Neopetrosiamides, peptides from the marine sponge Neopetrosia sp. that inhibit amoeboid invasion by human tumor cells.

[structure: see text] Neopetrosiamdes A (1) and B (2), two diastereomeric tricyclic peptides that inhibit amoeboid invasion of human tumor cells, have been isolated from the marine sponge Neopetrosia sp. collected in Papua New Guinea. The structures of the neopetrosiamides were elucidated by analysis of MS and NMR data and confirmed by chemical degradation.

[1]  C. Bewley,et al.  Lithistid Sponges: Star Performers or Hosts to the Stars. , 1998, Angewandte Chemie.

[2]  R. Andersen,et al.  Strongylophorine-26, a new meroditerpenoid isolated from the marine sponge Petrosia (Strongylophora) corticata that exhibits anti-invasion activity. , 2004, Journal of natural products.

[3]  David E. Williams,et al.  Motuporin, A Potent Protein Phosphatase Inhibitor Isolated from the Papua New Guinea Sponge Theonella swinhoei Gray , 1992 .

[4]  Shigeki Matsunaga and Nobuhiro Fusetani.  Nonribosomal Peptides from Marine Sponges , 2003 .

[5]  David E. Williams,et al.  Motuporamines, anti-invasion and anti-angiogenic alkaloids from the marine sponge Xestospongia exigua (Kirkpatrick): isolation, structure elucidation, analogue synthesis, and conformational analysis. , 2002, The Journal of organic chemistry.

[6]  M. K. Harper,et al.  Microcionamides A and B, bioactive peptides from the philippine sponge Clathria (Thalysias) abietina. , 2004, The Journal of organic chemistry.

[7]  Peter Friedl,et al.  Compensation mechanism in tumor cell migration , 2003, The Journal of cell biology.

[8]  S. Akiyama,et al.  Kendarimide A, a novel peptide reversing P-glycoprotein-mediated multidrug resistance in tumor cells, from a marine sponge of Haliclona sp. , 2004 .

[9]  F. Bovey,et al.  Carbon-13 magnetic resonance spectroscopy. Spectrum of proline in oligopeptides , 1973 .

[10]  L. Pannell,et al.  Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei, collected in Papua New Guinea , 1999 .

[11]  I. Siemion,et al.  Influence of the Distance of the Proline Carbonyl from the β and γ Carbon on the 13C Chemical Shifts , 1975 .

[12]  P. Friedl.  Prespecification and plasticity: shifting mechanisms of cell migration. , 2004, Current opinion in cell biology.

[13]  Erik Sahai,et al.  Differing modes of tumour cell invasion have distinct requirements for Rho/ROCK signalling and extracellular proteolysis , 2003, Nature Cell Biology.

[14]  Michel Roberge,et al.  Dominicin, a cyclic octapeptide, and laughine, a bromopyrrole alkaloid, isolated from the Caribbean marine sponge Eurypon laughlini. , 2005, Journal of natural products.

[15]  A. Karsan,et al.  Inhibition of tumor cell invasion and angiogenesis by motuporamines. , 2001, Cancer research.

[16]  R. Andersen,et al.  Strongylophorine-26, a Rho-dependent inhibitor of tumor cell invasion that reduces actin stress fibers and induces nonpolarized lamellipodial extensions , 2005, Molecular Cancer Therapeutics.

[17]  F. Bovey,et al.  Proton coupled carbon-13 magnetic resonance spectra. Simple amides , 1973 .