Abstract
Although boron neutron capture therapy (BNCT) is currently in clinical trials in several countries around the world, the continued development of BNCT for the treatment of cancer patients is dependent on the production of new compounds which exhibit biological characteristics exceeding that of the currently utilized disodium mercaptoundecahydro-closo-dodecaborate (BSH) or para-boronophenylalanine (p-BPA). Specifically, the compounds being developed should have an enhanced tumor uptake and retention, as well as exhibit a higher degree of specificity, particularly in terms of the tumor to blood boron ratio and tumor to normal brain boron ratio. Additionally, the degree of enhancement must be sufficiently significant to invest the resources necessary to produce the quantities required for clinical trials. Thorough reviews of the development of boron-containing compounds for application in BNCT have been published in recent years.1,2 The focus of this review is the research which has been accomplished since the Seventh International Symposium on Neutron Capture Therapy for Cancer, held in Zurich, Switzerland in September, 1996.
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M.F. Hawthorne, “The Role of Chemistry in the Development of Boron Neutron Capture Therapy of Cancer,” Angew. Chem. Int. Ed. Engl. 32:950–984, 1993.
A.H. Soloway, W. Tjarks, B.A. Barnum, F. Rong, R.F. Barth, I.M. Codogni, and J.G. Wilson, Chem. Rev. 98:1515–1562, 1998.
E. Binello, S. Shortkroff, A.G. Jones, C. Viveiros, G. Young, A. Davison, C.B. Sledge, and J.C. Yanch, In vitro Analysis of 10B Uptake for Boron Neutron Capture Synovectomy,” in: Advances in Neutron Capture Therapy: Vol. II, Chemistry and Biology,” B. Larsson, J. Crawford, and R. Weinrich, ed., Elsevier, Netherlands, pp. 609–613, 1997.
G.E. Laramore, “The Use of Neutrons in Cancer Therapy: A Historical Perspective Through the Modern Era,” Seminars in Oncology, 24(6):672–685, 1997.
H. Nemoto, J. Cai, N. Asao, S. Iwamoto, and Y. Yamamoto, Synthesis and Biological Properties of Water-Soluble p-Boronophenylalanine Derivatives. Relationship between Water Solubility, Cytotoxicity, and Cellular Uptake, J. Med. Chem. 38, 1673–1678, 1996.
M. Takagaki, K. Ono, Y. Oda, H. Kikuchi, H. Nemoto, S. Iwamoto, J. Cai, and Y. Yamamoto, “Hydroxylforms of P-Boronophenylalanine as Potential Boron Carriers on Boron Neutron Capture Therapy for Malignant Brain Tumors,” Cancer Research 56:2017–2020, 1996.
A.H. Soloway, H. Hatanaka, and M.A. David, J. Med. Chem. 10:714, 1967.
T. Peymann, C.B. Knobler, and M.F. Hawthorne, unpublished results.
J. Cai, and A.H. Soloway, “Synthesis of Carboranyl Polyamines for DNA Targeting,” Tetrahedron Letters, 37(52):9283–9286, 1996.
J. Cai, A.H. Soloway, R.F. Barth, D.M. Adams, J.R. Hariharan, I.M. Wyzlic, and K. Radcliffe, “Boron-Containing Polyamines as DNA Targeting Agents for Neutron Capture Therapy of Brain Tumors: Synthesis and Biological Evaluation,” J. Med. Chem. 40:3887–3896, 1997.
A.H. Soloway, unpublished results.
H. Ghaneolhosseini, W. Tjarks, and S. Sjoberg, “Synthesis of Novel Boronated Acridines and Spermidines as Possible Agents for BNCT,” Tetrahedron, 54(15):3877–3884, 1998.
R.R. Srivastava, R.R. Singhaus, and G.W. Kabalka, “l-Amino-3-[2-(1,7-dicarba-closo-dodecaboran(12)-l-yl)ethyl]cyclobutanecarboxylic Acid: A Potential BNCT Agent,” J. Org. Chem. 62:4476–4478, 1997.
R.R. Srivastava, and G.W. Kabalka, “Syntheses of l-Amino-3-[2-(7-(2-hydroxyethyl)-1,7-dicarba-closo-dodecaboran(12)-l-yl)ethyl]cyclobutanecarboxylic Acid and Its nido-Analogue: Potential BNCT Agents,”J. Org. Chem. 62:8730–8734, 1997.
R.R. Srivastava, and G.W. Kabalka, unpublished results.
K. Shelly, D.A. Feakes, M.F. Hawthorne, P.G. Schmidt, T.A. Krisch, and W.F. Bauer, “Model Studies Directed Toward the Boron Neutron-Capture Therapy of Cancer: Boron Delivery to Murine Tumors with Liposomes,” Proc. Natl. Acad. Sci. USA, 89:9039–9043, 1992.
D.A. Feakes, K. Shelly, C.B. Knobler, and M.F. Hawthorne, “Na3[B20H17NH3]: Synthesis and Liposomal Delivery to Murine Tumors,” Proc. Natl. Acad. Sci. USA, 91:3029–3033, 1994.
D.A. Feakes, K. Shelly, and M.F. Hawthorne, “Selective Boron Delivery to Murine Tumors By Lipophilic Species Incorporated in the Membranes of Unilamellar Liposomes,” Proc. Natl. Acad. Sci. USA, 92:1367–1370, 1995.
F. Li, K. Shelly, C.B. Knobler, and M.F. Hawthorne, “Formation of a Novel Amidinium-Bridged Polyhedral Borane Ion by Incorporation of an Acetonitrile Solvent Molecule,” Angew. Chem. Int. Ed. 37(13–14):1865–1867, 1998.
F. Li, K. Shelly, C.B. Knobler, and M.F. Hawthorne, “A New Isomer of the [B20H18]2- Ion: Synthesis, Structure, and Reactivity of cis-[B20H18]2- and cis-[B20H17NH3]-,” Angew. Chem. Int. Ed. 37(13–14):1868–1871, 1998.
D.A. Feakes, F.R. Harris, D.K. Hathaway, and V.S. Morton, “Preparation of Hydrophilic Boron-Containing Compounds for Incorporation into Liposomes,” in: Advances in Neutron Capture Therapy: Vol. II, Chemistry and Biology, B. Larsson, J. Crawford, and R. Weinrich, ed., Elsevier, Netherlands, pp. 95–100, 1997.
D.A. Feakes, R.C. Waller, D.K. Hathaway, and V.S. Morton, unpublished results.
N.S. Hosmane, A. Franken, G. Zhang, R.R. Srivastava, R.Y. Smith, and B.F. Spielvogel, “Synthesis and Crystal Structure of a Novel Fused Polyhedral Borane Dianion, [B22H22]2-: Potential Precursor for Use in Boron Neutron Capture Therapy (BNCT) of Cancer,” Main Group Metal Chemistry, 21(6):319–324, 1998.
R.G. Fairchild, S.B. Kahl, B.H. Laster, J. Kalef-Ezra, and E.A. Popenoe, Cancer Res. 50:4860, 1990.
S. Ruf, J. Osterloh, and D. Gabel, unpublished results.
Y. Yamamoto, “New Reactions of Carboranes and Synthesis of a Carborane-Gadolinium Complex for BNCT,” Special Publication of the Royal Society of Chemistry (Advances in Boron Chemistry), 201:281–288, 1997.
G.E. Laramore, P. Wootton, J.C. Livesey, D.S. Wilbur, R. Risler, M. Phillips, J. Jacky, T.A. Buchholz, T.W. Griffin, and S. Brossard, “Boron Neutron Capture Therapy: A Mechanism for Achieving A Concomitant Tumor Boost in Fast Neutron Radiotherapy,” Int. J. Radiation Oncology Biol. Phys. 28(5): 1135–1142, 1994.
K.J. Stelzer, P.R. Gavin, R. Risler, H. Kippenes, M.F. Hawthorne, D.W. Nigg, and G.E. Laramore, unpublished results.
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Feakes, D.A. (2001). Chemistry and Pharmacology of Agents for BNCT. In: Hawthorne, M.F., Shelly, K., Wiersema, R.J. (eds) Frontiers in Neutron Capture Therapy. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-1285-1_3
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DOI: https://doi.org/10.1007/978-1-4615-1285-1_3
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