CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2012, Vol. 84, No. 11, pp. 2289-2298

http://dx.doi.org/10.1351/PAC-CON-11-11-02

Published online 2012-05-22

Imitation and modification of bioactive lead structures via integration of boron clusters

Sven Stadlbauer1, René Frank1, Matthias Scholz1, Solveig Boehnke1, Verena M. Ahrens2, Annette G. Beck-Sickinger2 and Evamarie Hey-Hawkins1*

1 Institute of Inorganic Chemistry, Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany
2 Institute of Biochemistry, Universität Leipzig, Brüderstraße 34, D-04103 Leipzig, Germany

References

  • 1. N. S. Hosmane (Ed.). Boron Science, New Technologies and Applications, CRC Press, Boca Raton (2011).
  • 2a. S. Bauer, S. Tschirschwitz, P. Lönnecke, R. Frank, B. Kirchner, M. L. Clarke, E. Hey-Hawkins. Eur. J. Inorg. Chem. 2776 (2009). (http://dx.doi.org/10.1002/ejic.200900304)
  • 2b. S. Bauer, E. Hey-Hawkins. “Phosphorus-substituted carbaboranes in catalysis”, in Boron Science, New Technologies and Applications, N. S. Hosmane (Ed.), Chap. 22, pp. 513–559, CRC Press, Boca Raton (2011).
  • 2c. S. E. Lyubimov, E. A. Rastorguev, T. A. Verbitskaya, P. V. Petrovskii, E. Hey-Hawkins, V. N. Kalinin, V. A. Davankov. Polyhedron 30, 1258 (2011). (http://dx.doi.org/10.1016/j.poly.2011.02.003)
  • 2d. S. E. Lyubimov, I. V. Kuchurov, A. A. Tyutyunov, P. V. Petrovskii, V. N. Kalinin, S. G. Zlotin, V. A. Davankov, E. Hey-Hawkins. Catal. Commun. 11, 419 (2010). (http://dx.doi.org/10.1016/j.catcom.2009.11.012)
  • 2e. S. E. Lyubimov, V. A. Davankov, K. N. Gavrilov, T. B. Grishina, E. A. Rastorguev, A. A. Tyutyunov, T. A. Verbitskaya, V. N. Kalinin, E. Hey-Hawkins. Tetrahedron Lett. 51, 1682 (2010). (http://dx.doi.org/10.1016/j.jorganchem.2008.09.032)
  • 2e. S. E. Lyubimov, V. A. Davankov, P. V. Petrovskii, E. Hey-Hawkins, A. A. Tyutyunov, E. G. Rys, V. N. Kalinin. J. Organomet. Chem. 693, 3689 (2008).
  • 3. T. M. Keller. Carbon 40, 225 (2002). (http://dx.doi.org/10.1016/S0008-6223(01)00092-6)
  • 4. J. F. Valliant, K. J. Guenther, A. S. King, P. Morel, P. Schaffer, O. O. Sogbein, K. A. Stephenson. Coord. Chem. Rev. 232, 173 (2002). (http://dx.doi.org/10.1016/S0010-8545(02)00087-5)
  • 5. G. W. Kabalka, M. L. Yao. Anticancer Agents Med. Chem. 6, 111 (2006). (http://dx.doi.org/10.2174/187152006776119144)
  • 6. R. F. Barth, J. A. Coderre, M. G. Vicente, T. E. Blue. Clin. Cancer Res. 11, 3987 (2005). (http://dx.doi.org/10.1158/1078-0432.CCR-05-0035)
  • 7. K. Yokoyama, S.-I. Miyatake, Y. Kajimoto, S. Kawabata, A. Doi, T. Yoshida, T. Asano, M. Kirihata, K. Ono, T. Kuroiwa. J. Neurooncol. 78, 227 (2006). (http://dx.doi.org/10.1007/s11060-005-9099-4)
  • 8. R. F. Barth. Appl. Radiat. Isot. 67, S3 (2009). (http://dx.doi.org/10.1016/j.apradiso.2009.03.102)
  • 9. M. F. Hawthorne, M. W. Lee. J. Neurooncol. 62, 33 (2003).
  • 10. A. F. Armstrong, J. F. Valliant. Dalton Trans. 4240 (2007). (http://dx.doi.org/10.1039/b709843j)
  • 11. M. F. Hawthorne, A. Maderna. Chem. Rev. 99, 3421 (1999). (http://dx.doi.org/10.1021/cr980442h)
  • 12. V. I. Bregadze, I. B. Sivaev, S. A. Glazun. Anticancer Agents Med. Chem. 6, 75 (2006). (http://dx.doi.org/10.2174/187152006776119180)
  • 13. I. B. Sivaev, V. I. Bregadze. Eur. J. Inorg. Chem. 1433 (2009). (http://dx.doi.org/10.1002/ejic.200900003)
  • 14. Z. J. Leśnikowski. Collect. Czech. Chem. Commun. 72, 1646 (2007). (http://dx.doi.org/10.1135/cccc20071646)
  • 15. M. F. Hawthorne, A. Maderna. Chem. Rev. 99, 3421 (1999). (http://dx.doi.org/10.1021/cr980442h)
  • 16. Y. Endo, T. Yoshimi, Y. Yamakoshi. Chem. Pharm. Bull. (Tokyo) 48, 312 (2000). (http://dx.doi.org/10.1248/cpb.48.312)
  • 17a. M. Scholz, E. Hey-Hawkins. Chem. Rev. 111, 7035 (2011). (http://dx.doi.org/10.1021/cr200038x)
  • 17b. E. Hey-Hawkins, M. Scholz. PCT/EP2008/056702.
  • 18. C. G. Wermuth, C. R. Ganellin, P. Lindberg, L. A. Mitscher. Pure Appl. Chem. 70, 1129 (1998). (http://dx.doi.org/10.1351/pac199870051129)
  • 19. F. Issa, M. Kassiou, L. M. Rendina. Chem. Rev. 111, 5701 (2011). (http://dx.doi.org/10.1021/cr2000866)
  • 20. M. F. Hawthorne. Angew. Chem., Int. Ed. 32, 950 (1993).
  • 21. A. H. Soloway, W. Tjarks, B. A. Barnum, F. G. Rong, R. F. Barth, I. M. Codogni, J. G. Wilson. Chem. Rev. 98, 1515 (1998). (http://dx.doi.org/10.1021/cr941195u)
  • 22. N. Gupta, R. A. Gahbauer, T. E. Blue, B. Albertson. J. Neurooncol. 62, 197 (2003).
  • 23. K. Hideghéty, W. Sauerwein, A. Wittig, C. Götz, P. Paquis, F. Grochulla, K. Haselsberger, J. Wolbers, R. Moss, R. Huiskamp, H. Fankhauser, M. de Vries, D. Gabel. J. Neurooncol. 62, 145 (2003).
  • 24. S. Stadlbauer, E. Hey-Hawkins. PCT/EP2008/060649.
  • 25. R. A. Bechtold, A. Kaczmarczyk. J. Med. Chem. 18, 371 (1975). (http://dx.doi.org/10.1021/jm00238a010)
  • 26. J. J. Benedict. EP 0068584 A1 (1981).
  • 27. M. W. Lee, K. Shelly, R. R. Kane, M. F. Hawthorne. Advances in Neutron Capture Therapy 2006, Proceedings of ICNCT-12, Chemistry and Pharmacy, Y. Nakagawa, T. Kobayashi, H. Fukuda (Eds.), pp. 234–236 (2006).
  • 28. W. Tjarks, R. F. Barth, J. H. Rotaru, D. M. Adams, W. Yang, R. G. Kultyshev, J. Forrester, B. A. Barnum, A. H. Soloway, S. G. Shore. Anticancer Res. 21, 841 (2001).
  • 29. S. Stadlbauer, P. Welzel, E. Hey-Hawkins. Inorg. Chem. 48, 5005 (2009). (http://dx.doi.org/10.1021/ic9004278)
  • 30. S. Stadlbauer, P. Lönnecke, P. Welzel, E. Hey-Hawkins. Eur. J. Org. Chem. 3129 (2010). (http://dx.doi.org/10.1002/ejoc.201000213)
  • 31. S. Stadlbauer, P. Lönnecke, P. Welzel, E. Hey-Hawkins. Eur. J. Org. Chem. 6301 (2009). (http://dx.doi.org/10.1002/ejoc.200900813)
  • 32a. S. Stadlbauer, E. Hey-Hawkins. “Bioconjugates of carbaboranyl phosphonates”, in Boron Science: New Technologies and Applications, N. S. Hosmane (Ed.), Chap. 2, pp. 21–40, CRC Press, Boca Raton (2011).
  • 32b. S. Stadlbauer, P. Lönnecke, E. Hey-Hawkins. “Phosphonate-substituted carbaboranes for potential use in BNCT”, in Advances in Neutron Capture Therapy 2006, Proceedings of ICNCT-12, Chemistry and Pharmacy, Y. Nakagawa, T. Kobayashi, H. Fukuda (Eds.), pp. 215–216 (2006).
  • 33. E. Justus, D. Awad, M. Hohnholdt, T. Schaffran, K. Edwards, G. Karlsson, L. Damian, D. Gabel. Bioconjugate Chem. 18, 1287 (2007). (http://dx.doi.org/10.1021/bc070040t)
  • 34. J. Kunig, P. Lönnecke, E. Hey-Hawkins. Carbohydr. Res. 346, 1154 (2011). (http://dx.doi.org/10.1016/j.carres.2011.03.035)
  • 35a. J. Capala, R. F. Barth, M. Bendayan, M. Lauzon, D. M. Adams, A. H. Soloway, R. A. Fenstermaker, J. Carlsson. Bioconjug. Chem. 7, 7 (1996). (http://dx.doi.org/10.1021/bc950077q)
  • 35b. R. F. Barth, W. Yang, D. M. Adams, J. H. Rotaru, S. Shukla, M. Sekido, W. Tjarks, R. A. Fenstermaker, M. Ciesielski, M. M. Nawrocky, J. A. Coderre. Cancer Res. 62, 3159 (2002).
  • 36. I. U. Khan, A. G. Beck-Sickinger. Anticancer Agents Med. Chem. 8, 186 (2008).
  • 37. K. Tatemoto, M. Carlquist, V. Mutt. Nature 296, 659 (1982). (http://dx.doi.org/10.1038/296659a0)
  • 38. I. Böhme, J. Stichel, C. Walther, K. Mörl, A. G. Beck-Sickinger. Cell Signalling 20, 1740 (2008). (http://dx.doi.org/10.1016/j.cellsig.2008.05.017)
  • 39. M. C. Michel, A. G. Beck-Sickinger, H. Cox, H. N. Doods, H. Herzog, D. Larhammar, R. Quirion, T. Schwartz, T. Westfall. Pharmacol. Rev. 50, 143 (1998).
  • 40a. P. M. Rose, P. Fernandes, J. S. Lynch, S. T. Frazier, S. M. Fisher, K. Kodukula, B. Kienzle, R. Seethala. J. Biol. Chem. 270, 22661 (1995).
  • 40b. erratum: P. M. Rose, P. Fernandes, J. S. Lynch, S. T. Frazier, S. M. Fisher, K. Kodukula, B. Kienzle, R. Seethala. J. Biol. Chem. 270, 29038 (1995).
  • 41. J. C. Reubi, M. Gugger, B. Waser, J. C. Schaer. Cancer Res. 61, 4636 (2001).
  • 42. R. M. Söll, M. C. Dinger, I. Lundell, D. Larhammer, A. G. Beck-Sickinger. Eur. J. Biochem. 268, 2828 (2001). (http://dx.doi.org/10.1046/j.1432-1327.2001.02161.x)
  • 43. V. M. Ahrens, R. Frank, S. Stadlbauer, A. G. Beck-Sickinger, E. Hey-Hawkins. J. Med. Chem. 54, 2368 (2011). (http://dx.doi.org/10.1021/jm101514m)
  • 44. J. F. Valliant, P. Schaffer, K. A. Stephenson, J. F. Britten. J. Org. Chem. 67, 383 (2002). (http://dx.doi.org/10.1021/jo0158229)
  • 45. R. C. Reynolds, S. R. Campbell, R. G. Fairchild, R. L. Kisliuk, P. L. Micca, S. F. Queener, J. M. Riordan, W. D. Sedwick, W. R. Waud, A. K. Leung, R. W. Dixon, W. J. Suling, D. W. Borhani. J. Med. Chem. 50, 3283 (2007). (http://dx.doi.org/10.1021/jm0701977)
  • 46. R. L. Julius, O. K. Farha, J. Chiang, L. J. Perry, M. F. Hawthorne. Proc. Natl. Acad. Sci. USA 104, 4808 (2007). (http://dx.doi.org/10.1073/pnas.0700316104)
  • 47a. R. J. Flower. Nat. Rev. Drug. Discov. 2, 179 (2003). (http://dx.doi.org/10.1038/nrd1034)
  • 47b. B. Hinz, K. Brune. J. Pharmacol. Exp. Ther. 300, 367 (2002). (http://dx.doi.org/10.1124/jpet.300.2.367)
  • 48a. J. R. Vane, R. J. Flower, R. M. Botting. Stroke 21, IV12 (1990).
  • 48b. G. P. Hochgesang Jr., S. W. Rowlinson, L. J. Marnett. J. Am. Chem. Soc. 122, 6514 (2000). (http://dx.doi.org/10.1021/ja0003932)
  • 48c. M. Lecomte, O. Laneuville, C. Ji, D. L. DeWitt, W. L. Smith. J. Biol. Chem. 269, 13207 (1994).
  • 49. M. Scholz, K. Bensdorf, R. Gust, E. Hey-Hawkins. ChemMedChem 4, 746 (2009). (http://dx.doi.org/10.1002/cmdc.200900072)
  • 50. M. V. R. Reddy, M. R. Mallireddigari, V. R. Pallela, P. Venkatapuram, R. Boominathan, S. C. Bell, E. P. Reddy. Bioorg. Med. Chem. 13, 1715 (2005). (http://dx.doi.org/10.1016/j.bmc.2004.12.005)
  • 51. M. Scholz, M. Steinhagen, J. T. Heiker, A. G. Beck-Sickinger, E. Hey-Hawkins. ChemMedChem 6, 89 (2011). (http://dx.doi.org/10.1002/cmdc.201000368)
  • 52. M. Scholz, G. N. Kaluđerović, H. Kommera, R. Paschke, J. Will, W. S. Sheldrick, E. Hey-Hawkins. Eur. J. Med. Chem. 46, 1131 (2011). (http://dx.doi.org/10.1016/j.ejmech.2011.01.030)
  • 53a. P. Brozic, J. Cesar, A. Kovac, M. Davies, A. P. Johnson, C. W. Fishwick, T. Lanisnik Rizner, S. Gobec. Chem. Biol. Interact. 178, 158 (2009). (http://dx.doi.org/10.1016/j.cbi.2008.10.019)
  • 53b. A. B. Reddy, S. K. Srivastava, K. V. Ramana. Cytokine 48, 170 (2009). (http://dx.doi.org/10.1016/j.cyto.2009.07.004)
  • 53c. T. L. Rizner, T. Smuc, R. Rupreht, J. Sinkovec, T. M. Penning. Mol. Cell. Endocrinol. 248, 126 (2006). (http://dx.doi.org/10.1016/j.mce.2005.10.009)
  • 54. O. A. Barski, K. H. Gabbay, K. M. Bohren. Biochemistry 35, 14276 (1996). (http://dx.doi.org/10.1021/bi9619740)
  • 55. O. A. Barski, K. H. Gabbay, C. E. Grimshaw, K. M. Bohren. Biochemistry 34, 11264 (1995). (http://dx.doi.org/10.1021/bi00035a036)
  • 56. F. D. Hart, P. L. Boardman. Br. Med. J. 2, 965 (1963). (http://dx.doi.org/10.1136/bmj.2.5363.965)
  • 57. A. S. Kalgutkar, A. B. Marnett, B. C. Crews, R. P. Remmel, L. J. Marnett. J. Med. Chem. 43, 2860 (2000). (http://dx.doi.org/10.1021/jm000004e)
  • 58. A. S. Kalgutkar, B. C. Crews, S. W. Rowlinson, A. B. Marnett, K. R. Kozak, R. P. Remmel, L. J. Marnett. Proc. Natl. Acad. Sci. USA 97, 925 (2000). (http://dx.doi.org/10.1073/pnas.97.2.925)
  • 59. P. J. Loll, D. Picot, O. Ekabo, R. M. Garavito. Biochemistry 35, 7330 (1996). (http://dx.doi.org/10.1021/bi952776w)
  • 60. W. C. Black, C. Bayly, M. Belley, C. C. Chan, S. Charleson, D. Denis, J. Y. Gauthier, R. Gordon, D. Guay, S. Kargman, C. K. Lau, Y. Leblanc, J. Mancini, M. Ouellet, D. Percival, P. Roy, K. Skorey, P. Tagari, P. Vickers, E. Wong, L. Xu, P. Prasit. Bioorg. Med. Chem. Lett. 6, 725 (1996). (http://dx.doi.org/10.1016/0960-894X(96)00100-X)
  • 61. M. Scholz, A. L. Blobaum, L. J. Marnett, E. Hey-Hawkins. Bioorg. Med. Chem. 19, 3242 (2011). (http://dx.doi.org/10.1016/j.bmc.2011.03.054)
  • 62. M. Scholz, A. L. Blobaum, L. J. Marnett, E. Hey-Hawkins. Bioorg. Med. Chem. Submitted for publication.