Examination of Stability of p-, m-, o-Boronophenylalanine in Blood with High Performance Liquid Chromatography

  • Kazuo Yoshino
  • Naoko Koike
  • Yuko Kuroda
  • Yoshihiro Mori
  • Masamitsu Ichihashi
  • Hidetake Kakihana
  • Yutaka Mishima

Abstract

Many pharmacokinetic experiments were carried out with tumor-bearing animals and patients using p-Boronophenylalanine(p-BPA)-fructose complex, and the selective boron accumulation property in the tumors was confirmed.1,2 As the results, p-BPA fructose complex has been used for Boron Neutron Capture Therapy (BNCT) of malignant melanoma and brain tumors.3,4 But, mechanism studies about the accumulation properties are few.5 Recently, we have proposed a chemical model representing boron accumulation in and its release from melanoma.6 This mechanism is based on the facts that p-BPA is complexed by Dopa, which is greatly produced in melanoma cells, that the complex is then decomposed by tyrosinase to form boric acid. Although the above-mentioned chemical reactions had been rally observed in test tubes, it was still ambiguous whether these reactions do occur or not in a human body. The present paper deals with this point. One of the methods of confirming the phenomena in vivo is 11B-NMR. Since the signal width of boric acid is sharp compared with that of p-BPA and the chemical shift of boric acid is different from that of p-BPA, we can examine whether the decomposition occurs. But, the application of 11B-NMR to the human tissue is not so easy. Improvement of the sample tube and of the NMR module are required.

Keywords

High Performance Liquid Chromatography High Performance Liquid Chromatography Boric Acid Boron Neutron Capture Therapy High Performance Liquid Chromatography Column 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. I. C. Honda, M. Shiono, N. Wadabayashi, S. Hatta, M. Ichihashi, Y. Mishima, K. Yoshino, T. Kobayashi, K. Kanda, and Y. Hori, 1°B1-BPA administration to human melanoma patients: boron analytical studies for neutron capture therapy. Kyoto Univ. Res. Reactor Inst. T.R. 357: 7–18, 1991.Google Scholar
  2. 2.
    C. Honda, M. Shiono, N. Wadabayashi, M. Ichihashi, Y. Mishima, T. Kobayashi, K. Kanda, Y. Hori, and K. Yoshino, Increased selective 10B-uptake by malignant melanoma using systematic administration of 10B1-BPA-fructose complex. in: “Progress in Neutron Capture Therapy for Cancer”, B. J. Allen et al. eds., Plenum Press, New York, 1992, pp. 421–424.CrossRefGoogle Scholar
  3. 3.
    H. Fukuda, J. Hiratsuka, C’. Honda, T. Kobayashi, K. Yoshino, H. Karashima, J. Takahashi, Y. Abe, K.. Kanda, M. Ichihashi, and Y. Mishima, Boron neutron capture therapy of malignant melanoma using 10B-paraboronophenylalanine with special reference to evaluation of radiation dose and damage to the normal skin, Radiation Research 138: 435–442, 1994.PubMedCrossRefGoogle Scholar
  4. 4.
    S. Ueda, Y. Imahori, Y. Ohmori, K. Ono, T. Kobayashi, M. Takagaki, Y. Oda, T. Ido, and Y Mishima. Positron emission tomography and boron neutron capture therapy system to a patient with brain tumor. This symposium proceedings.Google Scholar
  5. 5.
    M. Shiono, T. Shibata, M. Ichihashi, Y. Mishima, The mechanism of the selective affinity of 10B1paraboronophenylalanine for malignant melanoma…!. Kobe Unis. School of Medicine, 53 (1): 35–41, 1992.Google Scholar
  6. 6.
    K. Yoshino, Y. Mori, H. Kakihana, H. Takahashi, Y. Mishima and M. Ichihashi, Chemical modeling with p-Boronophenylalanine for boron accumulation to and release from Melanoma. This symposium proceedings.Google Scholar
  7. 7.
    K. Yoshino, M. Okamoto, II. Kakihana, T. Nakanishi, M. Ichihashi, and Y. Mishima, Spectrophotometric determination of trace boron in biological materials after alkali fusion decomposition, Final. Client. 56; 839–842, 1984.Google Scholar
  8. 8.
    K. Yoshino, T. Takasoh, H. Hatanaka, F. Komada, K. Okumura, Y. Mishima. C. Honda, and Y. Mori, Determination ofp-Boronophenylalanine in biological tissues with high performance liquid chromatography, in: “Advances in Neutron Capture Therapy”, A. H. Soloway et al. eds., Plenum Press, New York, 1993, pp. 465–468.CrossRefGoogle Scholar
  9. 9.
    K. Yoshino, N. Watanabe, H. Takahashi, S. Watanabe, Y. Mori, H. Kakihana, Y. Mishima, and M. Ichihashi, Chemical properties of p-, in-, o-Boronophenylalanine. This symposium proceedings.Google Scholar
  10. 10.
    unpublished data.Google Scholar

Copyright information

© Springer Science+Business Media New York 1996

Authors and Affiliations

  • Kazuo Yoshino
    • 1
  • Naoko Koike
    • 1
  • Yuko Kuroda
    • 1
  • Yoshihiro Mori
    • 1
  • Masamitsu Ichihashi
    • 2
  • Hidetake Kakihana
    • 3
  • Yutaka Mishima
    • 4
  1. 1.Department of Chemistry, Faculty of ScienceShinshu UniversityAsahi Matsumoto 390Japan
  2. 2.Kobe University School of MedicineKobe 650Japan
  3. 3.Energy Research CenterTsuruga 914Japan
  4. 4.Mishima Institute for Dermatological ResearchMishima Skin ClinicKobe 657Japan

Personalised recommendations