ArticleEuropean journal of medicinal chemistry2015
Wittig derivatization of sesquiterpenoid polygodial leads to cytostatic agents with activity against drug resistant cancer cells and capable of pyrrolylation of primary amines.
Article in European journal of medicinal chemistry, 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, 19 citations in OpenAlex.
- Semisynthetic Derivatives of Polygodial as α-Glucosidase and α-Amylase Inhibitors: In Vitro Evaluation, Molecular Docking and Molecular Dynamics Simulation.Pharmaceutics · 2026Article
- Metal Ion Signaling in Biomedicine.Chemical reviews · 2025Review
- Anticancer Activity of Natural and Semi-Synthetic Drimane and Coloratane Sesquiterpenoids.Molecules (Basel, Switzerland) · 2022Review
- Polygodial and Ophiobolin A Analogues for Covalent Crosslinking of Anticancer Targets.International journal of molecular sciences · 2021Article
- Activity of natural and synthetic polygodial derivatives againstNatural product research · 2021Article
- Novel polygodial analogs P3 and P27: Efficacious therapeutic agents disrupting mitochondrial function in oral squamous cell carcinoma.International journal of oncology · 2018Article
- Polygodial analog induces apoptosis in LNCaP prostate cancer cells.European journal of pharmacology · 2018Article
- Covalent modification of biological targets with natural products through Paal-Knorr pyrrole formation.Natural product reports · 2017Review
- Targeting calcium signaling in cancer therapy.Acta pharmaceutica Sinica. B · 2017Review
- DNA Repair Genes ERCC1 and BRCA1 Expression in Non-Small Cell Lung Cancer Chemotherapy Drug Resistance.Medical science monitor : international medical journal of experimental and clinical research · 2016Article
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Authors and funding
25 authors at 13 institutions in 6 countries.
Funding
Abstract
Many types of cancer, including glioma, melanoma, non-small cell lung cancer (NSCLC), among others, are resistant to proapoptotic stimuli and thus poorly responsive to current therapies based on the induction of apoptosis in cancer cells. The current investigation describes the synthesis and anticancer evaluation of unique C12-Wittig derivatives of polygodial, a sesquiterpenoid dialdehyde isolated from Persicaria hydropiper (L.) Delabre. These compounds were found to undergo an unprecedented pyrrole formation with primary amines in a chemical model system, a reaction that could be relevant in the biological environment and lead to the pyrrolation of lysine residues in the target proteins. The anticancer evaluation of these compounds revealed their promising activity against cancer cells displaying various forms of drug resistance, including resistance to proapoptotic agents. Mechanistic studies indicated that compared to the parent polygodial, which displays fixative general cytotoxic action against human cells, the C12-Wittig derivatives exerted their antiproliferative action mainly through cytostatic effects explaining their activity against apoptosis-resistant cancer cells. The possibility for an intriguing covalent modification of proteins through a novel pyrrole formation reaction, as well as useful activities against drug resistant cancer cells, make the described polygodial-derived chemical scaffold an interesting new chemotype warranting thorough investigation.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.