Tetrazine ligation for chemical proteomics

Kang, Kyung‐Tae; Park, Jongmin; Kim, Eunha

doi:10.1186/s12953-017-0121-5

Cited by 36 publications

(31 citation statements)

References 78 publications

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“…Thanks to its fast reaction kinetics, rivalling those of CuAAC, while retaining a superior level of selectivity, the iEDDA has attracted immense interest in the fields of bioconjugation and bioorthogonal chemistry [ 73 ]. A variety of dienophiles and a range of differently substituted tetrazines have been reported in the literature, as well as a number of ‘turn-on’ probes that make use of the convenient ability of tetrazines to quench conjugated fluorophores and thereby achieve fluorogenicity upon iEDDA reaction (see, for recent reviews, [ 74 , 75 ]).…”

Section: Overview Of Bioorthogonal Reactions In Abppmentioning

confidence: 99%

Bioorthogonal Reactions in Activity-Based Protein Profiling

Verhelst

Bonger²,

Willems

2020

Molecules

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Activity-based protein profiling (ABPP) is a powerful technique to label and detect active enzyme species within cell lysates, cells, or whole animals. In the last two decades, a wide variety of applications and experimental read-out techniques have been pursued in order to increase our understanding of physiological and pathological processes, to identify novel drug targets, to evaluate selectivity of drugs, and to image probe targets in cells. Bioorthogonal chemistry has substantially contributed to the field of ABPP, as it allows the introduction of tags, which may be bulky or have unfavorable physicochemical properties, at a late stage in the experiment. In this review, we give an overview of the bioorthogonal reactions that have been implemented in ABPP, provide examples of applications of bioorthogonal chemistry in ABPP, and share some thoughts on future directions.

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Section: Overview Of Bioorthogonal Reactions In Abppmentioning

confidence: 99%

Bioorthogonal Reactions in Activity-Based Protein Profiling

Verhelst

Bonger²,

Willems

2020

Molecules

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“…In addition to the existing bioorthogonal reactions, guidelines to construct new bioorthogonal reagents have been suggested to extend the bioorthogonal toolbox [20,21]. Among the twenty unique reactions compliant with the features listed above, two have received considerable interest: the strain promoted azide-alkyne cycloaddition (SPAAC) and the inverse-electron demand Diels-Alder (IEDDA) reaction [22] ( Figure 2). The SPAAC is a copper-free variant of the azide-alkyne cycloaddition which is less toxic and therefore more compatible with biological environments, whereas the IEDDA is a reaction between a strained dienophile and a diene that is sufficiently reactive to proceed at physiological temperature and pressure conditions.…”

Section: Labelled Chemical Probesmentioning

confidence: 99%

Labelled Chemical Probes for Demonstrating Direct Target Engagement in Living Systems

Prevet

Collins

2019

Future Med. Chem.

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Demonstrating target engagement in living systems can help drive successful drug discovery. Target engagement and occupancy studies in cells confirm direct binding of a ligand to its intended target protein and provide the binding affinity. Combined with biomarkers to measure the functional consequences of target engagement, these experiments can increase confidence in the relationship between in vitro pharmacology and observed biological effects. In this review, we focus on chemically and radioactively labelled probes as key reagents for performing such experiments. Using recent examples, we examine how the labelled probes have been employed in combination with unlabelled ligands to quantify target engagement in cells and in animals. Finally, we consider future developments of this emerging methodology.

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“…In classical Diels–Alder reaction, HOMO of the diene adds to the LUMO of dienophile, while in iEDDA, it is the HOMO of the dienophile which adds to the LUMO of the diene. This constitutes the inverse electron demand in iEDDA reactions, which are almost instantaneous and gives quantitative yields even in inside living cells .…”

Section: Crosslinkers For Antibody Drug Conjugatesmentioning

confidence: 99%

Chemical Crosslinking‐Mass Spectrometry (CXL‐MS) for Proteomics, Antibody‐Drug Conjugates (ADCs) and Cryo‐Electron Microscopy (cryo‐EM)

2018

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Chemical crosslinking-mass spectrometry (CXL-MS) has emerged as a powerful tool in structural biology to elucidate protein-protein interactions. This review throws light on the advent of these technologies incorporating chemical crosslinking in proteomics, structural biology and extended to studies and applications of antibody-drug conjugates (ADCs). Monoclonal ASCs are known to target their specific receptors, where the drug could be released for vastly improved therapeutic effect. Cryo-electron microscopy (cryo-EM) is being referred to as the "revolution of the century" as it can help attain almost atomic resolution, while preserving the biological samples at near-native state and has been recognized by the Nobel award 2017. CXL-MS and appropriate bioinformatics tools in combination with cryo-EM reveal better 3D information about dynamic interactions in proteins, interactive domains and motifs, among others in ADCs and in viruses like Zika virus, Rota virus, Dengue virus and also spliceosomes at resolutions, especially below 3 Å. © 2018 IUBMB Life, 70(10):947-960, 2018.

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Tetrazine ligation for chemical proteomics

Cited by 36 publications

References 78 publications

Bioorthogonal Reactions in Activity-Based Protein Profiling

Bioorthogonal Reactions in Activity-Based Protein Profiling

Labelled Chemical Probes for Demonstrating Direct Target Engagement in Living Systems

Chemical Crosslinking‐Mass Spectrometry (CXL‐MS) for Proteomics, Antibody‐Drug Conjugates (ADCs) and Cryo‐Electron Microscopy (cryo‐EM)

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