Analogs of cyclosporin a modified at the d-ala8 position

The Journal of Antibiotics

Volumn 45, Issue 1, 1992, Pages 94-102

  Patchett, Arthur A ^a   Taub, David ^a   Hensens, Otto D ^a   Goegelman, Robert T ^a   Yang, Lihu ^a   Dumont, Francis ^a   Peterson, Larry ^a   Sigal, Nolan H ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOSPORIN A; DRUG ANALOG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; INTRAVENOUS DRUG ADMINISTRATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; REGIONAL PERFUSION; STEREOCHEMISTRY; T LYMPHOCYTE ACTIVATION;

ANIMAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; CYCLOSPORINS; FEMALE; IMMUNOSUPPRESSIVE AGENTS; LYMPHOCYTE ACTIVATION; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED C57BL; MOLECULAR CONFORMATION; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; T-LYMPHOCYTES;

EID: 0026557370     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.7164/antibiotics.45.94     Document Type: Article

References (23)

1. Borel, J. F.: Pharmacology of cyclosporine (Sandimmune) IV. Pharmacological properties in vivo. Pharmacol. Rev. 41: 259-371, 1989
2. Mason, J.: Pharmacology of cyclosporine (Sandimmune) VII. Pathophysiology and toxicology of cyclosporine in humans and animals. Pharmacol. Rev. 41: 423-434, 1989
3. Wenger, R. M.: Pharmacology of cyclosporine (Sandimmune) II. Chemistry. Pharmacol. Rev. 41: 243-247, 1989
4. Wenger, R. M.: Synthesis of cyclosporin and analogues: Structural and conformational requirements for immunosuppressive activity. Prog. Allergy 38: 46-64, 1986
5. Wenger, R. M.; T. G. Payne & M. H. Schreier: Cyclosporine: Chemistry, structure-activity relationships and mode of action. In Progress in Clinical Biochemistry. Vol. 3, pp. 157-191, Springer-Verlag, 1986
6. Traber, R.; H. Hofmann & H. Kobel: Cyclosporins-new analogues by precursor directed biosynthesis. J. Antibiotics 42: 591-597, 1989
7. Lawen, A.; R. Traber, D. Geyl, R. Zocher & H. Kleinkauf: Cell-free biosynthesis of new cyclosporins. J. Antibiotics 42: 1283-1289, 1989
8. Wenger, R.; R. P. Traber, H. Kobel & H. Hofmann (Sandoz): Novel cyclosporins. U.S. 4,639,434, Jan. 27, 1987
9. Wenger, R.: Cyclosporine and analogues: Structural requirements for immunosuppressive activity. Transplant. Proc. 28 (Suppl. 5): 213-218, 1986
10. Quesniaux, V. F. J.; M. H. Schreier, R. M. Wenger, P. C. Hiestand, M. W. Harding & M. H. V. van Regenmortel: Molecular characteristics of cyclophilin-cyclosporine interactions. Transplantation 46: 235-275, 1988
11. Fesik, S. W.; R. T. Gampe, Jr., T. F. Holzman, D. A. Egan, R. Edalji, J. R. Luly, R. Helfrich, V. Kishore & D. H. Rich: Isotope-edited NMR of cyclosporin A bound to cyclophilin: evidence for a trans 9,10 amide bond. Science 250: 1406-1409, 1990
12. Schreiber, S. L.: Chemistry and biology of the immunophilins and their immunosuppressive ligands. Science 251: 283-287, 1991
13. Hensens, O. D.; R. F. White, R. T. Goegelman, E. S. Inamine & A. A. Patchett: The preparation of [2-deutero-3-fluoro-d-Ala8]cyclosporin A by directed biosynthesis. J. Antibiotics 45: 133-135, 1992
14. Seebach, D. (Sandoz): Novel cyclosporins. U.S. 4,703,033, Oct. 27, 1987
15. Seebach, D.; W. Murtiashaw, R. Naef, S. I. Shoda, M. Krieger, P. Bollinger, A. Leutwiler & R. M. Wenger: Aktive cyclosporinderivate durch C-alkylierung unter ersatz von H-re der sarkosin-einheit. Erzeugung polylithüerter peptide. Presented at the Swiss Chem. Soc. Mtg., Berne, Oct. 18, 1985 [Cited by Wenger, R. M.: Pharmacology of cyclosporin (Sandimmune) II. Chemistry. Pharmacol. Rev. 41: 243-247, 1989]
16. Walsh, C: Suicide substrates: mechanism-based enzyme inactivators. Tetrahedron 38: 871-909, 1982
17. Kessler, H.; H.-R. Loosli & H. Oschkinat: Assignment of the 1H-, 13C-, and 15N-NMR spectra of cyclosporin A in CDC13 and C6D6 by a combination of homo-and heteronuclear two-dimensional techniques. Helv. Chim. Acta 68: 661-681, 1985
18. Loosli, H. R.; H. Kessler, H. Oschkinat, H.-P. Weber, T. J. Petcher & A. Widmer: The conformation of 'cyclosporin A' in the crystal and in solution. Helv. Chim. Acta 68: 682-703, 1985
19. Durette, P. L.; J. Boger, F. Dumont, R. Firestone, R. A. Frankshun, S. L. Koprak, C. S. Lin, M. R. Melino, A. A. Pessolano, J. Pisano, J. A. Schmidt, N. H. Sigal, M. J. Staruch & B. E. Witzel: A study of the correlation between cyclophilin binding and in vitro immunosuppressive activity of cyclosporine A and analogues. Transplant. Proc. 20 (Suppl. 2): 51-57, 1988
20. Dumont, F. J.; M. J. Staruch, S. L. Koprak, M. R. Melino & N. H. Sigal: Distinct mechanisms of suppression of murine T cell activation by the related macrolides FK-506 and rapamycin. J. Immunol. 144: 251-259, 1990
21. States, D. J.; R. A. Haberkorn & D. J. Reuben: A two dimensional nuclear Overhauser experiment with pure absorption phase in four quadrants. J. Magn. Reson. 48: 286-293, 1982
22. Kessler, H.; M. Gerhke, J. Lautz, M. Kock, D. Seebach & A. Thaler: Complexation and medium effects on the conformation of cyclosporin A studied by NMR spectroscopy and molecular dynamics calculations. In NMR Methods for Elucidating Macromolecule-Ligand Interactions: An Approach to Drug Design. Eds., R. E. Schumacher & I. M. Armitage, pp. 169-173, Pergamon Press, 1990
23. Wenger, R. M.: Total synthesis of cyclosporin A and cyclosporin H, two fungal metabolites isolated from the species Tolypocladium inflatum Gams. Helv. Chim. Acta 67: 502-525, 1984