5B Boron Compounds as Therapeutic Drugs

Metallotherapeutic Drugs and Metal-Based Diagnostic Agents: The Use of Metals in Medicine

Volumn , Issue , 2005, Pages 19-49

  Rana, Geeta ^a   Vyakaranam, Kamesh ^a   Maguire, John A ^b   Hosmane, Narayan S ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

^b SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

BNCT agents; Boranated polyamines; Boron neutron capture therapy (BNCT); Boron containing phenanthridinium analogues; Boronated anthraquinones; Cyclic thiourea derivatives; Fast neutron therapy; Pyrophosphates; Radiation sensitizers

Indexed keywords

EID: 84889496632     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/0470864052.ch2     Document Type: Chapter

References (105)

1. K. Vyakaranam; G. Rana; N.S. Hosmane and B.F. Spielvogel,Metal-Based Drugs, 3, 145 (2001).
2. K. Vyakaranam; G. Rana; B.F. Spielvogel and N.S. Hosmane,Inorg. Chem. Commun., 4, 629 (2001).
3. A. Hasan; H. Li; J. Tomasz and B.R. Shaw,Nucl. Acid Res., 24, 2150 (1996).
4. H. Li; K. Porter; F. Huang and B.R. Shaw,Nucl. Acid Res., 23, 4495 (1995).
5. A. Sood; B.R. Shaw and B.F. Spielvogel,J. Am. Chem. Soc., 112, 9000 (1990).
6. A. Sood; B.F. Spielvogel and B.R. Shaw,J. Am. Chem. Soc., 111, 9234 (1989).
7. B.F. Spielvogel; A. Sood; B.R. Shaw et al.,Progress in Neutron Capture Therapy for Cancer, Proceedings of International Symposium, Sydney, Australia, 4 (1992), pp. 211-213
8. B.R. Shaw; J. Madison; A. Sood and B.F. Spielvogel,Methods Mol. Biol., 20, 225 (1993).
9. R.R. Kane; K. Drechsel and M.F. Hawthorne,J. Am. Chem. Soc., 115, 8853 (1993).
10. B.F. Spielvogel; A. Sood; B.R. Shaw and I.H. Hall,Pure Appl. Chem., 63, 415 (1991).
11. B.F. Spielvogel; A. Sood; J. Tomasz et al., In Advances in Neutron Capture Therapy; Soloway, A.H., Barth, R.F. and Carpenter, D.E., Eds; Plenum Press, New York, Vol. 5, 1993, pp. 361-365
12. M. Takagaki; W. Powell; A. Sood et al.,Radiat. Res., 156, 118 (2001).
13. R.R. Kane; R.H. Pack and M.F. Hawthorne,J. Org. Chem., 58, 991 (1993).
14. I.H. Hall; E.S. Hall; L. Chi et al.,Anticancer Res., 12, 1091 (1992).
15. G. Rana; K. Vyakaranam; B.F. Spielvogel et al.,Inorg. Chim. Acta, 342, 255 (2003).
16. A. Sood; B.F. Spielvogel; B.R. Shaw et al.,Anticancer Res., 12, 335 (1992).
17. A. Sood; B.R. Shaw; B.F. Spielvogel et al.,Pharmazie, 47, 833 (1992).
18. B.F. Spielvogel; A. Sood; B.R. Shaw and I.H. Hall, Curr. Top. Chem. Boron, Kabalka, G.W., Ed.; Royal Society of Chemistry: Cambridge, United Kingdom, 1994 (SP. PUBL. 143), pp. 193-198
19. K.G. Rajendran; B.S. Burnham; S.Y. Chen et al.,J. Pharm. Sci., 83, 1391 (1994).
20. J.Tomasz; B.R. Shaw;K.W. Porter et al.,Angew. Chem., Int. Ed. Engl., 31, 1373 (1992).
21. G.L. Locker,Am. J. Roentgenol. Radiat. Ther., 36, 1 (1936).
22. M. Javid; G.L. Brownell and W.H. Sweet,J. Clin. Invest., 31, 604 (1952).
23. G. Friedlander; J.W. Kennedy; E.S. Macias and J.M. Miller, Nucl. Radiochem., 3rd edn, John Wiley & Sons, New York, 1981.
24. R.F. Barth; A.H. Soloway and R.M. Brugger,Cancer Invest., 14, 534 (1996).
25. R.G. Zamenhof; A.M. Kalend and W.D. Bloomer,J. Natl. Cancer Inst., 84, 1290 (1992).
26. A.H. Soloway; W. Tjarks; B.A. Barnum et al.,Chem. Rev., 98, 1515 (1998).
27. See http://www.cnea.gov.ar/xxi/bnct/eng/. Last date visited. April 14, 2003.
28. W. Tjarks; A.K.M. Anisuzzaman; L. Liu et al.,J. Med. Chem., 35, 1628 (1992).
29. H. Ghaneolhosseini; W. Tjarks and S. Sjoberg,Tetrahedron, 54, 3877 (1998).
30. Z.J. Lesnikowski and R.F. Schinazi,Pol. J. Chem., 69, 827 (1995).
31. Y. Yamamoto and K.I. Imamura,Bioorg. Med. Chem. Lett., 6, 1855 (1996). (c) F.G. Rong; A.H. Soloway; S. Ikeda and D.H. Ives, Nucleosides Nucleotides Nucleic Acids, 16, 379 (1997). 24. (a) M.F. Hawthorne; R.J. Wiersema and M. Takasugi, J. Med. Chem., 15, 449 (1972). (b) E.A. Mizusawa; H.L. Dahlman; S.J. Bennett and M.F. Hawthorne, Proc. Natl. Acad. Sci. USA, 79, 3011 (1982).
32. S.B. Kahl and M.S. Koo,J. Chem. Soc., Chem. Commun., 1769 (1990).
33. K. Shelly; D.A. Feakes; M.F. Hawthorne et al.,Proc. Natl. Acad. Sci. USA, 89, 9039 (1992). 27. (a) J.L. Fauchere; O. Leukart; A. Eberle and R. Schwyzer, Helv. Chim. Acta, 62, 1382 (1979). (b) J. Malmqist and S. Sjoberg, Tetrahedron, 52, 9207 (1996).
34. W.H. Sweet; A.H. Soloway and G.L. Brownell,Acta Union Int. Contre Cancer, 16, 1216 (1960).
35. D.A. Allen and T.D. Beynon,Phys. Med. Biol., 40, 807 (1995).
36. J.A. Coderre; M.S. Makar; P.L. Micca et al., Abstracts of the Fifth International Symposium on Neutron Capture Therapy for Cancer; Columbus, OH, 1992.
37. T. Hartman and J. Carllson,Radiother. Oncol., 31, 61 (1994).
38. P.J. Perry; M.A. Read; R.T. Davies et al.,J. Med. Chem., 42, 2679 (1999).
39. P.J. Perry; A.P. Reszka; A.A. Wood et al., J. Med. Chem., 41, 4873 (1998)
40. K. Vyakaranam; G. Rana; J.A. Maguire and N.S. Hosmane, Organometallics, 21, 3905 (2002)
41. F. Wellmann; R. Abraham; R. Muller and D. Gabel, Z. Naturforsch. C, 46, 252 (1991).
42. M. Miura; D. Gabel; G. Oenbrink and R.G. Fairchild, Tetrahedron Lett., 31, 2247 (1990).
43. F. Li; K. Shelly; R.R. Kane et al.,J. Am. Chem. Soc., 118, 6506 (1996).
44. R.A. Watson-Clark; C.B. Knobler and M.F. Hawthorne, Inorg. Chem., 35, 2963 (1996).
45. F. Haslinger and A.H. Soloway,J. Med. Chem., 9, 792 (1966).
46. W. Tjarks;H.Ghaneolhosseini; C.L.A. Henssen et al.,Tetrahedron Lett., 37, 6905 (1996).
47. K. Yoshino; T. Maruyama; H. Takahashi et al., Advances in Neutron Capture Therapy; Plenum Press, New York, 1993.
48. Y. Mori; A. Suzuki; K. Yoshino and H. Kakihana,Pigment Cell Res., 2, 273 (1989).
49. H. Nemoto; S. Iwamoto;H.Nakamura and Y. Yamamoto,Chem. Lett., 22, 465 (1993).
50. B.F. Spielvogel; A.T. McPhail; M.K. Das and I.H. Hall,J. Am. Chem. Soc., 102, 6343 (1980).
51. K.H. Scheller; R.B. Martin; B.F. Spielvogel and A.T. McPhail,Inorg. Chim. Acta, 57, 227 (1982)
52. W. Karnbrock; H.J. Musiol and L. Moroder, Tetrahedron, 51, 1187 (1995).
53. S. Sjoberg; M.F. Hawthorne; P. Lindstrom et al., In Advances in Neutron Capture Therapy; Soloway, A.H., Barth, R.F. and Carpenter, D.E., Eds.; Plenum Press, New York, Vol. 5, 1993, pp. 269-272.
54. I.M. Wyzlic and A.H. Soloway, Tetrahedron Lett., 33, 7489 (1992).
55. P.A. Radel and S.B. Kahl, J. Org. Chem., 61, 4582 (1996).
56. J.K. Prashar and D.E. Moore, J. Chem. Soc., Perkin. Trans., 1051 (1993).
57. Y. Yamamoto, Pure Appl. Chem., 63, 423 (1991).
58. G. Palmisano and M. Santagostino, Tetrahedron, 49, 2533 (1993).
59. A.H. Soloway; A.K.M. Anisuzzaman; F. Alam et al.,Pure Appl. Chem., 63, 411 (1991).
60. B. Selverstone; W.H. Sweet and C. Robinson,Ann. Surg., 130, 643 (1949).
61. K.C. John; A. Kaczmarczyk and A.H. Soloway,J. Med. Chem., 12, 54 (1969).
62. D.S. Matteson and T.C. Cheng,J. Org. Chem., 33, 3055 (1968).
63. K. Shelly; M.F. Hawthorne and C.B. Knobler, Inorg. Chem., 31, 2889 (1992).
64. G. Rana; K. Vyakaranam; S.C. Ledger et al., Appl. Organomet. Chem., 17, 361 (2003).
65. H. Fleish, Drugs., 42, 919 (1991).
66. G. Rana; K. Vyakaranam; B.F. Spielvogel et al., Inorg. Chim. Acta, 344C, 249 (2003).
67. A.E. Pegg and P.P. McCann, Am. J. Physiol., C212 (1982).
68. C.W. Tabor and H. Tabor, Annu. Rev. Biochem., 53, 749 (1984).
69. B.K. Chang; P.R. Libby; R.J. Bergeron and C.W. Porter,Biochem. Biophys. Res. Commun., 157, 264 (1988).
70. P.A. Stark; B.D. Thrall; G.G. Meadows and M.M. Abdel-Monem,J. Med. Chem., 35, 4264 (1992).
71. J.L.A. Mitchell; R.R. Diveley and A. Bareyal-Leyser,Biochem. Biophys. Res. Commun., 186, 81 (1992).
72. N.A. Khan; V. Quemener and J.-P. Moulinoux,Cell Biol. Int. Rep., 15, 9 (1991).
73. J.C. Zhuo; J. Cai; A.H. Soloway et al., J. Med. Chem., 42, 1282 (1999).
74. J. Cai; A.H. Soloway; R.F. Barth et al., J. Med. Chem., 40, 3887 (1997).
75. J.R. Mangiardi, In Brain Tumors: An Encyclopedic Approach. Kaye, A.H. and Laws, E.R. Jr, Eds; Churchill Livingstone, Edinburgh, p. 99, 1995.
76. T. Peymann, Sauerstoff und Schwefel am Undecahydro-closo-dodecaborate (2-) als Nucleophile; Ph.D. Thesis, University of Bremen, Germany, 1995.
77. M.F. Hawthorne,Pure Appl. Chem., 63, 327 (1991).
78. Y.K. Ho; R.G. Smith; M.S. Brown and J.L. Goldstein,Blood, 52, 1099 (1978).
79. S.B. Kahl, Proceedings of the Workshop of the Radiation Research Program of NCI; Annapolis, Maryland and Zink, S., Eds; National Cancer Institute, Bethesda, MD; March 3-4, 1988.
80. M. Kallio; J. Callaway; E. Saario and S. Kahl, Cancer Neutron Capture Therapy, Mishima, Y., Ed.; Plenum Press, New York, 1996.
81. P. Lemmen and B. Werner,Chem. Phys. Lipids, 62, 185 (1992).
82. K.A. Kennedy,Anticancer Drug Des., 2, 181 (1987).
83. M. Scobie and M.D. Threadgill, J. Chem. Soc., Perkin. Trans., 203 (1994).
84. P.J. Wood; M. Scobie and M.D. Threadgill,Int. J. Radiat. Biol., 70, 587 (1996).
85. D.H. Swenson; B.H. Laster and R.L. Metzger,J. Med. Chem., 39, 1540 (1996).
86. J.R. Whittaker,J. Biol. Chem., 111, 6217 (1971).
87. W. Tjarks, Borhaltige Thioharnstoffe in der Neutroneneinfangtherapie; Ph.D. Thesis, University of Bremen, Germany, 1989.
88. B.S. Larsson; K. Olander; L. Dencker and L. Br. Holmquist,J. Cancer, 46, 538 (1982).
89. R.G. Fairchild; D. Greenberg; K.P. Watts et al.,Cancer Res., 42, 556 (1982).
90. T. Nakagawa and K. Aono,Chem. Pharm. Bull., 24, 778 (1976).
91. T. Rosenblum and A. Stein, Biochem. Biopharmacol., 12, 1453 (1963).
92. M.I. Phillips, Ed., Antisense Technology Part A: General Methods, Methods of Delivery and RNA Studies; Methods in Enzymology 313; Academic Press, New York, 226, 2000.
93. M.I. Phillips, Antisense Technology Part B: Applications; Methods in Enzymology 314; Academic Press, New York, 237, 1999.
94. E. Uhlman and A. Peyman, Chem. Rev., 90, 543-548 (1990).
95. R.W. Wagner, Nature, 372, 333-335 (1994).
96. J.F. Milligan; M.D. Matteucci and J.C. Martin, J. Med. Chem., 36, 1923-1937 (1993).
97. Z.J. Lesnikowski and R.F. Schinazi,J. Org. Chem., 58, 6531 (1993).
98. B.F. Spielvogel; W. Powell and A. Sood,Main Group Met. Chem., 19, 699 (1996).
99. B.F. Spielvogel; G. Rana; K. Vyakaranam et al.,Collect. Czech. Chem. Commun., 67, 1095 (2002).
100. K. Vyakaranam; G. Rana; B.F. Spielvogel et al., Nucleosides Nucleotides Nucleic Acids, 21, 581 (2002).
101. K. Vyakaranam and N.S. Hosmane, Bioinorg. Chem. Appl., 2, 31 (2004).
102. F. Sweet,Steroids, 37, 223 (1981).
103. F. Wellmann and D. Gabel, Proc. First Int. Symp. Neutron Capture Ther; Brookhaven Natl. Lab. BNL, BNL 51730, 1983.
104. L. Schneiderova; O. Strouf; B. Gruner et al.,Collect. Czech. Chem. Commun., 57, 463 (1992).
105. M.F. Hawthorne, Cancer Neutron Capture Therapy, Mishima, Y., Ed.; Plenum Press, New York, 1996.