Photochemistry of the Organoselenium Compound Ebselen: Direct Photolysis and Reaction with Active Intermediates of Conventional Reactive Species Sensitizers and Quenchers
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Hopanna, Mamatha; Kelly, Lisa; Blaney, Lee; Photochemistry of the Organoselenium Compound Ebselen: Direct Photolysis and Reaction with Active Intermediates of Conventional Reactive Species Sensitizers and Quenchers; Environmental Science & Technology 2020, 54, 18, 11271–11281; https://pubs.acs.org/doi/10.1021/acs.est.0c03093
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This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in Environmental Science & Technology, copyright © American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.est.0c03093.
This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in Environmental Science & Technology, copyright © American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.est.0c03093.
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Abstract
Ebselen (EBS), 2-phenyl-1,2-benzisoselenazol-3(2H)-one, is an organoselenium pharmaceutical with antioxidant and anti-inflammatory properties. Furthermore, EBS is an excellent scavenger of reactive oxygen species. This property complicates conventional protocols for sensitizing and quenching reactive species because of potential generation of active intermediates that quickly react with EBS. In this study, the photochemical reactivity of EBS was investigated in the presence of (1) ¹O₂ and ˙OH sensitizers [rose Bengal (RB), perinaphthanone, and H₂O₂] and (2) reactive species scavenging and quenching agents (sorbic acid, isopropanol, sodium azide, and tert-butanol) that are commonly employed to study photodegradation mechanisms and kinetics. The carbon analogue of EBS, namely, 2-phenyl-3H-isoindol-1-one, was included as a reference compound to confirm the impact of the selenium atom on EBS photochemical reactivity. EBS does not undergo acid dissociation, but pH-dependent kinetics were observed in RB-sensitized solutions, suggesting EBS reaction with active intermediates (³RB²⁻*, O₂˙⁻, and H₂O₂) that are not kinetically relevant for other compounds. In addition, the observed rate constant of EBS increased in the presence of sorbic acid, isopropanol, and sodium azide. These findings suggest that conventional reactive species sensitizers, scavengers, and quenchers need to be carefully applied to highly reactive organoselenium compounds to account for reactions that are typically slow for other organic contaminants.