Nido-Dicarbaborate Induces Potent and Selective Inhibition of Cyclooxygenase-2

ChemMedChem

Volumn 11, Issue 2, 2016, Pages 175-178

  Neumann, Wilma ^a   Xu, Shu ^b   Sárosi, Menyhárt B ^a   Scholz, Matthias S ^a,e   Crews, Brenda C ^b   Ghebreselasie, Kebreab ^b   Banerjee, Surajit ^c,d   Marnett, Lawrence J ^b   Hey Hawkins, Evamarie ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c Department of Obstetrics Gynecology   (United States)

^d ARGONNE NATIONAL LABORATORY   (United States)

^e UNIVERSITY OF BONN   (Germany)

Author keywords

carbaboranes; carboranes; cyclooxygenases; drug design; enzymes; inhibitors; selectivity

Indexed keywords

BORANE DERIVATIVE; CYCLOOXYGENASE 2 INHIBITOR; DICARBABORATE DERIVATIVE; INDOMETACIN; UNCLASSIFIED DRUG; CYCLOOXYGENASE 2;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STABILITY; ENZYME INHIBITION; PHARMACOPHORE; PRIORITY JOURNAL; ANIMAL; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; MOLECULAR MODEL; MOUSE; SHEEP; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; BORANES; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; INDOMETHACIN; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SHEEP; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84955401024     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201500199     Document Type: Article

References (28)

1. M. F. Hawthorne, Angew. Chem. Int. Ed. Engl. 1993, 32, 950;
2. Angew. Chem. 1993, 105, 997;
3. A. H. Soloway, W. Tjarks, B. A. Barnum, F. G. Rong, R. F. Barth, I. M. Codogni, J. G. Wilson, Chem. Rev. 1998, 98, 1515;
4. J. F. Valliant, K. J. Guenther, A. S. King, P. Morel, P. Schaffer, O. O. Sogbein, K. A. Stephenson, Coord. Chem. Rev. 2002, 232, 173;
5. Boron Science: New Technologies and Applications (Ed.:, N. S. Hosmane,), CRC Press, Boca Raton, 2011.
6. F. Issa, M. Kassiou, L. M. Rendina, Chem. Rev. 2011, 111, 5701;
7. M. Scholz, E. Hey-Hawkins, Chem. Rev. 2011, 111, 7035.
8. J. Fanfrlík, M. Lepšík, D. Horinek, Z. Havlas, P. Hobza, ChemPhysChem 2006, 7, 1100.
9. P. Řezáčoá, P. Cígler, P. Matějíček, M. Lepšík, J. Pokorná, B. Grüner, J. Konvalinka, in Boron Science: New Technologies and Applications (Ed.:, N. S. Hosmane,), CRC Press, Boca Raton, 2011, pp. 41.
10. 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. W. Leung, R. W. Dixon, W. J. Suling, D. W. Borhani, J. Med. Chem. 2007, 50, 3283;
11. J. Brynda, P. Mader, V. Šícha, M. Fábry, K. Poncová, M. Bakardiev, B. Grüner, P. Cígler, P. Řezáčová, Angew. Chem. Int. Ed. 2013, 52, 13760;
12. Angew. Chem. 2013, 125, 14005;
13. S. M. Wilkinson, H. Gunosewoyo, M. L. Barron, A. Boucher, M. McDonnell, P. Turner, D. E. Morrison, M. R. Bennett, I. S. McGregor, L. M. Rendina, M. Kassiou, ACS Chem. Neurosci. 2014, 5, 335;
14. M. E. El-Zaria, A. R. Genady, N. Janzen, C. I. Petlura, D. R. Beckford Vera, J. F. Valliant, Dalton Trans. 2014, 43, 4950.
15. M. Scholz, K. Bensdorf, R. Gust, E. Hey-Hawkins, ChemMedChem 2009, 4, 746;
16. M. Scholz, A. L. Blobaum, L. J. Marnett, E. Hey-Hawkins, Bioorg. Med. Chem. 2011, 19, 3242;
17. M. Scholz, A. L. Blobaum, L. J. Marnett, E. Hey-Hawkins, Bioorg. Med. Chem. 2012, 20, 4830;
18. M. Laube, W. Neumann, M. Scholz, P. Lönnecke, B. Crews, L. J. Marnett, J. Pietzsch, T. Kniess, E. Hey-Hawkins, ChemMedChem 2013, 8, 329.
19. D. L. Simmons, R. M. Botting, T. Hla, Pharmacol. Rev. 2004, 56, 387.
20. C. Michaux, C. Charlier, Mini-Rev. Med. Chem. 2004, 4, 603.
21. 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 2000, 97, 925;
22. A. S. Kalgutkar, A. B. Marnett, B. C. Crews, R. P. Remmel, L. J. Marnett, J. Med. Chem. 2000, 43, 2860.
23. 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. 1996, 6, 725.
24. J. J. Schaeck, S. B. Kahl, Inorg. Chem. 1999, 38, 204.
25. W. Neumann, R. Frank, E. Hey-Hawkins, Dalton Trans. 2015, 44, 1748.
26. J. J. Talley, S. R. Bertenshaw, D. L. Brown, J. S. Carter, M. J. Graneto, C. M. Koboldt, J. L. Masferrer, B. H. Norman, D. J. Rogier, Jr., B. S. Zweifel, K. Seibert, Med. Res. Rev. 1999, 19, 199.
27. R. G. Kurumbail, A. M. Stevens, J. K. Gierse, J. J. McDonald, R. A. Stegeman, J. Y. Pak, D. Gildehaus, J. M. Miyashiro, T. D. Penning, K. Seibert, P. C. Isakson, C. W. Stallings, Nature 1996, 384, 644.
28. C. A. Harman, M. V. Turman, K. R. Kozak, L. J. Marnett, W. L. Smith, R. M. Garavito, J. Biol. Chem. 2007, 282, 28096.