Advertisement

Synthesis of Boronated Uridine Derivatives for Boron Neutron Capture Therapy

  • G. W. Kabalka
  • N. Kesavulu Reddy
  • C. Narayana

Abstract

The effectiveness of boron neutron capture therapy would be maximized if the capture reaction occurred in the cell nucleus.1 Thus boronated nucleic acid precursors may be ideal agents for achieving high selective boron concentrations in the nucleus of tumor cells since they should be readily taken up by rapidly proliferating malignant cells and incorporated into cellular DNA or RNA.

Keywords

Boron Neutron Capture Therapy Lithium Iodide Tetrabutylammonium Fluoride Retrosynthetic Analysis Nucleic Acid Precursor 
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. 1.
    T. Kobayashi and K. Kanda, Analytical calculation of boron-10 dosage in cell nucleus for neutron capture therapy, Radiat. Res. 91: 77–94 (1982)PubMedCrossRefGoogle Scholar
  2. 2.
    A. Sood, B.R. Shaw, and B.F. Spielvogel, Boron-Containing Nucleic Acids. 2.2 Synthesis of Oligodeoxynucloside Boronophosphates. J. Am. Chem. Soc. 112: 9000–9001 (1990)CrossRefGoogle Scholar
  3. 3.
    A. Sood, B.F. Spielvogel, and B.R. Shaw, Boron-Containing Nucleic Acids; Synthesis of Cyanoborane Adducts of 2’-Deoxynucleosides. J. Am. Chem. Soc. 111: 9234–9235 (1989)CrossRefGoogle Scholar
  4. 4.
    Y. Yamamoto, T. Seko, and H. Nemoto, New Method for the Synthesis of Boron-10 Containing Nucleoside Derivatives for Neutron-Capture Therapy via Palladium-Catalyzed Reaction. J. Org. Chem. 54: 4734–4736 (1989).CrossRefGoogle Scholar
  5. 5.
    Y. Yamamoto, T. Seko, F.G. Rong, and H. Nemoto. Boron-10 Carriers for NCT. A New Synthetic Method via Condensation with Aldehydes having Boronic Moiety. Tetrahedron Lett. 30: 7191–7194 (1989).Google Scholar
  6. 6.
    R.F. Schinazi, and W.H. Prusoff, Synthesis of 5-(Dihydroxyboryl)-2’-deoxyuridine and Related Boron-Containing Pyrimidines. J. Org. Chem. 50: 841–847 (1985)Google Scholar
  7. 7.
    Y. Yamamoto, Molecular Design and Synthesis of B-10 Carriers for Neutron Capture Therapy. Pure. Appl. Chem. 63: 423–426 (1991).CrossRefGoogle Scholar
  8. 8.
    W. Tjarks, A.K.M. Anisuzzaman, L. Liu, A.H. Soloway, R.F. Barth, D.J. Perkins, and D.M. Adams, Synthesis and in Vitro Evaluation of Boronated Uridine and Glucose Derivatives for Boron Neutron Capture Therapy. J. Med. Chem. 35: 1628–1633 (1992).PubMedCrossRefGoogle Scholar
  9. 9.
    R.F. Schinazi, S. Kusuma, B.H. Laster, E. Popenoe, and R.G. Fairchild, Rational Design of Pyrimidines and Nucleosides for Neutron Capture Therapy. Boron Compounds Suitable for Neutron Capture Therapy for the Treatment of Cancer; Proceedings of the Workshop of the Radiation Research Program of NCI, Annapolis, May 3–4, 1988.Google Scholar
  10. 10.
    Y. Yamamoto, T. Seko, H. Nakamura, H. Nemoto, H. Hojo, N. Mukai, and Y. Hashimoto, Synthesis of Carboranes Containing Nucleoside Bases. Unexpectedly High Cytostatic and Cytocidal Toxicity toward Cancer Cells. J. Chem. Soc., Chem Commun. 157 (1992)Google Scholar
  11. 11.
    G.F.Kattan, Z.J. Lesnikowski, S. Yao, F. Tanious, W.D. Wilson, and R.F. Schinazi, Carboranyl Oligonucleotides. 2. Synthesis and Physicochemical Properties of Dodecathymidylate Containing 5-(o-Carborany-l-yl)-2’-deoxyuridine. J. Am. Chem. Soc. 116: 7494–7501 (1994)CrossRefGoogle Scholar
  12. 12.
    L. Otvos, J. Szecsi, J.Sagi, and T. Kovacs, Substrate Specificity Of DNA Polymerases. II. 5-(1-Alkynyl)dUTPs as Substrates of Klenow DNA Polymerase enzyme. Nucleic Acid Research, Symposium Series, 18: 125–129 (1987)Google Scholar
  13. 13.
    F.A. Gomez, and M.F. Hawthorne, A Simple Route to C-Monosubstituted Carborane Derivatives, J. Org. Chem. 57:1384–1390 (1992)Google Scholar
  14. 14.
    G.W. Kabalka, N.K. Reddy, and C. Narayana, Lithium Iodide-Catalyzed Alkylation of Carboranes, Tetrahedron Lett. 33: 7687–7688 (1992).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1996

Authors and Affiliations

  • G. W. Kabalka
    • 1
  • N. Kesavulu Reddy
    • 1
  • C. Narayana
    • 1
  1. 1.Departments of Chemistry and RadiologyUniversity of TennesseeKnoxvilleUSA

Personalised recommendations