Conditionally Activatable Visible-Light Photocages

Bojtár, Márton; Németh, Krisztina; Domahidy, Farkas; Knorr, Gergely; Verkman, András; Kállay, Mihály; Kele, Péter

doi:10.1021/jacs.0c07508

Cited by 66 publications

(60 citation statements)

References 56 publications

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“… 470 Visible-light activated liberation of carboxylic acid LGs from coumarin 55j was demonstrated to occur only after bioorthogonal transformation of the modulating tetrazine moiety. 471 …”

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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“… 470 Visible-light activated liberation of carboxylic acid LGs from coumarin 55j was demonstrated to occur only after bioorthogonal transformation of the modulating tetrazine moiety. 471 …”

Section: Photorelease From Organic Photoactivatable Compoundsmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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“…Moreover, the employment of exogenous trigger containing a reporter like fluorophore or radioactive isotope for drug activation can simultaneously provide imaging signals to achieve diagnosis and treatment. In addition, recent examples about conditional activation with multiple controls, such as singlet oxygen and light, are expected to provide improved spatial and temporal resolution [117,118]. Furthermore, there are still many challenges in establishing bioorthogonal platforms for multi-drug release and clinical applications in theranostics [119], which will likely require further developments in bioorthogonal chemistry and biomaterials.…”

Section: Discussionmentioning

confidence: 99%

Activation and Delivery of Tetrazine-Responsive Bioorthogonal Prodrugs

Wang

Zhang

et al. 2020

Molecules

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Prodrugs, which remain inert until they are activated under appropriate conditions at the target site, have emerged as an attractive alternative to drugs that lack selectivity and show off-target effects. Prodrugs have traditionally been activated by enzymes, pH or other trigger factors associated with the disease. In recent years, bioorthogonal chemistry has allowed the creation of prodrugs that can be chemically activated with spatio-temporal precision. In particular, tetrazine-responsive bioorthogonal reactions can rapidly activate prodrugs with excellent biocompatibility. This review summarized the recent development of tetrazine bioorthogonal cleavage reaction and great promise for prodrug systems.

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“…Later, Kele et al developed new IEDDA-activatable fluorogenic photocages based on a vinylene linked coumarinyl-Tz, which could be activated through the IEDDA reaction with a strained alkyne. Live-cell photouncaging was demonstrated by pretargeting the cells with an alkyne (TPP-BCN) followed by the addition of the fluorogenic rhodol-coumarinyl-Tz agent, resulting in fluorescence signal located in cell mitochondria [ 116 ].…”

Section: Applicationsmentioning

confidence: 99%

IEDDA: An Attractive Bioorthogonal Reaction for Biomedical Applications

2021

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The pretargeting strategy has recently emerged in order to overcome the limitations of direct targeting, mainly in the field of radioimmunotherapy (RIT). This strategy is directly dependent on chemical reactions, namely bioorthogonal reactions, which have been developed for their ability to occur under physiological conditions. The Staudinger ligation, the copper catalyzed azide-alkyne cycloaddition (CuAAC) and the strain-promoted [3 + 2] azide–alkyne cycloaddition (SPAAC) were the first bioorthogonal reactions introduced in the literature. However, due to their incomplete biocompatibility and slow kinetics, the inverse-electron demand Diels-Alder (IEDDA) reaction was advanced in 2008 by Blackman et al. as an optimal bioorthogonal reaction. The IEDDA is the fastest bioorthogonal reaction known so far. Its biocompatibility and ideal kinetics are very appealing for pretargeting applications. The use of a trans-cyclooctene (TCO) and a tetrazine (Tz) in the reaction encouraged researchers to study them deeply. It was found that both reagents are sensitive to acidic or basic conditions. Furthermore, TCO is photosensitive and can be isomerized to its cis-conformation via a radical catalyzed reaction. Unfortunately, the cis-conformer is significantly less reactive toward tetrazine than the trans-conformation. Therefore, extensive research has been carried out to optimize both click reagents and to employ the IEDDA bioorthogonal reaction in biomedical applications.

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Conditionally Activatable Visible-Light Photocages

Cited by 66 publications

References 56 publications

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Activation and Delivery of Tetrazine-Responsive Bioorthogonal Prodrugs

IEDDA: An Attractive Bioorthogonal Reaction for Biomedical Applications

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