PNA Molecular Beacons Assembled by Post‐Synthetic Click Chemistry Functionalization

Wang, Xiaoxiao; Hudson, Robert

doi:10.1002/cbic.201500248

Cited by 10 publications

(12 citation statements)

References 38 publications

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“…1 and 2). The same approach was then used for the production of a PNA probe similar to PNA F, but using an azide-containing monomer, which was earlier exploited in the solid phase insertion of nucleobase surrogates 29 or the production of molecular beacons, 30 and which allowed subsequent modification in solution to give PNA f (Fig. 1).…”

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confidence: 99%

Furan-PNA: a mildly inducible irreversible interstrand crosslinking system targeting single and double stranded DNA

et al. 2016

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confidence: 99%

Furan-PNA: a mildly inducible irreversible interstrand crosslinking system targeting single and double stranded DNA

et al. 2016

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“…Two or more pyrene labels may be conveniently placed anywhere in the PNA molecule by attaching them to a C5-functionalized thymine via amide or click chemistries, and applications for the detection of DNA by duplex [ 54 ] or triplex [ 69 ] formation have been demonstrated. Alternatively, the pyrene label can be placed onto the PNA backbone as a base replacement (in aegPNA) [ 55 ] or as a tethered label through a flexible linker (in acpcPNA) [ 70 ].…”

Section: Reviewmentioning

confidence: 99%

Fluorogenic PNA probes

Vilaivan¹

2018

Beilstein J. Org. Chem.

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Fluorogenic oligonucleotide probes that can produce a change in fluorescence signal upon binding to specific biomolecular targets, including nucleic acids as well as non-nucleic acid targets, such as proteins and small molecules, have applications in various important areas. These include diagnostics, drug development and as tools for studying biomolecular interactions in situ and in real time. The probes usually consist of a labeled oligonucleotide strand as a recognition element together with a mechanism for signal transduction that can translate the binding event into a measurable signal. While a number of strategies have been developed for the signal transduction, relatively little attention has been paid to the recognition element. Peptide nucleic acids (PNA) are DNA mimics with several favorable properties making them a potential alternative to natural nucleic acids for the development of fluorogenic probes, including their very strong and specific recognition and excellent chemical and biological stabilities in addition to their ability to bind to structured nucleic acid targets. In addition, the uncharged backbone of PNA allows for other unique designs that cannot be performed with oligonucleotides or analogues with negatively-charged backbones. This review aims to introduce the principle, showcase state-of-the-art technologies and update recent developments in the areas of fluorogenic PNA probes during the past 20 years.

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“…Light-up systems based on molecular beacons (MBs), i.e., structured pyrene-modified oligonucleotide probes, are powerful tools for sensitive fluorescence detection of a broad spectrum of different targets [ 66 , 85 , 92 , 93 , 94 , 95 , 96 , 97 ]. Originally, MBs are oligonucleotides forming a stem-loop-structure and labeled by a fluorescent group and a quencher at opposite ends of the probe to display an on/off output pattern [ 98 ].…”

Section: Fluorescent Biosensorsmentioning

confidence: 99%

Recent Advances in Nucleic Acid Targeting Probes and Supramolecular Constructs Based on Pyrene-Modified Oligonucleotides

et al. 2017

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In this review, we summarize the recent advances in the use of pyrene-modified oligonucleotides as a platform for functional nucleic acid-based constructs. Pyrene is of special interest for the development of nucleic acid-based tools due to its unique fluorescent properties (sensitivity of fluorescence to the microenvironment, ability to form excimers and exciplexes, long fluorescence lifetime, high quantum yield), ability to intercalate into the nucleic acid duplex, to act as a π-π-stacking (including anchoring) moiety, and others. These properties of pyrene have been used to construct novel sensitive fluorescent probes for the sequence-specific detection of nucleic acids and the discrimination of single nucleotide polymorphisms (SNPs), aptamer-based biosensors, agents for binding of double-stranded DNAs, and building blocks for supramolecular complexes. Special attention is paid to the influence of the design of pyrene-modified oligonucleotides on their properties, i.e., the structure-function relationships. The perspectives for the applications of pyrene-modified oligonucleotides in biomolecular studies, diagnostics, and nanotechnology are discussed.

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PNA Molecular Beacons Assembled by Post‐Synthetic Click Chemistry Functionalization

Cited by 10 publications

References 38 publications

Furan-PNA: a mildly inducible irreversible interstrand crosslinking system targeting single and double stranded DNA

Furan-PNA: a mildly inducible irreversible interstrand crosslinking system targeting single and double stranded DNA

Fluorogenic PNA probes

Recent Advances in Nucleic Acid Targeting Probes and Supramolecular Constructs Based on Pyrene-Modified Oligonucleotides

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