Biologically active biotin derivatives of schweinfurthin F

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 22, 2010, Pages 6716-6720

  Ulrich, Natalie C ^a   Kuder, Craig H ^b   Hohl, Raymond J ^b   Wiemer, David F ^a,b  

^a E11 SSH   (United States)

^b UNIVERSITY OF IOWA   (United States)

Author keywords

Anti proliferative; Biotin; Conjugate; Schweinfurthin; Synthesis

Indexed keywords

BIOTIN DERIVATIVE; NATURAL PRODUCT; SCHWEINFURTHIN F; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL MODIFICATION; CONJUGATE; CONTROLLED STUDY; CYTOTOXICITY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BIOTIN; CELL LINE, TUMOR; HUMANS; STILBENES;

EID: 77958023336     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.143     Document Type: Article

References (46)

1. G.C. Terstappen, C. Schlupen, R. Raggiaschi, and G. Gaviraghi Nat. Rev. Drug Disc. 6 2007 891
2. For a recent review, cf: F. Becker, K. Murthi, C. Smith, J. Come, N. Costa-Roldán, C. Kaufmann, U. Hanke, C. Degenhart, S. Baumann, W. Wallner, A. Huber, S. Dedier, S. Dill, D. Kinsman, M. Hediger, N. Bockovich, S. Meier-Ewert, A.F. Kluge, and N. Kley Chem. Biol. 11 2004 211
3. For a recent review, cf: S. Rossenu, D. Dewitte, J. Vandekerckhove, and C. Ampe J. Protein Chem. 16 1997 499
4. For a recent review, cf: H. Zhu, and M. Snyder Curr. Opin. Chem. Biol. 7 2003 55
5. P. Cuatrecasas Proc. Natl. Acad. Sci. U.S.A. 69 1972 1277
6. K. Hofmann, and F.M. Finn Ann. N.Y. Acad. Sci. 447 1985 359
7. For a recent review, cf: B.J. Leslie, and P.J. Hergenrother Chem. Soc. Rev. 37 2008 1347
8. M. McPherson, Y. Yang, P.W. Hammond, and B.L. Kreider Chem. Biol. 9 2002 691
9. S. Bach, M. Knockaert, J. Reinhardt, O. Lozach, S. Schmitt, B. Baratte, M. Koken, S.P. Coburn, L. Tang, T. Jiang, D. Liang, H. Galons, J. Dierick, L.A. Pinna, F. Meggio, F. Totzke, C. Schächtele, A.S. Lerman, A. Carnero, Y. Wan, N. Gray, and L. Meijer J. Biol. Chem. 280 2005 31208
10. S. Sato, Y. Kwon, S. Kamisuki, N. Srivastava, Q. Mao, Y. Kawazoe, and M. Uesugi J. Am. Chem. Soc. 129 2007 873
11. K. Godl, J. Wissing, A. Kurtenbach, P. Habenberger, S. Blencke, H. Gutbrod, K. Salassidis, M. Stein-Gerlach, A. Missio, M. Cotten, and H. Daub Proc. Natl. Acad. Sci. U.S.A. 100 2003 15434
12. J.E. Wulff, R. Siegrist, and A.G. Myers J. Am. Chem. Soc. 129 2007 14444
13. A.V. Statsuk, R. Bai, J.L. Baryza, V.A. Verma, E. Hamel, P.A. Wender, and S.A. Kozmin Nat. Chem. Biol. 1 2005 383
14. G. Wang, L. Shang, A.W.G. Burgett, P.G. Harran, and X. Wang Proc. Natl. Acad. Sci. U.S.A. 104 2007 2068
15. B. Nare, J.J. Allocco, R. Kuningas, S. Galuska, R.W. Myers, M.A. Bednarek, and D.M. Schmatz Anal. Biochem. 267 1999 390
16. P. Klausmeyer, Q.N. Van, J. Jato, T.G. McCloud, and J.A. Beutler J. Nat. Prod. 73 2010 479
17. J.A. Beutler, J.G. Jato, G. Cragg, D.F. Wiemer, J.D. Neighbors, M.S. Salnikova, M. Hollingshead, D.A. Scudiero, and T.G. McCloud R.J. Bogers, The Schweinfurthins: Issues in Development of a Plant-Derived Anticancer Lead Medicinal and Aromatic Plants 2006 Springer
18. J.A. Beutler, J. Jato, G.M. Cragg, and M.R. Boyd Nat. Prod. Lett. 14 2000 399
19. B.J. Yoder, S. Cao, A. Norris, J.S. Miller, F. Ratovoson, J. Razafitsalama, R. Andriantsiferana, V.E. Rasamison, and D.G.I. Kingston J. Nat. Prod. 70 2007 342
20. J.A. Beutler, R.H. Shoemaker, T. Johnson, and M.R. Boyd J. Nat. Prod. 61 1998 1509
21. K.D. Paull, R.H. Shoemaker, L. Hodes, A. Monks, D.A. Scudiero, L. Rubinstein, J. Plowman, and M.R. Boyd J, Natl. Cancer Inst. 81 1989 1088
22. H. Lin, Z. Wang, J. Wu, N. Shi, H. Zhang, W. Chen, S. Morris-Natschke, and A. Lin J. Nat. Prod. 70 2007 1114
23. W.K. Liu, F.W.K. Cheung, and C. Che J. Nat. Prod. 69 2006 934
24. J.Y. Su, Y.H. Meng, L.M. Zeng, X. Fu, and F.J. Schmitz J. Nat. Prod. 57 1994 1450
25. F. Raeppel, J. Weibel, and D. Heissler Tetrahedron Lett. 40 1999 6377
26. B.R. Moser J. Nat. Prod. 71 2008 487
27. A. Rudy, N. López-Antón, V.M. Dirsch, and A.M. Vollmar J. Nat. Prod. 71 2008 482
28. G.R. Pettit, M. Inoue, Y. Kamano, D.L. Herald, C. Arm, C. Dufresne, N.D. Christie, J.M. Schmidt, D.L. Doubek, and T.S. Krupa J. Am. Chem. Soc. 110 1988 2006
29. Y. Zhou, C. Garcia-Prieto, D.A. Carney, R.H. Xu, H. Pelicano, Y. Kang, W. Yu, C. Lou, S. Kondo, J. Liu, D.M. Harris, Z. Estrov, M.J. Keating, Z. Jin, and P. Huang J. Natl. Cancer Inst. 29 2005 1781
30. N.C. Ulrich, J.G. Kodet, N.R. Mente, C.H. Kuder, J.A. Beutler, R.J. Hohl, and D.F. Wiemer Bioorg. Med. Chem. 18 2010 1676
31. J.J. Topczewski, J.D. Neighbors, and D.F. Wiemer J. Org. Chem. 74 2009 6965
32. N.R. Mente, J.D. Neighbors, and D.F. Wiemer J. Org. Chem. 73 2008 7963
33. N.R. Mente, A.J. Wiemer, J.D. Neighbors, J.A. Beutler, R.J. Hohl, and D.F. Wiemer Bioorg. Med. Chem. Lett. 17 2007 911
34. J.D. Neighbors, J.A. Beutler, and D.F. Wiemer J. Org. Chem. 70 2005 925
35. E.M. Treadwell, J.D. Neighbors, and D.F. Wiemer Org. Lett. 4 2002 3639
36. E.M. Treadwell, S.C. Cermak, and D.F. Wiemer J. Org. Chem. 64 1999 8718
37. J.D. Neighbors, M.S. Salnikova, J.A. Beutler, and D.F. Wiemer Bioorg. Med. Chem. 14 2006 1771
38. C.H. Kuder, J.D. Neighbors, R.J. Hohl, and D.F. Wiemer Bioorg. Med. Chem. 17 2009 4718
39. J.D. Neighbors, M.S. Salnikova, and D.F. Wiemer Tetrahedron Lett. 46 2005 1321
40. M.J. Davies, J.C. Heslin, and C.J. Moody J. Chem. Soc., Perkin Trans. 1: Org. Bioorg. Chem. [1972-1999] 1989 2473
41. J.A. Marshall, J. Lebreton, B.S. DeHoff, and T.M. Jenson Tetrahedron Lett. 28 1987 723
42. K. Qian, D. Yu, C. Chen, L. Huang, S. Morris-Natschke, T.J. Nitz, K. Salzwedel, M. Reddick, G.P. Allaway, and K. Lee J. Med. Chem. 52 2009 3248
43. D.M. Lambert, G.K.E. Scriba, J.H. Poupaert, and P. Dumont Eur. J. Pharm. Sci. 4 1996 159
44. P. Rajan, I. Vedernikova, P. Cos, D. Vanden Berghe, K. Augustyns, and A. Haemers Bioorg. Med. Chem. Lett. 11 2001 215
45. T. Nakazawa, and K. Ohsawa J. Nat. Prod. 61 1998 993
46. B.J. Shorey, V. Lee, and J.E. Baldwin Tetrahedron 63 2007 5587