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Literature DB >> 17929935

Latrunculin with a highly oxidized thiazolidinone ring: structure assignment and actin docking.

Safwat A Ahmed¹, Srinivas Odde, Pankaj R Daga, John J Bowling, Mostafa K Mesbah, Diaa T Youssef, Sherief I Khalifa, Robert J Doerksen, Mark T Hamann.

Abstract

A new latrunculin, oxalatrunculin B (3), was isolated from Red Sea sponge Negombata corticata. Extensive spectroscopic analysis revealed an unprecedented heterocycle in which the rare thiazolidinone ring found in latrunculins was oxidized with three additional oxygens. An actin polymerization inhibition assay agreed with MM-PBSA free energy calculations that 3 binds more weakly than latrunculin B to actin. Significant antifungal and anticancer activity of 3 was found, suggesting an alternate target in addition to actin for latrunculin bioactivity.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2007 PMID： 17929935 PMCID： PMC2529398 DOI： 10.1021/ol7020675

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

7 in total

1. Toward computing relative configurations: 16-epi-latrunculin B, a new stereoisomer of the actin polymerization inhibitor latrunculin B.

Authors: Thomas R Hoye; Seif-Eldin N Ayyad; Brian M Eklov; Nadia E Hashish; W Thomas Shier; Khalid A El-Sayed; Mark T Hamann
Journal: J Am Chem Soc Date: 2002-06-26 Impact factor: 15.419

2. Actin crystal dynamics: structural implications for F-actin nucleation, polymerization, and branching mediated by the anti-parallel dimer.

Authors: Robbie Reutzel; Craig Yoshioka; Lakshmanan Govindasamy; Elena G Yarmola; Mavis Agbandje-McKenna; Michael R Bubb; Robert McKenna
Journal: J Struct Biol Date: 2004-06 Impact factor: 2.867

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Journal: Science Date: 1983-02-04 Impact factor: 47.728

Review 4. Regulation of cancer cell motility through actin reorganization.

Authors: Daisuke Yamazaki; Shusaku Kurisu; Tadaomi Takenawa
Journal: Cancer Sci Date: 2005-07 Impact factor: 6.716

5. Intramolecular Diels-Alder Reaction of N-Alkyl-2-cyano-1-azadienes: A Study of the Eschenmoser Cycloreversion of Dihydrooxazines as a Route to N-Alkyl-2-cyano-1-azadienes.

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Journal: J Org Chem Date: 1997-04-04 Impact factor: 4.354

6. Latrunculin analogues with improved biological profiles by "diverted total synthesis": preparation, evaluation, and computational analysis.

Authors: Alois Fürstner; Douglas Kirk; Michaël D B Fenster; Christophe Aïssa; Dominic De Souza; Cristina Nevado; Tell Tuttle; Walter Thiel; Oliver Müller
Journal: Chemistry Date: 2007 Impact factor: 5.236

7. Bioactive natural and semisynthetic latrunculins.

Authors: Khalid A El Sayed; Diaa T A Youssef; Dario Marchetti
Journal: J Nat Prod Date: 2006-02 Impact factor: 4.050

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

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4. Antiepileptic ceramides from the Red Sea sponge Negombata corticata.

Authors: Safwat A Ahmed; Sherief I Khalifa; Mark T Hamann
Journal: J Nat Prod Date: 2008-03-21 Impact factor: 4.050

Review 5. A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.

Authors: Koneni V Sashidhara; Kimberly N White; Phillip Crews
Journal: J Nat Prod Date: 2009-03-27 Impact factor: 4.050

6. Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.

Authors: Taro Amagata; Tyler A Johnson; Robert H Cichewicz; Karen Tenney; Susan L Mooberry; Joseph Media; Matthew Edelstein; Frederick A Valeriote; Phillip Crews
Journal: J Med Chem Date: 2008-11-27 Impact factor: 7.446

7. Semisynthetic latrunculin B analogs: studies of actin docking support a proposed mechanism for latrunculin bioactivity.

Authors: Sucheta Kudrimoti; Safwat A Ahmed; Pankaj R Daga; Amir E Wahba; Sherief I Khalifa; Robert J Doerksen; Mark T Hamann
Journal: Bioorg Med Chem Date: 2009-09-16 Impact factor: 3.641