Water‐Soluble, Donor–Acceptor Biphenyl Derivatives in the 2‐(<i>o</i>‐Nitrophenyl)propyl Series: Highly Efficient Two‐Photon Uncaging of the Neurotransmitter γ‐Aminobutyric Acid at <i>λ</i>=800 nm

Donato, Loïc; Mourot, Alexandre; Davenport, Christopher M.; Herbivo, Cyril; Warther, David; Léonard, Jérémie; Bolze, Frédéric; Nicoud, Jean‐François; Krämer, Richard; Goeldner, Maurice; Specht, Alexandre

doi:10.1002/anie.201106559

Cited by 108 publications

(112 citation statements)

References 41 publications

(33 reference statements)

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“…Power response curves implied that DEAC450-Glu was uncaged by two-photon excitation at 900 nm (Figure 2c), just as MNI-Glu and NDBF-EGTA at 720 nm 32,36 . Similar to other caged Glu and GABA probes 24,29,30 , DEAC450-Glu had off-target pharmacological side effects upon GABA-A receptor currents. We found the EC 50 for blocking evoked GABA-A receptor cur- rents on layer 2/3 pyramidal neurons was about 33 µM.…”

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confidence: 67%

“…Furthermore, the absorption minimum of DEAC450 is at the maximum for the CDNI 28,29 chromophore (Figure 1b). The relative absorption at the λ min is 9% of the λ max ; no such distinct minima exist for other caged compounds (Figure 1c) that have been recently shown to be two-photon sensitive 24,30,31 . This relative difference in linear absorption is further enhanced in the two-photon domain; the DEAC450 chromophore is >60x more fluorescent at 900 nm than 720 nm.…”

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confidence: 92%

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Optically Selective Two-Photon Uncaging of Glutamate at 900 nm

et al. 2013

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We have synthesized a 7-diethylaminocoumarin (DEAC) derivative that allows wavelength selective, two-photon uncaging at 900 nm versus 720 nm. This new caging chromophore, called DEAC450, has an extended π-electron moeity at the 3-position that shifts the absorption spectrum maximum of DEAC from 375 nm to 450 nm. Two-photon excitation at 900 nm was more than 60-fold greater than at 720 nm. Two-photon uncaging of DEAC450-Glu at 900 nm at spine heads on pyramidal neurons in acutely isolated brain slices generated postsynaptic responses that were similar to spontaneous postsynaptic excitatory miniature currents, whereas significantly higher energies at 720 nm evoked no currents. Since many nitroaromatic caged compounds are two-photon active at 720 nm, optically selective uncaging of DEAC450-caged biomolecules at 900 nm may allow facile two-color optical interrogation of bimodal signaling pathways in living tissue with high resolution for the first time.

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confidence: 67%

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confidence: 92%

Optically Selective Two-Photon Uncaging of Glutamate at 900 nm

et al. 2013

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“…The three-dimensional resolution opportunities provided by TPE have extensively been exploited in neuroscience both in tissue samples and in vivo [43][44][45][46][47][48][49][50]. The NIR TPE induced uncaging of neurotransmitters such as glutamate (figure 4) and has allowed the functional mapping of the respective receptors in neurons with high-resolution (μm), sub-cellular precision Figure 4.…”

Section: Some Therapeutic Applications Of Two-photon Excitationmentioning

confidence: 99%

Multi-photon excitation in uncaging the small molecule bioregulator nitric oxide

Garcia

Zhang

Ford

2013

Phil. Trans. R. Soc. A.

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Multi-photon excitation allows one to use tissue transmitting near-infrared (NIR) light to access excited states with energies corresponding to single-photon excitation in the visible or ultraviolet wavelength ranges. Here, we present an overview of the application of both simultaneous and sequential multi-photon excitation in studies directed towards the photochemical delivery (‘uncaging’) of bioactive small molecules such as nitric oxide (NO) to physiological targets. Particular focus will be directed towards the use of dyes with high two-photon absorption cross sections and lanthanide ion-doped upconverting nanoparticles as sensitizers to facilitate the uncaging of NO using NIR excitation.

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“…Reported PRPGs used for two-photon excitation processes: DMNB, [ 57 ] DBDHC, [ 53 ] NDBF, [ 52 ] CM, [ 58 ] RuBP, [ 56 ] NBPP, [ 56 ] and BNSF. [ 55 ] The applied photolysis wavelength ( λ ), the two-photon uncaging cross-section ( δ u ), and the protected functional groups are specifi ed.…”

Section: Caged Functional Layers With Spatial Resolution: Surface Patmentioning

confidence: 99%

Light‐Triggered Multifunctionality at Surfaces Mediated by Photolabile Protecting Groups

Cui

Miguel

Campo

2012

Macromol. Rapid Commun.

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Photoremovable protecting groups (PRPGs) are applied to organic surfaces, thin polymer films, and hydrogels to achieve light-based remote control of their (bio)chemical and physical properties. These can be localized (i.e. patterned), tunable by exposure dose, and generated on-demand. Using PRPGs with independent response to different wavelengths, multifunctional materials with a number of individually addressable functional states can be generated. Light-triggered polymerization, crosslinking, and degradation processes as well as release of attached molecules can be realized. Light-responsive surfaces and materials based on PRPGs open interesting possibilities for the next generation of instructive materials for cell culture and tissue regeneration.

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Water‐Soluble, Donor–Acceptor Biphenyl Derivatives in the 2‐(o‐Nitrophenyl)propyl Series: Highly Efficient Two‐Photon Uncaging of the Neurotransmitter γ‐Aminobutyric Acid at λ=800 nm

Cited by 108 publications

References 41 publications

Optically Selective Two-Photon Uncaging of Glutamate at 900 nm

Optically Selective Two-Photon Uncaging of Glutamate at 900 nm

Multi-photon excitation in uncaging the small molecule bioregulator nitric oxide

Light‐Triggered Multifunctionality at Surfaces Mediated by Photolabile Protecting Groups

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