Ratiometric Fluorescent Signaling of Small Molecule, Environmentally Sensitive Dye Conjugates for Detecting Single‐Base Mutations in DNA

Wang, Chun Xia; Sato, Yusuke; Kudo, Megumi; Nishizawa, Seiichi; Teramae, Norio

doi:10.1002/chem.201200219

Cited by 24 publications

(19 citation statements)

References 42 publications

(20 reference statements)

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“…Nakatani and Teramae developed oligonucleotide probe systems that take advantage of the interaction between a fluorescent heterocycle and an unpaired nucleobase within a probe ⋅ target assembly . The synthesis of the fluorescence‐labelled probe can be omitted.…”

Section: Figurementioning

confidence: 99%

“…Ideally,t he method would combine the high fluorescence response and stabilityp rovided by fluorogenic hybridization probeswith the very high sequence specificity offered by reactive probes.Nakatani and Te ramaed eveloped oligonucleotide probe systems that take advantage of the interaction between af luorescent heterocycle and an unpairedn ucleobase within ap robe· target assembly. [17][18][19][20] The synthesis of the fluorescence-labelled probe can be omitted. The formation of the complexes resulted in up to tenfoldi ntensificationo ff luorescence.…”

mentioning

confidence: 99%

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Bivalent Display of Dicysteine on Peptide Nucleic Acids for Homogenous DNA/RNA Detection through in Situ Fluorescence Labelling

Fang

Seitz

2016

ChemBioChem

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Fluorogenic probes that signal the presence of specific DNA or RNA sequences are key enabling tools for molecular disease diagnosis and imaging studies. Usually, at least one fluorophore is attached through covalent bonding to an oligonucleotide probe. However, the additional conjugation step increases costs. Here we introduce a method that avoids the requirement for the preparation of fluorescence-labelled oligonucleotides and provides the opportunity to alter the fluorogenic reporter dye without resynthesis. The method is based on adjacent hybridization of two dicysteine-containing peptide nucleic acid (PNA) probes to form a bipartite tetracysteine motif that binds profluorescent bisarsenical dyes such as FIAsH, ReAsH or CrAsH. Binding is accompanied by strong increases in fluorescence emission (with response factors of up to 80-fold and high brightness up to 50 mL mol cm ). The detection system provides sub-nanomolar limits of detection and allows discrimination of single nucleotide variations through more than 20-fold changes in fluorescence intensity. To demonstrate its usefulness, the FIAsH-based readout of the bivalent CysCys-PNA display was interfaced with a rolling-circle amplification (RCA) assay used to detect disease-associated microRNA let-7a.

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Section: Figurementioning

confidence: 99%

mentioning

confidence: 99%

Bivalent Display of Dicysteine on Peptide Nucleic Acids for Homogenous DNA/RNA Detection through in Situ Fluorescence Labelling

Fang

Seitz

2016

ChemBioChem

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“…Fluorescent Signaling 25 Ratiometric fluorescent probes have now come to be recognized as a promising tool for biosensing and bioimaging studies. [43][44][45][46] Significant efforts have been devoted to develop this class of probes for a wide range of analytes, including metal ions, 43,47 inorganic and organic anions, 48,49 enzyme activities, 50 and nucleic acids.…”

Section: Dna-binding Small Ligand For Ratiometricmentioning

confidence: 99%

“…These include a derivative of 3,5-diaminopyrazines and pteridines for a surface plasmon resonance (SPR) sensor, 24 and a derivative of 2-amino-1,8-naphthyridines for ratiometric fluorescent signaling. 25 The binding and sensing properties of these systems are discussed as a basis for the advanced design of DNA-binding small molecules for gene detection. [31][32][33][34][35][36][37][38] Significant efforts have been devoted to achieve sufficient selectivity and sensitivity, based on a combination of coupled bio-conjugates, 33 DNA-modified gold nanoparticles [34][35][36] and/or surface enzyme reactions.…”

Section: Introductionmentioning

confidence: 99%

Recent Progress in Abasic Site-binding Small Molecules for Detecting Single-base Mutations in DNA

2014

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“…Teramae's group has designed and synthesized a series of environmentally sensitive fluorescent probes which bind selectively to AP sites in ds-DNA. The binding was manifested by either fluorescence quenching or enhancement [9][10][11][12][13][14]. Wu et al reported an AP site selective fluorescent probe, sanguinarine with a large emission shift [15].…”

Section: Introductionmentioning

confidence: 99%

A chemical toxicity sensor based on the electrochemiluminescence quantification of apurinic/apyrimidinic sites in double-stranded DNA monolayer

Feng

Liang

Guo

et al. 2017

Sensors and Actuators B: Chemical

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a b s t r a c tA new chemical toxicity sensor was developed based on the electrochemiluminescence (ECL) quantification of apurinic/apyrimidinic sites (AP sites) in a DNA monolayer with a covalent aldehyde reactive probe (ARP). In the sensor, a uracil-containing DNA duplex was first immobilized on a gold electrode by self-assembly. The duplex was then reacted with uracil-DNA glycosylase (UDG) to convert uracils into AP sites. ARP was employed to tag the AP site with a biotin. After reacting with a ruthenium complex labeled streptavidin, ECL was measured for quantitative analysis. The DNA monolayer was characterized by cyclic voltammetry, electrochemical impedance spectroscopy and chronocoulometry, and its density was measured to be 2.89 × 10 −12 mol/cm 2 . Characterization of the reaction product between ARP and DNA AP sites in solution by nondenaturing polyacrylamide gel electrophoresis and mass spectrometry confirmed successful biotinylation. ECL intensity of the labeled DNA monolayer on the electrode was found to correlate with the number of AP sites, and the detection limit was estimated to be about 1 lesion in 512 DNA bases, which meant that 8.5 fmol AP bases on the electrode were detected. ECL response of the DNA monolayers containing either 8-oxodGuo or methylated bases was very low, indicating that ARP-based AP sites detection method was highly selective. The sensor successfully detected the AP sites in normal DNA induced by methylmethane sulfonate, a carcinogenic chemical. The novel combination of covalent probe and ECL measurement in a sensor configuration therefore provides unique advantages in selectivity and sensitivity, and can be potentially employed in the screening of chemicals for their genetic toxicity.

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Ratiometric Fluorescent Signaling of Small Molecule, Environmentally Sensitive Dye Conjugates for Detecting Single‐Base Mutations in DNA

Cited by 24 publications

References 42 publications

Bivalent Display of Dicysteine on Peptide Nucleic Acids for Homogenous DNA/RNA Detection through in Situ Fluorescence Labelling

Bivalent Display of Dicysteine on Peptide Nucleic Acids for Homogenous DNA/RNA Detection through in Situ Fluorescence Labelling

Recent Progress in Abasic Site-binding Small Molecules for Detecting Single-base Mutations in DNA

A chemical toxicity sensor based on the electrochemiluminescence quantification of apurinic/apyrimidinic sites in double-stranded DNA monolayer

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