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Isolation and structural elucidation of the cytostatic linear and cyclo-depsipeptides dolastatin 16, dolastatin 17, and dolastatin 18

Pettit, G.R.; Xu, J.P.ng

Official Gazette of the United States Patent and Trademark Office Patents 1246(5)

2001

ISSN/ISBN: 0098-1133
Accession: 035190462
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Cytostatic linear and cyclo-depsipeptides, "Dolastatin 16", "Dolastatin 18", and "Dolastatin 17", are disclosed which are obtained from Indian Ocean shelless mollusk Dolabella auricularia. Methods of using the substances to inhibit malignant cell growth associated with neoplastic diseases in animals and humans are also disclosed, as well as pharmaceutical preparations containing Dolastatin 16, Dolastatin 17, and Dolastatin 18.

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Related References

Winterhalter, B.R.; Berger, D.P.; Pettit, G.R.; Fiebig, H.H. 1991: Cytotoxicity of dolastatin 10 dolastatin 15 and dolastatin k333 human tumor xenografts in vitro Proceedings of the American Association for Cancer Research Annual Meeting 32: 402
Quentmeier, H.; Brauer, S.; Pettit, G.R.; Drexler, H.G. 1992: Cytostatic effects of dolastatin 10 and dolastatin 15 on human leukemia cell lines Leukemia and Lymphoma 6(3): 245-250
Pettit, G.R.; Kamano, Y.; Dufresne, C.; Cerny, R.L.; Herald, C.L.; Schmidt, J.M. 1989: Isolation and structure of the cytostatic linear depsipeptide dolastatin 15 Journal of Organic Chemistry 54(26): 6005-6006
Steube, K.G.; Grunicke, D.; Pietsch, T.; Gignac, S.M.; Pettit, G.R.; Drexler, H.G. 1992: Dolastatin 10 and dolastatin 15: effects of two natural peptides on growth and differentiation of leukemia cells Leukemia 6(10): 1048-1053
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Nogle, L.M.; Gerwick, W.H. 2002: Isolation of Four New Cyclic Depsipeptides, Antanapeptins AD, and Dolastatin 16 from a Madagascan Collection of Lyngbya m ajuscula Journal of Natural Products 65(1): 21-24
Nogle, L.M.; Gerwick, W.H. 2002: Isolation of four new cyclic depsipeptides, antanapeptins A-D, and dolastatin 16 from a Madagascan collection of Lyngbya majuscula Journal of Natural Products 65(1): 21-24
Pettit, GR.; Kamano, Y.; Herald, CL.; Dufresne, C.; Cerny, RL.; Herald, DL.; Schmidt, JM.; Kizu, H. 1989: Isolation and structure of the cytostatic depsipeptide dolastatin 13 from the sea hare Dolabella auricularia Journal of the American Chemical Society 1133: 5015-5016
Pettit, G.R.; Kamano, Y.; Herald, C.L.; Dufresne, C.; Cerny, R.L.; Herald, D.L.; Schmidt, J.M.; Kizu, H. 1989: Isolation and structure of the cytostatic depsipeptide dolastatin 13 from the sea hare Dolabella auricularia Journal of the American Chemical Society 111(13): 5015-5017
Roux, F.; Maugras, I.; Poncet, J.; Niel, G.; Jouin, P. 1994: Synthesis of dolastatin 10 and -dolastatin 10 Tetrahedron 50(18): 5345-5360
Holzapfel, C.W.; Van Zyl, W.J.; Roos, M. 1990: The synthesis and conformation in solution of cyclo l pro l leu l gln thz gly thz l val dolastatin 3 Tetrahedron 46(2): 649-660
Hu, M.K.; Huang, W.S. 1999: Synthesis and cytostatic properties of structure-simplified analogs of dolastatin 15 Journal of Peptide Research: Official Journal of the American Peptide Society 54(6): 460-467
Pettit, G.R.; Barkoczy, J. 2000: Elucidation and synthesis of antineoplastic tetrapeptide phenethylamides of dolastatin 10 Official Gazette of the United States Patent and Trademark Office Patents 1232(1)
Schmidt, U.; Dipl.-Chem. Utz, R. 1984: Synthetic studies on the elucidation of the structure and configuration of dolastatin 3 Angewandte Chemie International Edition 23(9): 725-726
Pettit, G.R.; Singh, S.B.; Hogan, F.; Burkett, D.D. 1990: Chiral modifications of dolastatin 10: the potent cytostatic peptide (19aR)-isodolastatin 10 Journal of Medicinal Chemistry 33(12): 3132-3133
Bredenkamp, M.W.; Holzapfel, C.W.; Van Zyl, W.J. 1990: The synthesis and analysis of the conformation in solution of the dolastatin 3 diastereomer cyclo[-L-Pro-L-Leu-D-(Gln)Thz-(Gly)Thz-L-Val-] Liebigs Annalen der Chemie (9): 871-875
Stezowski, J.J.; Poehlmann, H.W.; Haslinger, E.; Kalchhauser, H.; Schmidt, U.; Pozolli, B. 1987: The conformation of cyclo l pro l leu l val gly thz a dolastatin 3 analog in the crystalline and solution states Tetrahedron 43(17): 3923-3930
Bredenkamp, M.W.; Holzapfel, C.W.; Van Zyl, W.J. 1990: The synthesis and analysis of the conformation in solution of the dolastatin 3 diastereomer cyclo l pro l leu d gln thz gly thz l val Liebigs Annalen der Chemie 9: 871-876
Stezowski, J.J.; Pohlmann, H.W.; Haslinger, E.; Kalchhauser, H.; Schmidt, U.; Pozolli, B. 1987: The conformation of cyclo[L-Pro-L-Leu-L-Val-(gly)Thz-(gly)Thz], a dolastatin 3 analog, in the crystalline and solution states Tetrahedron (Oxford. Print) 43(17): 3923-3930