. Soc. 116, 1292 (1994)

    Article  Google Scholar 

  54. S. Khene, A. Ogunsipe, E. Antunes, T. Nyokong, J. Porphyrins Phthalocyanines 11, 109 (2007)

    Article  CAS  Google Scholar 

  55. S. Moeno, T. Nyokong, J. Photochem. Photobiol. A: Chem. 201, 228 (2009)

    Article  CAS  Google Scholar 

  56. K. Ishii, N. Kobayashi, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Porphyrin Handbook (Academic Press, New York, 2003) 1, 16

    Google Scholar 

  57. J.W. Borst, M.A. Hink, A. van Hoek, A.J. Visser, J. Fluoresc. 15(2), 153 (2005)

    Article  CAS  Google Scholar 

  58. C. Tregidgo, J.A. Levitt, K. Suhling, J. Biomed. Opt. 13(3), 31218 (2008)

    Article  Google Scholar 

  59. R.S. Sarpal, M. Belletete, G. Durocher, J. Photochem. Photobiol. A: Chem. 88, 153 (1995)

    Article  CAS  Google Scholar 

  60. M.G. Debacker, O. Deleplanque, B. Van Vlieberge, F.X. Sauvage, Laser Chem. 8(1), 1 (1988)

    Article  CAS  Google Scholar 

  61. N. Nombona, W. Chidawanyika, T. Nyokong, Polyhedron 30, 654 (2011)

    Article  CAS  Google Scholar 

  62. S.L. Murov, I. Carmichael, G.L. Hug, Handbook of Photochemistry, 2nd edition (M. Decker, New York, 1993)

    Google Scholar 

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Correspondence to Mopelola A. Idowu.

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Idowu, M.A., Arslanoğlu, Y. & Nyokong, T. Spectral properties and photophysical behaviour of water soluble cationic Mg(II) and Al(III) phthalocyanines. cent.eur.j.chem. 12, 403–415 (2014). https://doi.org/10.2478/s11532-013-0388-z

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