Synthesis and cytostatic activities of didemnin derivatives

Journal of Peptide Research

Volumn 54, Issue 2, 1999, Pages 146-161

  Schmidt, U ^a   Griesser, H ^a   Haas, G ^a   Kroner, M ^a   Riedl, B ^a   Schumacher, A ^a   Sutoris, F ^a   Haupt, A ^b   Emling, F ^c  

^a UNIVERSITY OF STUTTGART   (Germany)

^b BASF SE   (Germany)

^c Knoll AG   (Germany)

Author keywords

Cyclopeptides; Cyclopeptolides; Cytostatic agents; Non proteinogenic amino acids

Indexed keywords

AMIDE; AMINO ACID; CYCLOPEPTIDE; CYTOSTATIC AGENT; DIAMINOBUTYRIC ACID; DICHLOROMETHANE; DIDEMNIN A; ESTER; TETRAHYDROFURAN; THREONINE; TRIACYLGLYCEROL LIPASE;

AMINO ACID SEQUENCE; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CYTOSTASIS; DIASTEREOISOMER; DRUG SYNTHESIS; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOSUPPRESSIVE TREATMENT; PRIORITY JOURNAL; SEQUENCE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, THIN LAYER; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES, CYCLIC; TUMOR CELLS, CULTURED;

EID: 0032783046     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00097.x     Document Type: Article

References (26)

1. Schmidt, U., Schumacher, A., Mittendorf, J. & Riedl, B. (1998) Contribution to the synthesis of aureobasidin A. Synthesis of cyclopeptolides containing the sequence leucyl-N-methyl-β-hydroxyvalyl-(2R) - pentanoic acid. J. Peptide Res. 52, 143-154.
2. Sakai, R., Rinchart, K.L., Kishore, V., Kundu, B., Faircloth, G., Gloer, J.B., Carney, J.R., Namikoshi, M., Sun, F., Hughes, R.G. Jr, Gravalos, D.G., de Quesada, T.G., Wilson, G.R. & Heid, R.M. (1996) Sructure-Activity relationships of the didemnins. J. Med. Chem. 39, 2819-2834.
3. Jouin, P., Poncet, J., Dufour, M.N., Aumelas, A., Pantaloni, A., Cros, S. & Francois, G. (1991) Antineoplastic activity of didemnin congeners: nordidemnin and modified chain analogues. J. Med. Chem. 34, 486-491.
4. Mayer, S.C., Ramanjulu, J., Vera, M.D., Pfizenmayer, A.J. & Joulliē, M.M. (1994) Synthesis of new didemnin B analogs for investigations of structure/biological activity relationships. J. Org. Chem. 59, 5192-5205.
5. Jouin, P., Poncet, J., Dufour, M.N., Pantaloni, A. & Castro, B. (1988) Synthesis of the cyclodepsipeptide nordidemnin B, a cytotoxic minor product isolated from the sea tunicate trididemnum cyanophorum. J. Org. Chem. 54, 617-627.
6. Mayer, S.C., Pfizenmayer, A.J. & Joullié, M.M. (1996) Synthetic routes to a constrained ring analog of didemnin B. J. Org. Chem. 61, 1655-1664.
7. Ramanjulu, J.M., Ding, X., Joullié, M.M. & Li, W. (1997) Synthesis of a reduced ring analog of didemnin B. J. Org. Chem. 62, 4961-4969.
8. Furukubo, S., Hamada, Y. & Shioiri, T. (1992) Synthesis of lower analogs of didemnins: cytotoxic cyclic depsipeptides. Pept. Chem. Proc. Jpn Symp. 2nd 1992. (published 1993) 140-141, -CA120, 1171.
9. Rinchart, K.L. Jr, Kishore, V., Nagarajan, S., Lake, R.J., Gloer, J.B., Bozich, F.A., Li, K,M., Maleczka, R.E. Jr, Todsen, W.L., Munro, M.H.G., Sullins, D.W. & Sakai, R. (1987) Total synthesis of didemnins A, B and C. J. Am. Chem. Soc. 109, 6846-6848;
10. Helm, D. v. d. (1987) Meeting Intern. Congress of Crystallography, Perth, Australia, Paper C-52/03.2-8.
11. Schmidt, U., Kroner, M. & Griesser, H. (1988) Total synthesis of the didemnins - 1. synthesis of the peptolide ring. Tetrahedron Lett. 29, 3057-3060.
12. Schmidt, U., Kroner, M. & Griesser, H. (1988) Total synthesis of the didemnins. - 2. synthesis of didemnin A, B, C and prolyldidemnin A. Tetrahedron Lett. 29: 4407-4408.
13. Schmidt, U., Kroner, M. & Griesser, H. (1988) Total synthesis of the didemnins - iii. synthesis of protected (2R,3S)-alloisoleucine and (3S,4R,5S) isostatine derivatives amino acids from hydroxy acids. Synthesis, 832-835.
14. Schmidt, U., Kroner, M. & Griesser, H. (1988) Total synthesis of the didemnins - iv. synthesis of the peptolide ring and construction of the side chain. Synthesis, 294-300.
15. Schmidt, U. & Langner, J. (1997) A summary of this reaction is given in: Cyclotetrapeptides and cyclopentapeptides: occurrence and synthesis. J. Peptide Res. 49, 67-73.
16. Kessler, H., Mronga, S., Will, M. & Schmidt, U. (1990) Solution structure of [Me-L-Leu-7] didemnin B determined by NMR spectroscopy and refined by MD calculation. Helv. Chim. Acta. 73, 25-47.
17. Schmidt, U., Griesser, H., Haas, G., Kroner, M., Riedl, B., Emling, F., Haupt, A. & Kluge, M. Ger. Offen D.E. 4,120 (1992) 327. C. A., 119, 117837.
18. Schmidt, U. & Schefenacker, K. (1985) Über Aktivierte N,N-Dimethylaminosäuren. - Synthese von Enkephalinen mit N,N- Dimethyltyrosin. Liebigs Ann. Chem. 1254- 1262.
19. Schmidt, U. & Potzolli, B. (1987) Peptidsynthese durch N- oder O-Aktivierung von Aminosäuren mit 1,2-Dihydro- 4,6-dimethyl-2-thioxo-3-pyridincarbonitril Synthese des Cyclosporin-8-11-Tetrapeptid- Segments. Liebigs Ann. Chem., 935-942.
20. a. Sutoris, H.F. (1995) Thesis Universität Stuttgart.
21. Schmidt, U., Riedl, B., Haas, G., Griesser, H., Vetter, A. & Weinbrenner, S. (1993) Enantioselective and diastereoselective formation of syn-3-Hydroxy-4-amino Acids (syn-Statines) via Tetramic Acids, and literature cited therein. Synthesis, 216-220.
22. Schmidt; U., Mundinger, K., Riedl, B., Haas, G. & Lau, R. (1992) Synthesis of enantiomerically pure and compatibly protected (2S,3R) - and (bv2Sev,3R) diaminobutyric acid. Synthesis, 1201-1202.
23. Flick, D.A. & Glifford, G.E. (1984) Comparison of in vitro cell cytotoxic assays for tumor necrosis factor. J. Immunol. Meth. 68, 167-175.
24. 23. Haas, G. (1991) Synthese von Didemninderivaten und Totalsynthese von Dolastatin 3. Thesis, Universität Stuttgart.
25. Riedl, B. (1991) Synthese von Didemninderivaten und acylietten Tetrahydropyridazinderivaten. Thesis, Universität Stuttgart.
26. Sutoris, H.F. (1995) Synthesen biologisch aktiver Cyclopeptide und nichtribosomaler Aminosäuren. Thesis, Universität Stuttgart.