Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan

Korzycka, Karolina A.; Bennett, Philip M.; Cueto-Díaz, Eduardo J.; Wicks, Geoffrey; Drobizhev, Mikhail; Blanchard‐Desce, Mireille; Rebane, Aleksander; Anderson, Harry L.

doi:10.1039/c4sc03775h

Cited by 56 publications

(64 citation statements)

References 60 publications

(29 reference statements)

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“…(b) Two-photon excited photocleavage and uncaging of photolabile protecting groups: (i) two-photon excitation, (ii) dye donates an electron to the release unit, (iii) this unit undergoes a photochemical reaction ending in cargo release. Reprinted from ref 68; copyright 2015, permission from The Royal Society of Chemistry.…”

Section: Figurementioning

confidence: 99%

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

et al. 2017

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Nanotechnology has begun to play a remarkable role in various fields of science and technology. In biomedical applications, nanoparticles have opened new horizons, especially for biosensing, targeted delivery of therapeutics, and so forth. Among drug delivery systems (DDSs), smart nanocarriers that respond to specific stimuli in their environment represent a growing field. Nanoplatforms that can be activated by an external application of light can be used for a wide variety of photoactivated therapies, especially light-triggered DDSs, relying on photoisomerization, photo-cross-linking/un-cross-linking, photoreduction, and so forth. In addition, light activation has potential in photodynamic therapy, photothermal therapy, radiotherapy, protected delivery of bioactive moieties, anticancer drug delivery systems, and theranostics (i.e., real-time monitoring and tracking combined with a therapeutic action to different diseases sites and organs). Combinations of these approaches can lead to enhanced and synergistic therapies, employing light as a trigger or for activation. Nonlinear light absorption mechanisms such as two-photon absorption and photon upconversion have been employed in the design of light-responsive DDSs. The integration of a light stimulus into dual/multiresponsive nanocarriers can provide spatiotemporal controlled delivery and release of therapeutic agents, targeted and controlled nanosystems, combined delivery of two or more agents, their on-demand release under specific conditions, and so forth. Overall, light-activated nanomedicines and DDSs are expected to provide more effective therapies against serious diseases such as cancers, inflammation, infections, and cardiovascular disease with reduced side effects and will open new doors toward the treatment of patients worldwide.

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Section: Figurementioning

confidence: 99%

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

et al. 2017

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“…By combining two 7‐nitroindolinyl (NI)‐caged glutamates with a hydrophilic quadrupolar tailored 2P chromophore, we prepared triads affording a tenfold greater 2P‐induced release of glutamate ( δ u =0.5 GM at 730 nm) in comparison with the parent NI‐protecting group. Pursuing the same goal, triads operating by intramolecular electron transfer have been very recently reported as 2P sensitive protecting groups of amino acids with record 2P uncaging sensitivity . Aiming at further increasing the 2PA ability in the 700–800 nm region and assuming that the presence of a second caging unit within the triad could affect the 2P uncaging efficiency of the overall architecture (due to excitation energy trapping by the cage byproduct), we recently elaborated dissymmetric synergic dyads incorporating a nitroveratryl (NV)‐derived protecting group.…”

Section: Introductionmentioning

confidence: 99%

Cooperative Veratryle and Nitroindoline Cages for Two‐Photon Uncaging in the NIR

Cueto-Díaz

Picard

Klausen

et al. 2016

Chemistry A European J

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Tandem uncaging systems in which a two-photon absorbing module and a cage moiety, linked via a phosphorous clip, that act together by Förster resonance energy transfer (FRET) have been developed. A library of these compounds, using different linkers and cages (7-nitroindolinyl or nitroveratryl) has been synthesized. The investigation of their uncaging and two-photon absorption properties demonstrates the scope and versatility of the engineering strategy towards efficient two-photon cages and reveals surprising cooperative and topological effects. The interactions between the 2PA module and the caging moiety are found to promote cooperative effects on the 2PA response while additional processes that enhance the uncaging efficiency are operative in well-oriented nitroindoline-derived dyads. These synergic effects combine to lead to record two-photon uncaging cross-section values (i.e., up to 20 GM) for uncaging of carboxylic acids.

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“…As no charge‐transfer intermediates were detected in laser flash photolysis experiments, neither significant fluorescence was observed, authors suggested that the competing back electron transfer was the main deactivation path that occurred faster than the bond cleavage . Also, a fluorene‐sensitized picolinium derivative sensitive to two‐photon activation has been prepared by the Anderson group . The construct suffered, however, hydrolytic instability and low uncaging efficiency, presumably due to the fast back electron transfer, as was hypothesized in the earlier experiment.…”

Section: Introductionmentioning

confidence: 91%

Photoinduced Electron Transfer (PET)‐Mediated Fragmentation of Picolinium‐Derived Redox Probes

Barosi

Dhimane

Maurel

et al. 2018

Chemistry A European J

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The photolysis of covalently linked N-alkyl picolinium phenylacetate-carbazole dyads was analyzed experimentally and by using density functional theory (DFT) and time dependent-DFT (TD-DFT) calculations. In contrast to earlier observations efficient one and two-photon fragmentations conditions were found for 15 c (δ =0.16 GM at 730 nm) opening the way for the design of a novel class of "caged" compounds.

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Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan

Abstract: We present a modular approach to photo-labile protecting groups based on photoinduced electron transfer, providing high sensitivity to two-photon excitation.

Cited by 56 publications

References 60 publications

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light

Cooperative Veratryle and Nitroindoline Cages for Two‐Photon Uncaging in the NIR

Photoinduced Electron Transfer (PET)‐Mediated Fragmentation of Picolinium‐Derived Redox Probes

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