Small Correspondence

Stable Dioxetane Precursors as Selective Trap-and-Trigger Chemiluminescent Probes for Singlet Oxygen

Laura A. MacManus-Spencer, Douglas E. Latch, Kim M. Kroncke, and Kristopher McNeill*
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455
Anal. Chem., 2005, 77 (4), pp 1200–1205
DOI: 10.1021/ac048293s
Publication Date (Web): January 15, 2005
Copyright © 2005 American Chemical Society
*

 Corresponding author. Phone:  (612) 625-0781. Fax:  (612) 626-7541. E-mail:  mcneill@chem.umn.edu.

Abstract

A set of highly selective chemiluminescent probes has been developed for the detection and quantitation of singlet oxygen (1O2), a reactive oxygen species that is known to transform organic pollutants in the aquatic environment and elicits cytotoxic effects in biological systems. In this study, a trap-and-trigger detection method is employed, based on the reaction of 1O2 with a spiroadamantyl-substituted vinyl ether probe to form the corresponding thermally stable dioxetane, which undergoes chemiluminescent decomposition upon addition of a chemical trigger. The detection method is highly selective for 1O2 relative to superoxide anion and hydrogen peroxide. The sensitivity of this method allows for the accurate measurement of environmentally relevant (picomolar) steady-state 1O2 concentrations in relatively short exposure times. The detection method was used to detect and quantify 1O2 production in the reaction of dibenzoyl peroxide with superoxide anion.

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History

  • Published In Issue February 15, 2005
  • Received for review November 17, 2004. Accepted January 2, 2005.

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