ArticleACS chemical biology2013
Synthesis and SAR of Lehualide B: a marine-derived natural product with potent anti-multiple myeloma activity.
Article in ACS chemical biology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Antitumor natural products targeting mitochondrial NADH: ubiquinone oxidoreductase (complex I): a review.Frontiers in pharmacology · 2026Review
- An Estrogen Receptor β Agonist with AR Antagonist Activity from a Modern AsymmetricACS medicinal chemistry letters · 2025Article
- Multiple Myeloma: Possible Cure from the Sea.Cancers · 2022Review
- TheGenes · 2018Review
- Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.Tetrahedron · 2016Article
- The unique chemistry and biology of the piericidins.The Journal of antibiotics · 2016Review
- Kalkitoxin inhibits angiogenesis, disrupts cellular hypoxic signaling, and blocks mitochondrial electron transport in tumor cells.Marine drugs · 2015Article
- Development and Investigation of a Site Selective Palladium-Catalyzed 1,4-Difunctionalization of Isoprene using Pyridine-Oxazoline Ligands.Chemical science · 2015Article
- A Highly Chemo-, Regio-, and Stereoselective Metallacycle-Mediated Annulation Between a Conjugated Enyne and an Ene-Diyne.ARKIVOC : free online journal of organic chemistryArticle
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
We report a concise and convergent laboratory synthesis of the rare marine natural product lehualide B that has led to the discovery that (1) this compound has low nanomolar activity against human multiple myeloma cells and (2) the anticancer effects of lehualide B and its analogues are selective (i.e., they are approximately 2-3 orders of magnitude less toxic to human breast cancer cells). Synthetic lehualide B is shown to be an effective inhibitor of complex I of the mitochondrial electron transport chain, with potency similar to that observed for the terrestrial natural products piericidin A1 and rotenone, an observation that led to the discovery that piericidin A1 is also selectively cytotoxic toward human multiple myeloma cells. Interestingly, synthetic derivatives of lehualide B that resemble verticipyrone (an established complex I inhibitor composed of a γ-pyrone and a simple monounsaturated hydrophobic chain) lack the potent antimyeloma activity of the natural product. Finally, the synthesis and evaluation of a collection of lehualide-inspired analogues led to the elucidation of structure-activity relationships for this rare natural product that established important roles for the substituted γ-pyrone headgroup and the skipped polyene side chain.
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