Sceptrin, a marine natural compound, inhibits cell motility in a variety of cancer cell lines

ACS Chemical Biology

Volumn 5, Issue 2, 2010, Pages 195-202

  Cipres, Angel ^a,c   O'Malley, Daniel P ^b   Li, Ke ^b   Finlay, Darren ^a   Baran, Phil S ^b   Vuori, Kristiina ^a  

^a BURNHAM INSTITUTE   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c CENTRO NACIONAL DE BIOTECNOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BROMOSCREPTIN; DEBROMOSCREPTIN; DIBROMOSCREPTIN; NATURAL PRODUCT; OXYSCREPTIN; SCEPTRIN; UNCLASSIFIED DRUG;

AGELAS; ARTICLE; CANCER CELL CULTURE; CELL MOTILITY; CELL PROLIFERATION; CELL SURVIVAL; CONTROLLED STUDY; CYTOSKELETON; DRUG INHIBITION; DRUG MECHANISM; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL;

AGELAS; ANIMALS; BIOLOGICAL PRODUCTS; CELL LINE, TUMOR; CELL MOVEMENT; CELL PROLIFERATION; CELL SURVIVAL; CHEMOTAXIS; HELA CELLS; HUMANS; PSEUDOPODIA; PYRROLES;

AGELAS NAKAMURAI;

EID: 77449150089     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb900240k     Document Type: Article

References (31)

1. Newman, D. J., and Cragg, G. M. (2004) Marine natural products and related compounds in clinical and advanced preclinical trials, J. Nat. Prod. 67, 1216-1238.
2. Butler, M. S. (2008) Natural products to drugs: natural productderived compounds in clinical trials, Nat. Prod. Rep. 25, 475-516.
3. Laport, M. S., Santos, O. C., and Muricy, G. (2009) Marine sponges: potential sources of new antimicrobial drugs, Curr. Pharm. Biotechnol. 10, 86-105.
4. Faulkner, D. J. (2000) Marine natural products, Nat. Prod. Rep. 17, 7-55.
5. Aiello, A., Fattorusso, E., Giordano, A., Menna, M., Muller, W. E., Perovic-Ottstadt, S., and Schroder, H. C. (2007) Damipipecolin and damituricin, novel bioactive bromopyrrole alkaloids from the Mediterranean sponge Axinella damicornis, Bioorg. Med. Chem. 15, 5877-5887.
6. Walker RP, F. D., Van Engen, D, and Clardy, J. (1981) Sceptrin, an antimicrobial agent from the sponge Agelas sceptrum, J. Am. Chem. Soc. 103, 6772-6773.
7. Bernan, V. S., Roll, D. M., Ireland, C. M., Greenstein, M., Maiese, W. M., and Steinberg, D. A. (1993) A study on the mechanism of action of sceptrin, an antimicrobial agent isolated from the South Pacific sponge Agelas mauritiana, J. Antimicrob. Chemother. 32, 539-550.
8. Bickmeyer, U., Drechsler, C., Kock, M., and Assmann, M. (2004) Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation, Toxicon 44, 45-51.
9. Rosa, R., Silva, W., Escalona de Motta, G., Rodriguez, A. D., Morales, J. J., and Ortiz, M. (1992) Anti-muscarinic activity of a family of C11N5 compounds isolated from I sponges, Experientia 48, 885-887.
10. Mohammed, R., Peng, J., Kelly, M., and Hamann, M. T. (2006) Cyclic heptapeptides from the Jamaican sponge Stylissa caribica, J. Nat. Prod. 69, 1739-1744.
11. Vassas, A., Bourdy, G., Paillard, J. J., Lavayre, J., Pais, M., Quirion, J. C., and Debitus, C. (1996) Naturally occurring somatostatin and vasoactive intestinal peptide inhibitors. Isolation of alkaloids from two marine sponges, Planta Med. 62, 28-30.
12. Keifer, P. A. S., R. E., Koker, M. E. S., Hughes, R. G., Jr., Rittschof, D., and Rinehart, K. L. (1991) Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera, J. Org. Chem. 56, 2965-2975.
13. Rodriguez, A. D., Lear, M. J., and La Clair, J. J. (2008) Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol, J. Am. Chem. Soc. 130, 7256-7258.
14. Baran, P. S., Zografos, A. L., and O'Malley, D. P. (2004) Short total synthesis of (±)-sceptrin, J. Am. Chem. Soc. 126, 3726-3727.
15. Baran, P. S., Li, K., O'Malley, D. P., and Mitsos, C. (2005) Short, enantioselective total synthesis of sceptrin and ageliferin by programmed oxaquadricyclane fragmentation, Angew. Chem., Int. Ed. 45, 249-252.
16. O'Malley, D. P., Li, K., Maue, M., Zografos, A. L., and Baran, P. S. (2007) Total synthesis of dimeric pyrrole-imidazole alkaloids: sceptrin, ageliferin, nagelamide e, oxysceptrin, nakamuric acid, and the axinellamine carbon skeleton, J. Am. Chem. Soc. 129, 4762-4775.
17. Ridley, A. J., Schwartz, M. A., Burridge, K., Firtel, R. A., Ginsberg, M. H., Borisy, G., Parsons, J. T., and Horwitz, A. R. (2003) Cell migration: integrating signals from front to back, Science 302, 1704-1709.
18. Small, J. V., Rottner, K., Kaverina, I., and Anderson, K. I. (1998) Assembling an actin cytoskeleton for cell attachment and movement, Biochim. Biophys. Acta 1404, 271-281.
19. Kreis, T. E., and Birchmeier, W. (1980) Stress fiber sarcomeres of fibroblasts are contractile, Cell 22, 555-561.
20. Isenberg, G., and Wohlfarth-Bottermann, K. E. (1976) Transformation of cytoplasmic actin. Importance for the organization of the contractile gel reticulum and the contraction-relasation cycle of cytoplasmic actomyosin, Cell Tissue Res. 173, 495-528.
21. Ishizaki, T., Maekawa, M., Fujisawa, K., Okawa, K., Iwamatsu, A., Fujita, A., Watanabe, N., Saito, Y., Kakizuka, A., Morii, N., and Narumiya, S. (1996) The small GTP-binding protein Rho binds to and activates a 160 kDa Ser/Thr protein kinase homologous to myotonic dystrophy kinase, EMBO J. 15, 1885-1893.
22. Leung, T., Manser, E., Tan, L., and Lim, L. (1995) A novel serine/threonine kinase binding the Ras-related RhoA GTPase which translocates the kinase to peripheral membranes, J. Biol. Chem. 270, 29051-29054.
23. Giry, M., Popoff, M. R., von Eichel-Streiber, C., and Boquet, P. (1995) Transient expression of RhoA, -B, and -C GTPases in HeLa cells potentiates resistance to Clostridium difficile toxins A and B but not to Clostridium sordellii lethal toxin, Infect. Immun. 63, 4063-4071.
24. Paterson, H. F., Self, A. J., Garrett, M. D., Just, I., Aktories, K., and Hall, A. (1990) Microinjection of recombinant p21rho induces rapid changes in cell morphology, J. Cell Biol. 111, 1001-1007.
25. Chardin, P., Boquet, P., Madaule, P., Popoff, M. R., Rubin, E. J., and Gill, D. M. (1989) The mammalian G protein rhoC is ADP-ribosylated by Clostridium botulinum exoenzyme C3 and affects actin microfilaments in Vero cells, EMBO J. 8, 1087-1092.
26. Narumiya, S., Tanji, M., and Ishizaki, T. (2009) Rho signaling, ROCK and mDia1, in transformation, metastasis and invasion, Cancer Metastasis Rev. 12, 65-76.
27. Watanabe, N., Madaule, P., Reid, T., Ishizaki, T., Watanabe, G., Kakizuka, A., Saito, Y., Nakao, K., Jockusch, B. M., and Narumiya, S. (1997) p140mDia, a mammalian homolog of Drosophila diaphanous, is a target protein for Rho small GTPase and is a ligand for profilin, EMBO J. 16, 3044-3056.
28. Chernyavsky, A. I., Arredondo, J., Wess, J., Karlsson, E., and Grando, S. A. (2004) Novel signaling pathways mediating reciprocal control of keratinocyte migration and wound epithelialization through M3 and M4 muscarinic receptors, J. Cell Biol. 166, 261-272.
29. Chernyavsky, A. I., Nguyen, V. T., Arredondo, J., Ndoye, A., Zia, S., Wess, J., and Grando, S. A. (2003) The M4 muscarinic receptorselective effects on keratinocyte crawling locomotion, Life Sci. 72, 2069-2073.
30. Molinski, T. F., Dalisay, D. S., Lievens, S. L., and Saludes, J. P. (2009) Drug development from marine natural products, Nat. Rev. Drug Discovery 8, 69-85.
31. Volkmann, N., Hanein, D., Ouyang, G., Trybus, K. M., DeRosier, D. J., and Lowey, S. (2000) Evidence for cleft closure in actomyosin upon ADP release, Nat. Struct. Biol. 7, 1147-1155.