Antineoplastic Agents. 520. Isolation and Structure of Irciniastatins A and B from the Indo-Pacific Marine Sponge Ircinia ramosa

Journal of Medicinal Chemistry

Volumn 47, Issue 5, 2004, Pages 1149-1152

  Pettit, George R ^a   Xu, Jun Ping ^a   Chapuis, Jean Charles ^a   Pettit, Robin K ^a   Tackett, Larry P ^a   Doubek, Dennis L ^a   Hooper, John N A ^b   Schmidt, Jean M ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

^b QUEENSLAND MUSEUM   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; IRCINIASTATIN A; IRCINIASTATIN B; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CONCENTRATION RESPONSE; DRUG ISOLATION; HUMAN; IRCINIA RAMOSA; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELLS, CULTURED; COUMARINS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PORIFERA; UMBILICAL VEINS;

EID: 1242296319     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030207d     Document Type: Article

References (33)

1. For contribution 519, refer to: Nabha et al. Combretastatin A-4 prodrug induces mitotic catastrophe in chronic lymphocytic leukemia cell line independent of caspase activation and poly (ADP-ribose) polymerase cleavage. Clin. Cancer Res. 2002, 8, 2735-2741.
2. (a) Pettit, G. R.; Herald, C. L.; Hogan, F. Biosynthetic products for anticancer drug design and treatment: The bryostatins. In Anticancer Drug Design; Baguley, B., Ed.; Academic Press: San Diego, CA, 2002; pp 203-235.
3. (b) Clamp, A.; Jayson, G. C. The clinical development of the bryostatins. Anti-Cancer Drugs 2002, 13, 673-683.
4. (c) O'Brien, M.; Taylor, N. H.; Thomas, E. J. Synthesis of the C(1)-C(16) fragment of bryostatins. Tetrahedron Lett. 2002, 43, 5491-5494.
5. (d) Saad, E. D.; Kraut, E. H.; Hoff, P. M.; Moore, D. F.; Jones, D.; Pazdur, R.; Abbruzzese, J. L. Phase II study of dolastatin 10 as first-line treatment for advanced colorectal cancer. Am. J. Clin. Oncol. 2002, 25, 451-453.
6. (e) van Kesteren, C.; Twelves, C.; Bowman, A.; Hoekman, K.; López-Lázaro, L.; Jimeno, J.; Guzman, C.; Mathôt, R. A. A.; Simpson, A.; Vermorken, J. B.; Smyth, J.; Schellens, J. H. M.; Hillebrand, M. J. X.; Rosing, H.; Beijnen, J. H. Clinical pharmacology of the novel marine-derived anticancer agent ecteinascidin 743 administered asa 1- and 3-h infusion in a phase I study. Anti-Cancer Drugs 2002, 13, 381-393.
7. (f) Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. Total synthesis of ecteinascidin 743. J. Am. Chem. Soc. 2002, 124, 6552-6554.
8. (g) Jimeno, J. M. A clinical armamentarium of marine-derived anticancer compounds. Anti-Cancer Drugs 2002, 13, S15-S19.
9. (h) Paterson, I.; Coster, M. J. Total synthesis of altohyrtin A (spongistatin 1): An alternative synthesis of the CD-spiroacetal subunit. Tetrahedron Lett. 2002, 43, 3285-3289.
10. (i): Crimmins, M. T.; Katz, J. D.; Washburn, D. G.; Allwein, S. P.; McAtee, L. F. Asymmetric total synthesis of spongistatins 1 and 2. J. Am. Chem. Soc. 2002, 124, 5661-5663.
11. (j) Cragg, G. M.; Newman, D. J. Medicinals for the millennia. Ann. New York Acad. Sci. 2001, 953, 3-25.
12. (k) Vedejs, E.; Kongkittingam, C. A total synthesis of (-)-hemiasterlin using N-Bts methodology. J. Org. Chem. 2001, 66, 7355-7364.
13. (l) Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 2001, 18, 1-49.
14. (m) Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 2000, 17, 7-55.
15. (a) Pettit, G. R. Evolutionary Biosynthesis of Anticancer Drugs. In Anticancer Agents: Frontiers in Cancer Chemotherapy; Ojima, I., Vite, G. D., Altmann, K.-H., Eds.; American Chemical Society, Washington, DC, 2001; pp 16-42.
16. (b) Pettit, G. R.; Day, J. F.; Hartwell, J. L.; Wood, H. B. Antineoplastic components of marine animals. Nature 1970, 227, 962-963.
17. (a) Gosliner, T. M.; Behrens, D. W.; Williams, G. C. Coral Reef Animals of the Indo-Pacific; Sea Challengers: Monterey, CA, 1996; p 25.
18. (b) Colin, P. L.; Arneson, C. Tropical Pacific Invertebrates; Coral Reef Research Foundation: Beverly Hills, CA, 1995; p 53.
19. (a) Kuramoto, M.; Fujita, T.; Ono, N. Ircinamine, a novel cytotoxic alkaloid from Ircinia sp. Chem. Lett. 2002, 4, 464-465.
20. (b) Salama, A. M.; Estrada, M. G.; Orjuela, M. P. Antimicrobial and antitumor activity of variabiline and its enanthiomers isolated from Ircinia felix. Revista Colombiana Ciencias Quim.-Farm. 2001, 30, 74-80.
21. (c) Yan, S.-J.; Zhang, G.-W.; Su, J.-Y.; Zeng, L.-M. Rare long conjugated diterpene ketene from the marine sponge Ircinia selaginea (Lamark). Gaodeng Xuexiao Huaxue Xuebao 2001, 22, 949-951.
22. (d) Takada, N.; Sato, H.; Suenaga, K.; Arimoto, H.; Yamada, K.; Ueda, K. ; Uemura, D. Isolation and structures of haterumalides NA, NB, NC, ND, and NE, novel macrolides from an Okinawan sponge Ircinia sp. Tetrahedron Lett. 1999, 40, 6309-6312.
23. (e) Prokoféva, N. G.; Kalinovskaya, N. I.; Lukýanov, P. A. ; Kuznetsova, T. A. Membranotropic effects of cyclic lipopeptides produced by a marine isolate of the bacteria Bacillus pumilus. Biologiya Morya (Vladivostok) 1996, 22, 179-182.
24. (f) Mau, C. M. S.; Nakao, Y.; Yoshida, W. Y.; Scheuer, P. J.; Kelly-Borges, M. Waiakeamide, a cyclic hexapeptide from the sponge Ircinia dendroides. J. Org. Chem. 1996, 61, 6302-6304.
25. (g) Kondo, K.; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Kobayashi, J.; Sasaki, T. Structures of ircinals A and B, novel alkaloids from the Okinawan marine sponge Ircinia sp. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1992, 34, 463-469.
26. (h) Kamimura, D.; Yamada, K. Novel antitumor sesterterpenoids. Jpn. Kokai Tokkyo Koho 1993, JP 92-40445 19920131.
27. (i) Kondo, K.; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. Ircinals A and B from the Okinawan marine sponge Ircinia sp.: Plausible biogenetic precursors of manzamine alkaloids. J. Org. Chem. 1992, 57, 2480-2483.
28. (j) Mihopoulos, N.; Vagias, C.; Chinou, I.; Roussakis, C.; Scoullos, M.; Harvala, C.; Roussis, V. Ircinia spinosula. Z. Naturforsch., C: Biosci. 1999, 54, 417-423.
29. (h) De Rosa, S.; De Giulio, A.; Iodice, C. Biological effects of prenylated hydroquinones: Structure-activity relationship studies in antimicrobial, brine shrimp, and fish lethality assays. J. Nat. Prod. 1994, 57, 1711-1716.
30. Bligh, E. G.; Dyer, W. J. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 1959, 37, 912.
31. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paul, K.; Vestica, D.; Hose, C.; Langley, J.; Cronise, P.; Vaigro-Wolff, A. Feasibility of high-flux anticancer screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. 1991, 83, 757-766.
32. National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Approved Standard M7-A5. NCCLS: Wayne, PA, 2000.
33. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standard M27-A. NCCLS: Wayne, PA, 1997.