Potent cytotoxic peptides from the Australian marine sponge Pipestela candelabra

Marine Drugs

Volumn 12, Issue 6, 2014, Pages 3399-3415

  Tran, Trong D ^a   Pham, Ngoc B ^a   Fechner, Gregory A ^a   Hooper, John N A ^a   Quinn, Ronald J ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Cytotoxicity; Geodiamolide; Hemiasterlin; Milnamide; Peptide; Pipestela candelabra; Prostate cancer

Indexed keywords

CYTOTOXIC AGENT; DOXORUBICIN; GEODIAMOLIDE D; GEODIAMOLIDE E; GEODIAMOLIDE F; HEMIASTERLIN; HEMIASTERLIN A; HEMIASTERLIN D; MILNAMIDE A; MILNAMIDE C; MILNAMIDE D; MILNAMIDE E; MILNAMIDE F; MILNAMIDE G; PACLITAXEL; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; PEPTIDE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; AUSTRALIA; CANCER INHIBITION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; IC 50; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PIPESTELA CANDELABRA; PROSTATE CANCER CELL LINE; SKIN FIBROBLAST; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; FIBROBLAST; IC50; ISOLATION AND PURIFICATION; MALE; METABOLISM; NEWBORN; PATHOLOGY; PENIS; PROSTATIC NEOPLASMS; SPECTROSCOPY; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; AUSTRALIA; CELL LINE, TUMOR; FIBROBLASTS; HUMANS; INFANT, NEWBORN; INHIBITORY CONCENTRATION 50; MALE; PENIS; PEPTIDES; PORIFERA; PROSTATIC NEOPLASMS; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84903537693     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12063399     Document Type: Article

References (27)

1. Alvarez, B.; Hooper, J.N.A.; Soest, R.W.M.V. Pipestela, a new genus of Axinellidae (Polifera: Demospongiae: Halichondrida) and description of three new species. Mem. Queensl. Mus. 2008, 52, 105-118.
2. Hooper, J.; Soest, R.V. Systema Porifera: A Guide to the Classification of Sponges; Kluwer Academic/Plenum: New York, NY, USA, 2002.
3. Sorres, J.; Martin, M.T.; Petek, S.; Levaique, H.; Cresteil, T.; Ramos, S.; Thoison, O.; Debitus, C.; Mourabit, A.A. Pipestelides A-C: Cyclodepsipeptides from the Pacific marine sponge Pipestela candelabra. J. Nat. Prod. 2012, 75, 759-763.
4. Talpir, R.; Benayahu, Y.; Kasman, Y.; Pannell, L.; Schleyer, M. Hemiasterlin and Geodiamolide TA; Two new cytotoxic peptides from the marine sponge Hemiasterella minor (Kirkpatrick). Tetrahedron Lett. 1994, 35, 4453-4456. (Pubitemid 24195061)
5. Coleman, J.E.; Silva, E.D.D.; Kong, F.; Andersen, R.J.; Allen, T.M. Cytotoxic peptides from the marine sponge Cymbastela sp. Tetrahedron 1995, 51, 10653-10662.
6. Gamble, W.R.; Durso, N.A.; Fuller, R.W.; Westergaard, C.K.; Johnson, T.R.; Sachkett, D.L.; Hamel, E.; Cardellina, J.H.; Boyd, M.R. Cytotoxic and tubulin-interative hemiasterlins from Auletta sp. and Siphonochalina spp. sponges. Bioorg. Med. Chem. 1999, 7, 1611-1615. (Pubitemid 29347127)
7. Crews, P.; Farias, J.J.; Emrich, R.; Keifer, P.A. Milnamide A, an unusual cytotoxic tripeptide from the marine sponge Auletta cf. constricta. J. Org. Chem. 1994, 59, 2932-2934. (Pubitemid 24216863)
8. Sonnenschein, R.N.; Farias, J.J.; Tenney, K.; Mooberry, S.L.; Lobkovsky, E.; Clardy, J.; Crews, P. A further study of the cytotoxic constituents of a milnamide-producing sponge. Org. Lett. 2004, 6, 779-782. (Pubitemid 38387974)
9. Chevallier, C.; Richardson, A.D.; Edler, M.C.; Hamel, E.; Harper, M.K.; Ireland, C.M. A new cytotoxic and tubulin-interactive milnamide derivative from a marine sponge Cymbastela sp. Org. Lett. 2003, 5, 3737-3739. (Pubitemid 37289568)
10. Nieman, J.A.; Coleman, J.E.; Wallace, D.J.; Piers, E.; Lim, L.Y.; Roberge, M.; Andersen, R.J. Synthesis and antimitotic/cytotoxic activity of hemiasterlin analogues. J. Nat. Prod. 2003, 66, 183-199. (Pubitemid 36278228)
11. Kowalczyk, J.J.; Kuznetsov, G.; Schiller, S.; Seletsky, B.M.; Spyvee, M.; Yang, H. Hemiasterlin Derivatives and Uses Thereof. US Patent US7,064,211B2, 20 June 2006.
12. Kowalczyk, J.J.; Kuznetsov, G.; Schiller, S.; Seletsky, B.M.; Spyvee, M.; Yang, H. Hemiasterlin Derivatives and Uses Thereof. US Patent US7,192,972B2, 20 March 2007.
13. Campagna, S.A.; Fang, F.G.; Kowalczyk, J.J.; Schiller, S.; Seletsky, B.M.; Spyvee, M.; Yang, H. Hemiasterlin Derivatives and Uses Thereof. US Patent US7,585,976B2, 8 September 2009.
14. Newman, D.J.; Cragg, G.M. Marine Natural Products and Related Compounds in Clinical and Advanced Preclinical Trials. J. Nat. Prod. 2004, 67, 1216-1238. (Pubitemid 39145623)
15. Molinski, T.F.; Dalisay, D.S.; Lievens, S.L.; Saludes, J.P. Drug development from marine natural products. Nat. Rev. Drug Discov. 2009, 8, 69-85.
16. Kuznetsov, G.; TenDyke, K.; Towle, M.J.; Cheng, H.; Liu, J.; Marsh, J.P.; Schiller, S.E.R.; Spyvee, M.R.; Yang, H.; Seletsky, B.M.; et al. Tubulin-based antimitotic mechanism of E7974, a novel analogue of the marine sponge natural product hemiasterlin. Mol. Cancer Ther. 2009, 8, 2852-2860.
17. Lima, C.M.R.; Bayraktar, S.; MacIntyre, J.; Raez, L.; Flores, A.M.; Ferrell, A.; Rubin, E.H.; Poplin, E.A.; Tan, A.R.; Lucarelli, A.; et al. A phase 1 trial of E7974 administered on day 1 of a 21-day cycle in patients with advanced solid tumors. Cancer 2012, 118, 4262-4270.
18. Camp, D.; Davis, R.A.; Campitelli, M.; Ebdon, J.; Quinn, R.J. Drug-like properties: Guiding principles for the design of natural product libraries. J. Nat. Prod. 2012, 75, 72-81.
19. Silva, E.D.D.; Andersen, R.J.; Allen, T.M. Geodiamolide C to F, new cytotoxic cyclodepsipeptides from the marine sponge Pseudodaxinyssa sp. Tetrahedron Lett. 1990, 31, 489-492. (Pubitemid 20040767)
20. Coleman, J.E.; Soest, R.V.; Andersen, R.J., New geodiamolides from the sponge Cymbastela sp. collected in Papua New Guinea. J. Nat. Prod. 1999, 62, 1137-1141. (Pubitemid 29418340)
21. Couperus, P.A.; Clague, A.D.H.; van Dongen, J.P.C.M. 13C Chemical shifts of some model olefins. Org. Magn. Reson. 1976, 8, 426-431.
22. Kashman, Y.; Groweiss, A. New diterpenoids from the soft corals Xenia macrospiculata and Xenia obscuronata. J. Org. Chem. 1980, 45, 3841-3824.
23. Graber, M.A.; Gerwick, W.H. Kalkipyrone, a toxic γ-pyrone from an assemblage of the marine cyanobacteria Lyngbya majuscula and Tolypothrix sp. J. Nat. Prod. 1998, 61, 677-680. (Pubitemid 28262046)
24. Liu, C.; Masuno, M.N.; MacMillan, J.B.; Molinski, T.F. Enantioselective total synthesis of (+)-milnamide A and evidence of its autoxidation to (+)-milnamide D. Angew. Chem. Int. Ed. 2004, 43, 5951-5954. (Pubitemid 39551330)
25. Marfey, P. Determination of D-Amino Acids. II. Use of a Bifunctional Reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 1984, 49, 591-596.
26. Kochhar, S.; Christen, P. Amino acid analysis by high-performance liquid chromatography after derivatization with 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide. Anal. Biochem. 1989, 178, 17-21. (Pubitemid 19095997)
27. Tran, T.D.; Pham, N.B.; Fechner, G.; Zencak, D.; Vu, H.T.; Hooper, J.N. A.; Quinn, R.J. Cytotoxic cyclic depsipeptides from the Australian marine sponge Neamphius huxleyi. J. Nat. Prod. 2012, 75, 2200-2208.