Karborany i metalokarborany. Część 1, Karborany

Olejniczak, A.

Artykuł - szczegóły

Tytuł artykułu

Karborany i metalokarborany. Część 1, Karborany

Autorzy

Olejniczak A.

Wybrane pełne teksty z tego czasopisma

Identyfikatory

Warianty tytułu

Carboranes and metallacarboranes. Part 1, Carboranes

Języki publikacji

Abstrakty

Polyhedral clusters containing boron, alone or in combination with other elements, have been know for nearly a century and intensive studies of their structures, bonding, and reactivity have been under way for more than half that period. Carboranes are boron cage system in which one or more carbon atoms belong as an integral part to an electron-delocalized borane framework. The term "carboranes" includes both closed polyhedral and open-cage structures. Polyhedral carboranes of general formula C2Bn-1Hn have been characterized from n=2 to n=12. One of the most striking features of the carboranes is the capability of the two carbon atoms and ten boron atoms to adopt the icosahedral geometry in which the carbon and boron atoms are hexacoordinate. This feature of the icosahedral structure gives rise to the unusual properties of these molecules and their derivatives. Because of their unique physical and chemical properties, carboranes have been used to prepare catalysts, radiopharmaceuticals, polymers and an assortment of coordination compounds and materials for nanotechnology. The medicinal chemistry of carboranes is centered on their use in boron neutron capture therapy of tumors (BNCT).

Słowa kluczowe

karborany nazewnictwo właściwości fizykochemiczne zastosowanie karboranów

carboranes physical properties chemical properties

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2004

Tom

[Z] 58, 11-12

Strony

895--913

Opis fizyczny

Bibliogr. 103 poz., rys.

Twórcy

autor

Olejniczak A.

Laboratorium Wirusologii Molekularnej i Chemii Biologicznej, Centrum Biologii Medycznej PAN, ul. Lodowa 106, 93-232 Łódź

Bibliografia

[1] Z.J. Leśnikowski, R.F. Schinazi, Pol. J. Chem., 1995,69, 827.
[2] M.F. Hawthorne, Angew. Chem. Int. Ed. Engl., 1993,32, 950.
[3] R.F. Barth, R.G. Fairchild, R.M. Brugger, Boron Neutron Capture Therapy of Cancer: Present Realities and Future Prospects in Cancer Therapy into Twenty First Century, 1992, Huber B.S. Ed., Ventura Publishing Co., Inc.
[4] Y. Shibata, A. Matsumura, T. Yamamoto, H. Akutsu, S. Yasuda, K. Nakai, T. Nose, K Yamamoto, H. Kumada, N. Hori, S. Ohtake, Anticancer Res., 2003,23, 5231.
[5] H.E. Wang, A.H. Liao, W.P. Deng, P.F. Chang, J.C. Chen, F.D. Chen, R.S. Liu, J.S. Lee, J.J. Hwang, J. Nucl. Med., 2004, 45, 302.
[6] G. Peacock, R. Sidwell, G. Pan, S. Ole, D.R. Lu, J. Pharm. Sci., 2004, 93, 13.
[7] Y. Endo, T. Iijima, Y. Yamakoshi, H. Fukasawa, C. Miyaura, M. Inada, A. Kubo, A. Itai, Chem. Biol., 2001, 8, 341.
[8] K. Yamamoto, Y. Endo, Bioorg. Chem. Lett., 2 001,11,2389.
[9] B. Spielvogel, V. Povell, A. Sood, Main Group Met. Chem., 1996,19, 699.
[10] S.J. Hurwitz, L. Ma, A. Eleuteri, J. Wright, J. Moravek, R. F. Schinazi, Nucleos. Nucleot., 2000, 19, 691.
[11] Z.J. Leśnikowski, J. Shi, R.F. Schinazi, J. Organomet. Chem. 1999,581,156.
[12] J.L. Maurer, A J. Serino, M.F. Hawthorne, Organometallics, 1988, 7 ,2519.
[13] G.B. Giovenzana, L. Lay, D. Monti, G. Palmisano, L. Panza, Tetrahedron, 1999, 55, 14123.
[14] A.H. Soloway, W. Tjarks, B.A. Bamum, F.G. Rong, F.R. Barth, I.M. Codogni, J.G. Wilson, Chem. Rev., 1998,98, 1515.
[15] H.P. Hogenkamp, D.A. Collins, D. Live, L.M. Benson, S. Naylor, Nucl. Med. Biol., 2000, 27, 89.
[16] J. Cai, A.H. Soloway, R.F. Barth, D.M. Adams, J.R. Hariharan, I.M. Wyzlic, K. Radcliffe, J. Med. Chem., 1997,40, 3887.
[17] J.C. Zhuo, J. Cai, A.H. Soloway, R.F. Barth, D.M. Adams, W. Ji, W. Tjarks, J. Med. Chem., 1999, 42, 1282.
[18] K.Y. Rho, YJ. Cho, C.M. Yoon, H. Nakamura, Tetrahedron Lett., 1999,40, 4821.
[19] I.M. Wyzlic, A.H. Soloway, Tetrahedron Lett., 1992,33, 7489.
[20] RA. Radel, S.B. Kahl, J. Org. Chem., 1996,61,4582.
[21] G. Oros, I. Ujvaiy, R.J. Nachman, Amino Acids, 1999,17,357.
[22] W. Tjarks, A.K.M. Anisuzzaman, L. Liu, A.H. Soloway, R.F. Barth, D.J. Perkins, D.A. Adams, J. Med. Chem., 1992, 35, 1628.
[23] R-F. Schinazi, Z.J. Leśnikowski, Nucleos. Nucleot., 1998,17, 635.
[24] A.B. Olejniczak, M. Koziolkiewicz, Z.J. Leśnikowski, Antisense Nucl. Acid Drug Dev., 2002 12, 79.
[25] Z.J. Leśnikowski, Eur. J. Org. Chem., 2003,23,4489.
[26] B. Štibr, Chem. Rev., 1992,92, 225.
[27] R.N. Grimes, Carboranes, Academic Press, Inc, New York 1970.
[28] E. Pruchnik, Chemia metaloorganiczna. Pierwiastki przejściowe. PWN, Warszawa 1991.
[29] B. Gruner, Z. Plzak, J. Chromatogr. A, 1997,789,497.
[30] R.N. Grimes, Angew. Chem. Int. Ed. Engl, 2003,42, 1198.
[31] R.E. Williams, Chem. Rev., 1992, 92, 177.
[32] J. Casanova, The Borane, Carborane, Carbocation Continuum, John Willey and Sons, Inc, New York 1998.
[33] S. Hermanek, Chem. Rev., 1992,92, 325.
[34] W. Siebert, C.J. Maier, A. Maier, P. Greiwe, M.J. Bayer, M. Hofmann, H. Pritzkow, Pure Appl. Chem., 2003, 75, 1277.
[35] T. Dodge, M.A. Curtis, J.M. Russell, J. Am. Chem. Soc., 2000,122, 10573.
[36] K.E. Stockman, E.A. Boring, M. Sabat, M.G. Finn, R.N. Grimes, Organometallics, 2000,19,2200
[37] N.S. Hosmane, Pure Appl. Chem., 2003, 75, 1219.
[38] H. Yan, A. M. Beatty, T.P. Fehlner, J. Am. Chem. Soc., 2003,125, 16367.
[39] V.l. Bregadze, Chem. Rev., 1992, 92, 209.
[40] W. Mizerski, Tablice Chemiczne, Wydawnictwo Adamantan, Warszawa 1993.
[41] T.L. Heying, J.W. Ager, S.L. Clark, D.J. Mangold, H.L. Goldstein, M. Hillman, R.J. Polak, J.W. Szymański, Inorg. Chem., 1963, 2, 1089.
[42] M.M. Fein, J. Bobiński, N. Mayes, N. Schwartz, M.S. Cohen, Inorg. Chem., 1963,2, 1111.
[43] L.I. Zakharkin, V.l. Stańko, V.A. Brattsev, Y.A. Chapovskii, Y.T. Struchov, Izv. Akad. Nauk. SSSR. Ser. Khim., 1963, 2, 2069.
[44] L.I. Zakharkin, V.l. Stańko, V.A. Brattsev, Y.A. Chapovskii, O.Y. Okhlobystin, Izv. Akad. Nauk. SSSR. Ser. Khim., 1963,12, 2238.
[45] D. Grafstein, J. Bobiński, J. Dvorak, J.E. Paustian, H.F. Smith, S. Karlan, C. Vogel, M.M. Fein, Inorg. Chem., 1963, 2, 1120.
[46] R. Hoomann, W. N. Lipscomb, Inorg. Chem., 1963, 2, 231.
[47] S. Papetti, T.L. Heying, J. Am. Chem. Soc., 1964,86,2295.
[48] H.D. Kaesz, R. Bau, H.A. Beall, W.N. Lipscomb, J. Am. Chem. Soc., 1967,89,4218.
[49] B.F.G. Johnson, Y.V. Roberst, E. Parisini, Inorg. Chim. Acta, 1993,211, 17.
[50] L.I. Zakharkin, V.S. Kirillova, Izv. Akad. Nauk. SSSR. Ser. Khim., 1975,11,2596.
[51] H. Tomita, H. Luu, T. Onak, Inorg. Chem., 1 9 9 1,30,812.
[52] L.I. 7nl-wirin V.N. Kalinin, V.V. Gedymin, J. Oiganomet. Chem., 1969,16, 371.
[53] R.A. Kasar, G.M. Knudsen, S B. Kahl, Inorg. Chem., 1999,38, 2936.
[54] M.F. Hawthorne, D.C. Young, P.M. Garrett, D.A. Owen, S.G. Schwerin, F.N. Tebbe, P.A. Wegner, J. Am. Chem. Soc., 1968,90, 862.
[55] J.J. Schaeck, S. B. Kahl, Inorg. Chem., 1999,38, 204.
[56] S. Sjoberg, Advances in Neutron Capture Therapy. Vol. II, Chemistry and Biology, Proceeding of the Seventh International Symposium on Neutron Capture Therapy of Cancer, J. Larsson, R Crawford, R. Weinreich, Ed., Elsevier, Amsterdam 1997, 3-21.
[57] E.C. Reynhardt, J. Mag. Reson., 1986,69, 337.
[58] M.G. Davidson, T.G. Hibbert, J.A.K. Howard, A. Mackinnon, K. Wade, Chem. Commun., 1996, 2285.
[59] L.A. Leites, Chem. Rev., 1992, 92, 279.
[60] H. Nakamura, K. Aoyagi, Y. Yamamoto, J. Org. Chem., 1997, 62, 780.
[61] R.N. Grimes, J. Chem. Educ., 2004, 81, 657.
[62] P. Kaszyński, J. Huang, G.S. Jenkins, K.A. Bairamov, D. Lipiak, Mol. Cryst. Liq. Cryst., 1995, 260,315.
[63] P. Kaszyński, A.G. Douglass, J. Organometal. Chem., 1999 ,581, 28.
[64] J. Piesek, Chem. Rev., 1992,92,269.
[65] D.K. McLemore, D.A. Dixon, S.H. Strauss, Inorg. Chim. Acta, 1999, 294, 193.
[66] M.F. Hawthorne, A. Madema, Chem. Rev., 1999, 99,3421.
[67] B. Larsson, J. Crawford, R. Weinreich, Ed., Advances in Neutron Capture Therapy, Vol. II, Chemistry and Biology, Proc. Seventh International Symposium on Neutron Capture Therapy of Cancer, Elsevier, Amsterdam 1997.
[68] J.F. Valliant, KJ. Guenther, A.S. King, P. Morel, P. Schaffer, O.O. Sogbein, K.A. Stephenson, Coord. Chem. Rev., 2002,232, 173.
[69] S. Sjobeig, J. Carlsson, H. Ghaneolhosseini, L. Gedda, T. Hartman, J. Malmquist, C. Naeslund, P. Olsson, W. Tjarks, J. Neurooncol., 1997,33,41.
[70] M.R Hawthorne, M.W. Lee, J. Neurooncol. 2003, 62, 33.
[71] L. Maurer, R Berchier, AJ. Serino, C.B. Knobler, M.F. Hawthorne, J. Oxg. Chem., 1990,5,838
[72] L.R Hetze, U. Bothe, Chem. Eur. J., 1998,4,1179.
[73] L.R Tietze, U. Bothe, U. Griesbach, M. Nakaichi, T. Hasegawa, H. Nakamura, Y. Yamamoto, Bioorg. Med. Chem.,2001,9,1747.
[74] LJF. Tietze, U. Bothe, I. Schuberth, Chem. Eur. J., 2000, 6, 836.
[75] L.F. Tietze, U. Bothe, U. Griesbach, M. Nakaichi, T. Hasegawa, H. Nakamura, Y. Yamamoto, ChemBioChem., 2001,2, 326.
[76] T.F. Dougherty, Crit. Rev. Oncol. Hematol., 1984, 2, 83.
[77] R.K. Pandey, F.-Y. Shiau, C J. Medforlh, T.J. Dougherty, K. M. Smith, Tetrahedron Lett., 1990,31, 789.
[78] M.F. Isaac, S.B. Kahl, J. Organomet. Chem., 2003,680,232.
[79] T. Hartman, J. Carlsson, Radiother. Oncol., 1992, 31, 61.
[80] L. Gedda, H. Ghaneolhosseini, P. Nilsson, K. Nyholm, J. Pettersson, S. Sjoberg, J. Carlsson, Anti-Cancer Drug. Des., 2 000,15,277.
[81] A.K.M. Anisuzzaman, F. Alam, A.S. Soloway, Polyhedron, 1990,9, 891.
[82] W. Tjarks, A.K.M. Anisuzzaman, L. Liu, A.H. Soloway, RF. Barth, D.J. Perkins, D.M. Adams, J. Med. Chem., 1992,35, 1628.
[83] Y. Yamamoto, T. Seko, H. Nakamura, H. Nemoto, H. Hojo, N. Mukai, Y. Hashmioto, J. Chem. Soc. Chem. Commun., 1992,157.
[84] R.F. Schinazi, N. Goudgaon, J. Soria, D. C. Liotta, 5th International Symposium on Neutron Capture Therapy, Columbus, OH, Sept. 13-17, 1992, 11.
[85] Y. Yamamoto, H. Nemoto, H. Nakamura, S. Iwamoto, w G. W. Kabalka, Ed., Current Topics in The Chemistry of Boron, The Royal Society of Chemistry, Cambridge 1994, 149.
[86] K. Imamura, Y. Yamamoto, Bull. Chem. Soc. Jpn., 1997, 70, 3103.
[87] Y. El-Kattan, N.M. Goudagon, G. Fulcrand, D.C. Liotta, R.F. Schinazi, w G.W. Kabalka, Ed., Current Topics in The Chemistry of Boron, The Royal Society, Cambridge 1994, 181.
[88] F.G. Rong, A.H. Soloway, S. Ikeda, D.H. Ives, Nucleos. Nucleot., 1995,14,1873.
[89] G. Palmisano, M. Santagostino, Tetrahedron, 1993,49, 2533.
[90] F.G. Rong, A.H. Soloway, IMEBORON VIII, Knoxville, TN, July, 11-15,1993,116.
[91] F.G. Rong, A.H. Soloway, Nucleos. Nucleot., 1994,13, 2021.
[92] G.W. Kabalka, N.K. Reddy, C. Narayana, IMEBORON VIII, Knoxville, TN, July, 11-15, 1993, 144.
[93] Y. Yamamoto, T. Seko, H. Nakamura, Heteroatom Chem., 1992,3,239.
[94] K. Imamura, Y. Yamamoto, Bioorg. Med. Chem. Lett., 1996,6, 1855.
[95] J.C.G. Graciet, J. Shi, R.F. Schinazi, Nucleos. Nucleot., 1998,17, 711.
[96] N.M. Goudgaon, Y.A. El-Kattan, X.Y. Xia, J. McAtee, J. Soria, S.J. Wey, D.C. Liotta, R.F. Schinazi, Nucleos. Nucleot., 1997,16, 2133.
[97] A.B. Olejniczak, A. Semenuk, M. Kwiatkowski, Z. J. Leśnikowski, J. Organomet. Chem., 2003, 680, 124.
[98] Z.J. Leśnikowski, R.F. Schinazi, J. Org. Chem., 1993,58, 6531.
[99] Z.J. Leśnikowski, G. Fulcrand, R.M. Lloyd Jr., A. Juodawlkis, R.F. Schinazi, Biochemistry, 1996, 35,5741.
[100] R.A. Watson-Clark, M.L. Banquerino, K. Shelly, M.F. Hawthorne, E. Brahn, Proc. Natl. Acad. Sci. U. S.A. 1998,95, 2531
[101] J.F. Valliant, P. Schaffer, J.F. Britten, A. Davidson, A.G. Jones, J.C. Yanch, Tetrahedron Lett., 2 000,41, 1355.
[102] G.W. Kabalka, G.T. Smith, J.P. Dyke, W.S. Reid, C.P.D. Longford, T.G. Roberts, N.K Reddy, E. Buonocore, K.F. Hubner, J. Nucl. Med., 1997,38, 1762.
[103] Y. Imahori, S. Ueda, Y. Ohmori, K. Sakae, T. Kusuki, T. Kobayashi, M. Takagaki, K Ono, T. Ido, R. Fujii, Clin. Cancer. Res., 1998,4, 1825.

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Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUS2-0006-0045