A Glutathione Activatable Ion Channel Induces Apoptosis in Cancer Cells by Depleting Intracellular Glutathione Levels
- 12 February 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 59 (20) , 7944-7952
Abstract
Cancer cells use elevated glutathione (GSH) levels as an inner line of defense to evade apoptosis and develop drug resistance. In this study, we describe a novel 2,4‐nitrobenzenesulfonyl (DNS) protected 2‐hydroxyisophthalamide system that exploits GSH for its activation into free 2‐hydroxyisophthalamide forming supramolecular M + /Cl − channels. Better permeation of the DNS protected compound into MCF‐7 cells compared to the free 2‐hydroxyisophthalamide and GSH‐activatable ion transport resulted in higher cytotoxicity, which was associated with increased oxidative stress that further reduced the intracellular GSH levels and altered mitochondrial membrane permeability leading to the induction of the intrinsic apoptosis pathway. The GSH‐activatable transport‐mediated cell death was further validated in rat insulinoma cells ( INS‐1E ); wherein the intracellular GSH levels showed a direct correlation to the resulting cytotoxicity. Lastly, the active compound was found to restrict the growth and proliferation of 3D spheroids of MCF‐7 cells with efficiency similar to that of the anticancer drug doxorubicin.Keywords
Funding Information
- Anusandhan National Research Foundation (EMR/2016/001897)
- Anusandhan National Research Foundation (EMR/2016/001974)
- Department of Biotechnology, Ministry of Science and Technology, India (BT/HRD/NBA/36/06/2018)
- UGC-DAE Consortium for Scientific Research, University Grants Commission (F.4-5(18-FRP)(IV-Cycle)/2017(BSR))
This publication has 63 references indexed in Scilit:
- γ-Glutamylcysteine detoxifies reactive oxygen species by acting as glutathione peroxidase-1 cofactorNature Communications, 2012
- Drug Resistance and Cellular Adaptation to Tumor Acidic pH MicroenvironmentMolecular Pharmaceutics, 2011
- Milestoning without a Reaction CoordinateJournal of Chemical Theory and Computation, 2010
- Effects of sulfur dioxide on expressions of p53, bax and bcl-2 in lungs of asthmatic ratsInhalation Toxicology, 2009
- Expression of caspase and apoptotic signal pathway induced by sulfur dioxideEnvironmental and Molecular Mutagenesis, 2009
- What is the mitochondrial permeability transition pore?Journal of Molecular and Cellular Cardiology, 2009
- Directing cancer cells to self-destruct with pro-apoptotic receptor agonistsNature Reviews Drug Discovery, 2008
- Development of Bis(2‐picolyl)amine–Zinc Chelates for Imidazole ReceptorsEuropean Journal of Organic Chemistry, 2008
- A New Method for the Cytofluorometric Analysis of Mitochondrial Membrane Potential Using the J-Aggregate Forming Lipophilic Cation 5,5′,6,6′-Tetrachloro-1,1′,3,3′-tetraethylbenzimidazolcarbocyanine Iodide (JC-1)Biochemical and Biophysical Research Communications, 1993
- DNA base modifications in chromatin of human cancerous tissuesFEBS Letters, 1992