Abstract
The application of the cytotoxic 10B neutron-capture reaction [10B(n,α)7Li] to the treatment of human tumors has received much attention in recent years. The interaction of boron-10 isotope and thermal neutron produces an α-particle and recoils a lithium-7 ion bearing approximately 2,4 MeV (Eq. 1).
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
H. Hatanaka, “Boron Neutron Capture Therapy for Tumors,” Nishimura Co. Ltd., Niigata, Japan, 1986.
A.H. Soloway, R.F. Barth, and D.E. Carpenter, “Advances in Neutron Capture Therapy,” Plenum, New York, 1993.
Y. Mishima, C. Honda, M. Ichihashi, H. Ohara, J. Hiratsuka, N. Fukuda, H. Karashima, T. Kobayashi, K. Kanda, and K. Yoshino, Treatment of malignant melanoma by single neutron capture treatment with melanoma-seeking 1°B compound, Lancet 388, 1989.
For an excellent review, M.F. Hawthorne, The role of chemistry in the development of boron neutron capture therapy, Angew Chem. Int. Ed. Engl. 32: 950, 1993.
(a) A.K.M. Anisuzzaman, F. Alam, and A.H. Soloway, Synthesis of a carboranyl nucleoside for potential use in neutron capture therapy of cancer, Polyhedron 9: 891, 1990.
(b) 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.
(c) R.C. Reynolds, T.W. Trask, and W.D. Sedwick, 2,4- dichloro-5-(1-o-carborany]methyl)-6-methylpyrimidine: A potential synthon for 5-(l-o- Carboranylmethyl)pyrimidines, J. Org. Chem. 56: 2391, 1991.
(a) T.K. Liao, E.C. Podrebarac, and C.C. Cheng, Boron-substituted pyrimidines, J. Am. Chem. Soc. 86: 1869, 1964.
(b) R.F. Schinazi, and W.H. Prusoff, Synthesis and properties of boron and silicon substituted uracil or 2’-Deoxyuridine, Tetrahedron Lett. 4981, 1978; Synthesis of 5-(Dihydroxybory1)-2’-deoxyuridine and related boron-containing pyrimidines, J. Org. Chem. 50: 841, 1985.
(c) Y. Yamamoto, T. Seko, and H. Nemoto, A new method for the synthesis of boron-10 containing nucleoside derivatives for neutron capture therapy via palladium catalyzed reaction, J. Org. Chem. 54: 4734, 1989.
(d) Y. Yamamoto, T. Seko, F. Rong, and H. Nemoto, Boron-10 carriers for NCT. A new synthetic method via condensation with aldehydes having boronic moiety, Tetrahedron Lett. 30: 7191, 1989.
(e) Y. Yamamoto, Molecular design and synthesis of B-10 carriers for neutron capture therapy, Pure Appl. Chem. 63: 423, 1991.
(a) B.F. Spielvogel, A. Sood, B.R. Shaw, and I.H. Hall, From boron analogues of amino acids to boronated DNA: potential new pharmaceuticals and neutron capture agents, Pure Appl. Chem. 63: 415, 1991.
(b) A. Sood, B.R. Shaw, and B.F. Spielvogel, Boron-containing nucleic acids. 2. Synthesis of oligodeoxynucleoside boranophosphates, J. Am. Chem. Soc. 112: 9000, 1990.
(c) J. Tomasz, B.R. Shaw, K. Porter, B.F. Spielvogel, and A. Sood, 5’-P-Borane-substituted thymidine mono-phosphate and triphosphate, Angew. Chem. Int. Ed. Engl. 31: 1373, 1992.
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, 1989.
(a) W. Tjarks, and D. Gabel, Boron-containing thiouracil derivatives for neutron-capture therapy of melanoma, J. Med. Chem. 34: 315, 1991.
(b) H. Ketz, W. Tjarks, and D. Gabel, Synthesis ofnido-carborate containing thioureas, Tetrahedron Lett. 31: 4003, 1990.
T. Nakagawa, and K. Ando, Syntheses of chlorpromazine undecahydrododecaborate and nonahydrodecaborate — Promising agents for neutron capture therapy of malignant melanoma, Chem. Pharm. Bull. 24: 778, 1976.
J.K. Prashar, D.E. Moore, J.G. Wilson, and B.J. Allen, Synthesis of carborany]- phenylalanine for potential use in neutron capture therapy, Advances in Neutron Capture Ther, Ed. A.H. Soloway, R.F. Barth, and D.E. Carpenter, Plenum, New York, p 265, 1993.
F. Wellmann, R. Abraham, R. Mller, and D. Gabel, Synthesis and Biological Behavior of a boronated analogue of the antiestrogen U 23,469-M, Z. Naturforsch. 46: 252, C1991.
(a) M. Miura, D. Gabel, G. Oenbrink, and R.G. Fairchild, Preparation of carboranyl porphyrins for boron neutron capture therapy, Tetrahedron Lett. 31: 2247, 1990.
(b) S.B. Kahl, and M.-S. Koo, Synthesis of tetrakis-carborane-carboxylate esters of 2,4- bis-(a,(3-dihydroxyethyl)-deuteroporphyrin IX, J. Chem. Soc. Chem. Commun., 1769, 1990.
(a) R.R. Kane, R.H. Pak, and M.F. Hawthorne, Solution-phase segment. synthesis of boron-rich peptides, J. Org. Chem. 58: 991, 1993.
(b) R.R. Kane, C.S. Lee, K. Drechsel, and M.F. Hawthorne, Solution-phase synthesis of boron-rich phosphates, J. Org. Chem. 58: 3227, 1993.
(c) R.R. Kane, K. Drechsel, and M.F. Hawthorne, Automated syntheses of carborane-derived homogeneous oligophosphates: Reagents for use in the immunoprotein-mediated boron neutron capture therapy (BNCT) of cancer, J. Am. Chem. Soc. 115: 8853, 1993.
(a) A.D. Whittaker, D.P. Kelly, M. Pardee, and R.F. Martin, Synthesis of 1°B- and I57Gd-labelled DNA ligands for neutron capture therapy, Progress in Neutron Capture Thee. Cancer, Ed. B.J. Allen, D.E. Moore, and B.V. Harrington, Plenum, New York, p 231, 1992.
(b) A. Corder, R.F. Martin, A. Whittaker, D.P. Kelly, H. Meriaty, and B.J. Allen, Evaluation of a 10B-labelled DNA ligand, Advanced in Neutron Capture Thee, Ed. A.H. Soloway, R.F. Barth, and D.E. Carpenter, Plenum, New York, p 377, 1993.
For example, see R.S. Youngquist, and P.B. Dervan, Sequence-specific recognition of B-DNA by oligo(N-methylpyrrolecarboxamide)s, Proc. Natl. Acad. Sci. USA, 82: 2565, 1985.
E. Nishiwaki, S. Tanaka, H. Lee, and M. Shibuya, Efficient synthesis of oligo-N- methylpyrrolecarboxamides and related compounds, Heterocycles 27: 1945, 1988.
(a) H. Nemoto, J.G. Wilson, H. Nakamura, and Y. Yamamoto, Polyols of a cascade type as a water-solubilizing element of carborane derivatives for boron neutron capture therapy, J. Org. Chem. 57: 435, 1992.
(b) H. Nemoto, J. Cai, and Y. Yamamoto, Synthesis of a water-soluble o-Carborane bearing a uracil moiety via a palladium-catalyzed reaction under essentially neutron conditions, J. Chem. Soc. Chem. Commun. 577, 1994.
R.C. Haushalter, W.H. Butler, and R.W. Rudolph, The preparation and characterization of several meso-tetracarbonylporphyrins, J. Am. Chem. Soc. 103: 2620. 1981.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1996 Springer Science+Business Media New York
About this chapter
Cite this chapter
Yamamoto, Y., Cai, J., Nakamura, H., Sadayori, N., Nemoto, H. (1996). Netropsin and Distamycin Analogues Bearing Ortho-Carborane. In: Mishima, Y. (eds) Cancer Neutron Capture Therapy. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9567-7_25
Download citation
DOI: https://doi.org/10.1007/978-1-4757-9567-7_25
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4757-9569-1
Online ISBN: 978-1-4757-9567-7
eBook Packages: Springer Book Archive