Peptide nucleic acid-templated selenocystine–selenoester ligation enables rapid miRNA detection

Sayers, Jessica; Payne, Richard J.; Winssinger, Nicolas

doi:10.1039/c7sc02736b

Cited by 53 publications

(50 citation statements)

References 37 publications

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“…8), and selenophilicity produces a strong preference for diselenides over mixed selenosulfides. [29][30][31][32][33][34][35][36] As a result, 3-alkyl-1,2diselenolanes prefer to stay closed, and fast exchange makes it challenging to catch selenosulfides and demonstrate that 1,2-diselenolanes really do exchange with thiolates. [27] In the following, this question is clarified, also with regard to post-exchange rearrangements that may or may not account for the intriguing power of 3-alkyl-1,2-diselenolanes to enter into cells.…”

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confidence: 99%

The Opening of 1,2‐Dithiolanes and 1,2‐Diselenolanes: Regioselectivity, Rearrangements, and Consequences for Poly(disulfide)s, Cellular Uptake and Pyruvate Dehydrogenase Complexes

Laurent

Sakai

Matile

2019

Helvetica Chimica Acta

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The thiol‐mediated opening of 3‐alkyl‐1,2‐dithiolanes and diselenolanes is described. The thiolate nucleophile is shown to react specifically with the secondary chalcogen atom, against steric demand, probably because the primary chalcogen atom provides a better leaving group. Once released, this primary chalcogen atom reacts with the obtained secondary dichalcogenide to produce the constitutional isomer. Thiolate migration to the primary dichalcogenide equilibrates within ca. 20 ms at room temperature at a 3 : 2 ratio in favor of the secondary dichalcogenide. The clarification of this focused question is important for the understanding of multifunctional poly(disulfide)s obtained by ring opening disulfide exchange polymerization of 3‐alkyl‐1,2‐dithiolanes, to rationalize the cellular uptake mediated by 3‐alkyl‐1,2‐diselenolanes as molecular walkers and, perhaps, also of the mode of action of pyruvate dehydrogenase complexes. The isolation of ring‐opened diselenolanes is particularly intriguing because dominant selenophilicity disfavors ring opening strongly.

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confidence: 99%

The Opening of 1,2‐Dithiolanes and 1,2‐Diselenolanes: Regioselectivity, Rearrangements, and Consequences for Poly(disulfide)s, Cellular Uptake and Pyruvate Dehydrogenase Complexes

Laurent

Sakai

Matile

2019

Helvetica Chimica Acta

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“…Middel et al used photocleavable PNA templates to direct NCL to a glutamic acid side chain . Very recently, Sayers et al reported a templated ligation between PNA‐linked selenoesters and selenocysteine . The reaction is the fastest nucleic acid–templated reaction to date and has been used to detect miRNA within cell lysates by means of a paper strip assay.…”

Section: Termolecular Assemblies For Nucleic Acid–programmed Peptide mentioning

confidence: 99%

Templated chemistry for bioorganic synthesis and chemical biology

Seitz

2019

Journal of Peptide Science

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In light of the 2018 Max Bergmann Medal, this review discusses advancements on chemical biology–driven templated chemistry developed in the author's laboratories. The focused review introduces the template categories applied to orient functional units such as functional groups, chromophores, biomolecules, or ligands in space. Unimolecular templates applied in protein synthesis facilitate fragment coupling of unprotected peptides. Templating via bimolecular assemblies provides control over proximity relationships between functional units of two molecules. As an instructive example, the coiled coil peptide–templated labelling of receptor proteins on live cells will be shown. Termolecular assemblies provide the opportunity to put the proximity of functional units on two (bio)molecules under the control of a third party molecule. This allows the design of conditional bimolecular reactions. A notable example is DNA/RNA–triggered peptide synthesis. The last section shows how termolecular and multimolecular assemblies can be used to better characterize and understand multivalent protein‐ligand interactions.

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“…Optical readout formats mainly include fluorescence-based systems that can be monitored quantitatively using fluorescence microscopes/scanners or flow cytometers, and bioluminescence-based approaches that are detectable with luminescence spectrometers or with the naked eye [10]. OTRs with a colorimetric readout have also been reported on enzyme linked immunosorbent assay (ELISA) and paper-based formats [25] [26]. Finally, products of ligation-mediated templated reactions can be detected by size/molecular weight-based approaches that use gel electrophoresis (including denaturing polyacrylamide gel electrophoresis (PAGE)), high performance liquid chromatography (HPLC) and mass spectrometry systems such as the matrix assisted laser desorption and ionisation-time of flight (MALDI-TOF) technique [27] [28].…”

Section: General Merits Of Bio-orthogonal Otr-based Na Sensing Stratementioning

confidence: 99%

“…Another approach to improving the limitations of conventional LFAs would be to implement OTRs on paper, for rapid and low-cost detection of NA targets. Winssinger et al, recently reported the design of an LFA for rapid detection of the products of template-mediated bio-orthogonal ligations [26]. Two synthetic PNA probes were functionalised with probe heads that can undergo a peptide bond formation under a selenium-mediated ligation manifold exclusively upon simultaneous hybridisation to a unique NA target.…”

Section: Otrs In Lateral Flow Assays (Lfas)mentioning

confidence: 99%

Platforms for Bioorthogonal Oligonucleotide-templated Reactions: Translating Concepts into Devices

Pavagada

Ladame

2018

Chimia

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The exponential improvements made in DNA sequencing technologies, together with the rapidly declining associated costs, has increasingly led to the expansion of the field of personalised genomic medicine. Changes in the sequence or copy number of specific deoxyribonucleic acid (DNA) or ribonucleic acid (RNA) molecules represent key signatures for the diagnosis, prognosis, classification and monitoring of a broad range of pathologies, most notably cancer. Technologies that can detect these changes require analytical tools that can detect DNA or RNA with high sensitivity and high specificity. Sensing based on bio-orthogonal oligonucleotide-templated reactions (OTRs) has been recognised as an elegant strategy that satisfies these criteria and was successfully used for the quantitative detection of nucleic acids both in vitro and in vivo. Herein, we will focus on recent efforts to implement bio-orthogonal OTRs into clinically useful biosensors using probes immobilised on or embedded in customised materials and platforms.

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Peptide nucleic acid-templated selenocystine–selenoester ligation enables rapid miRNA detection

Abstract: A PNA-templated peptide ligation reaction has been developed between selenocystine and selenoesters. The methodology was used for the sequence specific detection of miRNA at low concentrations.

Cited by 53 publications

References 37 publications

The Opening of 1,2‐Dithiolanes and 1,2‐Diselenolanes: Regioselectivity, Rearrangements, and Consequences for Poly(disulfide)s, Cellular Uptake and Pyruvate Dehydrogenase Complexes

The Opening of 1,2‐Dithiolanes and 1,2‐Diselenolanes: Regioselectivity, Rearrangements, and Consequences for Poly(disulfide)s, Cellular Uptake and Pyruvate Dehydrogenase Complexes

Templated chemistry for bioorganic synthesis and chemical biology

Platforms for Bioorthogonal Oligonucleotide-templated Reactions: Translating Concepts into Devices

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