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Article: Aarhus Sensor Green: A Fluorescent Probe for Singlet Oxygen

Pedersen, Stephan K / Blaikie Frances H / Breitenbach Thomas / Gollmer Anita / Holmehave Jeppe / Jensen Henrik H / Ogilby Peter R

Journal of organic chemistry. 2014 Apr. 04, v. 79, no. 7

2014

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 ... ...

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, Oâ(aÂ¹Îg). 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 Ï2 + Ï4 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.
Keywords	anthracenes ; chemical bonding ; fluorescein ; mammals ; moieties ; organic chemistry ; oxygen ; pH ; singlet oxygen
Language	English
Dates of publication	2014-0404
Size	p. 3079-3087.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021%2Fjo500219y
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Article ; Online: Aarhus sensor green: a fluorescent probe for singlet oxygen.

Pedersen, Stephan K / Holmehave, Jeppe / Blaikie, Frances H / Gollmer, Anita / Breitenbach, Thomas / Jensen, Henrik H / Ogilby, Peter R

The Journal of organic chemistry

2014 Volume 79, Issue 7, Page(s) 3079–3087

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.
MeSH term(s)	Animals ; Anthracenes/chemical synthesis ; Anthracenes/chemistry ; Cycloaddition Reaction ; Fluorescent Dyes/chemistry ; HeLa Cells ; Humans ; Hydrogen-Ion Concentration ; Light ; Photosensitizing Agents/chemistry ; Singlet Oxygen/chemistry
Chemical Substances	Anthracenes ; Fluorescent Dyes ; Photosensitizing Agents ; Singlet Oxygen (17778-80-2) ; 9,10-diphenylanthracene (51BQ8IYQ9U) ; anthracene (EH46A1TLD7)
Language	English
Publishing date	2014-04-04
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo500219y
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Article: A mitochondria-targeted nitroxide is reduced to its hydroxylamine by ubiquinol in mitochondria.

Trnka, Jan / Blaikie, Frances H / Smith, Robin A J / Murphy, Michael P

Free radical biology & medicine

2008 Volume 44, Issue 7, Page(s) 1406–1419

Abstract: Piperidine nitroxides such as TEMPOL act as antioxidants in vivo due to their interconversion among nitroxide, hydroxylamine, and oxoammonium derivatives, but the mechanistic details of these reactions are unclear. As mitochondria are a significant site ... ...

Abstract	Piperidine nitroxides such as TEMPOL act as antioxidants in vivo due to their interconversion among nitroxide, hydroxylamine, and oxoammonium derivatives, but the mechanistic details of these reactions are unclear. As mitochondria are a significant site of piperidine nitroxide metabolism and action, we synthesized a mitochondria-targeted nitroxide, MitoTEMPOL, by conjugating TEMPOL to the lipophilic triphenylphosphonium cation. MitoTEMPOL was accumulated several hundred-fold into energized mitochondria where it was reduced to the hydroxylamine by direct reaction with ubiquinol. This reaction occurred by transfer of H() from ubiquinol to the nitroxide, with the ubisemiquinone radical product predominantly dismutating to ubiquinone and ubiquinol, together with a small amount reacting with oxygen to form superoxide. The piperidine nitroxides TEMPOL, TEMPO, and butylTEMPOL reacted similarly with ubiquinol in organic solvents but in mitochondrial membranes the rates varied in the order: MitoTEMPOL > butylTEMPOL > TEMPO > TEMPOL, which correlated with the extent of access of the nitroxide moiety to ubiquinol within the membrane. These findings suggest ways of using mitochondria-targeted compounds to modulate the coenzyme Q pool within mitochondria in vivo, and indicate that the antioxidant effects of mitochondria-targeted piperidine nitroxides can be ascribed to their corresponding hydroxylamines.
MeSH term(s)	Antioxidants/chemistry ; Biochemistry/methods ; Cations ; Chromatography, High Pressure Liquid ; Cyclic N-Oxides/chemistry ; Electron Spin Resonance Spectroscopy ; Hydroxylamine/chemistry ; Mass Spectrometry/methods ; Mitochondria/metabolism ; Models, Chemical ; Nitric Oxide/chemistry ; Oxidative Stress ; Spin Labels ; Superoxides/metabolism ; Time Factors ; Ubiquinone/analogs & derivatives ; Ubiquinone/chemistry
Chemical Substances	Antioxidants ; Cations ; Cyclic N-Oxides ; Spin Labels ; Superoxides (11062-77-4) ; Ubiquinone (1339-63-5) ; Hydroxylamine (2FP81O2L9Z) ; Nitric Oxide (31C4KY9ESH) ; ubiquinol (M9NL0C577Y) ; tempol (U78ZX2F65X)
Language	English
Publishing date	2008-01-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	807032-5
ISSN	1873-4596 ; 0891-5849
ISSN (online)	1873-4596
ISSN	0891-5849
DOI	10.1016/j.freeradbiomed.2007.12.036
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Article: Intracellular singlet oxygen photosensitizers: on the road to solving the problems of sensitizer degradation, bleaching and relocalization

da Silva, Elsa F. F / Arnaut, Luis G / Blaikie, Frances H / Bosio, Gabriela N / Bregnhøj, Mikkel / Breitenbach, Thomas / Etzerodt, Michael / Ogilby, Peter R / Pedersen, Brian W / Pimenta, Frederico M / Westberg, Michael

Integrative biology. 2016 Feb. 15, v. 8, no. 2

2016

Abstract: Selected singlet oxygen photosensitizers have been examined from the perspective of obtaining a molecule that is sufficiently stable under conditions currently employed to study singlet oxygen behavior in single mammalian cells. Reasonable predictions ... ...

Abstract	Selected singlet oxygen photosensitizers have been examined from the perspective of obtaining a molecule that is sufficiently stable under conditions currently employed to study singlet oxygen behavior in single mammalian cells. Reasonable predictions about intracellular sensitizer stability can be made based on solution phase experiments that approximate the intracellular environment (e.g., solutions containing proteins). Nevertheless, attempts to construct a stable sensitizer based solely on the expected reactivity of a given functional group with singlet oxygen are generally not sufficient for experiments in cells; it is difficult to construct a suitable chromophore that is impervious to all of the secondary and/or competing degradative processes that are present in the intracellular environment. On the other hand, prospects are reasonably positive when one considers the use of a sensitizer encapsulated in a specific protein; the local environment of the chromophore is controlled, degradation as a consequence of bimolecular reactions can be mitigated, and genetic engineering can be used to localize the encapsulated sensitizer in a given cellular domain. Also, the option of directly exciting oxygen in sensitizer-free experiments provides a useful complementary tool. These latter systems bode well with respect to obtaining more accurate control of the “dose” of singlet oxygen used to perturb a cell; a parameter that currently limits mechanistic studies of singlet-oxygen-mediated cell signaling.
Keywords	bleaching ; encapsulation ; genetic engineering ; mammals ; oxygen ; photosensitizing agents ; prediction ; proteins ; singlet oxygen
Language	English
Dates of publication	2016-0215
Size	p. 177-193.
Publishing place	The Royal Society of Chemistry
Document type	Article
ZDB-ID	2480063-6
ISSN	1757-9708 ; 1757-9694
ISSN (online)	1757-9708
ISSN	1757-9694
DOI	10.1039/c5ib00295h
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Intracellular singlet oxygen photosensitizers: on the road to solving the problems of sensitizer degradation, bleaching and relocalization.

da Silva, Elsa F F / Pimenta, Frederico M / Pedersen, Brian W / Blaikie, Frances H / Bosio, Gabriela N / Breitenbach, Thomas / Westberg, Michael / Bregnhøj, Mikkel / Etzerodt, Michael / Arnaut, Luis G / Ogilby, Peter R

Integrative biology : quantitative biosciences from nano to macro

2016 Volume 8, Issue 2, Page(s) 177–193

Abstract	Selected singlet oxygen photosensitizers have been examined from the perspective of obtaining a molecule that is sufficiently stable under conditions currently employed to study singlet oxygen behavior in single mammalian cells. Reasonable predictions about intracellular sensitizer stability can be made based on solution phase experiments that approximate the intracellular environment (e.g., solutions containing proteins). Nevertheless, attempts to construct a stable sensitizer based solely on the expected reactivity of a given functional group with singlet oxygen are generally not sufficient for experiments in cells; it is difficult to construct a suitable chromophore that is impervious to all of the secondary and/or competing degradative processes that are present in the intracellular environment. On the other hand, prospects are reasonably positive when one considers the use of a sensitizer encapsulated in a specific protein; the local environment of the chromophore is controlled, degradation as a consequence of bimolecular reactions can be mitigated, and genetic engineering can be used to localize the encapsulated sensitizer in a given cellular domain. Also, the option of directly exciting oxygen in sensitizer-free experiments provides a useful complementary tool. These latter systems bode well with respect to obtaining more accurate control of the "dose" of singlet oxygen used to perturb a cell; a parameter that currently limits mechanistic studies of singlet-oxygen-mediated cell signaling.
MeSH term(s)	Animals ; Cattle ; Fluorescent Dyes/chemistry ; Fullerenes/chemistry ; Genetic Engineering ; HeLa Cells ; Humans ; Oxygen/chemistry ; Photobleaching ; Photosensitizing Agents/chemistry ; Serum Albumin/chemistry ; Signal Transduction ; Singlet Oxygen/chemistry
Chemical Substances	Fluorescent Dyes ; Fullerenes ; Photosensitizing Agents ; Serum Albumin ; Singlet Oxygen (17778-80-2) ; Oxygen (S88TT14065)
Language	English
Publishing date	2016-02
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2480063-6
ISSN	1757-9708 ; 1757-9694
ISSN (online)	1757-9708
ISSN	1757-9694
DOI	10.1039/c5ib00295h
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Article ; Online: Antioxidant properties of MitoTEMPOL and its hydroxylamine.

Trnka, Jan / Blaikie, Frances H / Logan, Angela / Smith, Robin A J / Murphy, Michael P

Free radical research

2008 Volume 43, Issue 1, Page(s) 4–12

Abstract: Piperidine nitroxides such as TEMPOL have been widely used as antioxidants in vitro and in vivo. MitoTEMPOL is a mitochondria-targeted derivative of TEMPOL designed to protect mitochondria from the oxidative damage that they accumulate, but once there is ...

Abstract	Piperidine nitroxides such as TEMPOL have been widely used as antioxidants in vitro and in vivo. MitoTEMPOL is a mitochondria-targeted derivative of TEMPOL designed to protect mitochondria from the oxidative damage that they accumulate, but once there is rapidly reduced to its hydroxylamine, MitoTEMPOL-H. As little is known about the antioxidant efficacy of hydroxylamines, this study has assessed the antioxidant activity of both MitoTEMPOL and MitoTEMPOL-H. The hydroxylamine was more effective at preventing lipid-peroxidation than MitoTEMPOL and decreased oxidative damage to mitochondrial DNA caused by menadione. In contrast to MitoTEMPOL, MitoTEMPOL-H has no superoxide dismutase activity and its antioxidant actions are likely to be mediated by hydrogen atom donation. Therefore, even though MitoTEMPOL is rapidly reduced to MitoTEMPOL-H in cells, it remains an effective antioxidant. Furthermore, as TEMPOL is also reduced to a hydroxylamine in vivo, many of its antioxidant effects may also be mediated by its hydroxylamine.
MeSH term(s)	Animals ; Antioxidants/pharmacology ; Cyclic N-Oxides/pharmacology ; DNA, Mitochondrial/drug effects ; Hydroxylamine/pharmacology ; Lipid Peroxidation/drug effects ; Mice ; Mitochondria, Liver/drug effects ; Oxidation-Reduction/drug effects ; Polymerase Chain Reaction ; Rats ; Spin Labels ; Superoxide Dismutase/metabolism
Chemical Substances	Antioxidants ; Cyclic N-Oxides ; DNA, Mitochondrial ; Spin Labels ; Hydroxylamine (2FP81O2L9Z) ; Superoxide Dismutase (EC 1.15.1.1) ; tempol (U78ZX2F65X) ; TEMPOL-H (V55XB6IT82)
Language	English
Publishing date	2008-07-10
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1194130-3
ISSN	1029-2470 ; 1071-5762
ISSN (online)	1029-2470
ISSN	1071-5762
DOI	10.1080/10715760802582183
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Article ; Online: Singlet Oxygen Sensor Green®: photochemical behavior in solution and in a mammalian cell.

Gollmer, Anita / Arnbjerg, Jacob / Blaikie, Frances H / Pedersen, Brian Wett / Breitenbach, Thomas / Daasbjerg, Kim / Glasius, Marianne / Ogilby, Peter R

Photochemistry and photobiology

2011 Volume 87, Issue 3, Page(s) 671–679

Abstract: The development of efficient and selective luminescent probes for reactive oxygen species, particularly for singlet molecular oxygen, is currently of great importance. In this study, the photochemical behavior of Singlet Oxygen Sensor Green(®) (SOSG), a ... ...

Abstract	The development of efficient and selective luminescent probes for reactive oxygen species, particularly for singlet molecular oxygen, is currently of great importance. In this study, the photochemical behavior of Singlet Oxygen Sensor Green(®) (SOSG), a commercially available fluorescent probe for singlet oxygen, was examined. Despite published claims to the contrary, the data presented herein indicate that SOSG can, in fact, be incorporated into a living mammalian cell. However, for a number of reasons, caution must be exercised when using SOSG. First, it is shown that the immediate product of the reaction between SOSG and singlet oxygen is, itself, an efficient singlet oxygen photosensitizer. Second, SOSG appears to efficiently bind to proteins which, in turn, can influence uptake by a cell as well as behavior in the cell. As such, incorrect use of SOSG can yield misleading data on yields of photosensitized singlet oxygen production, and can also lead to photooxygenation-dependent adverse effects in the system being investigated.
MeSH term(s)	Artifacts ; Female ; Fluorescent Dyes/analysis ; Fluorescent Dyes/chemistry ; Fluorescent Dyes/metabolism ; HeLa Cells ; Humans ; Light ; Microscopy, Fluorescence ; Photochemical Processes/radiation effects ; Photosensitizing Agents/analysis ; Photosensitizing Agents/chemistry ; Photosensitizing Agents/metabolism ; Single-Cell Analysis/methods ; Singlet Oxygen/analysis ; Singlet Oxygen/metabolism ; Solutions/chemistry ; Solutions/metabolism ; Spectrum Analysis
Chemical Substances	Fluorescent Dyes ; Photosensitizing Agents ; Solutions ; Singlet Oxygen (17778-80-2)
Language	English
Publishing date	2011-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123540-0
ISSN	1751-1097 ; 0031-8655
ISSN (online)	1751-1097
ISSN	0031-8655
DOI	10.1111/j.1751-1097.2011.00900.x
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Article: Antioxidant Î²-Carotene Does Not Quench Singlet Oxygen in Mammalian Cells

Bosio, Gabriela N / Blaikie Frances H / Breitenbach Thomas / MaÌrtire Daniel O / Ogilby Peter R / Parisi Julieta / Pedersen Brian W / Reigosa Miguel / Silva Elsa F. F

Journal of the American Chemical Society. 2013 Jan. 09, v. 135, no. 1

2013

Abstract: Carotenoids, and Î²-carotene in particular, are important natural antioxidants. Singlet oxygen, the lowest excited state of molecular oxygen, is an intermediate often involved in natural oxidation reactions. The fact that Î²-carotene efficiently quenches ...

Abstract	Carotenoids, and Î²-carotene in particular, are important natural antioxidants. Singlet oxygen, the lowest excited state of molecular oxygen, is an intermediate often involved in natural oxidation reactions. The fact that Î²-carotene efficiently quenches singlet oxygen in solution-phase systems is invariably invoked when explaining the biological antioxidative properties of Î²-carotene. We recently developed unique microscope-based time-resolved spectroscopic methods that allow us to directly examine singlet oxygen in mammalian cells. We now demonstrate that intracellular singlet oxygen, produced in a photosensitized process, is in fact not efficiently deactivated by Î²-carotene. This observation requires a re-evaluation of Î²-caroteneâs role as an antioxidant in mammalian systems and now underscores the importance of mechanisms by which Î²-carotene inhibits radical reactions.
Keywords	antioxidant activity ; antioxidants ; beta-carotene ; mammals ; oxidation ; oxygen ; singlet oxygen ; spectroscopy
Language	English
Dates of publication	2013-0109
Size	p. 272-279.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021%2Fja308930a
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Article ; Online: Direct modification of the proinflammatory cytokine macrophage migration inhibitory factor by dietary isothiocyanates.

Brown, Kristin K / Blaikie, Frances H / Smith, Robin A J / Tyndall, Joel D A / Lue, Hongqi / Bernhagen, Jürgen / Winterbourn, Christine C / Hampton, Mark B

The Journal of biological chemistry

2009 Volume 284, Issue 47, Page(s) 32425–32433

Abstract: Isothiocyanates are a class of phytochemicals with widely reported anti-cancer and anti-inflammatory activity. However, knowledge of their activity at a molecular level is limited. The objective of this study was to identify biological targets of ... ...

Abstract	Isothiocyanates are a class of phytochemicals with widely reported anti-cancer and anti-inflammatory activity. However, knowledge of their activity at a molecular level is limited. The objective of this study was to identify biological targets of phenethyl isothiocyanate (PEITC) using an affinity purification approach. An analogue of PEITC was synthesized to enable conjugation to a solid-phase resin. The pleiotropic cytokine macrophage migration inhibitory factor (MIF) was the major protein captured from cell lysates. Site-directed mutagenesis and mass spectrometry showed that PEITC covalently modified the N-terminal proline residue of MIF. This resulted in complete loss of catalytic tautomerase activity and disruption of protein conformation, as determined by impaired recognition by a monoclonal antibody directed to the region that receptors and interacting proteins bind to MIF. The conformational change was supported by in silico modeling. Monoclonal antibody binding to plasma MIF was disrupted in humans consuming watercress, a major dietary source of PEITC. The isothiocyanates have significant potential for development as MIF inhibitors, and this activity may contribute to the biological properties of these phytochemicals.
MeSH term(s)	Amino Acid Sequence ; Antibodies, Monoclonal/chemistry ; Cell Membrane/metabolism ; Cytokines/metabolism ; Dose-Response Relationship, Drug ; Humans ; Inflammation ; Isothiocyanates/chemistry ; Jurkat Cells ; Macrophage Migration-Inhibitory Factors/metabolism ; Models, Biological ; Models, Chemical ; Molecular Sequence Data ; Mutagenesis, Site-Directed ; Protein Conformation
Chemical Substances	Antibodies, Monoclonal ; Cytokines ; Isothiocyanates ; Macrophage Migration-Inhibitory Factors
Language	English
Publishing date	2009-09-23
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2997-x
ISSN	1083-351X ; 0021-9258
ISSN (online)	1083-351X
ISSN	0021-9258
DOI	10.1074/jbc.M109.047092
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Article ; Online: Antioxidant β-carotene does not quench singlet oxygen in mammalian cells.

Bosio, Gabriela N / Breitenbach, Thomas / Parisi, Julieta / Reigosa, Miguel / Blaikie, Frances H / Pedersen, Brian W / Silva, Elsa F F / Mártire, Daniel O / Ogilby, Peter R

Journal of the American Chemical Society

2013 Volume 135, Issue 1, Page(s) 272–279

Abstract: Carotenoids, and β-carotene in particular, are important natural antioxidants. Singlet oxygen, the lowest excited state of molecular oxygen, is an intermediate often involved in natural oxidation reactions. The fact that β-carotene efficiently quenches ... ...

Abstract	Carotenoids, and β-carotene in particular, are important natural antioxidants. Singlet oxygen, the lowest excited state of molecular oxygen, is an intermediate often involved in natural oxidation reactions. The fact that β-carotene efficiently quenches singlet oxygen in solution-phase systems is invariably invoked when explaining the biological antioxidative properties of β-carotene. We recently developed unique microscope-based time-resolved spectroscopic methods that allow us to directly examine singlet oxygen in mammalian cells. We now demonstrate that intracellular singlet oxygen, produced in a photosensitized process, is in fact not efficiently deactivated by β-carotene. This observation requires a re-evaluation of β-carotene's role as an antioxidant in mammalian systems and now underscores the importance of mechanisms by which β-carotene inhibits radical reactions.
MeSH term(s)	Antioxidants/chemistry ; HeLa Cells ; Humans ; Singlet Oxygen/chemistry ; beta Carotene/chemistry
Chemical Substances	Antioxidants ; beta Carotene (01YAE03M7J) ; Singlet Oxygen (17778-80-2)
Language	English
Publishing date	2013-01-09
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/ja308930a
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