ArticleACS medicinal chemistry letters2016
Salinomycin Hydroxamic Acids: Synthesis, Structure, and Biological Activity of Polyether Ionophore Hybrids.
Article in ACS medicinal chemistry letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
8 citing papers in PubMed.
- Urea and Thiourea Derivatives of Salinomycin as Agents Targeting Malignant Colon Cancer Cells.Anti-cancer agents in medicinal chemistry · 2025Article
- Expeditive Synthesis of Potent C20-ACS organic & inorganic Au · 2022Article
- Rapid Access to Ironomycin Derivatives by Click Chemistry.ACS organic & inorganic Au · 2022Article
- Salinomycin as a potent anticancer stem cell agent: State of the art and future directions.Medicinal research reviews · 2022Review
- Single and double modified salinomycin analogs target stem-like cells in 2D and 3D breast cancer models.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2021Article
- Review
- The Molecular Basis for Inhibition of Stemlike Cancer Cells by Salinomycin.ACS central science · 2018Article
- Salinomycin kills cancer stem cells by sequestering iron in lysosomes.Nature chemistry · 2017Article
Corrections and comments
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Authors and funding
5 authors.
Funding
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Abstract
The polyether ionophore salinomycin has recently gained attention due to its exceptional ability to selectively reduce the proportion of cancer stem cells within a number of cancer cell lines. Efficient single step strategies for the preparation of hydroxamic acid hybrids of this compound varying in N- and O-alkylation are presented. The parent hydroxamic acid, salinomycin-NHOH, forms both inclusion complexes and well-defined electroneutral complexes with potassium and sodium cations via 1,3-coordination by the hydroxamic acid moiety to the metal ion. A crystal structure of an cationic sodium complex with a noncoordinating anion corroborates this finding and, moreover, reveals a novel type of hydrogen bond network that stabilizes the head-to-tail conformation that encapsulates the cation analogously to the native structure. The hydroxamic acid derivatives display down to single digit micromolar activity against cancer cells but unlike salinomycin selective reduction of ALDH(+) cells, a phenotype associated with cancer stem cells was not observed. Mechanistic implications are discussed.
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