Improved Stability and Targeted Cytotoxicity of Epigallocatechin-3-Gallate Palmitate for Anticancer Therapy
- 4 January 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Langmuir
- Vol. 37 (2), 969-977
- https://doi.org/10.1021/acs.langmuir.0c03449
Abstract
Although with high antioxidant activity, epigallocatechin-3-gallate (EGCG) was restricted by its poor chemical stability in practical applications. One of EGCG derivatives, EGCG palmitate, was synthesized with EGCG and palmitoyl chloride to overcome instability of EGCG. However, uncertainties still exist in chemical stability and cytotoxicity of EGCG palmitate, which are essential for further exploration in anticancer therapy. Our work aims to analyze the resistance of EGCG palmitate to oxidation and summarize its targeted inhibition efficiency on cancerous cells and normal cells. High-performance liquid chromatography analysis confirmed that EGCG palmitate remained stable in air and Dulbecco’s modified eagle medium (DMEM) for a longer time than EGCG. Antioxidative and pro-oxidative effects of EGCG palmitate on treated cells are proposed through reactive oxygen species (ROS) detection, respectively. It reveals that pro-oxidants by H2O2 production can exert antiproliferative and proapoptotic effects on cancerous cells and stimulate autophagy, while an antioxidant relieves oxidative stress caused by superoxide as compared to normal cells. Consequently, targeted cytotoxicity is adopted by EGCG palmitate-treated cancerous cells. Results above manifest that EGCG palmitate possesses potential to serve as a promising prodrug in anticancer treatment.Keywords
Funding Information
- Ministry of Science and Technology of the People's Republic of China (2017YFF0211002)
- Science and Technology Department of Zhejiang Province (2015C03034)
- National Natural Science Foundation of China (21473157, 22003038)
This publication has 37 references indexed in Scilit:
- Pro- and Antioxidant Effects of Vitamin C in Cancer in correspondence to Its Dietary and Pharmacological ConcentrationsOxidative Medicine and Cellular Longevity, 2019
- Epigallocatechin gallate (EGCG) suppresses growth and tumorigenicity in breast cancer cells by downregulation of miR-25Bioengineered, 2019
- Theaflavin and epigallocatechin‐3‐gallate synergistically induce apoptosis through inhibition of PI3K/Akt signaling upon depolymerizing microtubules in HeLa cellsJournal of Cellular Biochemistry, 2018
- Effects of (−)-epigallocatechin-3-gallate incorporation on the physicochemical and oxidative stability of myofibrillar protein–soybean oil emulsionsFood Chemistry, 2018
- Polyphenol contents and antioxidants activities of biscuits produced from ginger-enriched pigeon pea-wheat composite flour blendsJournal of Food Biochemistry, 2018
- Evaluation of epigallocatechin gallate and epicatechin gallate effects on acrylamide-induced neurotoxicity in rats and cytotoxicity in PC 12 cellsDrug and Chemical Toxicology, 2017
- Synergistic, antagonistic and additive interactions of green tea polyphenolsZeitschrift für Lebensmittel-Untersuchung und Forschung, 2015
- Differential prooxidative effects of the green tea polyphenol, (–)‐epigallocatechin‐3‐gallate, in normal and oral cancer cells are related to differences in sirtuin 3 signalingMolecular Nutrition & Food Research, 2014
- Epigallocatechin gallate induces embryonic toxicity in mouse blastocysts through apoptosisDrug and Chemical Toxicology, 2013
- Pro-oxidative activities and dose–response relationship of (−)-epigallocatechin-3-gallate in the inhibition of lung cancer cell growth: a comparative study in vivo and in vitroCarcinogenesis: Integrative Cancer Research, 2010