Antineoplastic agents 365. Dolastatin 10 SAR probes

Anti-Cancer Drug Design

Volumn 13, Issue 4, 1998, Pages 243-277

  Pettit, George R ^a   Srirangam, Jayaram K ^a   Barkoczy, Jozsef ^a   Williams, Michael D ^a   Boyd, Michael R ^b   Hamel, Ernest ^b   Pettit, Robin K ^c   Hogan, Fiona ^a   Bai, Ruoli ^b   Chapuis, Jean Charles ^a   McAllister, Shane C ^c   Schmidt, Jean M ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c WESTERN OREGON UNIVERSITY   (United States)

Author keywords

Antineoplastic agents; Dolastatin 10; Structural modifications

Indexed keywords

ANTINEOPLASTIC AGENT; DOLASTATIN 10;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; CRYPTOCOCCUS NEOFORMANS; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; MICE; MICROBIAL SENSITIVITY TESTS; MICROCOCCUS LUTEUS; OLIGOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUMOR CELLS, CULTURED;

ANASPIDEA; AURICULARIA; DOLABELLA AURICULARIA; LEPUS; MURINAE;

EID: 7144263706     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. ALATTIA, T., ROUX, F., PONCET, J. CAVE, A. & JOUIN, P. (1995). Conformational study of dolastatin 10. Tetrahedron, 51 (9), 2593.
2. BAI, R., PETTIT, G.R. & HAMEL, E. (1990a). Dolastatin 10, a powerful cytostatic peptide derived from a marine animal: inhibition of tubulin polymerization mediated through the vinca alkaloid binding domain. Biochemical Pharmacology, 39, 1941.
3. BAI, R., PETTIT, G.R. & HAMEL, E (1990b). Structure-activity studies with chiral isomers and with segments of the antimitotic marine peptide dolastatin 10. Biochemical Pharmacology, 40, 1859.
4. BAI, R., PETTIT, G.R. & HAMEL, E. (1990c). Binding of dolastatin 10 to tubulin at a distinct site for peptide antimitotic agents near the exchangeable nucleotide and vinca alkaloid sites. Journal of Biological Chemistry, 265, 17141.
5. BAI, R., ROACH, M.C., SRIRANGAM, J.K., BARKOCZY, J., PETTIT, G.R., LUDUENA R.F. & HAMEL, E. (1993). Differential effects of active isomers, segments, and analogs of dolastatin 10 on ligand interactions with tubulin. Biochemical Pharmacology, 45, 1503.
6. BAI, R., TAYLOR, G.F., SCHMIDT, J.M., WILLIAMS, M.D., KEPLER, J.A., PETTIT, G.R. &. HAMEL, E. (1995). Interaction of dolastatin 10 with tubulin: induction of aggregation and binding and dissociation reactions. Molecular Pharmacology, 47, 965.
7. BENEDETTI, E., CARLOMAGNO, T., FRATERNALI, F, HAMADA, Y., HAYASHI, K., PAOLILLO, L. & SHIOIRI, T (1995). Conformational analysis of dolastatin 10: an NMR and theoretical approach. Biopolymers, 35, 525.
8. BOYD, M.R. (1993). The future of new drug development. Section I. Introduction to cancer therapy. In Current Therapy in Oncology. Niederhuber, J.E. (ed.), p. 11. B.C. Decker, Inc.: Philadelphia, PA.
9. BOYD, M.R. & PAULL, K.D. (1995). Some practical considerations and applications of the NCI in vitro anticancer drug discovery screen. Drug Development Research, 34, 91.
10. BOYD, M.R., PAULL, K D. & RUBINSTEIN, L.R. (1992). Data display and analysis strategies for the NCI disease-oriented in vitro antitumor drug screen. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development. Valeriote, A., Corbett, T, Baker, L. (eds), p. 11. Kluwer Academic Publishers: Amsterdam.
11. FANTUCCI, P., MARINO, T., RUSSO, N. & VILLA, A.M. (1995). Conformational behavior of the antineoplastic peptide dolastatin 10 and two mutated derivatives. Journal of Computer Aided Molecular Design, 9, 425.
12. KIM, I.K., LEE, B.S., HONG, Y.T., CHOI, H S. & KWON, N.M. (1994). Synthesis of dolastatin 10 analogs. Journal of the Korean Chemical Society, 39, 763.
13. KOBAYASHI, M., NATSUME, T., TAMAOKI, S., WATANABE, J-I., ASANO, H., MIKAMI, T., MIYASAKA, K., MIYAZAKI, K., GONDO, M., SAKAKIBARA, K. & TSUKAGOSHI, S. (1997). Antitumor activity of TZT-1027, a novel dolastatin 10 derivative. Japanese Journal of Cancer Research, 88, 316.
14. MIYAZAKI, K., KOBAYASHI, M., NATSUME, T, GONDO, M , MIKAMI, T., SAKAKIBARA, K. & TSUKAGOSHI, S. (1995). Synthesis and antitumor activity of novel dolastatin 10 analogs. Chemical and Pharmaceutical Bulletin, 43, 1706.
15. NAKAMURA, M., SHIBATA, T., NAKANE, K. NEMOTO, T, OJIKA, M. &. YAMADA, K. (1995). Stereochemistry and total synthesis of dolastatin E. Tetrahedron Letters, 36, 5059.
16. NATIONAL COMMITTEE FOR CLINICAL LABORATORY STANDARDS (1990). Performance Standards for Antimicrobial Disk Susceptibility Tests, 4th edn. Approved Standard M2-A4, NCCLS: Villanova, PA.
17. NEWMAN, R.A., FUENTES, A. & COVEY, J.M. (1994). Preclinical pharmacology of the marine natural product dolastatin 10 (NSC 376128). Drug Metabolism and Disposition, 22, 428.
18. PETTIT, G.R., KAMANO, Y., HERALD, C.L , TUINMAN, A.A., BOETTNER, F.E., KIZU, H , SCHMIDT, J.M., BACZYNSKYI, L., TOMER, K.B. & BONTEMS, R.J. (1987). The isolation and structure of a remarkable marine animal antineoplastic constituent. Journal of American Chemical Society, 109, 6883.
19. PETTIT, G.R., SINGH, S.B., HOGAN, F., LLOYD-WILLIAMS, P., HERALD, D.L., BURKETT, D.D. & CLEWLOW P.J. (1989). The absolute configuration and synthesis of natural (-)-dolastatin 10. Journal of American Chemical Society, 111, 5463.
20. 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, 3132.
21. PETTIT, G.R., KAMANO, Y., HERALD, C.L., FUJII, Y., KIZU, H., BOYD, M.R., BOETTNER, F.E., DOUBEK, D.L., SCHMIDT, J.M., CHAPUIS, J.-C. & MICHEL, C. (1993). Isolation of dolastatins 10-15 from the marine mollusc Dolabella auricularia. Tetrahedron, 49, 9151.
22. PETTIT, G R., SINGH, S.B., SRIRANGAM, J.K., HOGAN, F. & WILLIAMS, M.D. (1994a). The dolastatins 19. Synthesis of dolaisoleuine. Journal of Organic Chemistry, 59, 1796.
23. PETTIT, G.R., BARKOCZY, J., SRIRANGAM, J.K., SINGH, S.B., HERALD, D.L., WILLIAMS M.D., KANTOCI, D., HOGAN, F. & GROY TL. (1994b). The dolastatins 22. Synthesis of Boc-dolaproinyl-dolaphenine and four related chiral isomers. Journal of Organic Chemistry, 59, 2935.
24. PETTIT, G.R., SINGH, S.B., HERALD, D.L., LLOYD-WILLIAMS, P., KANTOCI, D , BURKETT, D.D , BARKOCZY, J., HOGAN, F. & WARDLAW, T.R. (1994c). The dolastatins 17. Synthesis of dolaproine and related diastereoisomers. Journal of Organic Chemistry, 59, 6287.
25. PETTIT, G.R., SRIRANGAM, J.K., HERALD, D.L & HAMEL, E. (1994d). The dolastatins 21. Synthesis, X-ray crystal structure, and molecular modeling of (6R)-isodolastatin 10. Journal of Organic Chemistry, 59, 6127.
26. PETTIT, G R., HOGAN, F., BURKETT, D.D., SINGH, S B., KANTOCI, D., SRIRANGAM, J.K. & WILLIAMS, M.D. (1994e). The Dolastatins 16. Synthesis of dolaphenine. Heterocycles, 39, 81.
27. PETTIT, G.R., SRIRANGAM, J.K , BARKOCZY, J., WILLIAMS, M.D., DURKIN, K.P.M., BOYD, M.R., BAI, R , HAMEL, E., SCHMIDT, J.M. & CHAPUIS, J.-C. (1995). Antineoplastic agents 337. Synthesis of dolastatin 10 structural modifications. Anti-Cancer Drug Design, 10, 529.
28. PETTIT, GR., SRIRANGAM, J.K., SINGH, S B., WILLIAMS M.D., HERALD, D.L., BARKOCZY, J, KANTOCI, D. & HOGAN, F (1996), Dolastatins 24. Synthesis of (-)-dolastatin 10. X-ray molecular structure of N,N-dimethylvalyl-valyl-dolaisoleucine tert-butyl ester. Journal of Chemical Society, Perkin Transactions 1, 859.
29. ROUX, F., MAUGRAS, I., PONCET, J., JOUIN, G.N P. (1994). Synthese de la Dolastatine 10 et de la [R-DoeJ-Dolastatine 10. Tetrahedron, 50, 5345.
30. SONE, H, KONDO, T., KIRYU, M., ISHIWATA, H., OJIKA, M. & YAMADA, K. (1995). Dolabellin, a cytotoxic bisthiazole metabolite from the sea hare Dolabella auricularia: structural determination and synthesis. Journal of Organic Chemistry, 60, 4774.
31. TOPPMEYER, D.L, SLAPAK, C.A & KUFE, D.W (1994). Role of P-glycoprotein in dolastatin 10 resistance. Biochemical Pharmacology, 48, 609.
32. YAMADA, S., IKOTA, I, SHIORI, T. & TACHIBANA, S.J. (1975). Diphenyl phosphorazidate (DPPA) and diethyl phosphorocyanidate (DEPC). Two new reagents for solid-phase peptide synthesis and their application to the synthesis of porcine motilin. Journal of the American Chemical Society, 97, 7174.