Temporal Labeling of Nascent RNA Using Photoclick Chemistry in Live Cells

Nainar, Sarah; Kubota, Miles; McNitt, Christopher D.; Tran, Catherine; Popik, Vladimir V.; Spitale, Robert C.

doi:10.1021/jacs.7b03121

Cited by 52 publications

(32 citation statements)

References 23 publications

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“…of Fb-N 3 , its tumor-specific accumulation could be triggered by micro-wound made through surgery, RT, or ultrasonic (US) treatment 20 – 22 . Subsequently, the intravenously injected Ptb-DBCO was accumulated through bioorthogonal reaction between DBCO and N 3 groups 23 . Owing to the altered vascular structure, we expect that the accumulated Ptb would easily translate into active enzyme (thrombin) and induce coagulation.…”

Section: Introductionmentioning

confidence: 99%

Controllable gelation of artificial extracellular matrix for altering mass transport and improving cancer therapies

et al. 2020

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Global alterations in the metabolic network provide substances and energy to support tumor progression. To fuel these metabolic processes, extracellular matrix (ECM) plays a dominant role in supporting the mass transport and providing essential nutrients. Here, we report a fibrinogen and thrombin based coagulation system to construct an artificial ECM (aECM) for selectively cutting-off the tumor metabolic flux. Once a micro-wound is induced, a cascaded gelation of aECM can be triggered to besiege the tumor. Studies on cell behaviors and metabolomics reveal that aECM cuts off the mass transport and leads to a tumor specific starvation to inhibit tumor growth. In orthotopic and spontaneous murine tumor models, this physical barrier also hinders cancer cells from distant metastasis. The in vivo gelation provides an efficient approach to selectively alter the tumor mass transport. This strategy results in a 77% suppression of tumor growth. Most importantly, the gelation of aECM can be induced by clinical operations such as ultrasonic treatment, surgery or radiotherapy, implying this strategy is potential to be translated into a clinical combination regimen.

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Section: Introductionmentioning

confidence: 99%

Controllable gelation of artificial extracellular matrix for altering mass transport and improving cancer therapies

et al. 2020

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“… 26 Pioneered by this work, various photo-labile precursors of strained alkynes have been explored for photo-controllable generation of strained alkynes as the biorthogonal functionality. 27–30 Visible-light triggered active alkyne generation from cyclopropenones was established with the aid of visible light-responsive photocatalysts. 31 Caged phosphines have also been designed and prepared for UV or even visible light triggered generation of active phosphine for light-controllable Staudinger–Bertozzi ligation.…”

Section: Strategies To Realize Photo-control On Bioorthogonal Bond-forming Reactionsmentioning

confidence: 99%

“…Selective UV irradiation of cyclopropenone-caged oxadibenzocyclooctynes induced photo-SPAAC reactions with azide-modified RNAs. 27 Tetrazole-modified microRNAs after being transfected into live cells were found to be functional to suppress target gene expression. 58 We therefore applied intramolecular TEPC reactions for spatiotemporal labelling of microRNAs inside cells by controlling the UV irradiated area and time on live cells.…”

Section: Biological Applications Of Photo-controllable Bioorthogonal Reactionsmentioning

confidence: 99%

Photo-controllable bioorthogonal chemistry for spatiotemporal control of bio-targets in living systems

Kong

Zhu

et al. 2020

Chem. Sci.

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The establishment of bioorthogonal chemistry is one of the most significant advances in chemical biology using exogenous chemistry to perturb and study biological processes. Photo-modulation of biological systems has realized temporal and spatial control on biomacromolecules in living systems. The combination of photo-modulation and bioorthogonal chemistry is therefore emerging as a new direction to develop new chemical biological tools with spatiotemporal resolution. This minireview will focus on recent development of bioorthogonal chemistry subject to spatiotemporal control through photo-irradiation. Different strategies to realize photo-control on bioorthogonal bond-forming reactions and biological applications of photo-controllable bioorthogonal reactions will be summarized to give a perspective on how the innovations on photo-chemistry can contribute to the development of optochemical biology. Future trends to develop more optochemical tools based on novel photochemistry will also be discussed to envision the development of chemistry-oriented optochemical biology.

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“…However, the highly ring‐strained cycloalkenes/‐alkynes are usually susceptible to nucleophilic additions by native thiol‐containing biomolecules, resulting in their decaying in live cell environment [5] . Photo‐releasing of the strained cyclooctyne in situ provides an effective solution [3a,e] . Photo‐switchable cyclic alkenes could load the ring‐strain in situ via photo‐isomerization to promote the bioconjugation rate [6] .…”

Section: Introductionmentioning

confidence: 99%

Spatiotemporal Resolved Live Cell Membrane Tracking through Photo‐click Reactions Enriched in Lipid Phase

Deng

Guo

et al. 2021

Chemistry A European J

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A set of photo‐switchable monopeptides derived from cis‐β‐dibenzodiazocine‐l‐alanine (cis‐DBDAA) have been designed and synthesized, which are capable of photo‐click reacting with diaryltetrazoles or diarylsydnones in a hydrophobic phospholipid bilayer environment. The DBDAA monopeptides include both a hydrophobic tail on C‐terminal, providing high affinity toward lipid membrane, and a modularized functional moiety on N‐terminal, enabling rapid optimization of the self‐assembly strength to form multifunctional supramolecules. With the cis‐DBDAA monopeptides photo‐switched into trans‐configuration, we were able to disrupt the supramolecular assembly through an efficient photo‐click reaction across the lipid bilayer of liposomes. We reveal that the performance of the photo‐click reactions between the monopeptides and photo‐generated nitrile imine intermediates is significantly enhanced by enrichment of both reactants in the hydrophobic membrane lamel of liposomes. Enrichment of the DBDAA monopeptide in lipid phase serves as a convenient method to introduce bioorthogonal chemical handles on live cell membranes, which enables fluorescence labelling of single cell's membrane with high spatiotemporal resolution to facilitate the studies on cell membrane dynamics.

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Temporal Labeling of Nascent RNA Using Photoclick Chemistry in Live Cells

Cited by 52 publications

References 23 publications

Controllable gelation of artificial extracellular matrix for altering mass transport and improving cancer therapies

Controllable gelation of artificial extracellular matrix for altering mass transport and improving cancer therapies

Photo-controllable bioorthogonal chemistry for spatiotemporal control of bio-targets in living systems

Spatiotemporal Resolved Live Cell Membrane Tracking through Photo‐click Reactions Enriched in Lipid Phase

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