Latrunculin A and its C-17-O-carbamates inhibit prostate tumor cell invasion and HIF-1 activation in breast tumor cells

Journal of Natural Products

Volumn 71, Issue 3, 2008, Pages 396-402

  El Sayed, Khalid A ^a   Khanfar, Mohammad A ^a   Shallal, Hassan M ^a   Muralidharan, A ^a   Awate, Bhushan ^a   Youssef, Diaa T A ^b   Liu, Yang ^c   Zhou, Yu Dong ^c   Nagle, Dale G ^c   Shah, Girish ^a  

^a UNIVERSITY OF LOUISIANA AT MONROE   (United States)

^b Suez Canal University   (Egypt)

^c UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

17 O [N (2 BROMOETHYL)CARBAMOYL]LATRUNCULIN A; 17 O [N (2 CHLOROETHYL)CARBAMOYL]LATRUNCULIN A; 17 O [N (3 CHLOROPROPYL)CARBAMOYL]LATRUNCULIN A; 17 O [N (BENZYL)CARBAMOYL]LATRUNCULIN A; 17 O [N (PHENYL)CARBAMOYL]LATRUNCULIN A; ACTIN; ARGININE; C 17 O CARBAMATE; G ACTIN; HYPOXIA INDUCIBLE FACTOR 1; LATRUNCULIN A; MATRIGEL; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BREAST TUMOR; CANCER CELL CULTURE; CANCER INHIBITION; CANCER INVASION; CELL MIGRATION; CELL SHAPE; CHEMICAL REACTION; CONTROLLED STUDY; CYTOKINESIS; DRUG MECHANISM; DRUG SYNTHESIS; GENE ACTIVATION; HUMAN; HUMAN CELL; MALE; MICROFILAMENT; PHARMACOPHORE; POLYMERIZATION; PROSTATE TUMOR; TUMOR CELL;

ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; BREAST NEOPLASMS; CARBAMATES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1; MALE; MOLECULAR STRUCTURE; PORIFERA; PROSTATIC NEOPLASMS; THIAZOLIDINES;

NEGOMBATA MAGNIFICA;

EID: 42249093328     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np070587w     Document Type: Article

References (41)

1. Kashman, Y.; Groweiss, A.; Shmueli, U. Tetrahedron Lett. 1980, 21, 3629-3632.
2. Okka, M.; Tian, B.; Kaufman, P. L. Arch. Ophthalmol. 2004, 122, 1482-1488.
3. Kaufman, P. L.; Geiger, B. U.S. Patent 772,412, 2002.
4. El Sayed, K. A.; Youssef, D. T. A.; Marchetti, D. J. Nat. Prod. 2006, 69, 219-223.
5. Specter, I.; Shochet, N. R.; Blasberger, D.; Kashman, Y. Cell Motil. Cytoskel. 1989, 13, 127-144.
6. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2004, 67, 1216-1238.
7. Nakaseko, Y.; Yanagida, M. Nature 2001, 412, 291-292.
8. Gachet, Y.; Tournier, S.; Millar, J. B.; Hyams, J. S. Nature 2001, 412, 352-355.
9. Yarmola, E. G.; Somasundaram, T.; Boring, T. A.; Spector, I.; Bubb, M. R. J. Biol. Chem. 2000, 275, 28120-28127.
10. Morton, W. M.; Ayscough, K. R.; McLaughlin, P. J. Nat. Cell Biol. 2000, 2, 376-378.
11. Groweiss, A.; Shmueli, U.; Kashman, Y. J. Org. Chem. 1983, 48, 3512-3516.
12. Blasberger, D.; Carmely, S.; Cojocaru, M.; Spector, I.; Shochet, N. R.; Kashman, Y. Liebigs Ann. Chem. 1989, 12, 1171-1188.
13. (a) Shah, G. V.; Noble, M. J.; Austenfeld, M.; Weigel, J.; Deftos, L. J.; Mebust, W. K.; Winston, K. Prostate 1992, 21, 87-97.
14. (b) Thomas, S.; Chigurupati, S.; Anbalagan, M.; Shah, G. Mol. Endocrinol. 2006, 20, 1894-1911.
15. (c) Chien, J.; Ren, Y.; Wang, Y. Q.; Bordelon, W.; Thompson, E.; Davis, R.; Rayford, W.; Shah, G. Mol. Cell. Endocrinol. 2001, 181, 69-79.
16. (d) Thomas, S.; Chiriva-Internati, M.; Shah, G. V. Clin. Exp. Metastasis 2007, 24, 363-377.
17. (a) Cooper, C. R.; Chay, C. H.; Pienta, K. J. Neoplasia 2002, 4, 191-194.
18. (b) Ghosh, P. M.; Ghosh-Choudhury, N.; Moyer, M. L.; Mott, G. E.; Thomas, C. A.; Foster, B. A.; Greenberg, N. M.; Kreisberg, J. I. Oncogene 1999, 18, 4120-4130.
19. (c) Chen, Y.; Wang, Y.; Yu, H.; Wang, F.; Xu, W. Exp. Biol. Med. 2005, 230, 731-741.
20. (d) Alroy, I.; Yarden, Y. FEBS Lett. 1997, 410, 83-86.
21. (e) Hoevel, T.; Macek, R.; Swisshelm, K.; Kubbies, M. Int. J. Cancer 2004, 108, 374-383.
22. (a) Byers, H. R.; Etoh, T.; Doherty, J. R.; Sober, A. J.; Mihm, M. C. Am. J. Pathol. 1991, 139, 423-435.
23. (b) Hotulainen, P.; Paunola, E.; Vartiainen, M. K.; Lappalainen, P. Mol. Biol. Cell 2005, 16, 649-664.
24. (c) Cascone, I.; Giraudo, E.; Caccavari, F.; Napione, L.; Bertotti, E.; Collard, J. G.; Serini, G.; Bussolino, F. J. Biol. Chem. 2003, 278, 50702-50713.
25. (d) Yoshioka, K.; Nakamori, S.; Itoh, K. Cancer Res. 1999, 59, 2004-2010.
26. (e) Gondi, C. S.; Lakka, S. S.; Yanamandra, N.; Olivero, W. C.; Dinh, D. H.; Gujrati, M.; Tung, C. H.; Weissleder, R.; Rao, J. S. Cancer Res. 2004, 64, 4069-4077.
27. (a) Tatum, J. L.; Kelloff, G. J.; Gillies, R. J.; Arbeit, J. M.; Brown, J. M.; Chao, K. S.; Chapman, J. D.; Eckelman, W. C.; Fyles, A. W.; Giaccia, A. J.; Hill, R. P.; Koch, C. J.; Krishna, M. C.; Krohn, K. A.; Lewis, J. S.; Mason, R. P.; Melillo, G.; Padhani, A. R.; Powis, G.; Rajendran, J. G.; Reba, R.; Robinson, S. P.; Semenza, G. L.; Swartz, H. M.; Vaupel, P.; Yang, D.; Croft, B.; Hoffman, J.; Liu, G.; Stone, H.; Sullivan, D. Int. J. Radiat. Biol. 2006, 82, 699-757.
28. (b) Semenza, G. L. Nat. Rev. Cancer 2003, 3, 721-732.
29. (c) Maxwell, P. H.; Dachs, G. U.; Gleadle, J. M.; Nicholls, L. G.; Harris, A. L.; Stratford, I. J.; Hankinson, O.; Pugh, C. W.; Ratcliffe, P. J. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 8104-8109.
30. (d) Ryan, H. E.; Lo, J.; Johnson, R. S. EMBO J. 1998, 17, 3005-3015.
31. (e) Ryan, H. E.; Poloni, M.; McNulty, W.; Elson, D.; Gassmann, M.; Arbeit, J. M.; Johnson, R. S. Cancer Res. 2000, 60, 4010-4015.
32. (f) Kung, A. L.; Wang, S.; Klco, J. M.; Kaelin, W. G.; Livingston, D. M. Nat. Med. 2000, 6, 1335-1340.
33. (g) Kung, A. L.; Zabludoff, S. D.; France, D. S.; Freedman, S. J.; Tanner, E. A.; Vieira, A.; Cornell-Kennon, S.; Lee, J.; Wang, B.; Wang, J.; Memmert, K.; Naegeli, H. U.; Petersen, F.; Eck, M. J.; Bair, K. W.; Wood, A. W.; Livingston, D. M. Cancer Cell 2004, 6, 33-43.
34. (h) Unruh, A.; Ressel, A.; Mohamed, H. G.; Johnson, R. S.; Nadrowitz, R.; Richter, E.; Katschinski, D. M.; Wenger, R. H. Oncogene 2003, 22, 3213-3220.
35. (i) Moeller, B. J.; Dreher, M. R.; Rabbani, Z. N.; Schroeder, T.; Cao, Y.; Li, C. Y.; Dewhirst, M. W. Cancer Cell 2005, 8, 99-110.
36. (j) Semenza, G. L. Expert Opin. Ther. Targets 2006, 10, 267-280.
37. (k) Melillo, G. Cancer Metastasis Rev. 2007, 16, 341-352.
38. Dai, J.; Liu, Y.; Zhou, Y.-D.; Nagle, D. G. J. Nat. Prod. 2007, 70, 130-133.
39. Kelly-Borges, M.; Vacelet, J. Mem. Queensl. Mus. 1995, 38, 477-503.
40. Antunes, E. M.; Copp, B. R.; Davies-Coleman, M. T.; Samaai, T. Nat. Prod. Rep. 2005, 22, 62-72.
41. Hodges, T. W.; Hossain, F. C.; KJm, Y.-P.; Zhou, Y.-D.; Nagle, D. G. J. Nat. Prod. 2004, 67, 767-771.