ArticleBioorganic & medicinal chemistry2018
Anticancer activity profiling of parthenolide analogs generated via P450-mediated chemoenzymatic synthesis.
Article in Bioorganic & medicinal chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Radical-Mediated Regiodivergent C(Chem catalysis · 2024Article
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- Engineering Catalytically Self-Sufficient P450s.Biochemistry · 2023Review
- Combination Anticancer Therapies Using Selected Phytochemicals.Molecules (Basel, Switzerland) · 2022Review
- Nanoparticle-Mediated Delivery of Micheliolide Analogs to Eliminate Leukemic Stem Cells in the Bone Marrow.Advanced therapeutics · 2022Article
- The NLRP3 Inflammasome Pathway: A Review of Mechanisms and Inhibitors for the Treatment of Inflammatory Diseases.Frontiers in aging neuroscience · 2022Review
- A Promiscuous Bacterial P450: The Unparalleled Diversity of BM3 in Pharmaceutical Metabolism.International journal of molecular sciences · 2021Review
- 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
- Box-Behnken Design (BBD)-Based Optimization of Microwave-Assisted Extraction of Parthenolide from the Stems ofMolecules (Basel, Switzerland) · 2021Article
- Scalable biocatalytic C-H oxyfunctionalization reactions.Chemical Society reviews · 2020Review
- Chemoenzymatic Synthesis of Enantiomeric, Bicyclic δ-Halo-γ-lactones with a Cyclohexane Ring, Their Biological Activity and Interaction with Biological Membranes.Biomolecules · 2020Article
- Characterization of CYP71AX36 from Sunflower (Helianthus annuus L., Asteraceae).Scientific reports · 2019Article
- Review
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The plant-derived sesquiterpene lactone parthenolide (PTL) was recently found to possess promising anticancer activity but elaboration of this natural product scaffold for optimization of its pharmacological properties has proven challenging via available chemical methods. In this work, P450-catalyzed C-H hydroxylation of positions C9 and C14 in PTL was coupled to carbamoylation chemistry to yield a panel of novel carbamate-based PTL analogs ('parthenologs'). These compounds, along with a series of other C9- and C14-functionalized parthenologs obtained via O-H acylation, alkylation, and metal-catalyzed carbene insertion, were profiled for their cytotoxicity against a diverse panel of human cancer cell lines. These studies led to the discovery of several parthenologs with significantly improved anticancer activity (2-14-fold) compared to the parent molecule. Most interestingly, two PTL analogs with high cytotoxicity (LC
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