Synthesis and in Vitro Evaluation of Boronated Uridine and Glucose Derivatives for Boron Neutron Capture Therapy

Journal of Medicinal Chemistry

Volumn 35, Issue 9, 1992, Pages 1628-1633

  Tjarks, Wener ^a   Anisuzzaman, Abul K M ^a   Liu, Liang ^a   Soloway, Albert H ^a   Barth, Rolf F ^a   Perkins, Douglas J ^a   Adams, Dianne M ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' O (O CARBORAN 1 YLMETHYL)URIDINE; 3' O (O CARBORAN 1 YLMETHYL)GLUCOSE; 3' O (O CARBORAN 1 YLMETHYL)URIDINE; 5' O (O CARBORAN 1 YLMETHYL)URIDINE; BORON DERIVATIVE; SODIUM 7 (URIDIN 2' YLMETHYL) DODECAHYDRO 7,8 DICARBA NIDO UNDECABORATE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ANIMAL CELL; ARTICLE; CANCER CHEMOTHERAPY; CELL ACTIVITY; CELL LEVEL; DRUG ACTIVITY; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG UPTAKE; GLIOMA CELL; NONHUMAN; PRIORITY JOURNAL; RAT; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

ANIMAL; BORON; GLIOMA; GLUCOSE; NEUTRONS; RADIOTHERAPY, HIGH-ENERGY; RATS; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, NON-P.H.S.; SUPPORT, U.S. GOV'T, P.H.S.; TUMOR CELLS, CULTURED; URIDINE;

EID: 0026661314     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00087a019     Document Type: Article

References (28)

1. Barth, R. F.; Soloway, A. H.; Fairchild, R. G. Boron Neutron Capture Therapy of Cancer. Cancer Res. 1990, 50, 1061-1071.
2. Kobayashi, T.; Kanda, K. Analytical Calculation of Boron-10 Dosage in Cell Nucleus for Neutron Capture Therapy. Radiat. Res. 1982, 91, 77-94.
3. Gabel, D.; Foster, S.; Fairchild, R. G. The Monte-Carlo Simulation of the Biological Effect of the 10B(n,a)7Li Reaction in Cells and Tissues and its Implication for Boron Neutron Capture Therapy. Radiat. Res. 1987, 111, 14-25.
4. Matteson, D. S.; Biernbaum, M. S.; Bechthold, R. A.; Campbell, J. D.; Wilcsek, R. J. Synthesis of Boron-Substituted Pyrimidines and Borazaroquinazolines. J. Org. Chem. 1978, 43, 950-954.
5. Maitra, A. Boron Analogue of Uracil. Ind. J. Chem., Sect. B 1978, 16B, 85-86.
6. Chissick, S. S.; Dewar, M. J. S.; Maitlis, P. A Boron-containing Purine Analog. J. Am. Chem. Soc. 1959, 81, 6329-6330.
7. Chissick, S. S.; Dewar, M. J. S.; Maitlis, P. M. New Heteroaromatic Compounds. XIV. Boron-containing Analogs of Purine, Quinazoline and Perimidine. J. Am. Chem. Soc. 1961, 83, 2708-2711.
8. Zimmer, H.; Sill, A. D.; Andrews, E. R. Functional Organoboron Compounds. Naturwissenschaften 1960, 47, 378.
9. Matteson, D. S.; Soloway, A. H.; Tomlinson, D. W.; Campbell, J. D.; Nixon, G. A. Synthesis and Biological Evaluation of Water-Soluble 2-Boronoethylthio Compounds. J. Med. Chem. 1964, 7, 640-643.
10. Bielawski, J.; Niedenzu, K.; Stewart, J. S. Preparation and Characterization of Some Isoelectronic Boron-Nitrogen Analogs of Substituted Uracil. Z. Naturforsch. 1985,40b, 398-392.
11. Bielawski, J.; Niedenzu, K.; Weber, A.; Weber, W. Cyclic Boron Derivatives of Biufet. Z. Naturforsch. B: Anorg. Chem., Org. Chem. 1981, 36b, 470-473.
12. Liao, T. K.; Podrebarac, E. G.; Cheng, C. C. Boron-Substituted Pyrimidines. J. Am. Chem. Soc. 1964, 86, 1869-1870.
13. Sood, A.; Shaw, B. R.; Spielvogel, B. F. Boron-Containing Nucleic Acids. 2.1 Synthesis of Oligodeoxynucleoside Boranophosphates. J. Am. Chem. Soc. 1990, 112, 9000-9001.
14. Sood, A.; Spielvogel, B. F.; Shaw, B. R. Boron-Containing Nucleic Acids; Synthesis of Cyanoborane Adducts of 2′-Deoxynucleosides. J. Am. Chem. Soc. 1989, 111, 9234-9235.
15. Yamamoto, Y.; Seko, T.; Nemoto, H. New Method for the Synthesis of Boron-10 Containing Nucleoside Derivatives for Neutron-Capture Therapy via Palladium-Catalyzed Reaction. J. Org. Chem. 1989, 54, 4734-4736.
16. Yamamoto, Y.; Seko, T.; Rong, F. G.; Nemoto, H. Boron-10 Carriers for NCT. A New Synthetic Method via Condensation with Aldehydes having Boronic Moiety. Tetrahedron Lett. 1989, 30, 7191-7194.
17. Schinazi, R. F.; Prusoff, W. H. Synthesis of 5-(Dihydroxyboryl)-2′-deoxyuridine and Related Boron-Containing Pyrimidines. J. Org. Chem. 1985, 50, 841-847.
18. Yamamoto, Y. Molecular Design and Synthesis of B-10 Carriers for Neutron Capture Therapy. Pure Appl. Chem. 1991, 63, 423-426.
19. Schinazi, R. F.; Kusuma, S.; Laster, B. H.; Popenoe, E.; Fairchild, R. G. 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.
20. Anisuzzaman, A. K. M.; Alam, F.; Soloway, A. H. Synthesis of A Carboranyl Nucleoside for Potential Use in Neutron Capture Therapy of Cancer. Polyhedron 1990, 9, 891-892.
21. Soloway, A. H.; Anisuzzaman, A. K. M.; Alam, F.; Barth, R. F.; Liu, L. The Development of Carboranyl Nucleic Acid Precursors for Use in Neutron Capture Therapy of Tumors. Pure Appl. Chem. 1991, 63, 411-413.
22. Liu, L.; Barth, R. F.; Soloway, A. H.; Anisuzzaman, A. K. M.; Alam, F.; Tjarks, W.; Zha, X.-H.; Morrison, G. H. Cellular Uptake and Distribution of 2′-O-(o-Carboran-1-ylmethyl)-uridine (CBU). A Potential Delivery Agent for Boron Neutron Capture Therapy (BNCT). Proc. Am. Assoc. Cancer Res. 1991, 34, 2418.
23. Grimes, R. N. Carboranes. In Organometallic Chemistry. A Series of Monographs; Maitlis, P. M., Stone, F. G. A., West, R., Eds.; Academic Press, Inc.: New York, London, 1970; pp 92-95, pp 193-197.
24. Wagner, D.; Verheyden, J. P. H.; Moffatt, J. G. Preparation and Synthetic Utility of Some Organotin Derivatives of Nucleotides. J. Org. Chem. 1974, 39, 24-30.
25. Levene, P. A.; Stuart-Tipson, R. The Partial Synthesis of Ribose Nucleotides. I. Uridine 5-Phosphoric Acid. J. Biol. Chem. 1934, 106, 113-124.
26. Hawthorne, M. F.; Young, D. C.; Garrett, P. M.; Owen, D. A.; Schwerin, S. G.; Tebbe, F. N.; Wegner, P. A. The Preparation and Characterization of the (3)-1,2-and (3)-1,7-Dicarbadodecahydroundecaborate(-1) Ions. J. Am. Chem. Soc. 1968, 90, 862-868.
27. Ko, L.; Koestner, A.; Wechsler, W. Morphological Characterization of Nitrosourea-induced Glioma Cell Lines and Clones. Acta Neuropathol. 1980, 51, 23-31.
28. Barth, R. F.; Adams, D. M.; Soloway, A. H.; Mechetner, E. B.; Alam, F.; Anisuzzaman, A. K. M. Determination of Boron in Tissues and Cells Using Direct-Current Plasma Atomic Emission Spectroscopy. Anal. Chem. 1991, 63, 890-893.