A Highly Efficient Chemiluminescence Probe for the Detection of Singlet Oxygen in Living Cells

Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11793-11796. doi: 10.1002/anie.201705803. Epub 2017 Aug 16.

Abstract

Singlet oxygen is among the reactive oxygen species (ROS) with the shortest life-times in aqueous media because of its extremely high reactivity. Therefore, designing sensors for detection of 1 O2 is perhaps one of the most challenging tasks in the field of molecular probes. Herein, we report a highly selective and sensitive chemiluminescence probe (SOCL-CPP) for the detection of 1 O2 in living cells. The probe reacts with 1 O2 to form a dioxetane that spontaneously decomposes under physiological conditions through a chemiexcitation pathway to emit green light with extraordinary intensity. SOCL-CPP demonstrated promising ability to detect and image intracellular 1 O2 produced by a photosensitizer in HeLa cells during photodynamic therapy (PDT) mode of action. Our findings make SOCL-CPP the most effective known chemiluminescence probe for the detection of 1 O2 . We anticipate that our chemiluminescence probe for 1 O2 imaging would be useful in PDT-related applications and for monitoring 1 O2 endogenously generated by cells in response to different stimuli.

Keywords: chemiluminescence; dioxetanes; live-cell imaging; molecular probes; singlet oxygen.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • HeLa Cells
  • Humans
  • Luminescence*
  • Molecular Probes / metabolism*
  • Photosensitizing Agents / metabolism
  • Singlet Oxygen / metabolism*

Substances

  • Molecular Probes
  • Photosensitizing Agents
  • Singlet Oxygen