Aarhus Sensor Green: A Fluorescent Probe for Singlet Oxygen
| Autor: | Anita Gollmer, Henrik H. Jensen, Jeppe Holmehave, Frances H. Blaikie, Stephan K. Pedersen, Thomas Breitenbach, Peter R. Ogilby |
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| Rok vydání: | 2014 |
| Předmět: |
Anthracenes
Anthracene Photosensitizing Agents Cycloaddition Reaction Light Singlet Oxygen Singlet oxygen Organic Chemistry Hydrogen-Ion Concentration Photochemistry Fluorescence Cycloaddition chemistry.chemical_compound chemistry Covalent bond Yield (chemistry) Animals Humans Moiety Derivative (chemistry) Fluorescent Dyes HeLa Cells |
| Zdroj: | Pedersen, S K, Holmehave, J, Blaikie, F H, Gollmer, A, Breitenbach, T, Jensen, H H & Ogilby, P R 2014, ' Aarhus Sensor Green: A Fluorescent Probe for Singlet Oxygen ', Journal of Organic Chemistry, vol. 79, no. 7, pp. 3079-3087 . https://doi.org/10.1021/jo500219y |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo500219y |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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