Synthesis and biological evaluation of a targeted library of protein phosphatase inhibitors

Biotechnology and Bioengineering

Volumn 71, Issue 1, 2000, Pages 58-70

  Wipf, Peter ^a   Aslan, Diana C ^a   Luci, Diane K ^a   Southwick, Eileen C ^b   Lazo, John S ^b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

Author keywords

Alkylation of sulfonamides; Cdc25 dual specificity phosphatases; Phosphatase inhibitors; Reductive amination; Wang resin

Indexed keywords

ALKYLATION; AMINATION; CELL CULTURE; ENZYME INHIBITION; PHOSPHORUS COMPOUNDS; SYNTHESIS (CHEMICAL); TOXICITY;

PHOSPHATASE; SERINE; THREONINE; TYROSINE; WANG RESIN;

ENZYMES;

AMIDE; AMINE; CALYCULIN A; CYANOGINOSIN LR; LYSINE DERIVATIVE; OKADAIC ACID; PHOSPHOPROTEIN PHOSPHATASE; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; PROTEIN TYROSINE PHOSPHATASE; RESIN; SULFONAMIDE;

ARTICLE; BREAST CANCER; CELL PROLIFERATION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; PHARMACOPHORE; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

DATABASES; DRUG DESIGN; ENZYME INHIBITORS; ETHERS, CYCLIC; HUMANS; INDICATORS AND REAGENTS; KINETICS; MICROCYSTINS; MODELS, MOLECULAR; OKADAIC ACID; OXAZOLES; PEPTIDES, CYCLIC; PHOSPHOPROTEIN PHOSPHATASE; STRUCTURE-ACTIVITY RELATIONSHIP;

MAMMALIA;

EID: 0033964566     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(200024)71:1<58::AID-BIT9>3.0.CO;2-0     Document Type: Article

References (34)

1. Hung, D.T.; Jamison, T.F.; Schreiber, S.L. Chem Biol 1996, 3, 623-639.
2. Draetta, G.; Eckstein, J Biochim Biophys Acta 1997,1332, M53-M63.
3. Honkanen, R E.; Boynton, A.L. In Protein Kinase C; J.F. Kuo, Ed.; Oxford University Press: Oxford, 1994; Chapter 12; p. 305, and references cited therein.
4. Gunasekera, S.P.; McCarthy, P.J.; Kelly-Borges, M.; Lobkovsky, E.; Clardy, J. J Am Chem Soc 1996, 118, 8759-8760.
5. Galaktionov, K.; Lee, A.K.; Eckstein, J.; Draetta, G.; Meckler, J.; Loda, M.; Beach, D. Science 1995, 269, 1575-1577.
6. Todd, J.L.; Tanner, K.G.; Denu, J. M. J Biol Chem 1999, 274, 13271-13280.
7. Nagata, A.; Igarashi, M.; Jinno, S.; Suto, K.; Okayama, H. New Biologist 1991, 3, 959-968.
8. Gasparotto, D.; Maestro, R.; Piccinin, S.; Vukosavljevic, T.; Barzan, L.; Sulfaro, S.; Boiocchi, M., Cancer Res 1997, 57, 2366-2368.
9. El-Subbagh, H.I.; Abadi, A.H.; Al-Khawad, I.E.; Al-Rashood, K.A. Arch Pharm 1999, 332, 19-24.
10. Peng, H.; Zalkow, L.H. J Med Chem 1998, 41, 4677-4680.
11. Wipf, P.; Cunningham, A.; Rice, R.L.; Lazo, J.S. Bioorg Med Chem 1997, 5, 165-177.
12. Rice, R.L.; Rusnak, J.M.; Yokokawa, F.; Yokokawa, S.; Messner, D.J.; Boynton, A. L.; Wipf, P.; Lazo, J.S. Biochem 1997, 36, 15965-15974.
13. Glover, N.R.; Tracey, A.S. Biochem 1999, 38, 5256-5271.
14. Vogt, A.; Rice, R.L.; Settineri, C.E.; Yokokawa, F.; Yokokawa, S.; Wipf, P.; Lazo, J. S. J Pharmacol Exper Therap 1998, 287, 806-813.
15. Crivici, A.; Lajoie, G. Synth Comm 1993, 23, 49-53.
16. Guibé, F. Tetrahedron 1998, 54, 2967-3042.
17. Miller, S.C.; Scanlan, T.S. J Am Chem Soc 1997, 119, 2301-2302.
18. Miller, S.C.; Scanlan, T.S. J Am Chem Soc 1998, 120, 2690-2691.
19. Yang, L.; Chiu, K. Tetrahedron Lett 1997, 38, 7307-7310.
20. Reichwein, J.F.; Liskamp, R.M.J. Tetrahedron Lett 1998, 39, 1243-1246.
21. Nuss, J.M.; Desai, M.C.; Zuckermann, R.N.; Singh, R.; Renhowe, P.A.; Goff, D.A.; Chinn, J.P.; Wang, L.; Dorr, H.; Brown, E.G.; Subramanian, S. Pure Appl Chem 1997, 69, 447-452.
22. Wipf, P.; Henninger, T.C. J Org Chem 1997, 62, 1586-1587.
23. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6376.
24. Dankwardt, S.M.; Smith, D. B.; Porco, J.A.; Nguyen, C.H. Synlett 1997, 854-856.
25. Borch, R.F.; Bernstein M.D.; Durst, H.D. J Am Chem Soc 1971,93, 2897-2904.
26. Ley, S.V.; Mynett, D.M.; Koot, W.-J. Synlett 1995, 1017-1020.
27. Abdel-Magid, A.F.; Carson, K.G.; Harris, B.D.; Maryanoff, C.A.; Shah, R.D. J Org Chem 1996, 61, 3849-3862.
28. Bilodeau, M.T.; Cunningham, A.M. J Org Chem 1998, 63, 2800-2801.
29. Breitenbucher, J.G.; Hui, H.C. Tetrahedron Lett. 1998, 39, 8207-8210.
30. Khan, N.M.; Arumugam, V; Balasubramanian, S. Tetrahedron Lett 1996, 37, 4819-4822.
31. Szardenings, A.K.; Burkoth, T.S.; Look, G.C.; Campbell, D.A. J Org Chem. 1996, 61, 6720-6722.
32. Marchini, P; Liso, G; Reho, A. J. Org. Chem. 1975, 40, 3453-3456.
33. Advanced ChemTech Handbook of Combinatorial & Solid Phase Organic Chemistry; Bennett, W.D.; Christensen, J.W., Hamaker, L. K.; Peterson, M. L.; Rhodes, M. R.; Saneii, H. H., Eds.; Advanced ChemTech, 1998, p. 101.
34. Kaiser, E.; Colescot, R.L.; Bossinger, C.D.; Cook, P.I. Anal Biochem 1970, 34, 595-598.