Cited by 232Microbial Natural Products and BiosynthesisMarine Sponges and Natural ProductsChemical Synthesis and Analysis

Coibamide A, a Potent Antiproliferative Cyclic Depsipeptide from the Panamanian Marine Cyanobacterium Leptolyngbya sp.

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Medina, Rebecca A., Goeger, Douglas E., Hills, Patrice, Mooberry, Susan L., Huang, Nelson, Romero, Luz I., Ortega-Barría, Eduardo, Gerwick, William H. +1 more·2008·Journal of the American Chemical Society

Abstract

Coibamide A (1) is a new, potent antiproliferative depsipeptide which was isolated from a marine Leptolyngbya cyanobacterium collected from the Coiba National Park, Panama. The planar structure of 1 was elucidated by a combination of NMR spectroscopy and mass spectrometry. Exhaustive 1D and 2D NMR spectroscopy included natural abundance 15N and variable temperature experiments; mass spectrometry included TOF-ESI-MSn and FT-MSn experiments. Chemical degradation followed by chiral HPLC- and GC-MS analyses was used to assign the absolute configuration of 1. This highly methylated cyclized depsipeptide exhibited an unprecedented selectivity profile in the NCI 60 cancer cell line panel and appears to act via a novel mechanism.

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Crossref · 10.1021/ja801383f

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  • Coibamide A exerts cytotoxic effects via cell cycle inhibition.

    “A similar mechanistic effect was reported for the cyclic depsipeptide coibamide A, isolated from Leptolyngbya sp. [100], and lyngbyabellin B, isolated from Lyngbya majuscule [182].”

    From Marine Natural Products: A Source of Novel Anticancer Drugs (2019) · cites this paper as [100]

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Authors
Medina, R. A., Goeger, D. E., Hills, P., Mooberry, S. L., Huang, N., Romero, L. I., Ortega-Barría, E., Gerwick, W. H., & McPhail, K. L.
Affiliations
  • Texas Biomedical Research Institute (US)
  • College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, Southwest Foundation for Biomedical Research, San Antonio, Texas 78227, Chemical and Screening Sciences, Wyeth Research, Cambridge, Massachusetts 02140, Instituto de Investigaciones Científicas Avanzados y Sevicios de Alta Tecnología, Clayton, Panama 5, Republic of Panama, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093
Venue
Journal of the American Chemical Society
Published
2008-04-29
Volume
130
Issue
20
Pages
6324-6325
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
OpenAlex
W2079316190
Cited by
231
References
10
Citations by year
2026: 8 · 2025: 16 · 2024: 16 · 2023: 12 · 2022: 14 · 2021: 26 · 2020: 28 · 2019: 7 · 2018: 13 · 2017: 12 · 2016: 14 · 2015: 12 · 2014: 10 · 2013: 16 · 2012: 7
FWCI
4.67
Type
journal article
Language
en
Open access
Locations
  • Journal of the American Chemical Society (publishedVersion)
  • PubMed (publishedVersion)
  • PubMed Central (acceptedVersion)
Funders
  • National Cancer Institute (CA52955, U19CA052955)
  • Fogarty International Center (U01TW006634, TW006634)
  • National Institute of Environmental Health Sciences (P30ES000210, #P30-ES00210)
Topics
  • Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
Keywords
cyclic depsipeptides, marine cyanobacteria, Leptolyngbya, structure elucidation, absolute configuration, NCI-60 cell lines, cytotoxicity, Coiba National Park
MeSH terms
Cyanobacteria, Animals, Antineoplastic Agents, Chromatography, High Pressure Liquid, Humans, Lung Neoplasms, Gas Chromatography-Mass Spectrometry, HL-60 Cells, Nuclear Magnetic Resonance, Biomolecular, Spectrometry, Mass, Electrospray Ionization, Cell Line, Tumor, Depsipeptides, Mice

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