ArticleOrganic letters2014
Efficient and stereocontrolled synthesis of 1,2,4-trioxolanes useful for ferrous iron-dependent drug delivery.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Toward Tumor-Conditional Release of Histone Deacetylase Inhibitors from Nongenotoxic Drug Conjugates.ACS medicinal chemistry letters · 2026Article
- Article
- Three decades of selective product formationRSC advances · 2025Review
- Identifying a next-generation antimalarial trioxolane in a landscape of artemisinin partial resistance.Science advances · 2025Article
- A tandem activity-based sensing and labeling strategy reveals antioxidant response element regulation of labile iron pools.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- In vivo bioluminescence imaging of labile iron in xenograft models and liver using FeAL-1, an iron-activatable form of D-luciferin.Cell chemical biology · 2023Article
- Artefenomel Regioisomer RLA-3107 Is a Promising Lead for the Discovery of Next-Generation Endoperoxide Antimalarials.ACS medicinal chemistry letters · 2023Article
- Elevated labile iron in castration-resistant prostate cancer is targetable with ferrous iron-activatable antiandrogen therapy.European journal of medicinal chemistry · 2023Article
- Ferrous iron-activatable drug conjugate achieves potent MAPK blockade in KRAS-driven tumors.The Journal of experimental medicine · 2022Article
- Expanded scope of Griesbaum co-ozonolysis for the preparation of structurally diverse sensors of ferrous iron.RSC advances · 2021Article
- Emerging role of ferrous iron in bacterial growth and host-pathogen interaction: New tools for chemical (micro)biology and antibacterial therapy.Current opinion in chemical biology · 2021Review
- Ferrous Iron-Dependent Pharmacology.Trends in pharmacological sciences · 2021Review
- Antimalarial Trioxolanes with Superior Drug-Like Properties and In Vivo Efficacy.ACS infectious diseases · 2020Article
- Targeting Mobilization of Ferrous Iron inACS infectious diseases · 2019Article
- Versatile Histochemical Approach to Detection of Hydrogen Peroxide in Cells and Tissues Based on Puromycin Staining.Journal of the American Chemical Society · 2018Article
- FINONature chemical biology · 2018Article
- Activity-based sensing fluorescent probes for iron in biological systems.Current opinion in chemical biology · 2018Review
- In vivo bioluminescence imaging of labile iron accumulation in a murine model ofProceedings of the National Academy of Sciences of the United States of America · 2017Article
- Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane.Journal of medicinal chemistry · 2017Article
- A Novel Tumor-Activated Prodrug Strategy Targeting Ferrous Iron Is Effective in Multiple Preclinical Cancer Models.Journal of medicinal chemistry · 2016Article
Corrections and comments
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3 authors.
Funding
Abstract
Ferrous iron-promoted reduction of a hindered peroxide bond underlies the antimalarial action of the 1,2,4-trioxane artemisinin and the 1,2,4-trioxolane arterolane. In appropriately designed systems, a 1,2,4-trioxolane ring can serve as a trigger to realize ferrous iron-dependent and parasite-selective drug delivery, both in vitro and in vivo. A stereocontrolled, expeditious (three steps), and efficient (67-71% overall yield) synthesis of 1,2,4-trioxolanes possessing the requisite 3″ substitution pattern that enables ferrous iron-dependent drug delivery is reported. The key synthetic step involves a diastereoselective Griesbaum co-ozonolysis reaction to afford primarily products with a trans relationship between the 3″ substituent and the peroxide bridge, as confirmed by X-ray structural analysis of a 3″-substituted 4-nitrobenzoate analogue.
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