Synthesis, conformational analysis, and cytotoxicity of new analogues of the natural cyclodepsipeptide jaspamide

Journal of Natural Products

Volumn 67, Issue 8, 2004, Pages 1325-1331

  Terracciano, Stefania ^a   Bruno, Ines ^a   Bifulco, Giuseppe ^a   Copper, Jean E ^b   Smith, Charles D ^b   Gomez Paloma, Luigi ^a   Riccio, Raffaele ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHONDRAMIDE C; CYCLODEPSIPEPTIDE; DOLICULIDE; JASPAMIDE; JASPAMIDE 1; JASPAMIDE 2; JASPAMIDE 3; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; CONFORMATIONAL TRANSITION; CYTOSKELETON; CYTOTOXICITY; DRUG ACTIVITY; DRUG SYNTHESIS; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 4344619554     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np049955b     Document Type: Article

References (21)

1. Jordon, A.; Hadfield, J. A.; Lawrence, N. J,; McGown, A. T. Med. Res. Rev. 1998, 4, 259-296.
2. Jordan, M. A.; Wilson, L. Curr. Opin. Cell Biol. 1998, 10, 123-130.
3. Shi, Q.; Chen, K.; Morris-Natschke, S. L.; Lee, K. H. Curr. Pharm. Des. 1998, 4, 219-248.
4. Nicolau, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014-2045.
5. Zabriskie, T. M.; Klocke, J. A.; Ireland, C. M.; Marcus, A. H.; Molinski, T. F.; Faulkner, D. J.; Xu, C.; Clardy, J. C. J. Am. Chem. Soc. 1986, 108, 3123-4.
6. Crews, P.; Manes, L. V.; Boehler, M. Tetrahedron Lett. 1986, 27, 2797-2800.
7. Braekman, J. C.; Daloze, D.; Moussiaux, B.; Riccio, R. J. Nat. Prod. 1987, 50, 994-995.
8. Zampella, A.; Giannini, C.; Debitus, C.; Roussakis, C.; D'Auria, M. V. J. Nat. Prod. 1999, 62, 332-334.
9. Stingl, J.; Andersen, R. J.; Emerman, J. T. Cancer Chemother. Pharmacol. 1992, 30, 401-406.
10. Senderowicz, A. M.; Kaur, G.; Sainz, E.; Laing, C.; Inman, W. D.; Rodriguez, J.; Crews, P.; Malspeis, L.; Grever, M. R.; Sausville, E. A.; Duncan, K. L. J. Natl. Cancer Inst. 1995, 87, 46-51.
11. Bubb, M. R.; Spector, I.; Beyer, B.; Fosen, K. A. J. Biol. Chem. 2000, 275, 5163-5170.
12. Bubb, M. R.; Senderowicz, A. M.; Dunkan, K. L.; Korn, E. D. J. Biol. Chem. 1994, 269, 14869-14871.
13. Bai, R.; Covell, D. G.; Liu, C.; Ghosh, A. K.; Hamel, E. J. Biol. Chem. 2002, 277, 32165-32171.
14. Fairchild, C. R.; Ivy, S. P.; Kao-Shan, C. S.; Whang-Peng, J.; Rosen, N.; Israel, M. A.; Melera, P. W.; Cowan, K. H.; Golsith, M. E. Cancer Res. 1987, 47, 5141-5148.
15. Kahn, M.; Nakanishi, H.; Su, T.; Lee, J. H.; Johnson, M. Int. J. Peptide Protein Res. 1991, 38, 324-334.
16. Inman, W.; Crews, P. J. Am. Chem. Soc. 1989, 111, 2822-2829.
17. Dauber-Osguthorpe, P.; Roberts, V. A.; Osguthorpe, D. J.; Wolff, J.; Genest, M.; Hagler, A. T. Proteins: Struct., Funct., Genet. 1998, 4, 31-47.
18. Accelerys Inc. (US, U.K.) 9685 Scranton Rd., San Diego, CA 92121-3752.
19. Skehan, P.; Storeng, P.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
20. Smith, C. D.; Zhang, X.; Mooberry, S. L.; Patterson, G. M.; Moore, R. E. Cancer Res. 1994, 54, 3779-3784.
21. Zhang, X.; Minale, L.; Zampella, A.; Smith, C. D. Cancer Res. 1997, 57, 3751-3758.