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Synthesis of Boronated Uridine Derivatives for Boron Neutron Capture Therapy

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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.

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References

  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)

    Article  PubMed  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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)

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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. 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)

    CAS  Google Scholar 

  7. Y. Yamamoto, Molecular Design and Synthesis of B-10 Carriers for Neutron Capture Therapy. Pure. Appl. Chem. 63: 423–426 (1991).

    Article  CAS  Google Scholar 

  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).

    Article  PubMed  CAS  Google Scholar 

  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. 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. 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)

    Article  Google Scholar 

  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)

    CAS  Google Scholar 

  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. G.W. Kabalka, N.K. Reddy, and C. Narayana, Lithium Iodide-Catalyzed Alkylation of Carboranes, Tetrahedron Lett. 33: 7687–7688 (1992).

    Article  CAS  Google Scholar 

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© 1996 Springer Science+Business Media New York

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Kabalka, G.W., Reddy, N.K., Narayana, C. (1996). Synthesis of Boronated Uridine Derivatives for Boron Neutron Capture Therapy. In: Mishima, Y. (eds) Cancer Neutron Capture Therapy. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9567-7_21

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  • DOI: https://doi.org/10.1007/978-1-4757-9567-7_21

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4757-9569-1

  • Online ISBN: 978-1-4757-9567-7

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