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Updated: May 2, 2026

Imaging Approaches to Assessments of Toxicological Oxidative Stress Using Genetically-encoded Fluorogenic Sensors

Imaging Approaches to Assessments of Toxicological Oxidative Stress Using Genetically-encoded Fluorogenic Sensors

Published on: February 7, 2018

Aarhus sensor green: a fluorescent probe for singlet oxygen.

Stephan K Pedersen¹, Jeppe Holmehave, Frances H Blaikie

¹Center for Oxygen Microscopy and Imaging, Department of Chemistry, Aarhus University , Langelandsgade 140, Aarhus 8000, Denmark.

The Journal of Organic Chemistry

|March 11, 2014

Summary

A new fluorescent probe, Aarhus Sensor Green (ASG), has been developed for detecting singlet molecular oxygen. ASG offers advantages over existing probes by not producing singlet oxygen itself, making it a more benign option.

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Area of Science:

Photochemistry
Biomedical Engineering
Organic Chemistry

Background:

Singlet molecular oxygen (O2(a(1)Δg)) is a reactive oxygen species implicated in various biological processes.
Fluorescent probes are essential tools for detecting and quantifying singlet oxygen in biological systems.
Existing probes like Singlet Oxygen Sensor Green (SOSG) have limitations, including potential photosensitization.

Purpose of the Study:

To synthesize and characterize a novel fluorescent probe, Aarhus Sensor Green (ASG), for singlet molecular oxygen detection.
To evaluate the advantages of ASG over the commercially available SOSG.
To assess the suitability of ASG as a benign fluorescent probe for biological applications.

Main Methods:

Synthesis of a tetrafluoro-substituted fluorescein derivative linked to a 9,10-diphenyl anthracene moiety.
Characterization of the photophysical properties of the synthesized compound (ASG).
Comparative analysis of ASG and SOSG in terms of reactivity with singlet oxygen and photosensitization potential.

Main Results:

Aarhus Sensor Green (ASG) was successfully synthesized and its photophysical properties were characterized.
ASG reacts rapidly with singlet molecular oxygen via a π2 + π4 cycloaddition to form a highly fluorescent endoperoxide.
Unlike SOSG, ASG and its endoperoxide (ASG-EP) do not photosensitize singlet oxygen production at physiological pH.

Conclusions:

ASG is a promising fluorescent probe for singlet molecular oxygen with improved characteristics compared to SOSG.
ASG's benign nature, due to its lack of photosensitization, makes it a superior choice for biological studies.
Further investigation is required to fully understand ASG's behavior within complex cellular environments, despite its ability to enter mammalian cells.