Synthesis of a PNA-encoded cysteine protease inhibitor library

Tetrahedron

Volumn 60, Issue 39, 2004, Pages 8677-8690

  Debaene, François ^a   Mejias, Lorenzo ^a   Harris, Jennifer L ^b,c   Winssinger, Nicolas ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b GENOMICS INSTITUTE OF THE NOVARTIS RESEARCH FOUNDATION   (United States)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Combinatorial chemistry; Microarrays; Peptide nucleic acid; Protease inhibitors

Indexed keywords

CYSTEINE PROTEINASE; CYSTEINE PROTEINASE INHIBITOR; PEPTIDE NUCLEIC ACID;

ARTICLE; COMBINATORIAL LIBRARY; DNA MICROARRAY; DRUG SYNTHESIS; HYBRIDIZATION; PRIORITY JOURNAL;

EID: 4344690276     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.107     Document Type: Article

References (39)

1. Pirrung M.C. Angew. Chem. Int. Ed. 41:2002;1276-1289
2. Heller M.J. Ann. Rev. Biomed. Eng. 4:2002;129-153
3. DeRisi J., Penland L., Brown P.O., Bittner M.L., Meltzer P.S., Ray M., Chen Y., Su Y.A., Trent J.M. Nat. Genet. 14:1996;457-460
4. Lockhart D.J., Dong H., Byrne M.C., Follettie M.T., Gallo M.V., Chee M.S., Mittmann M., Wang C., Kobayashi M., Horton H., Brown E.L. Nat. Biotechnol. 14:1996;1675-1680
5. Lockhart D.J., Winzeler E.A. Nature. 405:2000;827-836
6. Zhu H., Snyder M. Curr. Opin. Chem. Biol. 7:2003;55-63
7. Wang D., Liu S., Trummer B.J., Deng C., Wang A. Nat. Biotechnol. 20:2002;275-281
8. Houseman B.T., Mrksich M. Chem. Biol. 9:2002;443-454
9. Fodor S.P.A., Read J.L., Pirrung M.C., Stryer L., Lu A.T., Solas D. Science. 251:1991;767-773
10. Tegge W.J., Frank R. Methods Mol. Biol. 87:1998;99-106
11. MacBeath G., Koehler A.N., Schreiber S.L. J. Am. Chem. Soc. 121:1999;7967-7968
12. Hergenrother P.J., Depew K.M., Schreiber S.L. J. Am. Chem. Soc. 122:2000;7849-7850
13. Salisbury C.M., Maly D.J., Ellman J.A. J. Am. Chem. Soc. 124:2002;14868-14870
14. Pellois J.P., Zhou X., Srivannavit O., Zhou T., Gulari E., Gao X. Nat. Biotechnol. 20:2002;922-926
15. Barnes-Seeman D., Park S.B., Koehler A.N., Schreiber S.L. Angew. Chem. Int. Ed. 42:2003;2376-2379
16. Falsey J.R., Renil M., Park S., Li S., Lam K.S. Bioconj. Chem. 12:2001;346-353
17. Houseman B.T., Huh J.H., Kron S.J., Mrksich M. Nat. Biotechnol. 20:2002;270-274
18. Zhu Q., Lesaicherre M.-L., Uttamchandani M., Chen G.Y.J., Yao S.Q. Bioorg. Med. Chem. Lett. 12:2002;2085-2088
19. Uttamchandani M., Li D., Lesaicherre M.L., Yao S.Q. Org. Lett. 5:2003;1257-1260
20. Lovrinovic M., Seidel R., Wacker R., Schroeder H., Seitz O., Engelhard M., Goody R.S., Niemeyer C.M. Chem. Commun. 2003;822-823
21. Winssinger N., Harris J.L., Backes B.J., Schultz P.G. Angew. Chem. Int. Ed. 40:2001;3152-3155
22. Winssinger N., Ficarro S., Schultz P.G., Harris J.L. Proc. Natl. Acad. Sci. U. S. A. 99:2002;11139-11144
23. Furka Á., Sebestyén F., Asgedom M., Dibó G. Int. J. Pept. Protein Res. 37:1991;487
24. Hernandez A.A., Roush W.R. Curr. Opin. Chem. Biol. 6:2002;459-465
25. Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305-341
26. Otto H.-H. Chem. Rev. 97:1997;133-171
27. Yan S., Sloane B.F. Biol. Chem. 384:2003;845-854
28. Yamashita D.S., Smith W.W., Zhao B., Janson C.A., Tomaszek T.A., Bossard M.J., Levy M.A., Oh H.-J., Carr T.J., Thompson S.K., Ijames C.F., Carr S.A., McQueney M., D'Alessio K.J., Amegadzie B.Y., Hanning C.R., Abdel-Meguid S., DesJarlais R.L., Gleason J.G., Veber D.F. J. Am. Chem. Soc. 119:1997;11351-11352
29. Hook V.Y.H., Toneff T., Aaron W., Yasothornsrikul S., Bundey R., Reisine T. J. Neurochem. 81:2002;237-256
30. Saito K.I., Elce J.S., Hamos J.E., Nixon R.A. Proc. Natl. Acad. Sci. U. S. A. 90:1993;2628-2632
31. Mjalli A.M.M., Chapman K.T., Zhao J., Thornberry N.A., Peterson E.P., MacCoss M. Bioorg. Med. Chem. Lett. 5:1995;1405-1408
32. Greenbaum D.C., Baruch A., Grainger M., Bozdech Z., Medzihradszky K.F., Engel J., DeRisi J., Holder A.A., Bogyo M. Science. 298:2002;2002-2006
33. Powers J.C., Asgian J.L., Ekici O.D., James K.E., Dragovich P.S. Chem. Rev. 102:2002;4639-4750
34. Webber S.E., Babine R.E., Fuhrman S.A., Patick A.K., Matthews D.A., Lee C.A., Reich S.H., Prins T.J., Marakovits J.T., Littlefield E.S., Zhou R., Tikhe J., Ford C.E., Wallace M.B., Meador J.W. 3rd, Ferre R.A., Brown E.L., Binford S.L., Harr J.E., DeLisle D.M., Worland S.T. J. Med. Chem. 41:1998;2806-2818
35. Fukuyama T., Lin S.-C., Li L. J. Am. Chem. Soc. 112:1990;7050-7051
36. Prolong exposure to base or excess of base led to cyclative cleavage
37. Bollhagen R., Schmiedberger M., Barlos K., Grell E. J. Chem. Soc., Chem. Commun. 1994;2559-2560
38. Sakaitani M., Ohfune Y. J. Org. Chem. 55:1990;870-873
39. Carpino L.A. J. Am. Chem. Soc. 115:1993;4397-4398