ArticleOrganic & biomolecular chemistry2015
Molecular characterization of the boron adducts of the proteasome inhibitor bortezomib with epigallocatechin-3-gallate and related polyphenols.
Article in Organic & biomolecular chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 33 citations in OpenAlex.
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- Comparative Investigation of Cytotoxic Effects of Structurally Diverse Small Molecules and In Silico Analysis of 1-Acetyl-4-(4-Hydroxyphenyl)piperazine.Journal of cellular and molecular medicine · 2026Article
- Synthesis and Evaluation of Boron-Containing Heterocyclic Compounds with Antimicrobial and Anticancer Activities.Molecules (Basel, Switzerland) · 2025Article
- Enhancing the Mechanical Properties of Injectable Nanocomposite Hydrogels by Adding Boronic Acid/Boronate Ester Dynamic Bonds at the Nanoparticle-Polymer Interface.Gels (Basel, Switzerland) · 2024Article
- Dynamic Covalent Boronic-Acid-Functionalized Alginate/PVA Hydrogels for pH and Shear-Responsive Drug Delivery.Gels (Basel, Switzerland) · 2024Article
- Technologies for Direct Detection of Covalent Protein-Drug Adducts.Pharmaceuticals (Basel, Switzerland) · 2023Review
- Proteostasis of Islet Amyloid Polypeptide: A Molecular Perspective of Risk Factors and Protective Strategies for Type II Diabetes.Chemical reviews · 2021Review
- Protein Carbonylation and Lipid Peroxidation in Hematological Malignancies.Antioxidants (Basel, Switzerland) · 2020Review
- Preclinical Pharmacological Activities of Epigallocatechin-3-gallate in Signaling Pathways: An Update on Cancer.Molecules (Basel, Switzerland) · 2020Review
- Repurposing the aldose reductase inhibitor and diabetic neuropathy drug epalrestat for the congenital disorder of glycosylation PMM2-CDG.Disease models & mechanisms · 2019Article
- Drug screens ofDisease models & mechanisms · 2019Article
- Effects of B2O3 (boron trioxide) on colon cancer cells: our first-step experience and in vitro results.Turkish journal of biology = Turk biyoloji dergisi · 2019Article
- Effect of Tea Polyphenol Compounds on Anticancer Drugs in Terms of Anti-Tumor Activity, Toxicology, and Pharmacokinetics.Nutrients · 2016Review
- Antiproliferative and Antiangiogenic Effects of Punica granatum Juice (PGJ) in Multiple Myeloma (MM).Nutrients · 2016Article
- EGCG antagonizes Bortezomib cytotoxicity in prostate cancer cells by an autophagic mechanism.Scientific reports · 2015Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
The green tea polyphenol epigallocatechin-3-gallate (EGCG) was reported to effectively antagonize the ability of Bortezomib (BZM) to induce apoptosis in cancer cells. This interaction was attributed to the formation of a covalent adduct between a phenolic moiety of EGCG with the boronic acid group of Bortezomib. However, the structural details of this boron adduct and the molecular factors that contribute to its formation and its ability to inhibit Bortezomib's activity remain unclear. This paper describes the use of NMR spectroscopy and cell assays to characterize the structures and properties of the boron adducts of EGCG and related polyphenols. The observed boron adducts included both boronate and borate derivatives, and their structural characteristics were correlated with cell-based evaluation of the ability of EGCG and other phenols to antagonize the anticancer activity of Bortezomib. The enhanced stability of the BZM/EGCG adduct was attributed to electronic and steric reasons, and a newly identified intramolecular interaction of the boron atom of BZM with the adjacent amide bond. The reported approach provides a useful method for determining the potential ability of polyphenols to form undesired adducts with boron-based drugs and interfere with their actions.
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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.