Bioorthogonal Enzymatic Activation of Caged Compounds

Ritter, Cornelia; Nett, Nathalie; Acevedo‐Rocha, Carlos G.; Lonsdale, Richard; Kräling, Katja; Dempwolff, Felix; Hoebenreich, Sabrina; Graumann, Peter L.; Reetz, Manfred T.; Meggers, Eric

doi:10.1002/anie.201506739

Cited by 44 publications

(39 citation statements)

References 63 publications

(24 reference statements)

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“…327 Enzymes have evolved to be efficient biocatalysts, and with the development of protein engineering, researchers have the potential obtain powerful tools to exploit more matallo-enzymes combined with natural proteins. 328 The undeniable advantage of signal amplification through catalytic turnover has been successfully exploited in the area of enzyme-based bio-imaging and sensing. 329 …”

Section: Ru(ii) Complexes For Bioorthogonal Catalysismentioning

confidence: 99%

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

et al. 2017

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Cancer is rapidly becoming the top killer in the world. Most of the FDA approved anticancer drugs are organic molecules, while metallodrugs are very scarce. The advent of first metal based therapeutic agent, cisplatin, launched a new era in the application of transition metal complexes for therapeutic design. Due to their unique and versatile biochemical properties, ruthenium-based compounds have emerged as promising anti-cancer agents that serve as alternatives to cisplatin and its derivertives. The ruthenium(III) complexes have successfully been used in clinical research and their mechanisms of anticancer action have been reported in large volumes over the past few decades. Ruthenium(II) complexes have also attracted significant attention as anticancer candidates; however, only few of them have been reported comprehensively. In this review, we discuss the development of ruthenium(II) complexes as anticancer candidates and biocatalysts, including arene ruthenium complexes, polypyridyl ruthenium complexes, and ruthenium nanomaterial complexes. This review focuses on the likely mechanisms of action of ruthenium(II)-based anticancer drugs and the relationship between their chemical structures and biological properties. This review also highlights the catalytic activity and the photoinduced activation of ruthenium(II) complexes, their targeted delivery, and their activity in nanomaterial systems.

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Section: Ru(ii) Complexes For Bioorthogonal Catalysismentioning

confidence: 99%

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

et al. 2017

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“…Proteins have been engineered with unnatural side chains capable of bioorthogonal coupling, 2 Recently, bioorthogonal enzymatic decaging has been described in which engineered P450 proteins catalyze reactions to release alcohols. 23 However, the use of an enzyme to create a bioorthogonal coupling partner had not been described. We considered that the enzyme horseradish peroxidase (HRP) might be an effective catalyst for the creation of compounds for bioorthogonal reactivity.…”

Section: Introductionmentioning

confidence: 99%

Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation

et al. 2016

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Rapid bioorthogonal reactivity can be induced by controllable, catalytic stimuli using air as the oxidant. Methylene blue (4 μM) irradiated with red light (660 nm) catalyzes the rapid oxidation of a dihydrotetrazine to a tetrazine thereby turning on reactivity toward trans-cyclooctene dienophiles. Alternately, the aerial oxidation of dihydrotetrazines can be efficiently catalyzed by nanomolar levels of horseradish peroxidase under peroxide-free conditions. Selection of dihydrotetrazine/tetrazine pairs of sufficient kinetic stability in aerobic aqueous solutions is key to the success of these approaches. In this work, polymer fibers carrying latent dihydrotetrazines were catalytically activated and covalently modified by trans-cyclooctene conjugates of small molecules, peptides and proteins. In addition to visualization with fluorophores, fibers conjugated to a cell adhesive peptide exhibited a dramatically increased ability to mediate contact guidance of cells.

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“…The bio-specificity of substrate 6 ensures that this strategy can be used in a wide variety of organisms and cell types; however, it is still possible that endogenous esterases can cause a non-specific background signal under certain conditions. Thus, the system can be optimized by modifying the PLE enzyme and/or the substrate, or by identifying a more bioorthogonal enzyme-substrate pair ( Sletten and Bertozzi, 2009 ; Ritter et al, 2015 ). At the same time, robust control experiments (for example, using knockout models) are an essential step in testing for non-specific background due to endogenous enzymes ( Qiao and Sanes, 2015 ).…”

Section: Hybrid Approaches Combined With Genetic Toolsmentioning

confidence: 99%

Gap Junctions in the Nervous System: Probing Functional Connections Using New Imaging Approaches

Dong

Liu

2018

Front. Cell. Neurosci.

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Gap junctions are channels that physically connect adjacent cells, mediating the rapid exchange of small molecules, and playing an essential role in a wide range of physiological processes in nearly every system in the body, including the nervous system. Thus, altered function of gap junctions has been linked with a plethora of diseases and pathological conditions. Being able to measure and characterize the distribution, function, and regulation of gap junctions in intact tissue is therefore essential for understanding the physiological and pathophysiological roles that gap junctions play. In recent decades, several robust in vitro and in vivo methods have been developed for detecting and characterizing gap junctions. Here, we review the currently available methods with respect to invasiveness, signal-to-noise ratio, temporal resolution and others, highlighting the recently developed chemical tracers and hybrid imaging systems that use novel chemical compounds and/or genetically encoded enzymes, transporters, channels, and fluorescent proteins in order to map gap junctions. Finally, we discuss possible avenues for further improving existing techniques in order to achieve highly sensitive, cell type-specific, non-invasive measures of in vivo gap junction function with high throughput and high spatiotemporal resolution.

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Bioorthogonal Enzymatic Activation of Caged Compounds

Cited by 44 publications

References 63 publications

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials

Rapid Bioorthogonal Chemistry Turn-on through Enzymatic or Long Wavelength Photocatalytic Activation of Tetrazine Ligation

Gap Junctions in the Nervous System: Probing Functional Connections Using New Imaging Approaches

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