ArticleLangmuir : the ACS journal of surfaces and colloids2014
Synergism between airborne singlet oxygen and a trisubstituted olefin sulfonate for the inactivation of bacteria.
Article in Langmuir : the ACS journal of surfaces and colloids, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 19 citations in OpenAlex.
- Photosensitized Oxidative Damage from a New Perspective: The Influence of Before-Light and After-Light Reaction Conditions.The Journal of organic chemistry · 2024Review
- Structurally Characterized BODIPY-Appended Oxidovanadium(IV) β-Diketonates for Mitochondria-Targeted Photocytotoxicity.ACS omega · 2020Article
- Mechanistic and Kinetic Study of Singlet O2 Oxidation of Methionine by On-Line Electrospray Ionization Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2016Article
- Air-Water Interface Effects on the Regioselectivity of Singlet Oxygenations of a Trisubstituted Alkene.Tetrahedron letters · 2015Article
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
Abstract
The reactivity of a trisubstituted alkene surfactant (8-methylnon-7-ene-1 sulfonate, 1) to airborne singlet oxygen in a solution containing E. coli was examined. Surfactant 1 was prepared by a Strecker-type reaction of 9-bromo-2-methylnon-2-ene with sodium sulfite. Submicellar concentrations of 1 were used that reacted with singlet oxygen by an "ene" reaction to yield two hydroperoxides (7-hydroperoxy-8-methylnon-8-ene-1 sulfonate and (E)-8-hydroperoxy-8-methylnon-6-ene-1 sulfonate) in a 4:1 ratio. Exchanging the H2O solution for D2O where the lifetime of solution-phase singlet oxygen increases by 20-fold led to an ∼2-fold increase in the yield of hydroperoxides pointing to surface activity of singlet oxygen with the surfactant in a partially solvated state. In this airborne singlet oxygen reaction, E. coli inactivation was monitored in the presence and absence of 1 and by a LIVE/DEAD cell permeabilization assay. It was shown that the surfactant has low dark toxicity with respect to the bacteria, but in the presence of airborne singlet oxygen, it produces a synergistic enhancement of the bacterial inactivation. How the ene-derived surfactant hydroperoxides can provoke (1)O2 toxicity and be of general utility is discussed.
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Registered trials
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