ArticleEuropean journal of medicinal chemistry2016
Silibinin derivatives as anti-prostate cancer agents: Synthesis and cell-based evaluations.
Article in European journal of medicinal chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers, 2 of them syntheses that pooled it.
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Who cites it
20 citing papers in PubMed, 2 syntheses or guidelines pooled it, 41 citations in OpenAlex.
- A comprehensive review of phytoconstituents in liver cancer prevention and treatment: targeting insights into molecular signaling pathways.Medical oncology (Northwood, London, England) · 2024Pooled it
- The Radiosensitizing Potentials of Silymarin/Silibinin in Cancer: A Systematic Review.Current medicinal chemistry · 2024Pooled it
- 7-Antioxidants (Basel, Switzerland) · 2024Article
- Comprehensive Review on Recent Strategies for Management of Prostate Cancer: Therapeutic Targets and SAR.Mini reviews in medicinal chemistry · 2024Review
- Core Structure-Activity Relationship Studies of 5,7,20-Pharmaceuticals (Basel, Switzerland) · 2023Article
- Design, Synthesis and Biological Evaluation of Glycosylated Derivatives of Silibinin as Potential Anti-Tumor Agents.Drug design, development and therapy · 2023Article
- Silibinin Therapy Improves Cholangiocarcinoma Outcomes by Regulating ERK/Mitochondrial Pathway.Frontiers in pharmacology · 2022Article
- PEG-ModifiedPharmaceutics · 2021Article
- 3-Molecules (Basel, Switzerland) · 2021Article
- Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners.International journal of molecular sciences · 2021Review
- Anti-NLRP3 Inflammasome Natural Compounds: An Update.Biomedicines · 2021Review
- Molecular Mechanisms of Glucocorticoid Resistance in Corticotropinomas: New Developments and Drug Targets.Frontiers in endocrinology · 2020Review
- Flaxseed Lignans as Important Dietary Polyphenols for Cancer Prevention and Treatment: Chemistry, Pharmacokinetics, and Molecular Targets.Pharmaceuticals (Basel, Switzerland) · 2019Review
- Naturally occurring anti-cancer compounds: shining from Chinese herbal medicine.Chinese medicine · 2019Review
- Article
- Silibinin inhibits migration and invasion of the rhabdoid tumor G401 cell line via inactivation of the PI3K/Akt signaling pathway.Oncology letters · 2017Article
- 5- or/and 20-O-alkyl-2,3-dehydrosilybins: Synthesis and biological profiles on prostate cancer cell models.Bioorganic & medicinal chemistry · 2017Article
- Cancer chemoprevention through dietary flavonoids: what's limiting?Chinese journal of cancer · 2017Review
- Anti‑proliferative activity of epigallocatechin‑3‑gallate and silibinin on soft tissue sarcoma cells.Molecular medicine reports · 2017Article
- 3-O-Alkyl-2,3-dehydrosilibinins: Two synthetic approaches and in vitro effects toward prostate cancer cells.Bioorganic & medicinal chemistry letters · 2016Article
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
This study aims to systematically explore the alkylation effect of 7-OH in silibinin and 2,3-dehydrosilibinin on the antiproliferative potency toward three prostate cancer cell lines. Eight 7-O-alkylsilibinins, eight 7-O-alkyl-2,3-dehydrosilibinins, and eight 3,7-O-dialkyl-2,3-dehydrosilibinins have been synthesized from commercially available silibinin for the in vitro cell-based evaluation. The WST-1 cell proliferation assay indicates that nineteen out of twenty-four silibinin derivatives have significantly improved antiproliferative potency when compared with silibinin. 7-O-Methylsilibinin (2) and 7-O-ethylsilibinin (3) have been identified as the most potent compounds with 98- and 123-fold enhanced potency against LNCaP human androgen-dependent prostate cancer cell line. Among 2,3-dehydrosilibinin derivatives, 7-O-methyl-2,3-dehydrosilibinin (10) and 7-O-ethyl-2,3-dehydrosilibinin (11) have been identified as the optimal compounds with the highest potency towards both androgen-dependent LNCaP and androgen-independent PC-3 prostate cancer cell lines. 7-O-Ethyl-2,3-dehydrosilibinin (11) was demonstrated to arrest PC-3 cell cycle at the G0/G1 phase and to induce PC-3 cell apoptosis. The findings in this study suggest that antiproliferative potency of silibinin and 2,3-dehydrosilibinin can be appreciably enhanced through suitable chemical modifications on the phenolic hydroxyl group at C-7 and that introduction of a chemical moiety with the potential to improve bioavailability through a linker to 7-OH in silibinin and 2,3-dehydrosilibinin would be a feasible strategy for the development of silibinin derivatives as anti-prostate cancer agents.
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Registered trials
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