ArticleAngewandte Chemie (International ed. in English)2015
C-H Oxidation of Ingenanes Enables Potent and Selective Protein Kinase C Isoform Activation.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 44 citations in OpenAlex.
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- Divergent synthesis of thapsigargin analogs.Bioorganic & medicinal chemistry letters · 2018Article
- Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters.Molecules (Basel, Switzerland) · 2017Article
- Scalable Synthesis of (-)-Thapsigargin.ACS central science · 2017Article
- Ingenol Disoxate: A Novel 4-Isoxazolecarboxylate Ester of Ingenol with Improved Properties for Treatment of Actinic Keratosis and Other Non-Melanoma Skin Cancers.Dermatology and therapy · 2016Article
- Radicals: Reactive Intermediates with Translational Potential.Journal of the American Chemical Society · 2016Review
- Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes.Angewandte Chemie (International ed. in English) · 2016Article
- Nineteen-step total synthesis of (+)-phorbol.Nature · 2016Article
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Authors and funding
8 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Ingenol derivatives with varying degrees of oxidation were prepared by two-phase terpene synthesis. This strategy has allowed access to analogues that cannot be prepared by semisynthesis from natural ingenol. Complex ingenanes resulting from divergent C-H oxidation of a common intermediate were found to interact with protein kinase C in a manner that correlates well with the oxidation state of the ingenane core. Even though previous work on ingenanes has suggested a strong correlation between potential to activate PKCδ and induction of neutrophil oxidative burst, the current study shows that the potential to activate PKCβII is of key importance while interaction with PKCδ is dispensable. Thus, key modifications of the ingenane core allowed PKC isoform selectivity wherein PKCδ-driven activation of keratinocytes is strongly reduced or even absent while PKCβII-driven activation of neutrophils is retained.
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