Karborany jako lipofilowe farmakofory

• Autorzy: Olejniczak A. , Burzyńska-Pedziwiatr I.

Warianty tytułu

EN

Carboranes as a lipophilic pharmacophores

• Języki publikacji: PL

Abstrakty

EN

Carboranes are boron cage systems in which one or more carbon atoms belong as an integral part to an elektron-delocalized borane framework. They are characterized by high boron content, remarkable thermal and chemical stability, spherical geometry and high hydrophobicity. Electropositivity of boron enables BH groups in carboranes to form unconventional hydrogen bonds defined also as proton - hydride bond. Another type of interaction was found for CH group of carborane - participating in hydrogen-bonded complexes, although these complexes are approximately 21 kJ/mol less stable than complexes formed by BH groups [2-8]. Proton - hydride bonds are formed mainly due to electrostatic interactions between boron--bound hydrogen atom bearing partial negative charge and hydrogen atom of a biomolecule bearing partial positive charge. It was found that carboranes forms proton - hydride bonds with biomolecules preferably with BH groups of the cage opposite to the carbon atom. Carboranes have been used as hydrophobic pharmacophores in design of analogues of biologically active compounds such as estradiol, retinoic acids, protein kinase C modulators and TNF-a activity modulators. Some of these carbo-rane containing biomolecules interact effectively with the corresponding receptor enzymes exhibiting equal or even higher biological activity than their endogenous counterparts and are characterized by remarkable resistance to catabolism.

Słowa kluczowe

PL

karborany; hydrofobowe farmakofory; receptory; leki

EN

carboranes; hydrophobic pharmacophore; receptors; drugs

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2007
• Tom: [Z] 61, 7-8
• Strony: 567--589
• Opis fizyczny: bibliogr. 60 poz., rys., wykr.

Twórcy

autor

Olejniczak A.

autor

Burzyńska-Pedziwiatr I.

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

Bibliografia

• [1] V.I. Bregadze, Chem. Rev., 1992, 92, 209.
• [2] L.I. Kruglyak, V.N. Kalinin, E.G. Rys, L.I. Zakharkin, A.I. Shatenstein, Zh. Obshch. Khim., 1972, 42, 2670.
• [3] L.A. Leites, Chem. Rev., 1992, 92, 279.
• [4] C.J. Cramer, W.L. Gladfelter, Inorg. Chem., 1997, 36, 5358.
• [5] P.L.A. Popelier, J. Phys. Chem., 1998, 102, 1873.
• [6] T.B. Richardson, S. deGala, R.H. Crabtree, P.E.M. Siegbahn, J. Am. Chem. Soc., 1995, 117, 12875.
• [7] H. Yamazaki, K. Ohta, Y. Endo, Tetrahedron Lett., 2005, 46, 3119.
• [8] J. Fanfrlik, M. Lepšik, D. Horinek, Z. Havlas, P. Hobza, Chemphyschem 2006, 7, 1100.
• [9] Y. Endo, T. Iijima, Y. Yamakoshi, A. Kubo, A. Itai, Bioorg. Med. Chem. Lett., 1999, 9, 3313.
• [10] Y. Endo, T. Yoshimi, T. Iijima, Y. Yamakoshi, Bioorg. Med. Chem. Lett, 1999, 9, 3387.
• [11] Y. Endo, T. Iijima, H. Kagechika, K. Ohta, E. Kawachi, K. Shudo, Chem. Pharm. Bull., 1999, 47, 585.
• [12] T. Iijima, Y. Endo, M. Tsuji, E. Kawachi, H. Kagechika, K. Shudo, Chem. Pharm. Bull., 1999, 47, 398.
• [13] M. Tsuji, Y. Koiso, H. Takahashi, Y. Hashimoto, Y. Endo, Biol. Pharm. Bull., 2000, 23, 513.
• [14] Y. Endo, T. Yoshimi, K. Kimura, A. Itai, Bioorg. Med. Chem. Lett., 1999, 9, 2561.
• [15] G. Patrich, Krótkie wykłady. Chemia leków, Wydawnictwo Naukowe PWN, Warszawa, 2004.
• [16] R.N. Grimes, Carboranes, Academic Press, Inc, New York, 1970.
• [17] J. Casanova, The Borane, Carborane, Carbocation Continuum, John Willey and Sons, Inc, New York, 1998.
• [18] A. Olejniczak, Wiad. Chem., 2004, 58, 889.
• [19] S. Sjöberg, Advances in Neutron Capture Therapy, Vol. II, Chemistry and Biology, Proceedings of the Seventh International Symposium on Neutron Capture Therapy of Cancer, J. Larsson, R. Crawford, R. Weinreich, Ed., Amsterdam 1997, 3-21.
• [20] Y. Endo, K. Ohta, T. Yoshimi, K. Yamaguchi, Phosphorus, Sulfur, and Silicon, 2004, 179, 799.
• [21] K. Ohta, H. Yamazaki, Y. Endo, Tetrahedron Lett., 2006, 47, 1937.
• [22] Y. Endo, T. Iijima, Y. Yamakoshi, M. Yamaguchi, H. Fukasawa, K. Shudo, J. Med. Chem., 1999, 42, 1501.
• [23] Y. Endo, T. Ijima, Y. Yamakoshi, H. Fukasawa, C. Miyaura, M. Inada, A. Kubo, A. Itai, Chem. Biol., 2001, 8, 341.
• [24] T. Ogawa, K. Ohta, T. Yoshimi, H. Yamazaki, T. Suzuki, S. Ohta, Y. Endo, Bioorg. Med. Chem. Lett., 2006, 16, 3943.
• [25] Y. Endo, T. Yoshimi, C. Miyaura, Pure Appl. Chem., 2003, 75, 1197.
• [26] J.F. Valliant, K.J. Guenther, A.S. King, P. Morel, P. Schaffer, O. Sogbein, K.A. Stephenson, Coord. Chem. Rev., 2002, 232, 173.
• [27] T. Meyers, R. Koope, E. von Angerer, H. Schonenberger, E.A. Holler, J. Cancer Res. Clin. Oncol., 1994, 120, 359.
• [28] Y. Endo, T. Yoshimi, Y. Yamakoshi, Chem. Pharm. Bull, 2000, 48, 312.
• [29] B.J.A. Furr, V.C. Jordan, Pharmacol Ther., 1984, 25, 127.
• [30] J.F. Valliant, P. Schaffer, K.A. Stephenson, J.F. Britten, J. Org. Chem., 2002, 67, 383.
• [31] M.B. Sporn, A.B. Roberts, D.S. Goldman, Eds., The retinoids, 2 nd ed., Raven Press, Inc., New York, 1994.
• [32] M. Petkovich, N.J. Brandt, A. Krust, P. Chambon, Nature, 1987, 330, 444.
• [33] S. Kaneko, H. Kagechika, E. Kawachi, Y. Hashimoto, K. Shudo, Med. Chem. Res., 1991, 1, 220.
• [34] Y. Endo, K. Yaguchi, E. Kawachi, H. Kagechika, Bioorg. Med. Chem. Lett., 2000, 10, 1733.
• [35] Y. Endo, T. Iijima, K. Yaguchi, E. Kawachi, N. Inoue, H. Kagechika, A. Kubo, A. Itai, Bioorg. Med. Chem. Lett., 2001, 11, 1307.
• [36] Y. Endo, K. Yaguchi, M. Tsuji, K. Yamaguchi, K. Shudo, Chem. Pharm. Bull., 1999, 47, 699.
• [37] J. Johnsamuel, Y. Byun, T.P. Jones, Y. Endo, W. Tjarks, J. Organomet. Chem., 2003, 680, 223.
• [38] J. Johnsamuel, Y. Byun, T.P. Jones, Y. Endo, W. Tjarks, Bioorg. Med. Chem. Lett., 2003, 13, 3213.
• [39] C.L. Ashendel, J.M. Staller, R.K. Boutwell, Cancer Res., 1983, 43, 4333.
• [40] Y. Endo, M. Ohno, M. Hirano, A. Itai, K. Shudo, J. Am. Chem. Soc., 1996, 118, 1841.
• [41] Y. Endo, M. Ohno, M. Hirano, M. Takeda, A. Itai, K. Shudo, Bioorg. Med. Chem. Lett., 1994, 4, 491.
• [42] Y. Endo, S. Takehana, M. Ohno, P.E. Driedger, S. Stabel, M.Y. Mizutani, N. Tomioka, A. Itai, K. Shudo, J. Med. Chem., 1998, 41, 1476.
• [43] A.D. Mooradian, J.E. Morley, S.G. Korenman, Endocr. Rev., 1987, 8, 1.
• [44] S. Fujii, Y. Hashimoto, T. Suzuki, S. Ohta, Y. Endo, Bioorg. Med. Chem. Lett., 2005, 15, 227.
• [45] S. Fujii, T. Goto, K. Ohta, Y. Hashimoto, T. Suzuki, S. Ohta, Y. Endo, J. Med. Chem., 2005, 48, 4654.
• [46] T. Goto, K. Ohta, T. Suzuki, S. Ohta, Y. Endo, Bioorg. Med. Chem., 2005, 13, 6414.
• [47] T. Ishioka, A. Kubo, Y. Koiso, K, Nagasawa, A. Itai, Y. Hashimoto, Bioorg. Med. Chem., 2002, 10, 1555.
• [48] N.E. Kohl, E.A. Emine, W.A. Schleif, L.J. Davis, J.C. Heimach, R.A.F. Dixon, E.M. Scolnik, I.S. Signal, Proc. Natl. Acad. Sci., USA, 1985, 4686.
• [49] J. Prejdova, M. Soucek, J. Konvalinka, Curr. Drug Targets Infect. Disord., 2004, 4, 137.
• [50] F. Clavel, A.J. Hance, N. Engl. J. Med., 2004, 350, 1023.
• [51] J.M. Coffin, Science, 1995, 267, 483.
• [52] A. Olejniczak, Wiad. Chem., 2005, 59, 3.
• [53] P. Cigler, M. Ko.i.ek, P. Rezáèova, J. Brynda, Z. Otwinowski, J. Pokorna, J. Ple.ek, B. Grüner, L. Doleèková-Marešová, M. Máša, J. Sedláèek, J. Bodem, H.G. Kraeusslich, V. Král, J. Konvalinka Proc. Natl. Acad. Sci., USA, 2005, 102, 15394.
• [54] Z.J. Lesnikowski, R.F. Schinazi, Pol. J. Chem., 1995, 69, 827.
• [55] Z.J. Lesnikowski, J. Shi, R.F. Schinazi, J. Organomet. Chem., 1999, 581, 156.
• [56] Z.J. Lesnikowski, Eur. J. Org. Chem., 2003, 4489.
• [57] A.B. Olejniczak, M. Koziołkiewicz, Z.J. Le.nikowski, Antisense Nucl. Acid Drug Develop., 2002, 12, 79.
• [58] B. Wojtczak, A. Semenyuk, A.B. Olejniczak, M. Kwiatkowski, Z.J. Lesnikowski, Tetrahedron Lett., 2005, 46, 3969.
• [59] A.B. Olejniczak, J. Plešek, Z.J. Lesnikowski, Chem. Eur. J., 2007, 13, 311.
• [60] Z.J. Leśnikowski, E. Paradowska, A.B. Olejniczak, M. Studzińska, P. Seekamp, U. Schübler, D. Gabel, R.F. Schinazi, J. Plešek, Bioorg. Med. Chem., 2005, 13, 4168.