Desmethoxymajusculamide C, a cyanobacterial depsipeptide with potent cytotoxicity in both cyclic and ring-opened forms

Journal of Natural Products

Volumn 72, Issue 6, 2009, Pages 1011-1016

  Simmons, T Luke ^a   Nogle, Lisa M ^b   Media, Joseph ^c   Valeriote, Frederick A ^c   Mooberry, Susan L ^d   Gerwick, William H ^a,e  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b OREGON STATE UNIVERSITY   (United States)

^c HENRY FORD HOSPITAL   (United States)

^d SOUTHWEST FOUNDATION FOR BIOMEDICAL RESEARCH   (United States)

^e UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIN; CYTOTOXIC AGENT; DEPSIPEPTIDE; DESMETHOXYMAJUSCULAMIDE C; NATURAL PRODUCT; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL KILLING; CELL STRAIN HCT116; CLONOGENIC ASSAY; CONTINUOUS INFUSION; CONTROLLED STUDY; CYANOBACTERIUM; DEGRADATION; DEPOLYMERIZATION; DERIVATIZATION; DISK DIFFUSION; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; FRACTIONATION; HUMAN; HUMAN CELL; HYDROLYSIS; IC 50; MASS SPECTROMETRY; MAXIMUM TOLERATED DOSE; MICROFILAMENT; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SCID MOUSE; SOLID TUMOR; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

AMINO ACID SEQUENCE; ANIMALS; ANTINEOPLASTIC AGENTS; CYANOBACTERIA; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; FIJI; HCT116 CELLS; HUMANS; MICE; STRUCTURE-ACTIVITY RELATIONSHIP;

CYANOBACTERIA; LYNGBYA MAJUSCULA; MUS;

EID: 67650225531     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np9001674     Document Type: Article

References (23)

1. Papakonstani, E. A.; Stournaras, C. Methods Enzymol. 2007, 428, 227-240.
2. Janmey, P. A.; Chaponnier, C. Curr. Opin. Cell Biol. 1995, 7, 111-117.
3. Jordan, M. A.; Wilson, L. Curr. Opin. Cell. Biol. 1998, 10, 123-130.
4. Sahai, E. Nat. Rev. Cancer 2007, 7, 737-749.
5. Simmons, T. L.; Andrianasolo, E.; McPhail, K. L.; Flatt, P.; Gerwick, W. H. Mol. Cancer Ther. 2005, 4, 333-342.
6. Simmons, T. L. Gerwick, W. H. Anticancer Drugs of Marine Origin. In Oceans and Human Health: Risks and Remedies from the Seas; Walsh, P. J., Smith, S., Fleming, L., Solo-Gabriele, H., Gerwick, W. H., Eds.; Elsevier Science and Technology: UK, 2008; p 431.
7. Bubb, M. R.; Senderowicz, A. M. J.; Sausville, E. A.; Duncan, K. L. K.; Korn, E. D. J. Biol. Chem. 1994, 269, 14869-14871.
8. Marquez, B. L.; Watts, K. S.; Yokochi, A.; Roberts, M. A.; Verdier- Pinard, P.; Jimenez, J. I.; Hamel, E.; Scheuer, P. J.; Gerwick, W. H. J. Nat. Prod. 2002, 65, 866-871.
9. Bai, R.; Covell, D. G.; Liu, C.; Ghosh, A. K.; Hamel, E. J. Chem. Biol. 2002, 277, 32165-32171.
10. Morton, W. M.; Ayscough, K. R.; McLaughlin, P. J. Nat. Cell Biol. 2000, 2, 376-378.
11. Klehchin, V. A.; Allingham, J. S.; King, R.; Tanaka, J.; Marriott, G.; Rayment, I. Nat. Struct. Biol. 2003, 10, 1058-1063.
12. Harrigan, G. G.; Yoshida, W. Y.; Moore, R. E.; Nagle, D. G.; Park, P. U.; Biggs, J.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H.; Valeriote, F. A. J. Nat. Prod. 1998, 61, 1221-1225.
13. Bai, R.; Verdier-Panard, P.; Gangwar, S.; Stessman, C. C.; McClure, K. J.; Sausville, E. A.; Pettit, G. R.; Bates, R. B.; Hamel, E. Mol. Pharmacol. 2001, 59, 462-469.
14. Carter, D. C.; Moore, R. E.; Mynderse, J. S.; Niemczura, W. P.; Todd, J. S. J. Org. Chem. 1984, 49, 236-241.
15. Pettit, G. R.; Kamano, Y.; Kizu, H.; et al. Heterocycles 1989, 28, 553-558.
16. Mynderse, J. S.; Hunt, A. H.; Moore, R. E. J. Nat. Prod. 1988, 51, 1299-1301.
17. Subramanian, B. N.; Tenney, K.; Crews, P.; Gunatilaka, L.; Valeriote, F. A. J. Exp. Ther. Oncol. 2006, 5, 195-204.
18. Spartan '02(Linux); Wavefunction Inc.: Irvine, CA.
19. Jorgenson, W. L.; Tirado-Rives, J. J. Am. Chem. Soc. 1988, 110, 1657-1666.
20. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-264.
21. Ali, M. A.; Bates, R. B.; Crane, Z. D.; Dicus, C. W.; Gramme, M. R.; Hamel, E.; Marcischak, J.; Martinez, D. S.; McClure, K. J.; Nakkiew, P.; Pettit, G. R.; Stessman, C. C.; Sufi, B. A.; Yarick, G. V. Bioorg. Med. Chem. 2005, 13, 4138-4152.
22. Mamer, O. A. Methods Enzymol. 2000, 324, 3-10.
23. Corbett, T.; Valeriote, F.; LoRosso, P. J. Pharmacogn. 1995, S33, 102-122.