ArticleBioorganic & medicinal chemistry2016
Chemoenzymatic synthesis and antileukemic activity of novel C9- and C14-functionalized parthenolide analogs.
Article in Bioorganic & medicinal chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 39 citations in OpenAlex.
- Article
- Choose Your Own Adventure: A Comprehensive Database of Reactions Catalyzed by Cytochrome P450 BM3 Variants.ACS catalysis · 2024Review
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- Engineering Catalytically Self-Sufficient P450s.Biochemistry · 2023Review
- Nanoparticle-Mediated Delivery of Micheliolide Analogs to Eliminate Leukemic Stem Cells in the Bone Marrow.Advanced therapeutics · 2022Article
- Engineered and Artificial Metalloenzymes for Selective C-H Functionalization.Current opinion in green and sustainable chemistry · 2021Article
- Synthetic utility of oxygenases in site-selective terpenoid functionalization.Journal of industrial microbiology & biotechnology · 2021Review
- Comprehensive Structure-Activity Profiling of Micheliolide and its Targeted Proteome in Leukemia Cells via Probe-Guided Late-Stage C-H Functionalization.ACS central science · 2021Article
- A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones.Journal of the American Chemical Society · 2021Article
- Characterization of CYP71AX36 from Sunflower (Helianthus annuus L., Asteraceae).Scientific reports · 2019Article
- Review
- Investigating chemoresistance to improve sensitivity of childhood T-cell acute lymphoblastic leukemia to parthenolide.Haematologica · 2018Article
- Anticancer activity profiling of parthenolide analogs generated via P450-mediated chemoenzymatic synthesis.Bioorganic & medicinal chemistry · 2018Article
- Stabilization of the Reductase Domain in the Catalytically Self-Sufficient Cytochrome P450Chembiochem : a European journal of chemical biology · 2018Article
- Catalyst-Controlled Site-Selective Bond Activation.Accounts of chemical research · 2017Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Parthenolide is a naturally occurring terpene with promising anticancer properties, particularly in the context of acute myeloid leukemia (AML). Optimization of this natural product has been challenged by limited opportunities for the late-stage functionalization of this molecule without affecting the pharmacologically important α-methylene-γ-lactone moiety. Here, we report the further development and application of a chemoenzymatic strategy to afford a series of new analogs of parthenolide functionalized at the aliphatic positions C9 and C14. Several of these compounds were determined to be able to kill leukemia cells and patient-derived primary AML specimens with improved activity compared to parthenolide, exhibiting LC50 values in the low micromolar range. These studies demonstrate that different O-H functionalization chemistries can be applied to elaborate the parthenolide scaffold and that modifications at the C9 or C14 position can effectively enhance the antileukemic properties of this natural product. The C9-functionalized analogs 22a and 25b were identified as the most interesting compounds in terms of antileukemic potency and selectivity toward AML versus healthy blood cells.
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Registered trials
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