peptide nucleic acids

Summary

Summary: DNA analogs containing neutral amide backbone linkages composed of aminoethyl glycine units instead of the usual phosphodiester linkage of deoxyribose groups. Peptide nucleic acids have high biological stability and higher affinity for complementary DNA or RNA sequences than analogous DNA oligomers.

Top Publications

  1. Milano G, Musumeci D, Gaglione M, Messere A. An alternative strategy to synthesize PNA and DNA magnetic conjugates forming nanoparticle assembly based on PNA/DNA duplexes. Mol Biosyst. 2010;6:553-61 pubmed publisher
  2. Ciobanu M, Huang K, Daguer J, Barluenga S, Chaloin O, Schaeffer E, et al. Selection of a synthetic glycan oligomer from a library of DNA-templated fragments against DC-SIGN and inhibition of HIV gp120 binding to dendritic cells. Chem Commun (Camb). 2011;47:9321-3 pubmed publisher
    ..A prototypical example from the selected pairs was shown to have enhanced binding. A dendrimer incorporating the selected motifs inhibited gp120's binding to dendritic cells with higher efficiency than mannan. ..
  3. Wiessler M, Waldeck W, Pipkorn R, Kliem C, Lorenz P, Fleischhacker H, et al. Extension of the PNA world by functionalized PNA monomers eligible candidates for inverse Diels Alder Click Chemistry. Int J Med Sci. 2010;7:213-23 pubmed
    ..This system is not restricted to medicament material, but appropriate for the development of new and highly efficient drugs for a sustainable pharmacy. ..
  4. Gasser G, Sosniak A, Metzler Nolte N. Metal-containing peptide nucleic acid conjugates. Dalton Trans. 2011;40:7061-76 pubmed publisher
    b>Peptide Nucleic Acids (PNAs) are non-natural DNA/RNA analogues with favourable physico-chemical properties and promising applications. Discovered nearly 20 years ago, PNAs have recently re-gained quite a lot of attention...
  5. Torres A, Fabani M, Vigorito E, Williams D, Al Obaidi N, Wojciechowski F, et al. Chemical structure requirements and cellular targeting of microRNA-122 by peptide nucleic acids anti-miRs. Nucleic Acids Res. 2012;40:2152-67 pubmed publisher
    ..Our findings are valuable for further design of PNAs and other oligonucleotides as potent anti-miR agents...
  6. Fabbri E, Brognara E, Borgatti M, Lampronti I, Finotti A, Bianchi N, et al. miRNA therapeutics: delivery and biological activity of peptide nucleic acids targeting miRNAs. Epigenomics. 2011;3:733-45 pubmed publisher
    b>Peptide nucleic acids (PNAs) are DNA/RNA mimics extensively used for pharmacological regulation of gene expression in a variety of cellular and molecular systems, and they have been described as excellent candidates for antisense and ..
  7. Wancewicz E, Maier M, Siwkowski A, Albertshofer K, Winger T, Berdeja A, et al. Peptide nucleic acids conjugated to short basic peptides show improved pharmacokinetics and antisense activity in adipose tissue. J Med Chem. 2010;53:3919-26 pubmed publisher
    ..second PNA-conjugate targeting the murine insulin receptor primary transcript showed a similar activity profile, suggesting that short basic peptides can generally be used to effectively deliver peptide nucleic acids to adipose tissue.
  8. Nielsen P. Sequence-selective targeting of duplex DNA by peptide nucleic acids. Curr Opin Mol Ther. 2010;12:184-91 pubmed
    ..Such modifications have also resulted in new approaches to targeted gene repair and sequence-selective double-strand cleavage of genomic DNA. ..
  9. Corradini R, Sforza S, Tedeschi T, Totsingan F, Manicardi A, Marchelli R. Peptide nucleic acids with a structurally biased backbone. Updated review and emerging challenges. Curr Top Med Chem. 2011;11:1535-54 pubmed
    b>Peptide nucleic acids (PNAs) are polyamidic oligonucleotide analogues which have been described for the first time almost twenty years ago and were immediately found to be excellent tool in binding DNA and RNA for diagnostics and gene ..

More Information

Publications62

  1. Berthold P, Shiraishi T, Nielsen P. Cellular delivery and antisense effects of peptide nucleic acid conjugated to polyethyleneimine via disulfide linkers. Bioconjug Chem. 2010;21:1933-8 pubmed publisher
    ..Finally, the method can be easily modified to allow for co-conjugation of other small molecules in a high-throughput screening assay that does not require a purification step. ..
  2. Sforza S, Corradini R, Tedeschi T, Marchelli R. Food analysis and food authentication by peptide nucleic acid (PNA)-based technologies. Chem Soc Rev. 2011;40:221-32 pubmed publisher
    ..Finally, the future perspectives for the use of PNAs in food analysis will be briefly discussed according to the most recent developments. ..
  3. Zhang N, Appella D. Advantages of peptide nucleic acids as diagnostic platforms for detection of nucleic acids in resource-limited settings. J Infect Dis. 2010;201 Suppl 1:S42-5 pubmed publisher
    b>Peptide nucleic acids are a class of nondegradable oligonucleotide mimics that can be used as probes for nucleic acid sequences and could convey the necessary stability to be a diagnostic tool for use in a resource-limited setting...
  4. Hall L, Le Febre K, Deml S, Wohlfiel S, Wengenack N. Evaluation of the Yeast Traffic Light PNA FISH probes for identification of Candida species from positive blood cultures. J Clin Microbiol. 2012;50:1446-8 pubmed publisher
    ..The YTL provides rapid, reliable identification of the five common Candida species found in blood cultures. ..
  5. Shiraishi T, Nielsen P. Nanomolar cellular antisense activity of peptide nucleic acid (PNA) cholic acid ("umbrella") and cholesterol conjugates delivered by cationic lipids. Bioconjug Chem. 2012;23:196-202 pubmed publisher
    Limited cellular uptake and low bioavailability of peptide nucleic acids (PNAs) have restricted widespread use of PNAs as antisense/antigene agents for cells in culture and not least for in vivo applications...
  6. Shin D, Nam M, Yoon Y, Kim M. Membrane-based hybridization capture of intracellular peptide nucleic acid. Anal Biochem. 2010;399:135-7 pubmed publisher
    ..This method is useful for evaluating the quality of synthetic PNA and determining its intracellular localization. ..
  7. Hejazi M, Pournaghi Azar M, Ahour F. Electrochemical detection of short sequences of hepatitis C 3a virus using a peptide nucleic acid-assembled gold electrode. Anal Biochem. 2010;399:118-24 pubmed publisher
    ..7 x 10(-11)M with a relative standard deviation of 1.4% in phosphate buffer solution, pH 7.0. This sensor exhibits high reproducibility and could be used for detection of the target DNA for seven times after the regeneration process. ..
  8. Brognara E, Fabbri E, Aimi F, Manicardi A, Bianchi N, Finotti A, et al. Peptide nucleic acids targeting miR-221 modulate p27Kip1 expression in breast cancer MDA-MB-231 cells. Int J Oncol. 2012;41:2119-27 pubmed publisher
  9. Zengeya T, Gupta P, Rozners E. Triple-helical recognition of RNA using 2-aminopyridine-modified PNA at physiologically relevant conditions. Angew Chem Int Ed Engl. 2012;51:12593-6 pubmed publisher
    b>Peptide nucleic acids containing thymidine and 2-aminopyridine (M) nucleobases form stable and sequence-selective triple helices with double-stranded RNA at physiologically relevant conditions...
  10. Mu Y, Shen Z, Jeon B, Dai L, Zhang Q. Synergistic effects of anti-CmeA and anti-CmeB peptide nucleic acids on sensitizing Campylobacter jejuni to antibiotics. Antimicrob Agents Chemother. 2013;57:4575-7 pubmed publisher
    ..Antisense peptide nucleic acids (PNAs) targeting the three components of CmeABC were evaluated for inhibition of CmeABC expression...
  11. Brognara E, Fabbri E, Bianchi N, Finotti A, Corradini R, Gambari R. Molecular methods for validation of the biological activity of peptide nucleic acids targeting microRNAs. Methods Mol Biol. 2014;1095:165-76 pubmed publisher
    ..In this respect appealing molecules are based on peptide nucleic acids (PNAs), displaying a pseudo-peptide backbone composed of N-(2-aminoethyl)glycine units and found to be ..
  12. Stadler A, Sun D, Maye M, Van Der Lelie D, Gang O. Site-selective binding of nanoparticles to double-stranded DNA via peptide nucleic acid "invasion". ACS Nano. 2011;5:2467-74 pubmed publisher
    ..This method significantly broadens the molecular toolbox for constructing nanoscale systems by including the most conventional not yet utilized DNA motif, double helix DNA. ..
  13. Tonelli A, Tedeschi T, Germini A, Sforza S, Corradini R, Medici M, et al. Real time RNA transcription monitoring by Thiazole Orange (TO)-conjugated Peptide Nucleic Acid (PNA) probes: norovirus detection. Mol Biosyst. 2011;7:1684-92 pubmed publisher
    ..The probes showed to be specific even in the presence of high concentrations of non-target RNA. ..
  14. Zhang K, Fang H, Shen G, Taylor J, Wooley K. Well-defined cationic shell crosslinked nanoparticles for efficient delivery of DNA or peptide nucleic acids. Proc Am Thorac Soc. 2009;6:450-7 pubmed publisher
    ..Packaging and delivery of plasmid DNA, oligonucleotides, and peptide nucleic acids were studied by dynamic light scattering, transmission electron microscopy, gel electrophoresis, ..
  15. Rogers F, Lin S, Hegan D, Krause D, Glazer P. Targeted gene modification of hematopoietic progenitor cells in mice following systemic administration of a PNA-peptide conjugate. Mol Ther. 2012;20:109-18 pubmed publisher
    ..Therefore, our approach may provide new options for individualized therapies in the treatment of monogenic hematologic diseases such as sickle cell anemia and thalassemia. ..
  16. Bezer S, Rapireddy S, Skorik Y, Ly D, Achim C. Coordination-driven inversion of handedness in ligand-modified PNA. Inorg Chem. 2011;50:11929-37 pubmed publisher
    ..This finding could be used as a tool in the design of functional nucleic-acid based nanostructures. ..
  17. Gupta P, Muse O, Rozners E. Recognition of double-stranded RNA by guanidine-modified peptide nucleic acids. Biochemistry. 2012;51:63-73 pubmed publisher
    ..Recently, we discovered that short peptide nucleic acids (PNA) bind strongly and sequence selectively to a homopurine tract of double-helical RNA via formation of ..
  18. Pipkorn R, Wiessler M, Waldeck W, Hennrich U, Nokihara K, Beining M, et al. Improved synthesis strategy for peptide nucleic acids (PNA) appropriate for cell-specific fluorescence imaging. Int J Med Sci. 2012;9:1-10 pubmed
    ..After ligation to the modular peptide-based BioShuttle carrier, which was utilized to facilitate the delivery of the functional modules into the cells' cytoplasm, the modules were scrutinized. ..
  19. Englund E, Wang D, Fujigaki H, Sakai H, Micklitsch C, Ghirlando R, et al. Programmable multivalent display of receptor ligands using peptide nucleic acid nanoscaffolds. Nat Commun. 2012;3:614 pubmed publisher
    ..Using L-lysine ?-substituted peptide nucleic acids, the multivalent effects of an integrin antagonist were examined over a range of 1-45 ligands...
  20. Panyutin I, Onyshchenko M, Englund E, Appella D, Neumann R. Targeting DNA G-quadruplex structures with peptide nucleic acids. Curr Pharm Des. 2012;18:1984-91 pubmed
    ..To address these problems, nucleic acid mimics such as peptide nucleic acids (PNA) have been developed...
  21. Machado A, Almeida C, Carvalho A, Boyen F, Haesebrouck F, Rodrigues L, et al. Fluorescence in situ hybridization method using a peptide nucleic acid probe for identification of Lactobacillus spp. in milk samples. Int J Food Microbiol. 2013;162:64-70 pubmed publisher
    ..in concentrations at which these potential probiotic bacteria are considered to have an effective benefit on human health. ..
  22. Nielsen P. Gene targeting and expression modulation by peptide nucleic acids (PNA). Curr Pharm Des. 2010;16:3118-23 pubmed
    b>Peptide nucleic acids (PNA) are artificial structural mimics of nucleic acids capable of sequence specific hybridization to both RNA and DNA. Thus they have obvious potential as gene targeting agents for drug discovery approaches...
  23. El Sagheer A, Brown T. Click chemistry with DNA. Chem Soc Rev. 2010;39:1388-405 pubmed publisher
    ..In this critical review we describe some of the pioneering work that has been carried out in this area (78 references)...
  24. Hatamoto M, Ohashi A, Imachi H. Peptide nucleic acids (PNAs) antisense effect to bacterial growth and their application potentiality in biotechnology. Appl Microbiol Biotechnol. 2010;86:397-402 pubmed publisher
    b>Peptide nucleic acids (PNAs) are nucleic acid analogs having attractive properties such as quiet stability against nucleases and proteases, and they form strong complexes with complementary strands of DNA or RNA...
  25. Ali M, Neumann R, Ensinger W. Sequence-specific recognition of DNA oligomer using peptide nucleic acid (PNA)-modified synthetic ion channels: PNA/DNA hybridization in nanoconfined environment. ACS Nano. 2010;4:7267-74 pubmed publisher
    ..In this context, we envision that the single conical nanochannels functionalized with a PNA probe will provide a biosensing platform for the detection and discrimination of short single-stranded DNA oligomer of unknown sequence. ..
  26. Calabretta A, Wasserberg D, Posthuma Trumpie G, Subramaniam V, van Amerongen A, Corradini R, et al. Patterning of peptide nucleic acids using reactive microcontact printing. Langmuir. 2011;27:1536-42 pubmed publisher
    PNAs (peptide nucleic acids) have been immobilized onto surfaces in a fast, accurate way by employing reactive microcontact printing...
  27. Chen J, Peterson K, Iancu Rubin C, Bieker J. Design of embedded chimeric peptide nucleic acids that efficiently enter and accurately reactivate gene expression in vivo. Proc Natl Acad Sci U S A. 2010;107:16846-51 pubmed publisher
  28. Oh S, Ju Y, Park H. A highly effective and long-lasting inhibition of miRNAs with PNA-based antisense oligonucleotides. Mol Cells. 2009;28:341-5 pubmed publisher
    ..b>Peptide nucleic acids (PNAs) are artificial oligonucleotides constructed on a peptide-like backbone...
  29. Joshi R, Jha D, Su W, Engelmann J. Facile synthesis of peptide nucleic acids and peptide nucleic acid-peptide conjugates on an automated peptide synthesizer. J Pept Sci. 2011;17:8-13 pubmed publisher
    b>Peptide nucleic acids (PNAs) are DNA mimics with a neutral peptide backbone instead of the negatively charged sugar phosphates...
  30. Manicardi A, Calabretta A, Bencivenni M, Tedeschi T, Sforza S, Corradini R, et al. Affinity and selectivity of C2- and C5-substituted "chiral-box" PNA in solution and on microarrays. Chirality. 2010;22 Suppl 1:E161-72 pubmed publisher
    Two peptide nucleic acids (PNAs) containing three adjacent modified chiral monomers (chiral box) were synthesized...
  31. Ura Y, Beierle J, Leman L, Orgel L, Ghadiri M. Self-assembling sequence-adaptive peptide nucleic acids. Science. 2009;325:73-7 pubmed publisher
    ..covalent anchoring of nucleobase recognition units onto simple oligo-dipeptide backbones [thioester peptide nucleic acids (tPNAs)] and undergoes dynamic sequence modification in response to changing templates in solution...
  32. Hu J, Dodd D, Hudson R, Corey D. Cellular localization and allele-selective inhibition of mutant huntingtin protein by peptide nucleic acid oligomers containing the fluorescent nucleobase [bis-o-(aminoethoxy)phenyl]pyrrolocytosine. Bioorg Med Chem Lett. 2009;19:6181-4 pubmed publisher
    ..We observe elevated melting temperatures, localization to cellular compartments, and allele-selective inhibition of mutant huntingtin protein expression. ..
  33. Morgan M, Marlowe E, Della Latta P, Salimnia H, Novak Weekley S, Wu F, et al. Multicenter evaluation of a new shortened peptide nucleic acid fluorescence in situ hybridization procedure for species identification of select Gram-negative bacilli from blood cultures. J Clin Microbiol. 2010;48:2268-70 pubmed publisher
    ..There was 100% concordance between the two protocols for each assay (368 of 368 and 370 of 370 results) and 99.7% (367 of 368 and 369 of 370 results) agreement with routine laboratory techniques. ..
  34. Onyshchenko M, Gaynutdinov T, Englund E, Appella D, Neumann R, Panyutin I. Stabilization of G-quadruplex in the BCL2 promoter region in double-stranded DNA by invading short PNAs. Nucleic Acids Res. 2009;37:7570-80 pubmed publisher
    ..To induce G-quadruplex formation, we used short peptide nucleic acids (PNAs) that bind to the complementary C-rich strand...
  35. Avitabile C, Moggio L, Malgieri G, Capasso D, Di Gaetano S, Saviano M, et al. ? Sulphate PNA (PNA S): highly selective DNA binding molecule showing promising antigene activity. PLoS ONE. 2012;7:e35774 pubmed publisher
    b>Peptide Nucleic Acids (PNAs), nucleic acid analogues showing high stability to enzyme degradation and strong affinity and specificity of binding toward DNA and RNA are widely investigated as tools to interfere in gene expression...
  36. Torres A, Threlfall R, Gait M. Potent and sustained cellular inhibition of miR-122 by lysine-derivatized peptide nucleic acids (PNA) and phosphorothioate locked nucleic acid (LNA)/2'-O-methyl (OMe) mixmer anti-miRs in the absence of transfection agents. Artif DNA PNA XNA. 2011;2:71-8 pubmed
    ..LNA/OMe PS anti-miRs were the most potent anti-miR chemistry tested in this study, an ON chemistry that has been little exploited so far as anti-miR agents towards therapeutics. ..
  37. Calabretta A, Tedeschi T, Di Cola G, Corradini R, Sforza S, Marchelli R. Arginine-based PNA microarrays for APOE genotyping. Mol Biosyst. 2009;5:1323-30 pubmed publisher
    ..Six different hybridisation patterns related to six different genotypes in the APOE gene were found to be clearly distinct in microarray experiments, demonstrating the potential of this approach for highly specific genetic analysis. ..
  38. Briones C, Moreno M. Applications of peptide nucleic acids (PNAs) and locked nucleic acids (LNAs) in biosensor development. Anal Bioanal Chem. 2012;402:3071-89 pubmed publisher
    ..review of the current state of the art concerning the use of nucleic acid analogues, in particular peptide nucleic acids (PNA) and locked nucleic acids (LNA), for the development of high-performance affinity biosensors...
  39. Janssen P, Meeuwenoord N, van der Marel G, Jabbari Farouji S, van der Schoot P, Surin M, et al. ssPNA templated assembly of oligo(p-phenylenevinylene)s. Chem Commun (Camb). 2010;46:109-11 pubmed publisher
  40. Heemstra J, Liu D. Templated synthesis of peptide nucleic acids via sequence-selective base-filling reactions. J Am Chem Soc. 2009;131:11347-9 pubmed publisher
    ..These findings represent an experimental foundation for nonenzymatic information transfer through base filling. ..
  41. D Agata R, Corradini R, Ferretti C, Zanoli L, Gatti M, Marchelli R, et al. Ultrasensitive detection of non-amplified genomic DNA by nanoparticle-enhanced surface plasmon resonance imaging. Biosens Bioelectron. 2010;25:2095-100 pubmed publisher
    ..method which combines the nanoparticle-enhanced surface plasmon resonance imaging (SPRI) biosensing to the peptide nucleic acids (PNAs) improved selectivity and sensitivity in targeting complementary DNA sequences...
  42. Gasser G, Pinto A, Neumann S, Sosniak A, Seitz M, Merz K, et al. Synthesis, characterisation and bioimaging of a fluorescent rhenium-containing PNA bioconjugate. Dalton Trans. 2012;41:2304-13 pubmed publisher
    ..Furthermore, Re-PNA could be detected in living cells using fluorescent microscopy...
  43. Almeida C, Azevedo N, Fernandes R, Keevil C, Vieira M. Fluorescence in situ hybridization method using a peptide nucleic acid probe for identification of Salmonella spp. in a broad spectrum of samples. Appl Environ Microbiol. 2010;76:4476-85 pubmed publisher
  44. Li M, Zengeya T, Rozners E. Short peptide nucleic acids bind strongly to homopurine tract of double helical RNA at pH 5.5. J Am Chem Soc. 2010;132:8676-81 pubmed publisher
    ..Herein, we show that peptide nucleic acids, as short as six nucleobases, bind very strongly (K(a) > 10(7)) and sequence selectively to a ..
  45. Chow S, Suzuki S, Matsunaga T, Lavery S, Jeffs A, Takeyama H. Investigation on natural diets of larval marine animals using peptide nucleic acid-directed polymerase chain reaction clamping. Mar Biotechnol (NY). 2011;13:305-13 pubmed publisher
    ..japonicus and P. longipes bispinosus collected around Ryukyu Archipelago, Japan. ITS1 sequences of a wide variety of animals (Ctenophora, Cnidaria, Crustacea, Teleostei, Mollusca, and Chaetognatha) were detected...
  46. Svensen N, Diaz Mochon J, Bradley M. Decoding a PNA encoded peptide library by PCR: the discovery of new cell surface receptor ligands. Chem Biol. 2011;18:1284-9 pubmed publisher
    ..This approach to ligand discovery facilitates screening for differences in surface-receptor ligands and/or receptor expression between different cell types, and opens up a practical approach to PNA-tag amplification. ..
  47. Fabbri E, Manicardi A, Tedeschi T, Sforza S, Bianchi N, Brognara E, et al. Modulation of the biological activity of microRNA-210 with peptide nucleic acids (PNAs). ChemMedChem. 2011;6:2192-202 pubmed publisher
    ..The efficient delivery of anti-miR PNAs through a suitable peptide carrier (Rpep-PNA-a210) leads to the inhibition of miR-210 activity, altering the expression of miR-210-regulated erythroid functions. ..
  48. Pensato S, Saviano M, Bianchi N, Borgatti M, Fabbri E, Gambari R, et al. gamma-Hydroxymethyl PNAs: Synthesis, interaction with DNA and inhibition of protein/DNA interactions. Bioorg Chem. 2010;38:196-201 pubmed publisher
  49. Rapireddy S, Bahal R, Ly D. Strand invasion of mixed-sequence, double-helical B-DNA by ?-peptide nucleic acids containing G-clamp nucleobases under physiological conditions. Biochemistry. 2011;50:3913-8 pubmed publisher
    b>Peptide nucleic acids (PNAs) make up the only class of nucleic acid mimics developed to date that has been shown to be capable of invading double-helical B-form DNA...
  50. Tedeschi T, Calabretta A, Bencivenni M, Manicardi A, Corrado G, Caramante M, et al. A PNA microarray for tomato genotyping. Mol Biosyst. 2011;7:1902-7 pubmed publisher
    ..The strength and the limitations of such a system for SNP recognition are thoroughly discussed. ..
  51. Zengeya T, Li M, Rozners E. PNA containing isocytidine nucleobase: synthesis and recognition of double helical RNA. Bioorg Med Chem Lett. 2011;21:2121-4 pubmed publisher
    ..Compared to non-modified PNA, PNA1 had lower affinity for its RNA target. ..
  52. Mitra R, Ganesh K. PNAs grafted with (?/?, R/S)-aminomethylene pendants: regio and stereo specific effects on DNA binding and improved cell uptake. Chem Commun (Camb). 2011;47:1198-200 pubmed publisher
    ..These are efficiently taken up by cells, with ?(S-am) aeg-PNA being the best in all properties. ..
  53. Banack S, Metcalf J, Jiang L, Craighead D, Ilag L, Cox P. Cyanobacteria produce N-(2-aminoethyl)glycine, a backbone for peptide nucleic acids which may have been the first genetic molecules for life on Earth. PLoS ONE. 2012;7:e49043 pubmed publisher
    ..Before RNA-based organisms arose, peptide nucleic acids may have been used to transmit genetic information by the earliest forms of life on earth...