ArticleThe Journal of organic chemistry2013
Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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17 citing papers in PubMed, 0 citations in OpenAlex.
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- TheMolecules (Basel, Switzerland) · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis.The Journal of organic chemistry · 2017Article
- Inhibition of Eukaryotic Translation by the Antitumor Natural Product Agelastatin A.Cell chemical biology · 2017Article
- Marine Invertebrate Metabolites with Anticancer Activities: Solutions to the "Supply Problem".Marine drugs · 2016Review
- Marine Natural Products from New Caledonia--A Review.Marine drugs · 2016Review
- The fibroblast Tiam1-osteopontin pathway modulates breast cancer invasion and metastasis.Breast cancer research : BCR · 2016Article
- Synthesis of 2-Aminoazoles from Thioesters via α-Heterosubstituted Ketones by Copper-Mediated Cross-Coupling.The Journal of organic chemistry · 2015Article
- 10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D.Angewandte Chemie (International ed. in English) · 2015Article
- Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.Tetrahedron letters · 2015Article
- Syntheses of Cyclic Guanidine-Containing Natural Products.Tetrahedron · 2015Article
- Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products.Beilstein journal of organic chemistry · 2015Article
- Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.Chemical communications (Cambridge, England) · 2014Review
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Authors and funding
5 authors at 3 institutions in 2 countries.
Funding
Abstract
The full details of our enantioselective total syntheses of (-)-agelastatins A-F (1-6), the evolution of a new methodology for synthesis of substituted azaheterocycles, and the first side-by-side evaluation of all known (-)-agelastatin alkaloids against nine human cancer cell lines are described. Our concise synthesis of these alkaloids exploits the intrinsic chemistry of plausible biosynthetic precursors and capitalizes on a late-stage synthesis of the C-ring. The critical copper-mediated cross-coupling reaction was expanded to include guanidine-based systems, offering a versatile preparation of substituted imidazoles. The direct comparison of the anticancer activity of all naturally occurring (-)-agelastatins in addition to eight advanced synthetic intermediates enabled a systematic analysis of the structure-activity relationship within the natural series. Significantly, (-)-agelastatin A (1) is highly potent against six blood cancer cell lines (20-190 nM) without affecting normal red blood cells (>333 μM). (-)-Agelastatin A (1) and (-)-agelastatin D (4), the two most potent members of this family, induce dose-dependent apoptosis and arrest cells in the G2/M-phase of the cell cycle; however, using confocal microscopy, we have determined that neither alkaloid affects tubulin dynamics within cells.
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