Antimitotic diterpenes from Erythropodium caribaeorum test pharmacophore models for microtubule stabilization

Organic Letters

Volumn 2, Issue 3, 2000, Pages 257-260

  Cinel, Bruno ^a   Roberge, Michel ^a   Behrisch, Hans ^b   Van Ofwegen, Leen ^c   Castro, Clovis B ^d   Andersen, Raymond J ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b LEIDEN UNIVERSITY MEDICAL CENTER   (Netherlands)

^c NATURALIS BIODIVERSITY CENTER   (Netherlands)

^d FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTINEOPLASTIC AGENT; DITERPENE; ELEUTHEROBIN;

ANIMAL; ARTICLE; CELL CYCLE; CELL DEATH; CHEMICAL STRUCTURE; CHEMISTRY; COELENTERATE; DRUG EFFECT; IC 50; ISOLATION AND PURIFICATION; MICROTUBULE; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL DEATH; CNIDARIA; DITERPENES; INHIBITORY CONCENTRATION 50; MICROTUBULES; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034628224     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9912027     Document Type: Article

References (17)

1. (a) Jordan, A.; Hadfield, J. A.; Lawrence, N. J.; McGowen, A. T. Med. Res. Rev. 1998, 18, 259-296.
2. (b) Hamel, E. Ibid. 1996, 16, 207-231.
3. Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325-2333.
4. ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243-250.
5. Mooberry, S. L.; Tien, G.; Hernandez, A. H.; Plubrukarn, A.; Davidson, B. S. Cancer Res. 1999, 59, 653-660.
6. (a) Lindel, T.; Jensen, P. R.; Fenical, W.; Long, B. H.; Casazza, A. M.; Carboni, J.; Fairchild, C. R. J. Am. Chem. Soc. 1997, 119, 8744-8745.
7. (b) Long, B. H.; Carboni, J. M.; Wasserman, A. J.; Cornell, L. A.; Casazza, A. M.; Jensen, P. R.; Lindel, T.; Fenical, W.; Fairchild, C. R. Cancer Res. 1998, 58, 1111-1115.
8. (c) Hamel, E.; Sackett, D. L.; Vourloumis, D.; Nicolaou, K. C. Biochemistry 1999, 38, 5490-5498.
9. Ojima, I.; Chakravarty, S.; Inoue, T.; Lin, S.; He, L.; Horwitz, S. W.; Kuduk, S. D.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4256-4261.
10. Roberge, M.; Cinel, B.; Anderson, H.; Lim, L.; Jiang, X.; Xu, L.; Kelly, M. T.; Andersen, R. J. Cancer Res. Submitted for publication.
11. For previous chemical studies of E. caribaeorum, see: (a) Maharaj, D.; Pascoe, K. O.; Tinto, W. F. J. Nat. Prod. 1999, 62, 313-314.
12. (b) Pathirana, C.; Fenical, W. F.; Corcoran, E.; Clardy, J. Tetrahedron Lett. 1993, 34, 3371-3372.
13. (c) Pordesimo E. O.; Schmitz, F. J.; Ciereszko, L. S.; Hossain, M. B.; Van der Helm, D. J. Org. Chem. 1991, 56, 2344-2357.
14. (d) Look, S. A.; Fenical, W. F.; Van Engen, D.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 5026-5027.
15. Sarcodictyin F, a related 4,7-oxaeunicellane diterpenoid, has a similarly functionalized cyclohexene ring, but with the opposite stereochemistry at C-11. See: D'Ambrosio, M.; Guerriero, A.; Pietra, F. Helv. Chim. Acta 1988, 71, 964-976.
16. (a) McDaid, H. M.; Bhattacharya, Chen, X.-T.; He, L.; Shen, H.-J.; Gutteridge, C. E.; Horowitz, S. B.; Danishefsky, S. J. Cancer Chemother. Pharmacol. 1999, 44, 131-137.
17. (b) Nicolaou, K. C; Winssinger, N.; Vourloumis, D.; Ohshima, T.; Kim, S.; Pfefferkorn, J.; Xu, J.-Y.; Li, T. J. Am. Chem. Soc. 1998, 120, 10814-10826.