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Absorption and luminescence spectroscopic analysis of tautomeric forms of protonatedN,N-dimethyl-N′-(1-nitro-9-acridinyl)-1,3-propanediamine (nitracrine) and its nitro isomers in poly(vinyl alcohol) films

Journal of Fluorescence volume 1, pages 57–68 (1991)Cite this article

Abstract

The electronic absorption, fluorescence, and phosphorescence excitation spectra, as well as the fluorescence and phosphorescence spectra, at either room or liquid nitrogen temperatures, were measured forN,N-dimethyl-N′-(1-nitro-9-acridinyl)-1,3-propanediamine and its three nitro isomers in acidified poly(vinyl alcohol) (PVA) film. The spectral characteristics obtained reveal the existence of the compounds studied in at least two structural forms. The results are interpreted in terms of the tautomeric phenomena which originate due to the migration of the hydrogen atom, which is bound to the nitrogen atom attached to the carbon atom (9), to the acridine ring nitrogen.

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References

  1. A. Albert (1972)Med. Chem. Ser. Monogr. 11, 229–242.

    Google Scholar 

  2. R. M. Acheson (1973)Acridines, 2nd ed., Interscience, New York.

    Google Scholar 

  3. P. Laugaa, M. Delepierre, P. Leon, C. Garbay-Jaureguiberry, J. Markovits, J. B. Le Pecq, and B. P. Reques (1986)Pontif. Acad. Sci. Varia 70, 275–294.

    Google Scholar 

  4. J. L. Jurlina, A. Lindsay, J. E. Packer, B. C. Baguley, and W. A. Denny (1987)J. Med. Chem. 30, 473–480.

    PubMed  Google Scholar 

  5. L. P. G. Wakelin, G. J. Atwell, G. W. Rewcastle, and W. A. Denny (1987)J. Med. Chem 30, 855–861.

    PubMed  Google Scholar 

  6. G. Klopman and O. T. Macina (1987)Mol. Pharmacol.,31, 457–476.

    PubMed  Google Scholar 

  7. W. M. Cholody, S. Martelli, J. Paradziej-Lukowicz, and J. Konopa (1990)J. Med. Chem.,33, 49–52.

    PubMed  Google Scholar 

  8. “Ledakrin” (1976)Mater. Med. Pol. 8, 237–251.

    Google Scholar 

  9. M. Gniazdowski, J. Filipski, and M. Chorazy (1979)Antibiotics (N. Y.) 5, 275–297.

    Google Scholar 

  10. W. R. Wilson, R. F. Anderson, and W. A. Denny (1989)J. Med. Chem. 32, 23–30.

    PubMed  Google Scholar 

  11. K. Pawlak, J. W. Pawlak, and J. Konopa (1984)Cancer. Res. 44, 4289–4296.

    PubMed  Google Scholar 

  12. J. M. Woynarowski and A. Bartoszek (1985)Biochim. Biophys. Acta 825, 244–253.

    PubMed  Google Scholar 

  13. W. R. Wilson, W. A. Denny, G. M. Stewart, A. Fenn, and J. C. Probert (1986)Int. J. Radiat. Oncol. Biol. Phys. 12, 1235–1238.

    PubMed  Google Scholar 

  14. Z. Mazerska, M. Cholody, J. Lukowicz, B. Wysocka-Skrzela, and A. Ledochowski (1987)Arzneim-Forsch. 37, 1276–1281.

    Google Scholar 

  15. A. Bartoszek and J. Konopa (1987)Biochem. Pharmacol. 36, 4169–4171.

    PubMed  Google Scholar 

  16. L. R. Ferguson and P. Van Zijl (1988)Mutat. Res. 204, 655–663.

    PubMed  Google Scholar 

  17. D. Wilmanska, L. Szmigiero, and M. Gniazdowski (1989)Z. Naturforsch. C 44, 307–311.

    PubMed  Google Scholar 

  18. L. R. Ferguson, W. A. Denny, and S. M. O'Rourke (1989)Mutat. Res. 223, 13–22.

    PubMed  Google Scholar 

  19. L. Szmigiero and K. Studzian (1989)Biochim. Biophys. Acta 1008, 339–345.

    PubMed  Google Scholar 

  20. W. R. Wilson, L. H. Thompson, R. F. Anderson, and W. A. Denny (1989)J. Med. Chem. 32, 31–38.

    PubMed  Google Scholar 

  21. J. Biedrzycki, J. Blazejowski, A. Ledochowski, and J. Szychlinski (1977)Rocz. Chem. 51, 379–384.

    Google Scholar 

  22. J. Biedrzycki, J. Blazejowski, J. Szychlinski, and A. Ledochowski (1984)Z. Naturforsch. A 39, 195–200.

    Google Scholar 

  23. J. J. Stezowski, P. Kollat, M. Bogucka-Ledochowska, and J. P. Glusker (1985)J. Am. Chem. Soc. 107, 2067–2007.

    Google Scholar 

  24. A. Tempczyk, J. Rak, and J. Blazejowski (1990)J. Chem. Soc., Perkin Trans. 2, 1501–1508.

    Google Scholar 

  25. Z. Dauter, M. Bogucka-Ledochowska, A. Hempel, A. Ledochowski, and Z. Kosturkiewicz (1975)Rocz. Chem. 49, 859–862; (1976)50, 1753–1586.

    Google Scholar 

  26. A. Hempel, S. E. Hull, Z. Dauter, M. Bogucka-Ledochowska, and A. Konitz (1979)Acta Crystallogr. B. 35, 477–479.

    Google Scholar 

  27. V. B. Pett, M. Rossi, J. P. Glusker, J. J. Stezowski, and M. Bogucka-Ledochowska (1982)Bioorg. Chem.,11, 443–456.

    Google Scholar 

  28. J. Rak, J. Blazejowski, and R. J. Zauhar, In press.

  29. D. V. Naik, and S. G. Schulman (1975)Anal. Chim. Acta 80, 67–74.

    PubMed  Google Scholar 

  30. K. Kikuchi, K. Uij-le, Y. Miyashita, and H. Kokubun (1977)Bull. Chem. Soc. Jpn. 50, 879–882.

    Google Scholar 

  31. A. Kellmann and Y. Lion (1979)Photochem. Photobiol. 29, 217–222.

    Google Scholar 

  32. Y., Kubota and Y. Motoda (1980)Biochemistry 19, 4189–4197.

    PubMed  Google Scholar 

  33. P. Gangola, N. B. Joshi, and D. D. Pant (1981)Chem. Phys. Lett. 80, 418–421.

    Google Scholar 

  34. K. Kasama, K. Kikuchi, K. Uij-le, S.-A. Yamamoto, and H. Kokubun (1982)J. Phys. Chem. 86, 4733–4737.

    Google Scholar 

  35. I. Gryczynski A. Kawski, K. Nowaczyk, and H. Cherek (1983)J. Photochem. 21, 81–85.

    Google Scholar 

  36. L. A. Diverdi and M. R. Topp (1984)J. Phys. Chem. 88, 3447–3451.

    Google Scholar 

  37. J. F. Constant P. Laugga, B. P. Roques, and J. Lhomme (1988)Biochemistry 27, 3997–4003.

    PubMed  Google Scholar 

  38. W. E. Lee and W. C. Galley (1988)Biophys. J. 54, 627–635.

    PubMed  Google Scholar 

  39. T. Hard, P. Fan, D. Magde, and D. R. Kearns (1989)J. Phys. Chem. 93, 4338–4345.

    Google Scholar 

  40. P. Fan, T. Hard, and D. R. Kearns (1989)J. Phys. Chem. 93, 6615–6622.

    Google Scholar 

  41. Y. Ni and D. R. Kearns (1989)J. Phys. Chem. 93, 6622–6625.

    Google Scholar 

  42. A. Ledochowski and B. Stefanska (1966)Rocz. Chem. 40, 301–306.

    Google Scholar 

  43. A. Ledochowski (1966)Rocz. Chem. 40, 1557–1559.

    Google Scholar 

  44. K. Koldej (1977) Ph.D. thesis, Technical University of Gdańsk, Gdańsk, Poland.

  45. Y. Tanizaki, T. Kobayashi, and N. Ando (1959)Bull. Chem. Soc. Jpan. 32, 119–124.

    Google Scholar 

  46. C. A. Finch (1973)Poly Vinyl Alcohol, John Wiley and Sons, New York.

    Google Scholar 

  47. A. Kawski and K. Nowaczyk (1991)Acta Phys. Polon A78, 379–392.

    Google Scholar 

  48. C.A. Parker (1968)Photoluminescence of Solutions, Elsevier, Amsterdam, London, New York.

    Google Scholar 

  49. J. R. Lakowicz (1983)Principles of Fluorescence, Spectroscopy, Plenum, New York.

    Google Scholar 

  50. J. Jankowska and M. Jankowski (1981)Przeglad metod i algorytmów numerycznych, WNT, Warszawa, Poland.

    Google Scholar 

  51. R. Larsson and B. Norden (1970)Acta Chem. Scand 24, 2583–2592.

    Google Scholar 

  52. R. W. Chambers, T. Kajiwara, and D. R. Kearns (1974)J. Phys. Chem. 78, 380–387.

    Google Scholar 

  53. D. D. Pant, G. C. Joshi, and H. B. Tripathi (1986)Pramana 27, 161–170.

    Google Scholar 

  54. G. Strauss, S. B. Broyde, and T. Kurucsev (1971)J. Phys. Chem. 75, 2727–2733.

    Google Scholar 

  55. Z. V. Pushkareva and Z. Yu. Kokoshko (1953)Dokl. Akad. Nauk SSSR 93, 77–80.

    Google Scholar 

  56. A. K. Sukhomlinov (1958)Zy. Obshch. Khim. 28, 1038–1045.

    Google Scholar 

  57. R. M. Acheson, M. L. Burstall, C. W. Jefford, and B. F. Sansom (1954)J. Chem. Soc. 3742–3746.

  58. A. V. Karyakin and A. v. Shablya (1957)Dokl. Akad. Nauk SSSR 116, 969–972.

    Google Scholar 

  59. Yu. N. Sheinker and E. M. Peresleni (1960)Dokl. Akad. Nauk SSSR 131, 1366–1369.

    Google Scholar 

  60. A. C. Capomacchia, J. Casper, and S. G. Schulman (1974)J. Pharm. Sci. 63, 1272–1276.

    PubMed  Google Scholar 

  61. S. G. Schulman, D. V. Naik, A. C. Capomacchia, and T. Roy (1975)J. Pharm. Sci. 64, 982–986.

    PubMed  Google Scholar 

  62. P. Singh and S. P. Gupta (1978)J. Pharm. Sci. 67, 706–709.

    PubMed  Google Scholar 

  63. J.-P. Galy, R. Faure, J. Barbe, and J. Elguero (1988)Spectrosc. Lett. 21, 809–818.

    Google Scholar 

  64. A. C. Capomacchia and S. G. Schulman (1975)J. Pharm. Sci. 64, 1256–1257.

    PubMed  Google Scholar 

  65. A. C. Capomacchia and S. G. Schulman (1975)Anal. Chim. Acta 77, 79–85.

    PubMed  Google Scholar 

  66. J. Heldt, D. Gormin, and M. Kasha (1989)Chem. Phys. 136, 321–334.

    Google Scholar 

  67. D. Gormin, J. Heldt, and M. Kasha (1990)J. Phys. Chem. 94, 1185–1189.

    Google Scholar 

  68. K. Uij-le, K. Kasama, K. Kikuchi, and H. Kokubun (1978)Chem. Lett. 247–250.

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Affiliations

  1. Institute of Chemistry, University of Gdańsk, 80-952, Gdańsk, Poland

    Janusz Rak & Jerzy Blazejowski

  2. Lumincscence Research Group, Institute of Experimental Physics, University of Gdańsk, 80-952, Gdańsk, Poland

    Kazimierz Nowaczyk & Alfons Kawski

Authors
  1. Janusz Rak
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  2. Kazimierz Nowaczyk
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  3. Jerzy Blazejowski
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  4. Alfons Kawski
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Rak, J., Nowaczyk, K., Blazejowski, J. et al. Absorption and luminescence spectroscopic analysis of tautomeric forms of protonatedN,N-dimethyl-N′-(1-nitro-9-acridinyl)-1,3-propanediamine (nitracrine) and its nitro isomers in poly(vinyl alcohol) films. J Fluoresc 1, 57–68 (1991). https://doi.org/10.1007/BF00865259

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  • DOI: https://doi.org/10.1007/BF00865259

Key Words

  • Nitracrine
  • absorption
  • fluorescence
  • phosphorescence
  • tautomers
  • PVA films