Jaspamide

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Ashok Bhandari - One of the best experts on this subject based on the ideXlab platform.

A. Zampella - One of the best experts on this subject based on the ideXlab platform.

  • Jaspamides M-P: new tryptophan modified Jaspamide derivatives from the sponge Jaspis splendans
    'Elsevier BV', 2009
    Co-Authors: F. Gala, M. V. D'auria, S. De Marino, V. Sepe, F. Zollo, C. D. Smith, S. N. Keller, A. Zampella
    Abstract:

    Four new Jaspamide derivs. (e.g. I, Jaspamide M) with antimicrofilament activity were isolated from the marine sponge Jaspis splendans. Their structures were elucidated by NMR and MS analalysis. A structure-activity relationship analalysis on all natural Jaspamides is also reporte

  • Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide
    'Elsevier BV', 2008
    Co-Authors: S. Terracciano, V. Sepe, C. D. Smith, A. Zampella, I. Bruno, E. D'amico, G. Bifulco, R. Riccio
    Abstract:

    In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological profile has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural equirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2–8, containing, as the parent compound, a b-amino acid in the cyclopeptide backbone. Their biological profile is also described

  • New Jaspamide Derivatives from the Marine Sponge Jaspis splendans Collected in Vanuatu
    'American Chemical Society (ACS)', 1999
    Co-Authors: A. Zampella, C. Giannini, C. Debitus, C. Roussakis, M. V. D'auria
    Abstract:

    Two new Jaspamide derivatives (1 and 2) along with Jaspamide have been isolated from the marine sponge Jaspis splendans collected in Vanuatu. Their chemical structures were determined from 1D and 2D NMR studies and MS data. These two compounds inhibited the in vitro growth of the NSCLC-N6 human tumor cell lines with IC50 values in the microg/mL range

Ali Al-mourabit - One of the best experts on this subject based on the ideXlab platform.

  • Pipestelides A-C: cyclodepsipeptides from the Pacific marine sponge Pipestela candelabra.
    Journal of Natural Products, 2012
    Co-Authors: Jonathan Sorres, Marie-thérèse Martin, Sylvain Petek, Hélène Levaique, Thierry Cresteil, Suzanne Ramos, Odile Thoison, Cécile Debitus, Ali Al-mourabit
    Abstract:

    Pipestelides A-C (2-4) are three new NRPS-PKS hybrid macrolides containing uncommon moieties, isolated from the Pacific marine sponge Pipestela candelabra. Their structures were elucidated on the basis of spectroscopic data. These cyclodepsipeptides appear to be biosynthetically related to Jaspamide (aka jasplakinolide) (1) by chemical modification of the building blocks of the polyketide or peptide chains. Pipestelides A-C (2-4) contain a bromotyrosine [3-amino-3-(bromo-4-hydroxyphenyl)propanoic acid] unit, a polypropionate with a Z double bond, and a 2-hydroxyquinolinone, respectively. Revised chemical shift assignments are provided for the co-isolated known jasplakinolide C(a) (5). In addition, compounds 2 and 3 exhibited cytotoxic activities in the micromolar range.

  • Pipestelides A–C: Cyclodepsipeptides from the Pacific Marine Sponge Pipestela candelabra
    2012
    Co-Authors: Jonathan Sorres, Sylvain Petek, Hélène Levaique, Thierry Cresteil, Suzanne Ramos, Odile Thoison, Cécile Debitus, Marie-thérèse Martin, Ali Al-mourabit
    Abstract:

    Pipestelides A–C (2–4) are three new NRPS–PKS hybrid macrolides containing uncommon moieties, isolated from the Pacific marine sponge Pipestela candelabra. Their structures were elucidated on the basis of spectroscopic data. These cyclodepsipeptides appear to be biosynthetically related to Jaspamide (aka jasplakinolide) (1) by chemical modification of the building blocks of the polyketide or peptide chains. Pipestelides A–C (2–4) contain a bromotyrosine [3-amino-3-(bromo-4-hydroxyphenyl)­propanoic acid] unit, a polypropionate with a Z double bond, and a 2-hydroxyquinolinone, respectively. Revised chemical shift assignments are provided for the co-isolated known jasplakinolide Ca (5). In addition, compounds 2 and 3 exhibited cytotoxic activities in the micromolar range

R. Riccio - One of the best experts on this subject based on the ideXlab platform.

  • Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide
    'Elsevier BV', 2008
    Co-Authors: S. Terracciano, V. Sepe, C. D. Smith, A. Zampella, I. Bruno, E. D'amico, G. Bifulco, R. Riccio
    Abstract:

    In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological profile has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural equirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2–8, containing, as the parent compound, a b-amino acid in the cyclopeptide backbone. Their biological profile is also described

  • Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide
    'Elsevier BV', 2008
    Co-Authors: S. Terracciano, I. Bruno, G. Bifulco, Elisabetta D’amico, Angela Zampella, Valentina Sepe, Charles D. Smith, R. Riccio
    Abstract:

    In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide 1, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological profile has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural requirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2–8, containing, as the parent compound, a beta-amino acid in the cyclopeptide backbone. Their biological profile is also described

  • Synthesis, conformational analysis, and cytotoxicity of new analogues of the natural cyclodepsipeptide Jaspamide.
    Journal of natural products, 2004
    Co-Authors: S. Terracciano, I. Bruno, G. Bifulco, Charles D. Smith, Jean E. Copper, Luigi Gomez-paloma, R. Riccio
    Abstract:

    Three analogues of the natural bioactive cyclodepsipeptide Jaspamide (3-5) were efficiently synthesized using a combination of solid and solution phase techniques. The preliminary design of the molecules has involved the rational substitution and/or simplification of the most critical structural features of the lead compound. The synthetic products were subjected to pharmacological assays, and the conformational properties were investigated by MM (molecular mechanics) and MD (molecular dynamics) calculations, to describe the potential pharmacophoric core responsible for the observed activities.

A. V. Rama Rao - One of the best experts on this subject based on the ideXlab platform.