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Isolation and Bioassay of Linear Veraguamides from a Marine Cyanobacterium ( Okeania sp.).

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  • Additional Information
    • Source:
      Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
    • Publication Information:
      Original Publication: Basel, Switzerland : MDPI, c1995-
    • Subject Terms:
      Cyanobacteria*/chemistry ; Antineoplastic Agents*/pharmacology ; Antineoplastic Agents*/chemistry ; Antineoplastic Agents*/isolation & purification; Humans ; Cell Line, Tumor ; HEK293 Cells ; MCF-7 Cells ; Molecular Structure ; Biological Assay ; Phylogeny
    • Abstract:
      Marine cyanobacteria have gained momentum in recent years as a source of novel bioactive small molecules. This paper describes the structure elucidation and pharmacological evaluation of two new (veraguamide O ( 1 ) and veraguamide P ( 2 )) and one known (veraguamide C ( 3 )) analogs isolated from a cyanobacterial collection made in the Las Perlas Archipelago of Panama. We hypothesized that these compounds would be cytotoxic in cancer cell lines. The compounds were screened against HEK-293, estrogen receptor positive (MCF-7), and triple-negative breast cancer (MDA-MB-231) cells as well as against a broad panel of membrane-bound receptors. The planar structures were determined based on NMR and MS data along with a comparison to previously isolated veraguamide analogs. Phylogenetic analysis of the collection suggests it to be an Okeania sp., a similar species to the cyanobacterium reported to produce other veraguamides. Veraguamide O shows no cytotoxicity (greater than 100 μM) against ER-positive cells (MCF-7) with 13 μM IC 50 against MDA-MB-231 TNBC cells. Interestingly, these compounds show affinity for the sigma2/TMEM-97 receptor, making them potential leads for the development of non-toxic sigma 2 targeting ligands.
    • Comments:
      Update of: bioRxiv. 2025 Jan 22:2025.01.18.633713. doi: 10.1101/2025.01.18.633713.. (PMID: 39896503)
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    • Grant Information:
      75N95023C00021 United States DA NIDA NIH HHS; P20 GM130456 United States GM NIGMS NIH HHS; R15 AT008060 United States AT NCCIH NIH HHS; 1R61NS127271-01A1 United States NH NIH HHS; 1P20GM130456-05A1 United States NH NIH HHS; R61 NS127271 United States NS NINDS NIH HHS; 1R15AT008060-02S1 United States NH NIH HHS; U01 TW006634 United States TW FIC NIH HHS
    • Contributed Indexing:
      Keywords: TMEM-97; cyanobacteria; sigma 2; veraguamide
    • Accession Number:
      0 (Antineoplastic Agents)
    • Publication Date:
      Date Created: 20250213 Date Completed: 20250507 Latest Revision: 20250507
    • Publication Date:
      20250508
    • Accession Number:
      PMC11819893
    • Accession Number:
      10.3390/molecules30030680
    • Accession Number:
      39942783