A metal-mediated base pair that discriminates between the canonical pyrimidine nucleobases

Jash, Biswarup; Scharf, Philipp; Sandmann, Nikolas; Guerra, Célia Fonseca; Megger, Dominik A.; Müller, Jens

doi:10.1039/c6sc03482a

Cited by 50 publications

(63 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…This becomes manifest in a decreasing T m upon the addition of Ag I . This decrease in melting temperature has been explained by the metalation of the artificial P residue and a concomitant extrusion of its complementary thymine nucleobase from the duplex due to a steric clash . The present melting studies indicate that the opposing effects of the addition of Ag I to duplexes bearing P–T and P–C pairs under acidic and near‐neutral conditions, as observed earlier, are universally valid .…”

Section: Resultssupporting

confidence: 80%

“…It can be clearly discerned that the fluorescence of the system increases significantly in the presence of ODN‐C, as a direct result of the formation of the highly stabilizing P–Ag I –C base pair. The fluorescence increase amounts to 218 ± 13 % for Beacon1 and 146 ± 11 % for Beacon2 , both of which are higher than the 102 ± 7 % reported for the generic beacon sequence investigated originally (Figure a) . Unexpectedly, Beacon1 shows an increase in fluorescence of 61 ± 4 % in the presence of the thymine‐containing complementary oligonucleotide ODN‐T, too.…”

Section: Resultsmentioning

confidence: 62%

“…In all cases, the standard deviation of the mean of three independent measurements is indicated. The term “original beacon” refers to a generic beacon sequence reported earlier …”

Section: Resultsmentioning

confidence: 99%

“…Towards this end, several artificial nucleobases have been developed for discrimination of canonical nucleobases by metal‐mediated base‐pairing . We recently reported the use of a phenanthroline‐derived nucleobase surrogate, 1 H ‐imidazo[4,5‐ f ][1,10]phenanthroline) (P), that is capable of discriminating the pyrimidine nucleobases cytosine (C) and thymine (T) . In the presence of Ag I ions, highly stabilizing P–Ag I –C base pairs are formed from P–C pairs (Figure , inset), whereas P–T pairs are strongly destabilized under acidic and neutral conditions upon the addition of Ag I .…”

Section: Introductionmentioning

confidence: 99%

“…Schematic representation of a molecular beacon for the discrimination of a single C→T or T→C transition within an oligonucleotide by the formation of a metal‐mediated base pair (FRET: Förster resonance energy transfer). Figure adapted from ref …”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Application of a Metal‐Mediated Base Pair to the Detection of Medicinally Relevant Single Nucleotide Polymorphisms

Jash

Müller

2017

Eur J Inorg Chem

Self Cite

View full text Add to dashboard Cite

A highly stabilizing metal‐mediated base pair formed from the canonical nucleobase cytosine (C), the transition metal ion AgI, and the artificial nucleobase 1H‐imidazo[4,5‐f][1,10]phenanthroline (P) was used in the generation of molecular beacons for the detection of medicinally relevant single nucleotide polymorphisms (SNPs) based on either a C→T or a T→C transition (T: thymine). The beacons exploit the fact that a P–C pair is strongly stabilized in the presence of AgI, whereas a P–T pair is significantly destabilized. A direct correlation of oligonucleotide sequence, duplex stability prior to the addition of AgI, stabilization due to metal‐mediated base pair formation, and performance of the molecular beacon was not observed. Nonetheless, the data show for the first time that metal‐mediated base pairing can be applied in the detection of medicinally relevant SNPs.

show abstract

Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 62%

“…In all cases, the standard deviation of the mean of three independent measurements is indicated. The term “original beacon” refers to a generic beacon sequence reported earlier …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Application of a Metal‐Mediated Base Pair to the Detection of Medicinally Relevant Single Nucleotide Polymorphisms

Jash

Müller

2017

Eur J Inorg Chem

Self Cite

View full text Add to dashboard Cite

show abstract

Metallmodifizierte Nukleinsäuren: Metallvermittelte Basenpaare, ‐tripel und ‐tetraden

2019

Self Cite

View full text Add to dashboard Cite

Das Einbringen von Metallionen in Nukleinsäuren mittels metallvermittelter Basenpaare stellt eine vielversprechende und weit verbreitete Methode zur ortsspezifischen Modifizierung dieser selbstassemblierenden Supramoleküle mit metallbasierter Funktionalität dar. In den vergangenen 20 Jahren wurden zahlreiche solcher Nukleosid‐Surrogate entwickelt, die die Bandbreite an Metallen durch perfekt zugeschnittene Metallbindungsstellen erweitert haben. In jüngster Vergangenheit rückten künstliche, von natürlichen Purin‐ und Pyrimidinbasen abgeleitete Nukleoside durch die erwartete Kompatibilität mit Watson‐Crick‐Basenpaaren in den Fokus AgI‐vermittelter Basenpaare. Dieser Kurzaufsatz fasst diese sowie weitere aktuelle Entwicklungen auf dem Gebiet metallvermittelter Basenpaare zusammen. Zudem befasst er sich mit weiteren Aspekten metallmodifizierter Nukleinsäuren, indem er eine Erweiterung des Konzepts auf metallvermittelte Basentripel (in Dreifachhelices und dreiarmigen DNA‐Kreuzungen) sowie ‐tetraden (in Quadruplexen) behandelt. Für alle Arten metallmodifizierter Nukleinsäuren werden darüber hinaus postulierte oder bereits erreichte Anwendungen kurz erwähnt.

show abstract

Metal‐Modified Nucleic Acids: Metal‐Mediated Base Pairs, Triples, and Tetrads

2019

Self Cite

View full text Add to dashboard Cite

The incorporation of metal ions into nucleic acids by means of metal‐mediated base pairs represents a promising and prominent strategy for the site‐specific decoration of these self‐assembling supramolecules with metal‐based functionality. Over the past 20 years, numerous nucleoside surrogates have been introduced in this respect, broadening the metal scope by providing perfectly tailored metal‐binding sites. More recently, artificial nucleosides derived from natural purine or pyrimidine bases have moved into the focus of AgI‐mediated base pairing, due to their expected compatibility with regular Watson–Crick base pairs. This minireview summarizes these advances in metal‐mediated base pairing but also includes further recent progress in the field. Moreover, it addresses other aspects of metal‐modified nucleic acids, highlighting an expansion of the concept to metal‐mediated base triples (in triple helices and three‐way junctions) and metal‐mediated base tetrads (in quadruplexes). For all types of metal‐modified nucleic acids, proposed or accomplished applications are briefly mentioned, too.

show abstract

A metal-mediated base pair that discriminates between the canonical pyrimidine nucleobases

Abstract: A molecular beacon has been developed that depends on the formation of a metal-mediated base pair.

Cited by 50 publications

References 58 publications

Application of a Metal‐Mediated Base Pair to the Detection of Medicinally Relevant Single Nucleotide Polymorphisms

Application of a Metal‐Mediated Base Pair to the Detection of Medicinally Relevant Single Nucleotide Polymorphisms

Metallmodifizierte Nukleinsäuren: Metallvermittelte Basenpaare, ‐tripel und ‐tetraden

Metal‐Modified Nucleic Acids: Metal‐Mediated Base Pairs, Triples, and Tetrads

Contact Info

Product

Resources

About