Molecular Engineering of Photoremovable Protecting Groups for Two‐Photon Uncaging

Gug, Sylvestre; Bolze, Frédéric; Specht, Alexandre; Bourgogne, Cyril; Goeldner, Maurice; Nicoud, Jean‐François

doi:10.1002/anie.200803964

Cited by 91 publications

(87 citation statements)

References 30 publications

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“…237 This has also been recently demonstrated by Goeldner and co-workers, who studied the photochemical properties of biphenyl-containing photoremovable protecting groups possessing the o -nitrobenzyl, phenacyl, and 2-( o -nitrophenyl)propyl functionalities. 238 …”

Section: Nitroaryl Groupsmentioning

confidence: 59%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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Section: Nitroaryl Groupsmentioning

confidence: 59%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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“…It can be seen that BNSF-Glu has easily the highest two-photon cross section(133), seemingly making it a very attractive probe for study of synaptic signaling in brain slices. However, it is sparingly soluble (0.1 mM), and this probably makes brain slice experiments tricky to perform on a day-to-day basis.…”

Section: Two-photon Uncaging Microscopymentioning

confidence: 99%

Two-Photon Microscopy for Chemical Neuroscience

Ellis‐Davies

2011

ACS Chem. Neurosci.

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Microscopes using non-linear excitation of chromophores with pulsed near-IR light can generate highly localized foci of molecules in the electronic singlet state that are concentrated in volumes of less than one femtoliter. The three-dimensional confinement of excitation arises from the simultaneous absorption of two IR photons of approximately half the energy required for linear excitation. Two-photon microscopy is especially useful for two types of interrogation of neural processes. First, uncaging of signaling molecules such as glutamate, as stimulation is so refined it can be used to mimic normal unitary synaptic levels. In addition, uncaging allows complete control of the timing and position of stimulation, so the two-photon light beam provides the chemical neuroscientist with an “optical conductor's baton” which can command synaptic activity at will. A second powerful feature of two-photon microscopy is that when used for fluorescence imaging it enables the visualization of cellular structure and function in living animals at depths far beyond that possible with normal confocal microscopes. In this review I provide a survey of the many important applications of two-photon microscopy in these two fields of neuroscience, and suggest some areas for future technical development.

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“…4,5-Dimethoxy-2-nitrobenzyl alcohol15 was chosen despite its low two-photon uncaging cross-section (0.01 GM)16 compared to 4-bromo-coumarins (1 GM)17 or fluorene-based systems (5 GM)18, because it is well-studied and readily available, making it a good proof-of-concept photolabile group.…”

mentioning

confidence: 99%

UV and Near-IR Triggered Release from Polymeric Nanoparticles

et al. 2010

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A new light-sensitive polymer containing multiple light-sensitive triggering groups along the backbone and incorporating a quinone-methide self-immolative moiety was developed and formulated into nanoparticles encapsulating a model dye Nile Red. Triggered burst-release of the payload upon irradiation and subsequent degradation of the nanoparticles was observed. This system is designed to be versatile where the triggering group can be sensitive to a number of wavelengths.

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Molecular Engineering of Photoremovable Protecting Groups for Two‐Photon Uncaging

Cited by 91 publications

References 30 publications

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Two-Photon Microscopy for Chemical Neuroscience

UV and Near-IR Triggered Release from Polymeric Nanoparticles

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