ArticleJournal of medicinal chemistry2014
Synthetic reactions with rare taccalonolides reveal the value of C-22,23 epoxidation for microtubule stabilizing potency.
Article in Journal of medicinal chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Pharmacokinetic and Biodistribution Studies of [ACS medicinal chemistry letters · 2025Article
- Taccalonolides: Structure, semi-synthesis, and biological activity.Frontiers in pharmacology · 2022Review
- Efficacy of a Covalent Microtubule Stabilizer in Taxane-Resistant Ovarian Cancer Models.Molecules (Basel, Switzerland) · 2021Article
- Review
- Review
- Elucidating target specificity of the taccalonolide covalent microtubule stabilizers employing a combinatorial chemical approach.Nature communications · 2020Article
- Taccalonolide Microtubule Stabilizers.Progress in the chemistry of organic natural products · 2020Review
- Current advances of tubulin inhibitors as dual acting small molecules for cancer therapy.Medicinal research reviews · 2019Review
- Identification of C-6 as a New Site for Linker Conjugation to the Taccalonolide Microtubule Stabilizers.Journal of natural products · 2019Article
- Taccalonolide Microtubule Stabilizers Generated Using Semisynthesis Define the Effects of Mono Acyloxy Moieties at C-7 or C-15 and Disubstitutions at C-7 and C-25.Journal of natural products · 2018Article
- Tubulin Inhibitor-Based Antibody-Drug Conjugates for Cancer Therapy.Molecules (Basel, Switzerland) · 2017Review
- Mechanism of microtubule stabilization by taccalonolide AJ.Nature communications · 2017Article
- Pharmacokinetic Analysis and in Vivo Antitumor Efficacy of Taccalonolides AF and AJ.Journal of natural products · 2017Article
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4 authors.
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Abstract
The taccalonolides are microtubule stabilizers isolated from plants of the genus Tacca. Taccalonolide AF is 231 times more potent than the major metabolite taccalonolide A and differs only by the oxidation of the C-22,23 double bond in A to an epoxy group in AF. In the current study, 10 other rare natural taccalonolides were epoxidized and in each case epoxidation improved potency. The epoxidation products of taccalonolide T and AI were the most potent, with IC50 values of 0.43 and 0.88 nM, respectively. These potent taccalonolides retained microtubule stabilizing effects, and T-epoxide demonstrated antitumor effects in a xenograft model of breast cancer. Additional reactions demonstrated that reduction of the C-6 ketone resulted in an inactive taccalonolide and that C-22,23 epoxidation restored its activity. These studies confirm the value of C-22,23 epoxidation as an effective strategy for increasing the potency of a wide range of structurally diverse taccalonolide microtubule stabilizers.
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