Alcohol Uncaging with Fluorescence Reporting: Evaluation of <i>o</i>-Acetoxyphenyl Methyloxazolone Precursors

Gagey, Nathalie; Emond, Matthieu; Neveu, Pierre; Benbrahim, Chouaha; Goetz, Bernard; Aujard, Isabelle; Baudin, Jean‐Bernard; Jullien, Ludovic

doi:10.1021/ol800284g

Cited by 48 publications

(43 citation statements)

References 30 publications

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“…This general design logic is extremely versatile and can easily be adapted to most of the main families of fluorescent probes with the aid of chemical synthesis. Indeed, photoactivatable acridinone [46], anthracene [47], benzofurazan [48], borondipyrromethene [49], chromone [50], coumarin [51][52][53][54][55][56], dihydrofuran [57][58][59], fluorescein [60][61][62][63][64][65][66][67], naphthalene [68], pyranine [69], pyrazolines [70], resorufin [71], rhodamine [66,[72][73][74][75][76], thioxanthone [77] and xanthone [78] derivatives have been developed on the basis of these operating principles. Furthermore, this general strategy has been adapted to activate also the luminescence of conjugated oligomers [79] and semiconductor quantum dots [80,81].…”

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

“…In some instances, however, the released fragment must associate with a supramolecular partner in order to discourage nonradiative decay and enable emission [67,68]. In other instances, the photochemical reaction does not release the intact fluorophore and, instead, generates an intermediate species that spontaneously rearranges into the final fluorescent fragment [50,52,54,56]. Alternatively, such photolytic events can be coupled with energy transfer to activate fluorescence [65,66].…”

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

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Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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Photoactivatable fluorophores switch from a nonemissive to an emissive state upon illumination at an activating wavelength and then emit after irradiation at an exciting wavelength. The interplay of such activation and excitation events can be exploited to switch fluorescence on in a defined region of space at a given interval of time. In turn, the spatiotemporal control of fluorescence translates into the opportunity to implement imaging and spectroscopic schemes that are not possible with conventional fluorophores. Specifically, photoactivatable fluorophores permit the monitoring of dynamic processes in real time as well as the reconstruction of images with subdiffraction resolution. These promising applications can have a significant impact on the characterization of the structures and functions of biomolecular systems. As a result, strategies to implement mechanisms for fluorescence photoactivation with synthetic fluorophores are particularly valuable. In fact, a number of versatile operating principles have already been identified to activate the fluorescence of numerous members of the main families of synthetic dyes. These methods are based on either the irreversible cleavage of covalent bonds or the reversible opening and closing of rings. This paper overviews the fundamental mechanisms that govern the behavior of these photoresponsive systems, illustrates structural designs for fluorescence photoactivation, and provides representative examples of photoactivatable fluorophores in actions.

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Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

Section: Mechanisms and Structural Designs For Irreversible Fluorescementioning

confidence: 99%

Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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“…We recently implemented a protocol relying on continuous illumination to face a similar situation that involved fast photochemical events. [47][48][49] Here we also adopted continuous illumination and a fluorescent probe both to generate the photochemical reactions and to report on their extent by the inner filter effect. After a series of preliminary experiments (see Figures 5S and 6S in the Supporting Information), we adopted the strongly fluorescent rhodamine B probe, which is soluble www.chemeurj.org in acetonitrile/water 1:1 (v/v); it weakly absorbs in and strongly emits beyond the absorption wavelength range of TH/CH (to report on TH/CH absorbance and to avoid any absorption of the fluorescence emission by TH/CH; see Figures 2Sa and b in the Supporting Information).…”

Section: Preliminary Photochemical Observationmentioning

confidence: 99%

2‐Hydroxyazobenzenes to Tailor pH Pulses and Oscillations with Light

Emond

Saux

Maurin

et al. 2010

Chemistry A European J

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This paper evaluates the 2-hydroxyazobenzene platform for tailoring proton concentration pulses and oscillations with monochromatic light. The easily prepared 2-hydroxyazobenzenes exhibit large absorptions in the near-UV range. Photoisomerization was investigated by UV/Vis absorption, (1)H NMR spectroscopy, and steady-state fluorescence emission. In the whole investigated series, the trans stereoisomer of the 2-hydroxyazobenzene motif provides the corresponding cis derivative with an action cross section in the 10(3) M(-1) cm(-1) range. At the same time, photoisomerization is accompanied by a significant pK drop of the phenol group. According to the phenyl-substituent pattern, cis-to-trans thermal back-isomerization can be tuned in the 10 ms-100 s range. Up to 2 units of reversible pH drops or pH oscillations on the 10 s timescale have been obtained by appropriately tailoring single-wavelength illumination of 2-hydroxyazobenzene solutions.

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“…[58] Ihr Einsatz ist jedoch auf Anwendungen beschränkt, bei denen die langsame Substratfreisetzung kein Problem darstellt.…”

Section: O-hydroxycinnamateunclassified

Von Ein‐ zu Zwei‐Photonen‐Sonden: photoaktivierbare Reagentien, Aktuatoren und Photoschalter

et al. 2013

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Molekulare Systeme, die mit Licht “ferngesteuert” werden können, sind von wachsender Bedeutung in der Zellbiologie, der Physiologie und den Neurowissenschaften. Der entscheidende Aspekt hierbei ist die hohe räumliche und zeitliche Präzision, die mit Methoden der Lasermikroskopie erreicht werden kann. Das Verfahren der Zwei‐Photonen‐Anregung hat signifikante Vorzüge bei der Visualisierung biologischer Gewebe, allerdings ist der gezielte Entwurf intelligenter Sonden, die mit der Zellphysiologie kompatibel sind, nicht trivial. Dieser Aufsatz diskutiert die “chemischen” Herausforderungen bei der Entwicklung von Zwei‐Photonen‐Sonden.

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Alcohol Uncaging with Fluorescence Reporting: Evaluation of o-Acetoxyphenyl Methyloxazolone Precursors

Cited by 48 publications

References 30 publications

Photoactivatable Fluorophores

Photoactivatable Fluorophores

2‐Hydroxyazobenzenes to Tailor pH Pulses and Oscillations with Light

Von Ein‐ zu Zwei‐Photonen‐Sonden: photoaktivierbare Reagentien, Aktuatoren und Photoschalter

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