Photochemical Cyclization with Release of Carboxylic Acids and Phenol from Pyrrolidino-Substituted 1,4-Benzoquinones Using Visible Light

Chen, Yugang; Steinmetz, Mark G.

doi:10.1021/ol051362k

Cited by 37 publications

(41 citation statements)

References 18 publications

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“…The first strategy to overcome the limit of a maximum of wavelength absorption lying below the 450 nm range requires the tailoring of new caging groups based on chromophores that absorb in the visible range. 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.…”

Section: Introductionmentioning

confidence: 99%

Coumarinylmethyl Caging Groups with Redshifted Absorption

Fournier

Aujard

Saux

et al. 2013

Chemistry A European J

113

141

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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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Section: Introductionmentioning

confidence: 99%

Coumarinylmethyl Caging Groups with Redshifted Absorption

Fournier

Aujard

Saux

et al. 2013

Chemistry A European J

113

141

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“…If the energy of the absorbed photons is not sufficient to directly induce changes in bonding, chemical cascades are another approach to induce the desired chemical transformations. [25][26][27][28] The absorption profile (in particular λ max ) is often considered a key predictor of photochemical yield, yet recent work has found that this is not always the case. Unique insights can be achieved using single wavelength tunable laser sources to generate action plots of photochemical yields.…”

Section: Red-shifting Photochemical Reactionsmentioning

confidence: 99%

Shining a Light on Bioorthogonal Photochemistry for Polymer Science

Boase

2020

Macromol. Rapid Commun.

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Bioorthogonal chemistry is revolutionizing the fields of biological chemistry and nanomedicine, providing tools to actively probe and perturb native biochemical processes. Photochemistry provides the opportunity to actively and non‐invasively control bioorthogonal reactions, providing sophisticated optochemical tools. Despite the opportunities in bioorthogonal photochemistry, there remain many significant challenges to the clinical translation of current research. This review aims to provide an overview of these challenges and highlight recent examples from the literature that are providing revolutionary solutions to overcoming these barriers. It will highlight new photochemical systems that can be triggered by near infrared light in aqueous solutions and have been demonstrated to function in complex biological systems, including in living animals. It will cover diverse classes of photochemical reactions including photopolymerization, uncaging, conjugation, and photoswitching. The discussion will detail how new approaches are being integrated into polymers or highlight unexploited opportunities. This review intends to showcase how the unique synergy of bioorthogonal photochemistry and polymer science provides vast opportunities in the fields of biomaterials, nanomedicine, and theranostics. This will hopefully provide inspiration to material scientists to integrate bioorthogonal photochemistry into new adaptable materials and ensure translation to solve clinical challenges.

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“…[200] Compound 144 can be synthesized on as olid-phase support and consists of an octa-arginine cell-penetrating peptides equence that mediates cellular uptake, an uclear localization signal (NLS) that allows uptake into cell nuclei, and photosensitive amino acid 143 coupled to as erine bearingt wo peptide fragments of an uclear export signal (NES) as well as af luorescent moietyt hat allows localization of the compounds to be imaged. [202,203] The fact that quinone moieties can be photochemically reduced to their corresponding dihydroquinones is long known, [204][205][206][207] and severale xamples for which photoreduction is mediated by an adjacent sulfide [208,209] or amine [210][211][212][213][214][215][216][217] functionhave been reported. [200] Photochemicalc leavage of the compound by subsequent irradiation with UV light leads to the formation of a NES through an O-N-acyl shifti nr eleased N-terminal peptide 145,a si llustrated in Scheme 33.…”

Section: Photosensitive Tml Systemsmentioning

confidence: 99%

“…[200] Recently,D oughertya nd co-workers have presented ag eneral strategy for the direct photoinduced decay of quinonebased TML systems. [202,203] The fact that quinone moieties can be photochemically reduced to their corresponding dihydroquinones is long known, [204][205][206][207] and severale xamples for which photoreduction is mediated by an adjacent sulfide [208,209] or amine [210][211][212][213][214][215][216][217] functionhave been reported.…”

Section: Photosensitive Tml Systemsmentioning

confidence: 99%

Trimethyl Lock: A Multifunctional Molecular Tool for Drug Delivery, Cellular Imaging, and Stimuli‐Responsive Materials

Okoh

Klahn

2018

ChemBioChem

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Trimethyl lock (TML) systems are based on ortho-hydroxydihydrocinnamic acid derivatives displaying increased lactonization reactivity owing to unfavorable steric interactions of three pendant methyl groups, and this leads to the formation of hydrocoumarins. Protection of the phenolic hydroxy function or masking of the reactivity as benzoquinone derivatives prevents lactonization and provides a trigger for controlled release of molecules attached to the carboxylic acid function through amides, esters, or thioesters. Their easy synthesis and possible chemical adaption to several different triggers make TML a highly versatile module for the development of drug-delivery systems, prodrug approaches, cell-imaging tools, molecular tools for supramolecular chemistry, as well as smart stimuliresponsive materials.

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Photochemical Cyclization with Release of Carboxylic Acids and Phenol from Pyrrolidino-Substituted 1,4-Benzoquinones Using Visible Light

Cited by 37 publications

References 18 publications

Coumarinylmethyl Caging Groups with Redshifted Absorption

Coumarinylmethyl Caging Groups with Redshifted Absorption

Shining a Light on Bioorthogonal Photochemistry for Polymer Science

Trimethyl Lock: A Multifunctional Molecular Tool for Drug Delivery, Cellular Imaging, and Stimuli‐Responsive Materials

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