jo500219y_si_001.pdf (613.72 kB)
Aarhus Sensor Green: A Fluorescent Probe for Singlet Oxygen
journal contribution
posted on 2014-04-04, 00:00 authored by Stephan
K. Pedersen, Jeppe Holmehave, Frances H. Blaikie, Anita Gollmer, Thomas Breitenbach, Henrik H. Jensen, Peter R. OgilbyA tetrafluoro-substituted fluorescein
derivative covalently linked
to a 9,10-diphenyl anthracene moiety has been synthesized, and its
photophysical properties have been characterized. This compound, denoted
Aarhus Sensor Green (ASG), has distinct advantages for use as a fluorescent
probe for singlet molecular oxygen, O2(a1Δg). In the least, ASG overcomes several limitations inherent
to the use of the related commercially available product called Singlet
Oxygen Sensor Green (SOSG). The functional behavior of both ASG and
SOSG derives from the fact that these weakly fluorescent compounds
rapidly react with singlet oxygen via a π2 + π4 cycloaddition to irreversibly yield a highly fluorescent
endoperoxide. The principal advantage of ASG over SOSG is that, at
physiological pH values, both ASG and the ASG endoperoxide (ASG-EP)
do not themselves photosensitize the production of singlet oxygen.
As such, ASG better fits the requirement of being a benign probe.
Although ASG readily enters a mammalian cell (i.e., HeLa) and responds
to the presence of intracellular singlet oxygen, its behavior in this
arguably complicated environment requires further investigation.