Rapidly photoactivatable ATP probes for specific labeling of tropomyosin within the actomyosin protein complex

Masuda, Souta; Tomohiro, Takenori; Hatanaka, Y.

doi:10.1016/j.bmcl.2011.02.113

Cited by 7 publications

(3 citation statements)

References 33 publications

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“…Hatanaka and co-workers used probes 13a – b for analyzing the interactions within the actomyosin complex, showing selective labeling of tropomyosin. The trifluoromethyl phenyldiazirine moiety and its biotinylated version were linked through a phosphoramide bond to an ATP moiety.…”

Section: Nucleotide-derived Probesmentioning

confidence: 99%

Phosphorus-Based Probes as Molecular Tools for Proteome Studies: Recent Advances in Probe Development and Applications

Joachimiak

Błażewska

2018

J. Med. Chem.

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Studies on the human proteome have engaged diverse techniques; however, none of them represent a predominant approach. Chemical biology has made a major contribution to our understanding of human biology, stimulating the generation of biological hypotheses. Tools such as functional probes have advanced studies on biological mechanisms and helped in elucidating off-target reactivity and potential toxicities of drugs and drug candidates. Here, we accentuate the recent developments in the design and applications of phosph(on)ate-containing probes. Phosphate esters and anhydrides are present in a number of vital cell constituents, and their significance can be reflected by a number of biological processes that involve phosphorus-bearing molecules. We discuss the use of phosph(on)ate-derived probes for (1) the identification of phosphate-requiring enzymes, their substrates, interacting partners; (2) developing screening assays; and (3) their potential as diagnostics. Limitations that as yet need to be overcome and possible measures to be undertaken will also be addressed.

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Section: Nucleotide-derived Probesmentioning

confidence: 99%

Phosphorus-Based Probes as Molecular Tools for Proteome Studies: Recent Advances in Probe Development and Applications

Joachimiak

Błażewska

2018

J. Med. Chem.

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“…Another probe design incorporates a photoactivatable moiety into the AdoR-targeted probe, which provides the ability to attach the probe into a chemically inert AdoR-binding pocket. Photoactivatable AdoR analogs described in the literature include the 8-azido adenosine nucleotides (8-N 3 -AMP, 8-N 3 -ADP, and 8-N 3 -ATP) and 5’-diazirine containing ATP analogs [ 14 , 18 , 19 ]. Probe 1 employed in our approach contains an 8-azido adenosine moiety as the reactive group that generates a reactive intermediate which can indiscriminately react with amino acids at the binding site of the probe and thus is less restricted than the affinity labels with electrophilic functional groups [ 20 – 22 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of a Novel Adenosine-Ribose Probe for Global-Scale Profiling of Nucleoside and Nucleotide-Binding Proteins

et al. 2015

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Proteomics is a powerful approach used for investigating the complex molecular mechanisms of disease pathogenesis and progression. An important challenge in modern protein profiling approaches involves targeting of specific protein activities in order to identify altered molecular processes associated with disease pathophysiology. Adenosine-binding proteins represent an important subset of the proteome where aberrant expression or activity changes of these proteins have been implicated in numerous human diseases. Herein, we describe an affinity-based approach for the enrichment of adenosine-binding proteins from a complex cell proteome. A novel N 6-biotinylated-8-azido-adenosine probe (AdoR probe) was synthesized, which contains a reactive group that forms a covalent bond with the target proteins, as well as a biotin tag for affinity enrichment using avidin chromatography. Probe specificity was confirmed with protein standards prior to further evaluation in a complex protein mixture consisting of a lysate derived from mouse neuroblastoma N18TG2 cells. Protein identification and relative quantitation using mass spectrometry allowed for the identification of small variations in abundance of nucleoside- and nucleotide-binding proteins in these samples where a significant enrichment of AdoR-binding proteins in the labeled proteome from the neuroblastoma cells was observed. The results from this study demonstrate the utility of this method to enrich for nucleoside- and nucleotide-binding proteins in a complex protein mixture, pointing towards a unique set of proteins that can be examined in the context of further understanding mechanisms of disease, or fundamental biological processes in general.

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“…3). The development of this new family opened a simple strategy for harnessing phenyldiazirine photophores to important classes of biological ligands such as peptides, 30) nucleotides, 31) carbohydrates, 32) and lipids 33) to produce corresponding diazirine probes 21-24 34) (Fig. 4).…”

Section: )mentioning

confidence: 99%

Development and Leading-Edge Application of Innovative Photoaffinity Labeling

Hatanaka

2015

Chem. Pharm. Bull.

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Rapidly photoactivatable ATP probes for specific labeling of tropomyosin within the actomyosin protein complex

Cited by 7 publications

References 33 publications

Phosphorus-Based Probes as Molecular Tools for Proteome Studies: Recent Advances in Probe Development and Applications

Phosphorus-Based Probes as Molecular Tools for Proteome Studies: Recent Advances in Probe Development and Applications

Synthesis and Evaluation of a Novel Adenosine-Ribose Probe for Global-Scale Profiling of Nucleoside and Nucleotide-Binding Proteins

Development and Leading-Edge Application of Innovative Photoaffinity Labeling

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