Solid-Phase Synthesis of Doubly Labeled Peptide Nucleic Acids as Probes for the Real-Time Detection of Hybridization

Seitz, Oliver

doi:10.1002/1521-3773(20000915)39:18<3249::aid-anie3249>3.0.co;2-m

Cited by 96 publications

(52 citation statements)

References 19 publications

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“…LightUp probes consist of a thiazole orange conjugated with a PNA oligomer, whereas LightSpeed probes are duallabelled PNAs with a fluorescent dye and a quencher dye bound to the opposing termini of the molecule. 28,29 Both LightUp and LightSpeed probes are unique reagents for real-time PCR, which combine fluorescent enhancement with the high sensitivity and specificity of PNAs. A singlebase mismatch in the target sequence is sufficient to prevent probe binding.…”

Section: Antisense and Antigene Applicationsmentioning

confidence: 99%

The peptide nucleic acids (PNAs), powerful tools for molecular genetics and cytogenetics

2004

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Peptide nucleic acids (PNAs) are synthetic mimics of DNA in which the deoxyribose phosphate backbone is replaced by a pseudo-peptide polymer to which the nucleobases are linked. PNAs hybridize with complementary DNAs or RNAs with remarkably high affinity and specificity, essentially because of their uncharged and flexible polyamide backbone. The unique physico-chemical properties of PNAs have led to the development of a variety of research assays, and over the last few years, the use of PNAs has proven their powerful usefulness in molecular biology procedures and diagnostic assays. The more recent applications of PNA involve their use as molecular hybridization probes. Thus, several sensitive and robust PNA-dependent methods have been designed for developing antigene and anticancer drugs, modulating PCR reactions, detecting genomic mutation or labelling chromosomes in situ.

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Section: Antisense and Antigene Applicationsmentioning

confidence: 99%

The peptide nucleic acids (PNAs), powerful tools for molecular genetics and cytogenetics

2004

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“…Molecular beacons represent a versatile tool in DNA diagnostics [24]. Although these molecules initially had a hairpin structure with a stem, it was later found, especially for PNA molecules, that a stem is not required for their functioning [25,26]. In contrast to DNA molecular beacons, stemless PNA beacons are less sensitive to ionic strength, and the quenched fluorescence of PNA is not affected by DNAbinding proteins.…”

Section: Detection By Means Of Labeled Probe Moleculesmentioning

confidence: 99%

Peptide nucleic acids on microarrays and other biosensors

Brandt¹,

Hoheisel²

2004

Trends in Biotechnology

102

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“…The complete replacement of the ribose phosphate backbone with an artificial pseudopeptide backbone results in a remarkably improved binding to complementary nucleic acid sequences occurring with both high affinity and selectivity [12][13][14][15][16][17][18][19]. The hybridization properties of PNA have attracted widespread interest in this class of compounds [20][21][22]. Several reviews have covered the literature concerning new chemically modified PNA [23].…”

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confidence: 99%

Synthesis and anti-hepatitis B virus activity of new pyrimidine peptide nucleic acid analogs

Alharbi

Abdel‐Rahman

2012

Chem Heterocycl Comp

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A series of 4-methylsulfanylpyrimidin-2(1H)-one peptide nucleic acid analogs were synthesized and tested for their antiviral activity against hepatitis B virus. Plaque reduction infectivity assay was used to determine the virus count reduction as a result of treatment with tested compounds.Keywords: peptide nucleic acid analogs, pyrimidine nucleobases, anti-hepatitis B virus activity.Synthetic compounds that specifically recognize and bind to a specific DNA or RNA sequence of interest are potentially useful as antisense and antigene drugs or molecular probes, which have numerous applications in the field of molecular and experimental medicine [1][2][3]. Particularly successful DNA binding agents are found in a recently developed class of DNA analogs, the peptide nucleic acids (PNA) [4][5][6][7][8][9]. PNA are oligonucleotide analogs, in which the phosphodiester pentose backbone of DNA or RNA is replaced by a polyamide or peptide backbone [10]. For example, the phosphoribose backbone of natural oligonucleotide has been replaced by N-(2-aminoethyl)glycine whereby the purine/pirimidine base pair is attached to the glycine nitrogen through a methylene carbonyl linker [11]. The complete replacement of the ribose phosphate backbone with an artificial pseudopeptide backbone results in a remarkably improved binding to complementary nucleic acid sequences occurring with both high affinity and selectivity [12][13][14][15][16][17][18][19]. The hybridization properties of PNA have attracted widespread interest in this class of compounds [20][21][22]. Several reviews have covered the literature concerning new chemically modified PNA [23]. Their biological and chemical stability and their superior hybridization properties relative to natural oligonucleotides make them attracttive as potential therapeutic and biomolecular tools. Owing to the described significance of PNA and in connection with our work on the synthesis of new α-amino acid derivatives [24-28] and investigating their antiviral potential [29], we report here the synthesis and anti-hepatitis B virus (HBV) activity of new PNA with 4-methylsulfanylpyrimidin-2(1H)-one as the heterocyclic nucleobase.The coupling reaction at one of the nitrogen atoms of the heterocyclic base is the most effective method for introducing certain substituents with desired functionalities attached to the heterocycle. Thus, reaction of 4-(methylsulfanyl)uracils 1a-c [30] with ethyl chloroacetate in the presence of potassium carbonate afforded the corresponding nucleobase-substituted acetates 2a-c in 71-75% yields. The 1 H NMR spectra of compounds 2a-c showed the characteristic signals of the ester ethyl group and a singlet peak for the remaining CH 2 group at

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Solid-Phase Synthesis of Doubly Labeled Peptide Nucleic Acids as Probes for the Real-Time Detection of Hybridization

Cited by 96 publications

References 19 publications

The peptide nucleic acids (PNAs), powerful tools for molecular genetics and cytogenetics

The peptide nucleic acids (PNAs), powerful tools for molecular genetics and cytogenetics

Peptide nucleic acids on microarrays and other biosensors

Synthesis and anti-hepatitis B virus activity of new pyrimidine peptide nucleic acid analogs

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