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Synthesis and biological evaluation of new jasplakinolide (jaspamide) analogs.

Arun K Ghosh1, Zachary L Dawson, Deuk Kyu Moon, Ruoli Bai, Ernest Hamel.   

Abstract

Synthesis and biological evaluation of jasplakinolide analogs are described. The synthesis of analogs utilized a diastereoselective syn-aldol reaction and an orthoester Claisen rearrangement as key steps. All synthetic analogs were evaluated for their ability to disrupt the actin cytoskeleton. Compounds 2, 3, and 4 essentially displayed similar activity to jasplakinolide. Copyright 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20678932      PMCID： PMC2925441          DOI： 10.1016/j.bmcl.2010.07.023

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  17 in total

1.  Synthesis of jasplakinolide analogues containing a novel omega-amino acid.

Authors:  Srinivasa Marimganti; Shazia Yasmeen; Daniela Fischer; Martin E Maier
Journal:  Chemistry       Date:  2005-11-04       Impact factor: 5.236

2.  Synthesis, solution structure, and bioactivity of six new simplified analogues of the natural cyclodepsipeptide jaspamide.

Authors:  Stefania Terracciano; Ines Bruno; Giuseppe Bifulco; Elvira Avallone; Charles D Smith; Luigi Gomez-Paloma; Raffaele Riccio
Journal:  Bioorg Med Chem       Date:  2005-09-01       Impact factor: 3.641

3.  Synthesis and structure-activity correlation of natural-product inspired cyclodepsipeptides stabilizing F-actin.

Authors:  René Tannert; Lech-Gustav Milroy; Bernhard Ellinger; Tai-Shan Hu; Hans-Dieter Arndt; Herbert Waldmann
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

4.  Conformational studies of free and Li+ complexed jasplakinolide, a cyclic depsipeptide from the Fijian marine sponge Jaspis splendens.

Authors:  Jioji N Tabudravu; Linda A Morris; Bruce F Milne; Marcel Jaspars
Journal:  Org Biomol Chem       Date:  2005-02-07       Impact factor: 3.876

5.  The chondramides: cytostatic agents from myxobacteria acting on the actin cytoskeleton.

Authors:  F Sasse; B Kunze; T M Gronewold; H Reichenbach
Journal:  J Natl Cancer Inst       Date:  1998-10-21       Impact factor: 13.506

6.  Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin.

Authors:  M R Bubb; A M Senderowicz; E A Sausville; K L Duncan; E D Korn
Journal:  J Biol Chem       Date:  1994-05-27       Impact factor: 5.157

7.  Enantioselective total synthesis of +-jasplakinolide.

Authors:  Arun K Ghosh; Deuk Kyu Moon
Journal:  Org Lett       Date:  2007-05-08       Impact factor: 6.005

8.  Solid-phase based synthesis of jasplakinolide analogs by intramolecular azide-alkyne cycloadditions.

Authors:  Tai-Shan Hu; René Tannert; Hans-Dieter Arndt; Herbert Waldmann
Journal:  Chem Commun (Camb)       Date:  2007-08-14       Impact factor: 6.222

9.  (-)-Doliculide, a new macrocyclic depsipeptide enhancer of actin assembly.

Authors:  Ruoli Bai; David G Covell; Chunfeng Liu; Arun K Ghosh; Ernest Hamel
Journal:  J Biol Chem       Date:  2002-06-20       Impact factor: 5.157

10.  Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide.

Authors:  Stefania Terracciano; Ines Bruno; Elisabetta D'Amico; Giuseppe Bifulco; Angela Zampella; Valentina Sepe; Charles D Smith; Raffaele Riccio
Journal:  Bioorg Med Chem       Date:  2008-05-10       Impact factor: 3.641
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  3 in total

1.  Capturing the essence of organic synthesis: from bioactive natural products to designed molecules in today's medicine.

Authors:  Arun K Ghosh
Journal:  J Org Chem       Date:  2010-10-11       Impact factor: 4.354

2.  Biostructural features of additional jasplakinolide (jaspamide) analogues.

Authors:  Katharine R Watts; Brandon I Morinaka; Taro Amagata; Sarah J Robinson; Karen Tenney; Walter M Bray; Nadine C Gassner; R Scott Lokey; Joseph Media; Frederick A Valeriote; Phillip Crews
Journal:  J Nat Prod       Date:  2011-01-11       Impact factor: 4.050

Review 3.  Current scenario of peptide-based drugs: the key roles of cationic antitumor and antiviral peptides.

Authors:  Kelly C L Mulder; Loiane A Lima; Vivian J Miranda; Simoni C Dias; Octávio L Franco
Journal:  Front Microbiol       Date:  2013-10-31       Impact factor: 5.640
  3 in total

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