Keywords: Oligodeoxyribonucleotide, Agar Gel Electrophoresis, Article, Cell Survival, Chemical Structure, Chemistry, Circular Dichroism, Drug Effect, Electrospray Mass Spectrometry, Hela Cell, High Performance Liquid Chromatography, Human, Reverse Transcription Polymerase Chain Reaction, Synthesis, Ultraviolet Spectrophotometry, High Pressure Liquid, Molecular Structure, Reverse Transcriptase Polymerase Chain Reaction, Electrospray Ionization, Eukaryota, Chemical Synthesis, Pharmacology,
Affiliations: *** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini, CNR via Mezzocannone 16, I-80134 Napoli, Italy.
Department of Biological Sciences, Federico II University of Naples, via Mezzocannone 16, I-80134 Napoli, Italy
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Nielsen, P. E., Egholm, M., Berg, R. M., Buchardt, O., Sequence-selective recognition of DNA by strand displacement with thymine-substituted polyamide (1991) Science, 254, pp. 1497-1500
Gangamani, B. P., Kumar, V. A., Ganesh, K. N., Chiral analogues of Peptide Nucleic Acids: Synthesis of 4-aminoprolyl nucleic acids and DNA complementation studies using UV/CD spectroscopy (1999) Tetrahedron, 55, pp. 177-192
Roviello, G. N., Moccia, M., Sapio, R., Valente, M., Bucci, E. M., Castiglione, M., Pedone, C., Musumeci, D., Synthesis, characterization and hybridization studies of new nucleo-gamma-peptides based on diaminobutyric acid (2006) J. Pept. Sci., 12, pp. 829-835
Roviello, G. N., Musumeci, D., Moccia, M., Castiglione, M., Sapio, R., Valente, M., Bucci, E. M., Pedone, C., DabPNA: Design, synthesis and DNA binding studies (2007) Nucleosides, Nucleotides Nucleic Acids, 26, pp. 1307-1310
Foster, J. G., Cress, W. D., Wright, S. F., Hess, J. L., Intracellular localization of the neurotoxin 2, 4-Diaminobutyric Acid in Lathyrus sylvestris L. leaf tissue (1987) Plant Physiol., 83 (4), pp. 900-904
Meierhenrich, U. J., Mu oz Caro, G. M., Bredeh ft, J. H., Jessberger, E. K., Thiemann, W. H. P., Identification of diamino acids in the Murchison meteorite (2004) Proc. Natl. Acad. Sci. U. S. A., 101, pp. 9182-9186
Ray, A., Nord n, B., Peptide nucleic acid (PNA): Its medical and biotechnical applications and promise for the future (2000) FASEB J., 14, pp. 1041-1060
Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity
As part of our research on new oligonucleotide analogs for therapeutic and diagnostic use, here we explored the ability of an alternate dab-aegPNA oligomer to bind complementary natural nucleic acids. The alternate homothymine dab-aegPNA, synthesized following a chirally safe procedure and fully characterized by ESIMS and CD, was capable of forming hybrids with complementary DNA and RNA with enhanced thermal stability in comparison to natural oligomers, as shown by CD and UV spectroscopies. The stoichiometry of the complexes formed was determined by CD titration experiments that suggested triple helices formation. With respect to an analogous t(12) strand composed entirely of aegPNA, the chiral alternate t(12) oligomer presented an enhanced solubility in aqueous medium and did not form aggregates. Human serum stability assays performed on the new alternate oligomer evidenced a noteworthy enzymatic resistance. Moreover, the efficiency of dab-aegPNA in interfering with the reverse transcription of eukaryotic mRNA, and the absence of cytotoxic effects of the new analog were demonstrated, encouraging us to further study this chiral PNA analog in view of its possible in vivo/in vitro biotechnological applications.
Alternate dab-aegPNAs: synthesis, nucleic acid binding studies and biological activity
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