Synergism between Airborne Singlet Oxygen and a Trisubstituted Olefin Sulfonate for the Inactivation of Bacteria
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- 作者：Rajib Choudhury ; Alexander Greer
- 刊名：Langmuir
- 出版年：2014
- 出版时间：April 1, 2014
- 年：2014
- 卷：30
- 期：12
- 页码：3599-3605
- 全文大小：312K
- 年卷期：v.30,no.12(April 1, 2014)
- ISSN：1520-5827
文摘
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 鈥渆ne鈥?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 1O2 toxicity and be of general utility is discussed.