Sep 18, 2012

Phenylalkyl isoselenocyanates vs phenylalkyl isothiocyanates: thiol reactivity and its implications

Chemico-biological Interactions
Melissa A CrampsieArun K Sharma

Abstract

Phenylalkyl isoselenocyanate (ISC) compounds were recently designed in our laboratory by incorporating the anticancer element selenium into a panel of phenylalkyl isothiocyanates (ITCs), known to have anticancer properties. A structural activity investigation was carried out to compare the ISC and ITC panels. Cell viability assay and Annexin V staining for apoptosis showed ISC compounds to be more potent in killing A549 lung adenocarcinoma cells. Both ITCs and ISCs were able to deplete reduced glutathione (GSH) in cells, ISCs more rapidly, but ITCs to a greater extent. ISC compounds had a higher rate of reaction to thiol (-SH) groups as determined by pseudo first order kinetics than the corresponding carbon chain length ITC. The equilibrium concentrations of the GSH and protein thiol conjugates did not differ significantly when comparing sulfur to selenium compounds of the same carbon chain length, and did follow the same trend of displaying decreasing reactivity with increasing carbon chain length for both ITCs and ISCs. Furthermore, only ITCs were able to induce cell cycle arrest, suggesting that protein targets inside the cell may differ for the S and Se panels. Finally, the panels were tested for their ability to redox cycl...Continue Reading

Mentioned in this Paper

Selenocyanate potassium
Metabolic Process, Cellular
Selenium Compounds, Inorganic
Flow Cytometry
Adenocarcinoma of Lung (Disorder)
Conjugation
Protein Binding
Annexin A5
Dimethyl Sulfoxide
Apoptosis, Intrinsic Pathway

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