A new fluorogenic reagent for carboxylic acids, 7-acetylamino-4-mercapto-2,1,3-benzoxadiazole (AABD-SH), derived from an empirical method for predicting fluorescence characteristics

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Tomofumi Santa, Taizo Okamoto, Seiichi Uchiyama, Kazuto Mitsuhashi and Kazuhiro Imai


Abstract

In our previous studies, we found a relationship between the fluorescence characteristics (the fluorescence intensity, the maximum excitation and emission wavelengths) and Hammett substituent constants (ςp) of the substituent groups at the 4- and 7-positions of benzofurazan compounds, which enabled us to predict the fluorescence characteristics of the benzofurazan compounds. This prompted us to design a new fluorogenic derivatization reagent having a benzofurazan skeleton for carboxylic acids along this line of thought. Accordingly, the fluorogenic reagent, 7-acetylamino-4-mercapto-2,1,3-benzoxadiazole (AABD-SH) was synthesized. The reagent itself fluoresced very weakly but fluoresced strongly after the reaction with carboxylic acids. AABD-SH reacted with carboxylic acids within 5 min at room temperature in the presence of triphenylphosphine and 2,2′-dipyridyl disulfide. The derivatives of five carboxylic acids were separated on a reversed phase column and detected fluorimetrically at 524 nm with excitation at 368 nm. The detection limits were 10–20 fmol (signal-to-noise ratio of 3).


References

  1. Y. Ohkura, M. Kai and H. Nohta, J. Chromatogr. B, 1994, 659, 85 CrossRef CAS.
  2. N. Seiler, in Handbook of Derivatives for Chromatography, ed. K. Blau and J. M. Halket, Wiley, Chichester, 2nd edn., 1993, pp. 175 Search PubMed.
  3. T. Toyo'oka, J. Chromatogr. B, 1995, 671, 91 CrossRef CAS.
  4. P. S. Mukherjee and T. Karnes, Biomed. Chromatogr., 1996, 10, 193 CrossRef CAS.
  5. W. Dunges, Anal. Chem., 1977, 49, 442 CrossRef CAS.
  6. R. Farinotti, P. Siard, J. Bouson, S. Kirkiacharian, B. Valeur and G. Mahuzier, J. Chromatogr., 1983, 217, 491.
  7. A. Takadate, T. Masuda, C. Murata, C. Haratake, A. Isobe, M. Irukura and S. Goya, Anal. Sci., 1992, 8, 663 CAS.
  8. A. Takadate, T. Masuda, C. Tajima, C. Murata, M. Irukura and S. Goya, Anal. Sci., 1992, 8, 695 CAS.
  9. H. Tsuchiya, T. Hayashi, H. Naruse and N. Takagi, J. Chromatogr., 1982, 234, 121 CrossRef CAS.
  10. M. Yamaguchi, S. Hara, R. Matsunaga, M. Nakamura and Y. Ohkura, Anal. Sci., 1985, 1, 295 CAS.
  11. W. D. Watkins and M. B. Peterson, Anal. Biochem., 1982, 125, 30 CAS.
  12. N. Nimura and T. Kinoshita, Anal. Lett., 1980, 13, 191 CAS.
  13. Y.-M. Lee, H. Nakashima and T. Nakajima, Anal. Sci., 1989, 5, 681 CAS.
  14. M. Yamaguchi, T. Iwata, K. Inoue, S. Hara and M. Nakamura, Analyst, 1990, 115, 1363 RSC.
  15. T. Iwata, K. Inoue, M. Nakamura and M. Yamaguchi, Biomed. Chromatogr., 1992, 6, 120 CAS.
  16. N. Nimura, T. Kinoshita, T. Yoshida, A. Uetake and C. Nakai, Anal. Chem., 1988, 60, 2067 CrossRef CAS.
  17. K. Nakashima, Y. Taguchi, N. Kuroda and S. Akiyama, J. Chromatogr., 1993, 619, 1 CAS.
  18. S. Hara, K. Inoue, M. Fukazawa, N. Ono, T. Kuroda and M. Yamaguchi, Anal. Sci., 1998, 14, 1173 CAS.
  19. Y. Yasaka, M. Tanaka, T. Shono, T. Tetsumi and J. Katakawa, J. Chromatogr., 1990, 508, 133 CrossRef CAS.
  20. K. Akasaka, H. Ohrui and H. Meguro, Analyst, 1993, 118, 765 RSC.
  21. T. Toyo'oka, M. Ishibashi, Y. Takeda, K. Nakashima, S. Akiyama, S. Uzu and K. Imai, J. Chromatogr., 1991, 588, 61 CrossRef CAS.
  22. T. Santa, K. Kimoto, T. Fukushima, H. Homma and K. Imai, Biomed. Chromatogr., 1996, 10, 183 CrossRef CAS.
  23. T. Santa, A. Takeda, S. Uchiyama, T. Fukushima, H. Homma, S. Suzuki, H. Yokosu, C. K. Lim and K. Imai, J. Pharm. Biomed. Anal., 1998, 17, 1065 CrossRef CAS.
  24. S. Uchiyama, T. Santa, T. Fukushima, H. Homma and K. Imai, J. Chem. Soc., Perkin Trans. 2, 1998, 2165 RSC.
  25. T. Toyo'oka and K. Imai, Analyst, 1984, 109, 1003 RSC.
  26. T. Toyo'oka, M. Ishibashi and T. Terao, Analyst, 1992, 117, 727 RSC.
  27. S. Fery-Forgues, J.-P. Fayet and A. Lopez, J. Photochem. Photobiol. A, 1993, 70, 229 CrossRef CAS.
  28. S. Uchiyama, T. Santa and K. Imai, J. Chem. Soc., Perkin Trans. 2, 1999, 569 RSC.
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