Geranyl and neryl triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 9, 2014, Pages 2791-2798

  Zhou, Xiang ^a   Ferree, Sarah D ^b   Wills, Veronica S ^a   Born, Ella J ^b   Tong, Huaxiang ^b   Wiemer, David F ^a,b   Holstein, Sarah A ^b  

^a University of Iowa   (United States)

^b UNIVERSITY OF IOWA   (United States)

Author keywords

GGDP synthase; Inhibition; Isoprenoid biosynthesis; Olefin stereochemistry

Indexed keywords

ALKENE; BISPHOSPHONIC ACID DERIVATIVE; ENZYME INHIBITOR; FARNESYL TRANS TRANSFERASE; PROTEIN BINDING; TRIAZOLE DERIVATIVE;

ANTAGONISTS AND INHIBITORS; CELL LINE; CHEMISTRY; HUMAN; ISOMERISM; METABOLISM; SYNTHESIS;

ALKENES; CELL LINE; DIPHOSPHONATES; ENZYME INHIBITORS; FARNESYLTRANSTRANSFERASE; HUMANS; ISOMERISM; PROTEIN BINDING; TRIAZOLES;

EID: 84899456383     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.03.014     Document Type: Article

References (32)

1. S.A. Holstein, and R.J. Hohl Lipids 39 2004 293
2. A.J. Wiemer, D.F. Wiemer, and R.J. Hohl Clin. Pharmacol. Ther. 90 2011 804
3. A. Dudakovic, A.J. Wiemer, K.M. Lamb, L.A. Vonnahme, S.E. Dietz, and R.J. Hohl J. Pharmacol. Exp. Ther. 324 2008 1028
4. Y.H. Zhang, W. Zhu, Y.L. Liu, H. Wang, K. Wang, K. Li, J.H. No, L. Ayong, A. Gulati, R. Pang, L. Freitas-Junior, C.T. Morita, and E. Oldfield ACS Med. Chem. Lett. 4 2013 423
5. S.A. Holstein, and R.J. Hohl Curr. Opin. Pharmacol. 12 2012 704
6. S.A. Holstein, D.M. Cermak, D.F. Wiemer, K. Lewis, and R.J. Hohl Bioorg. Med. Chem. 6 1998 687
7. R.J. Hohl, K.A. Lewis, D.M. Cermak, and D.F. Wiemer Lipids 33 1998 39
8. B.S. Gibbs, T.J. Zahn, Y.Q. Mu, J.S. Sebolt-Leopold, and R.A. Gibbs J. Med. Chem. 42 1999 3800
9. S.F. Sousa, P.A. Fernandes, and M.J. Ramos Curr. Med. Chem. 15 2008 1478
10. Z. Guo, Y.W. Wu, D. Das, C. Delon, J. Cramer, S. Yu, S. Thuns, N. Lupilova, H. Waldmann, L. Brunsveld, R.S. Goody, K. Alexandrov, and W. Blankenfeldt EMBO J. 27 2008 2444
11. S.A. Holstein, and R.J. Hohl Leuk. Res. 35 2011 551
12. C. Recchi, and M.C. Seabra Biochem. Soc. Trans. 40 2012 1398
13. X. Zhou, S.V. Hartman, E.J. Born, J.P. Smits, S.A. Holstein, and D.F. Wiemer Bioorg. Med. Chem. Lett. 23 2013 764
14. H. Skarpos, S.N. Osipov, D.V. Vorob'eva, I.L. Odinets, E. Lork, and G.V. Roschenthaler Org. Biomol. Chem. 5 2007 2361
15. K.B. Sharpless, and R.C. Michaels J. Am. Chem. Soc. 95 1973 6136
16. H.E.B. Lempers, A.R.I. Garcia, and R.A. Sheldon J. Org. Chem. 63 1998 1408
17. R.C. Gash, F. MacCorquodale, and J.C. Walton Tetrahedron 45 1989 5531
18. R. Caputo, L. Mangoni, O. Neri, and G. Palumbo Tetrahedron Lett. 22 1981 3551
19. P.E. Sonnet J. Org. Chem. 43 1978 1841
20. F. Bohlmann, R. Zeisberg, and E. Klein Org. Magn. Reson. 7 1975 426
21. A.J. Wiemer, H. Tong, K.M. Swanson, and R.J. Hohl Biochem. Biophys. Res. Commun. 353 2007 921
22. L.W. Shull, A.J. Wiemer, R.J. Hohl, and D.F. Wiemer Bioorg. Med. Chem. 14 2006 4130
23. A.J. Wiemer, J.S. Yu, K.M. Lamb, R.J. Hohl, and D.F. Wiemer Bioorg. Med. Chem. 16 2008 390
24. A.J. Wiemer, J.S. Yu, L.W. Shull, R.J. Barney, B.M. Wasko, K.M. Lamb, R.J. Hohl, and D.F. Wiemer Bioorg. Med. Chem. 16 2008 3652
25. S.A. Holstein, and R.J. Hohl The Enzymes Vol. 30 2011 Elsevier 301
26. G. Limberg, I. Lundt, and J. Zavilla Synthesis 1999 178
27. C. Bordier J. Biol. Chem. 256 1981 1604
28. B.M. Wasko, A. Dudakovic, and R.J. Hohl J. Pharmacol. Exp. Ther. 337 2011 540
29. H. Tong, S.A. Holstein, and R.J. Hohl Anal. Biochem. 336 2005 51
30. P.B. Cassidy, J.M. Dolence, and C.D. Poulter Methods Enzymol. 250 1995 30
31. W.C. Pickett, F.L. Zhang, C. Silverstrim, S.R. Schow, M.M. Wick, and S.S. Kerwar Anal. Biochem. 225 1995 60
32. M.C. Seabra, and G.L. James Methods Mol. Biol. 84 1998 251