Carboxyalkyl peptoid PNAs: synthesis and hybridization properties

Cola, Chiara De; Manicardi, Alex; Corradini, Roberto; Izzo, Irene; Riccardis, Francesco De

doi:10.1016/j.tet.2011.11.017

Cited by 14 publications

(10 citation statements)

References 34 publications

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“…The PNA probe has offered greater affinity in binding to complementary DNA. PNA is an invaluable tool in molecular biology due to its biological stability, the excellent nucleic acids binding properties and the appreciable chemical simplicity, and improved distinction between closely-related sequences (including single-base mismatches) [11]. Such mismatch discrimination has a particular importance in the detection of diseaserelated mutations [12].…”

Section: Introductionmentioning

confidence: 99%

A Review of Peptide Nucleic Acid

Siddiquee¹,

Rovina²,

Azriah³

2015

Adv Tech Biol Med

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Peptide Nucleic Acid (PNA) is a nucleobase oligomer in which the whole backbone is mainly replaced by N-(2aminoethyl) glycine units. PNA is considered as DNA with a neutral peptide backbone due to negative charged sugar-phosphate backbone. It is chemically stable and resistant to hydrolytic cleavage. PNA can be categorized specific sequences of DNA and RNA according to Watson-Crick hydrogen bonding structure. Hybridization process showed high thermal stability and unique ionic strength effects. It is formed a stable PNA/DNA/PNA triplex with a looped-out DNA strand. PNA hybridization technology is promptly developed within in situ hybridization. In our review paper was elaborated the PNA superior hybridization characteristics, importance's of PNA and major applications of PNA in the diagnostic and pharmaceutical fields. And also PNA could be replaced DNA in uses as a probe for many investigation purposes. PNAs antisense activities have found in nerve cells and even in rats upon injection into the brain, and in Escherichia coli.

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Section: Introductionmentioning

confidence: 99%

A Review of Peptide Nucleic Acid

Siddiquee¹,

Rovina²,

Azriah³

2015

Adv Tech Biol Med

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“…In recent years, some novel types of negatively charged PNAs have been reported, the and their charges are represented by N -alkyl-carboxyl groups in the achiral backbone [ 42 ] and sulfomethyl groups at the γ-positions [ 43 ]. γ- S -Sulfomethyl PNAs formed PNA 2 DNA triplexes and demonstrated good lipofectamine-mediated penetration into SKBR3 cells in model experiments.…”

Section: Introductionmentioning

confidence: 99%

“…It should be noted that all of the previous papers [ 13 , 40 , 42 – 43 ] describe PNA oligomers with negatively charged thymine monomers exclusively (with at most 3 residues in a chain). To summarize, the incorporation of negative charges into PNA oligomers is required to ensure PNA solubility and compatibility with standard cationic lipofection systems, whereas for an effective recognition of complementary NA sequences the configuration and the positions of chiral centres in the backbone are important.…”

Section: Introductionmentioning

confidence: 99%

Polyanionic Carboxyethyl Peptide Nucleic Acids (ce-PNAs): Synthesis and DNA Binding

et al. 2015

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New polyanionic modifications of polyamide nucleic acid mimics were obtained. Thymine decamers were synthesized from respective chiral α- and γ-monomers, and their enantiomeric purity was assessed. Here, we present the decamer synthesis, purification and characterization by MALDI-TOF mass spectrometry and an investigation of the hybridization properties of the decamers. We show that the modified γ-S-carboxyethyl-T10 PNA forms a stable triplex with polyadenine DNA.

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“…20 Amines of the amino alcohols were protected with a Cbz group by treatment of benzyl chloroformate (CbzCl). 39 Subsequent oxidation with Dess–Martin periodinane yielded 6a–b , 40 which were subjected to a reductive amination in the presence of 5 and sodium triacetoxyborohydride to produce 7a–b in 78–80% yield. Removal of the Cbz group by hydrogenation reaction from 7a – b led to 3a – b .…”

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confidence: 99%