Synthesis and phosphatase inhibitory activity of analogs of sulfircin

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 15, 1997, Pages 2015-2020

  Cebula, Regina E ^a   Blanchard, Jill L ^a   Boisclair, Michael D ^a   Pal, Kollol ^a   Bockovich, Nicholas J ^a  

^a GPC Biotech Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHATASE; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; SESQUITERPENE; SULFIRICIN; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ALBICANS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SPECIFICITY; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0030808130     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00357-0     Document Type: Article

References (14)

1. Wright, A. E.; McCarthy, P. J. U. S. Patent 4,870,099, 1989.
2. Wright, A. E.; McCarthy, P. J.; Schulte, G. K. J. Org. Chem. 1989, 54, 3472.
3. The cdc25 inhibitory activity of sulfircin was first discovered as part of a sponsored research collaboration between scientists at Harbor Branch Oceanographic Institute, Inc. (HBOI) and Mitotix. As part of this project, extracts of marine organisms were screened at HBOI for their ability to inhibit cdc25. This resulted in the identification of thirty-five active extracts. Bioassay-guided fractionation of an extract of a sponge of the genus Ircinia led to the purification of sulfircin as the major active compound.
4. Tonks, N. K.; Diltz, C. D.; Fischer, E. H. J. Biol. Chem. 1988, 263, 6722.
5. Ishibashi, T.; Bottaro, D. P.; Chan, A.; Miki, T.; Aaronson, S. A. Proc. Natl. Acad. Sci., U.S.A. 1992, 89, 12170.
6. Galaktionov, K.; Beach, D. Cell 1991, 67, 1181.
7. Carman, R. M.; Deeth, H. C. Aust. J. Chem. 1971, 24, 1099.
8. Cambie, R. C.; Joblin, K. N.; Preston, A. F. Aust. J. Chem. 1971, 24, 583.
9. Gonzalez-Sierra, M.; Ruveda, E. A.; Lopez, J. T.; Cortes, M. J. Heterocycles 1987, 26, 2801.
10. Vlad, P. F.; Kryshtal, G. V.; Lazur'evskii, G. V. Zh. Obshch. Khim. 1967, 37, 2187.
11. Tilley, J. W.; Danho, W.; Lovey, K.; Wagner, R.; Swistok, J.; Makofske, R.; Michalewsky, J.; Triscari, J.; Nelson, D.; Weatherford, S. J. Med. Chem. 1991, 34, 1125.
12. 1H NMR data.
13. The assay for Cdc25A is described in: Eckstein, J.; Beer-Romero, P.; Berdo, I. Protein Science 1996, 5, 5. The assays for PTP1B and VHR are described in: Gottlin, E. B.; Xu, X.; Epstein, D. M.; Burke, S. P.; Eckstein, J. W.; Ballou, D. P.; Dixon, J. E. J. Biol. Chem. 1996, 271, 27445.
14. The assay for Cdc25A is described in: Eckstein, J.; Beer-Romero, P.; Berdo, I. Protein Science 1996, 5, 5. The assays for PTP1B and VHR are described in: Gottlin, E. B.; Xu, X.; Epstein, D. M.; Burke, S. P.; Eckstein, J. W.; Ballou, D. P.; Dixon, J. E. J. Biol. Chem. 1996, 271, 27445.