Unexpected side chain effects at residue 8 of cyclosporin A derivatives allow photoswitching of immunosuppression

Journal of Biological Chemistry

Volumn 280, Issue 6, 2005, Pages 4842-4850

  Zhang, Yixin ^a   Erdmann, Frank ^a   Baumgrass, Ria ^a,b   Schutkowski, Mike ^a,c   Fischer, Gunter ^a  

^a M P Res U Enzymol Protein F   (Germany)

^b DEUTSCHES RHEUMA FORSCHUNGSZENTRUM   (Germany)

^c Jerini AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CELLS; DERIVATIVES; GENETIC ENGINEERING; IRRADIATION; PROTEINS;

CALCINEURIN (CAN); CELL PROLIFERATION; CYCLIC PEPTIDES; GENE ASSAY;

ENZYME INHIBITION;

CALCINEURIN; CYCLOPHILIN; CYCLOSPORIN A DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; ISOMERASE; SERINE;

ARTICLE; BINDING SITE; CHEMICAL MODIFICATION; CYTOKINE PRODUCTION; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IMMUNOSUPPRESSIVE TREATMENT; LIGHT IRRADIANCE; LYMPHOCYTE PROLIFERATION; PRIORITY JOURNAL; REPORTER GENE; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE; TRANSCRIPTION REGULATION;

CALCINEURIN; CARBON; CELL LINE; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; CYCLOPHILINS; CYCLOSPORINE; CYTOKINES; DNA-BINDING PROTEINS; DOSE-RESPONSE RELATIONSHIP, DRUG; GENES, REPORTER; GLUTATHIONE TRANSFERASE; HUMANS; IMMUNOSUPPRESSIVE AGENTS; INHIBITORY CONCENTRATION 50; JURKAT CELLS; LIGHT; LUCIFERASES; MODELS, CHEMICAL; MODELS, MOLECULAR; NFATC TRANSCRIPTION FACTORS; NUCLEAR PROTEINS; PEPTIDES; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; SERINE; T-LYMPHOCYTES; TIME FACTORS; TRANS-ACTIVATION (GENETICS); TRANSCRIPTION FACTORS;

EID: 14244258607     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M409178200     Document Type: Article

References (43)

1. Borel, J. F. (1989) Pharmacol. Rev. 41, 259-371
2. Fischer, G. (1994) Angew. Chem. Int. Ed. Engl. 33, 1415-1436
3. Sigal, N. H., Dumont, F., Durette, P., Siekierka, J. J., Peterson, L., Rich, D. H., Dunlap, B. E., Staruch, M. J., Melino, M. R., Koprak, S. L., Williams, D., Witzel, B., and Pisano, J. M. (1991) J. Exp. Med. 173, 619-628
4. Liu, J., Farmer, J. D., Jr., Lane, W. S., Friedman, J., Weissman, I., and Schreiber, S. L. (1991) Cell 66, 807-815
5. Schreiber, S. L., and Crabtree, G. R. (1992) Immunol. Today 13, 136-142
6. Zhu, J., and McKeon, F. (2000) Cell. Mol. Life Sci. 57, 411-420
7. Zhu, J., and McKeon, F. (1999) Nature 398, 256-260
8. Hemenway, C. S., and Heitman, J. (1999) Cell Biochem. Biophys. 30, 115-151
9. Colgan, J., Asmal, M., Neagu, M., Yu, B., Schneidkraut, J., Lee, Y., Sokolskaja, E., Andreotti, A., and Luban, J. (2004) Immunity 21, 189-201
10. Brazin, K. N., Mallis, R. J., Fulton, D. B., and Andreotti, A. H. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 1899-1904
11. Zhang, L. H., and Liu, J. O. (2001) J. Immunol. 166, 5611-5618
12. Zhang, L. H., Youn, H. D., and Liu, J. O. (2001) J. Biol. Chem. 276, 43534-43540
13. Clarke, S. J., McStay, G. P., and Halestrap, A. P. (2002) J. Biol. Chem. 277, 34793-34799
14. Fischer, G., and Aumuller, T. (2003) Rev. Physiol. Biochem. Pharmacol. 148, 105-150
15. Luban, J. (1996) Cell 87, 1157-1159
16. Thali, M., Bukovsky, A., Kondo, E., Rosenwirth, B., Walsh, C. T., Sodroski, J., and Gottlinger, H. G. (1994) Nature 372, 363-365
17. Baumgrass, R., Zhang, Y., Erdmann, F., Thiel, A., Radbruch, A., and Fischer, G. (2004) J. Biol. Chem. 279, 2470-2479
18. Huai, Q., Kim, H. Y., Liu, Y., Zhao, Y., Mondragon, A., Liu, J. O., and Ke, H. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 12037-12042
19. Jin, L., and Harrison, S. C. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 13522-13526
20. Liu, J., Albers, M. W., Wandless, T. J., Luan, S., Alberg, D. G., Belshaw, P. J., Cohen, P., MacKintosh, C., Klee, C. B., and Schreiber, S. L. (1992) Biochemistry 31, 3896-3901
21. Nelson, P. A., Akselband, Y., Kawamura, A., Su, M., Tung, R. D., Rich, D. H., Kishore, V., Rosborough, S. L., DeCenzo, M. T., Livingston, D. J., and Harding, M. W. (1993) J. Immunol. 150, 2139-2147
22. Adams, S. R., and Tsien, R. Y. (1993) Annu. Rev. Physiol. 55, 755-784
23. Marriott, G. (1994) Biochemistry 33, 9092-9097
24. Eberle, M. K., Hiestand, P., Jutzi-Eme, A. M., Nininger, F., and Zihlmann, H. R. (1995) J. Med. Chem. 38, 1853-1864
25. Fischer, G., Bang, H., and Mech, C. (1984) Biomed. Biochim. Acta 43, 1101-1111
26. Mondragon, A., Griffith, E. C., Sun, L., Xiong, F., Armstrong, C., and Lui, J. O. (1997) Biochemistry 36, 4934-4942
27. Baumgrass, R., Weiwad, M., Erdmann, F., Liu, J. O., Wunderlich, D., Grabley, S., and Fischer, G. (2001) J. Biol. Chem. 276, 47914-47921
28. Traber, R., Hofmann, H., and Kobel, H. (1989) J. Antibiot. (Tokyo) 42, 591-597
29. Fischer, G., Wittmann-Liebold, B., Lang, K., Kiefhaber, T., and Schmid, F. X. (1989) Nature 337, 476-478
30. Thiel, A., and Radbruch, A. (1999) Arthritis Res. 1, 25-29
31. Zenke, G., Strittmatter, U., Fuchs, S., Quesniaux, V. F., Brinkmann, V., Schuler, W., Zurini, M., Enz, A., Billich, A., Sanglier, J. J., and Fehr, T. (2001) J. Immunol. 166, 7165-7171
32. Wenger, R. M. (1985) Angew. Chem. Int. Ed. Engl. 24, 77-85
33. Wenger, R. M. (1988) Transplant Proc. 20, 313-318
34. Moss, M. L., Palmer, R. E., Kuzmic, P., Dunlap, B. E., Henzel, W., Kofron, J. L., Mellon, W. S., Royer, C. A., and Rich, D. H. (1992) J. Biol. Chem. 267, 22054-22059
35. Schote, U., Ganz, P., Fahr, A., and Seelig, J. (2002) J. Pharm. Sci. 91, 856-867
36. Etzkorn, F. A., Chang, Z. Y., Stolz, L. A., and Walsh, C. T. (1994) Biochemistry 33, 2380-2388
37. Mikol, V., Kallen, J., Pflugl, G., and Walkinshaw, M. D. (1993) J. Mol. Biol. 234, 1119-1130
38. Dumont, F. J., Staruch, M. J., Koprak, S. L., Melino, M. R., and Sigal, N. H. (1990) J. Immunol. 144, 251-258
39. Hultsch, T., Albers, M. W., Schreiber, S. L., and Hohman, R. J. (1991) Proc. Natl. Acad. Sci. U. S. A. 88, 6229-6233
40. Fanghanel, J., and Fischer, G. (2003) Biophys. Chem. 100, 351-366
41. Li, W., Llopis, J., Whitney, M., Zlokarnik, G., and Tsien, R. Y. (1998) Nature 392, 936-941
42. Kiani, A., Rao, A., and Aramburu, J. (2000) Immunity 12, 359-372
43. Furuta, T., Wang, S. S., Dantzker, J. L., Dore, T. M., Bybee, W. J., Callaway, E. M., Denk, W., and Tsien, R. Y. (1999) Proc. Natl. Acad. Sci. U. S. A. 96, 1193-1200