Aarhus sensor green: a fluorescent probe for singlet oxygen.

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.

[1]  S. Nonell,et al.  Naphthoxazole‐Based Singlet Oxygen Fluorescent Probes , 2013, Photochemistry and photobiology.

[2]  T. Majima,et al.  Photochemistry of singlet oxygen sensor green. , 2013, The journal of physical chemistry. B.

[3]  W. Nam,et al.  Ratiometric fluorescent probes for detection of intracellular singlet oxygen. , 2013, Organic letters.

[4]  P. Ogilby,et al.  Spatially resolved two-photon irradiation of an intracellular singlet oxygen photosensitizer: Correlating cell response to the site of localized irradiation , 2013, Free radical research.

[5]  P. Ogilby,et al.  Antioxidant β-carotene does not quench singlet oxygen in mammalian cells. , 2013, Journal of the American Chemical Society.

[6]  Frederico M. Pimenta,et al.  Singlet-oxygen-mediated cell death using spatially-localized two-photon excitation of an extracellular sensitizer. , 2012, The journal of physical chemistry. B.

[7]  M. Kuimova,et al.  Irradiation- and sensitizer-dependent changes in the lifetime of intracellular singlet oxygen produced in a photosensitized process. , 2012, The journal of physical chemistry. B.

[8]  P. Bastiaens,et al.  Development of highly potent inhibitors of the Ras-targeting human acyl protein thioesterases based on substrate similarity design. , 2011, Angewandte Chemie.

[9]  B. Tang,et al.  A selective near-infrared fluorescent probe for singlet oxygen in living cells. , 2011, Chemical communications.

[10]  M. Glasius,et al.  Singlet Oxygen Sensor Green®: Photochemical Behavior in Solution and in a Mammalian Cell , 2011, Photochemistry and photobiology.

[11]  Peter R Ogilby,et al.  Singlet oxygen: there is indeed something new under the sun. , 2010, Chemical Society reviews.

[12]  Patrizio Salice,et al.  Photophysics of squaraine dyes: role of charge-transfer in singlet oxygen production and removal. , 2010, The journal of physical chemistry. A.

[13]  C. B. Nielsen,et al.  Molecular tuning of phenylene-vinylene derivatives for two-photon photosensitized singlet oxygen production. , 2009, The Journal of organic chemistry.

[14]  Tetsuo Nagano,et al.  Bioimaging Probes for Reactive Oxygen Species and Reactive Nitrogen Species , 2009, Journal of clinical biochemistry and nutrition.

[15]  L. Tolbod,et al.  Influence of an intermolecular charge-transfer state on excited-state relaxation dynamics: solvent effect on the methylnaphthalene-oxygen system and its significance for singlet oxygen production. , 2009, The journal of physical chemistry. A.

[16]  S. Nonell,et al.  Singlet oxygen photosensitisation by the fluorescent probe Singlet Oxygen Sensor Green. , 2009, Chemical communications.

[17]  J. Lambert,et al.  Photosensitized production of singlet oxygen: spatially-resolved optical studies in single cells , 2009, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[18]  P. Ogilby,et al.  Time‐resolved Singlet Oxygen Phosphorescence Measurements from Photosensitized Experiments in Single Cells: Effects of Oxygen Diffusion and Oxygen Concentration , 2008, Photochemistry and photobiology.

[19]  É. Hideg A comparative study of fluorescent singlet oxygen probes in plant leaves , 2008, Central European Journal of Biology.

[20]  J. White,et al.  Structural studies on cycloadducts of furan, 2-methoxyfuran, and 5-trimethylsilylcyclopentadiene with maleic anhydride and N-methylmaleimide. , 2008, The Journal of organic chemistry.

[21]  J. Lambert,et al.  Measuring the lifetime of singlet oxygen in a single cell: addressing the issue of cell viability , 2007, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[22]  M. Schwab,et al.  A concise synthesis of the Pennsylvania Green fluorophore and labeling of intracellular targets with O6-benzylguanine derivatives. , 2007, Organic letters.

[23]  M. Tan,et al.  A europium(III) complex as an efficient singlet oxygen luminescence probe. , 2006, Journal of the American Chemical Society.

[24]  P. Ogilby,et al.  Two-Photon Singlet Oxygen Microscopy: The Challenges of Working with Single Cells , 2006, Photochemistry and photobiology.

[25]  O. Christiansen,et al.  Overview of Theoretical and Computational Methods Applied to the Oxygen–Organic Molecule Photosystem , 2006, Photochemistry and photobiology.

[26]  I. Kochevar,et al.  Spatially Resolved Cellular Responses to Singlet Oxygen , 2006, Photochemistry and photobiology.

[27]  P. Frederiksen,et al.  Two-photon photosensitized production of singlet oxygen: optical and optoacoustic characterization of absolute two-photon absorption cross sections for standard sensitizers in different solvents. , 2006, The journal of physical chemistry. A.

[28]  N. Soh Recent advances in fluorescent probes for the detection of reactive oxygen species , 2006, Analytical and bioanalytical chemistry.

[29]  E. A. Luk'yanets,et al.  Phthalocyanines and related compounds: XLI. Synthesis of 9,10-diphenylanthracene-2,3-dicarboxylic acid derivatives , 2006 .

[30]  B. Peterson,et al.  The Pennsylvania Green Fluorophore: a hybrid of Oregon Green and Tokyo Green for the construction of hydrophobic and pH-insensitive molecular probes. , 2006, Organic letters.

[31]  P. Ogilby,et al.  Phototoxic Phytoalexins. Processes that Compete with the Photosensitized Production of Singlet Oxygen by 9-Phenylphenalenones† , 2006, Photochemistry and photobiology.

[32]  Eduarda Fernandes,et al.  Fluorescence probes used for detection of reactive oxygen species. , 2005, Journal of biochemical and biophysical methods.

[33]  C. B. Nielsen,et al.  Synthesis and characterization of water-soluble phenylene-vinylene-based singlet oxygen sensitizers for two-photon excitation. , 2005, The Journal of organic chemistry.

[34]  A. Pace,et al.  Advances in Singlet Oxygen Chemistry , 2005 .

[35]  Yasuteru Urano,et al.  Evolution of fluorescein as a platform for finely tunable fluorescence probes. , 2005, Journal of the American Chemical Society.

[36]  K. Ohkubo,et al.  Rational principles for modulating fluorescence properties of fluorescein. , 2004, Journal of the American Chemical Society.

[37]  Deqing Zhang,et al.  4,5-dimethylthio-4'-[2-(9-anthryloxy)ethylthio]tetrathiafulvalene, a highly selective and sensitive chemiluminescence probe for singlet oxygen. , 2004, Journal of the American Chemical Society.

[38]  Reinhard Schmidt,et al.  Physical mechanisms of generation and deactivation of singlet oxygen. , 2003, Chemical reviews.

[39]  J. Kennedy,et al.  Photodynamic therapy using 5-aminolevulinic acid-induced protoporphyrin IX , 2003 .

[40]  L. Klotz,et al.  Singlet oxygen-induced signaling effects in mammalian cells , 2003, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[41]  Y. Urano,et al.  Development of Novel Fluorescence Probes That Can Reliably Detect Reactive Oxygen Species and Distinguish Specific Species* 210 , 2003, The Journal of Biological Chemistry.

[42]  Douglas Magde,et al.  Fluorescence Quantum Yields and Their Relation to Lifetimes of Rhodamine 6G and Fluorescein in Nine Solvents: Improved Absolute Standards for Quantum Yields¶ , 2002, Photochemistry and photobiology.

[43]  K Tanaka,et al.  Rational design of fluorescein-based fluorescence probes. Mechanism-based design of a maximum fluorescence probe for singlet oxygen. , 2001, Journal of the American Chemical Society.

[44]  Y. Urano,et al.  Novel Fluorescent Probes for Singlet Oxygen. , 1999, Angewandte Chemie.

[45]  K. Mikkelsen,et al.  Radiative Transitions of Singlet Oxygen: New Tools, New Techniques and New Interpretations , 1999 .

[46]  Richard P. Haugland,et al.  Synthesis of Fluorinated Fluoresceins , 1997 .

[47]  W.Phillip Helman,et al.  Rate Constants for the Decay and Reactions of the Lowest Electronically Excited Singlet State of Molecular Oxygen in Solution. An Expanded and Revised Compilation , 1995 .

[48]  F. Wilkinson,et al.  Picosecond absorption studies on the role of charge transfer interactions in the mechanism of quenching of triplet states by molecular oxygen , 1993 .

[49]  R. Scurlock,et al.  Charge-transfer state and singlet oxygen (1.DELTA.g O2) production in photoexcited organic molecule-molecular oxygen complexes , 1991 .

[50]  J. Dewit,et al.  Effects of Various Heat Treatments on Structure and Solubility of Whey Proteins , 1984 .

[51]  P. Ogilby,et al.  Chemistry of singlet oxygen. 42. Effect of solvent, solvent isotopic substitution, and temperature on the lifetime of singlet molecular oxygen (1.DELTA.g) , 1983 .

[52]  M L Walsh,et al.  Localization of mitochondria in living cells with rhodamine 123. , 1980, Proceedings of the National Academy of Sciences of the United States of America.

[53]  S. Singer,et al.  Association of mitochondria with microtubules in cultured cells. , 1978, Proceedings of the National Academy of Sciences of the United States of America.

[54]  B. Dickinson,et al.  Boronate-based fluorescent probes: imaging hydrogen peroxide in living systems. , 2013, Methods in enzymology.

[55]  B. Wilson,et al.  Feasibility Study on Quantitative Measurements of Singlet Oxygen Generation Using Singlet Oxygen Sensor Green , 2012, Journal of Fluorescence.

[56]  W.Phillip Helman,et al.  Quantum Yields for the Photosensitized Formation of the Lowest Electronically Excited Singlet State of Molecular Oxygen in Solution , 1993 .

[57]  J. Kanofsky,et al.  Singlet oxygen production by biological systems. , 1989, Chemico-biological interactions.