Fluorescein Analogues as Photoremovable Protecting Groups Absorbing at ∼520 nm

Šebej, Peter; Wintner, Jürgen; Müller, Pavel; Slanina, Tomáš; Anshori, Jamaludin Al; Antony, Lovely Angel Panamparambil; Klán, Petr; Wirz, Jakob

doi:10.1021/jo301455n

Cited by 83 publications

(61 citation statements)

References 36 publications

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“…This large number of engineering constraints has led to the introduction of new types of photolabile protecting groups. Present challenges in the field of caging groups concern: improving the uncaging action cross sections with one- and two-photon absorption[129, 130];driving the uncaging reaction with absorption in the visible range[129, 131–135]quantifying the amount of uncaging (e.g. by means of fluorescence reporting)[136–141];…”

Section: Photo-activable Molecules For the Control Of Physiological Pmentioning

confidence: 99%

Optical control and study of biological processes at the single-cell level in a live organism

Feng

Zhang

et al. 2013

Rep. Prog. Phys.

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Living organisms are made of cells that are capable of responding to external signals by modifying their internal state and subsequently their external environment. Revealing and understanding the spatio-temporal dynamics of these complex interaction networks is the subject of a field known as systems biology. To investigate these interactions (a necessary step before understanding or modelling them) one needs to develop means to control or interfere spatially and temporally with these processes and to monitor their response on a fast timescale (

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Section: Photo-activable Molecules For the Control Of Physiological Pmentioning

confidence: 99%

Optical control and study of biological processes at the single-cell level in a live organism

Feng

Zhang

et al. 2013

Rep. Prog. Phys.

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“…Guided by simple Hückel molecular orbital (MO) predictions, Wirz et al. were the first to report a new photocage based on visible‐light‐absorbing fluorophores . Since then, promising new PPGs have been developed based on the boron‐dipyrromethene (BODIPY) fluorophore .…”

Section: Introductionmentioning

confidence: 99%

A New Photocage Derived from Fluorene

Reinfelds

Cosel

Falahati

et al. 2018

Chemistry A European J

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Photolabile protecting groups (PPGs or photocages) are increasingly subject to molecular design to meet requirements such as absorbance in the visible spectral range, high molar absorption coefficients, and high quantum yields of leaving group release. Improvements in these properties for the promising 3-diethylaminobenzyl (DEAMb) photocage, the photoactivity of which is based on the Zimmerman meta effect, are reported. Expansion of the aromatic system with a second aromatic ring resulted in improved spectral properties. A systematic trend relating the electronic (π-donor or acceptor) properties of the new aryl substituent and its position in the DEAMb ring to changes in the spectral properties could be observed. Conclusions from the experimental results were supported by computations obtained by using time-dependent DFT. A second generation of DEAMb-based photocages was designed. A rigid linker was introduced to ensure more efficient conjugation of the aromatic ring π systems by limiting rotational freedom. The resulting fluorenol (9-hydroxyfluorene)-based photocages had superior spectral properties to those of simple biphenyl systems. The best uncaging cross section achieved was 5320 m cm (ϵΦ ).

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“…This approach has been implemented by Chen and Steinmetz, who adapted the rearrangement of an amino‐substituted 1,4‐benzoquinone to photorelease carboxylic acids and phenols upon illuminating at 542 nm 18. 19 Wirz and Klan have explored the xanthene chromophore with absorption maxima in the 520 nm range 20. Ruthenium complexes have been used by Etchenique et al.…”

Section: Introductionmentioning

confidence: 99%

Coumarinylmethyl Caging Groups with Redshifted Absorption

Fournier

Aujard

Saux

et al. 2013

Chemistry A European J

119

145

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The small and synthetically easily accessible coumarinylmethyl backbone has been modified to generate a family of photolabile protecting groups with redshifted absorption. We relied on introducing electron‐donating groups in the 7 position and electron‐withdrawing groups in the 2‐, and 2‐ and 3 positions. In particular, we showed that the diethylamino‐thiocoumarylmethyl and the diethylamino‐coumarylidenemalononitrilemethyl are relevant for uncaging with cyan light. They both exhibit a significant action cross section for uncaging in the 470–500 nm wavelength range and a low light absorption between 350 and 400 nm. These attractive features are favorable to perform chromatic orthogonal photoactivation with UV and blue‐cyan light sources, respectively.

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Fluorescein Analogues as Photoremovable Protecting Groups Absorbing at ∼520 nm

Cited by 83 publications

References 36 publications

Optical control and study of biological processes at the single-cell level in a live organism

Optical control and study of biological processes at the single-cell level in a live organism

A New Photocage Derived from Fluorene

Coumarinylmethyl Caging Groups with Redshifted Absorption

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