title: Aarhus sensor green: a fluorescent probe for singlet oxygen.
abstract: A 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(a(1)Δg). 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.
authors.affiliation: Center for Oxygen Microscopy and Imaging, Department of Chemistry, Aarhus University , Langelandsgade 140, Aarhus 8000, Denmark.
authors.forename: Stephan K
authors.initials: SK
authors.lastname: Pedersen
authors.forename: Jeppe
authors.initials: J
authors.lastname: Holmehave
authors.forename: Frances H
authors.initials: FH
authors.lastname: Blaikie
authors.forename: Anita
authors.initials: A
authors.lastname: Gollmer
authors.forename: Thomas
authors.initials: T
authors.lastname: Breitenbach
authors.forename: Henrik H
authors.initials: HH
authors.lastname: Jensen
authors.forename: Peter R
authors.initials: PR
authors.lastname: Ogilby
mesh_terms: D000818:Animals; D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry*; D061565:Cycloaddition Reaction; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D008027:Light; D017319:Photosensitizing Agents / Q000737:chemistry; D026082:Singlet Oxygen / Q000737:chemistry*
chemical_list: D000873:Anthracenes; D005456:Fluorescent Dyes; D017319:Photosensitizing Agents; D026082:Singlet Oxygen; C046961:9,10-diphenylanthracene; C034020:anthracene