ArticleACS omega2026
Electrochemical Investigation of the Redox Behavior of Isoquinoline Alkaloid Emetine.
Article in ACS omega, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Authors and funding
13 authors.
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Abstract
Emetine is a biologically active isoquinoline alkaloid with reported antiviral, anticancer, and antiparasitic properties; however, its broader therapeutic application remains limited by dose-dependent toxicity and an incomplete understanding of its oxidative behavior. The electrochemical oxidation of emetine at a glassy carbon electrode (GCE) under physiologically relevant conditions was investigated using cyclic voltammetry (CV), differential pulse voltammetry (DPV), controlled-potential electrolysis (CPE), UV-Vis and fluorescence spectroscopy, and high-resolution LC-QTOF-MS/MS. DPV revealed three irreversible anodic oxidation processes centered near +0.90, +1.01, and +1.25 V versus Ag/AgCl. Scan-rate studies showed that the two lower-potential processes are predominantly diffusion-controlled, whereas the higher-potential process exhibits greater contributions from surface-associated and interfacial phenomena. pH-dependent studies (pH 4.0-9.1) demonstrated that emetine oxidation is strongly influenced by the protonation state and proceeds through a complex multistep irreversible mechanism. CPE generated multiple oxidation products, and subsequent high-resolution LC-QTOF-MS/MS analysis revealed ten emetine-associated products (P1-P10). Tentative structural assignments for P1-P8 encompassed dehydrogenated, oxygenated/dehydrogenated, and nitrogen-containing products, whereas P9 and P10 remained structurally unresolved. Together with complementary spectroscopic evidence, these findings support a mechanistic model in which emetine oxidation is initiated at amine functionalities and adjacent benzylic carbon centers, followed by competing dehydrogenation, oxygen incorporation, and secondary product-forming reactions. This study establishes a mechanistic framework for emetine electrooxidation and demonstrates the utility of integrating electrochemistry with high-resolution mass spectrometry to investigate the oxidative chemistry of bioactive isoquinoline alkaloids.
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