Affinity and selectivity of C2- and C5-substituted 'chiral-box' PNA in solution and on microarrays
| Autor: | Tullia Tedeschi, Roberto Corradini, Mariangela Bencivenni, Stefano Sforza, Alessandro Calabretta, Alex Manicardi, Rosangela Marchelli |
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| Rok vydání: | 2010 |
| Předmět: |
Models
Molecular Peptide Nucleic Acids Pharmacology chemistry.chemical_classification Circular dichroism Molecular Structure Chemistry Oligonucleotide Stereochemistry Circular Dichroism Organic Chemistry Stereoisomerism Peptide Microarray Analysis Catalysis Analytical Chemistry Solutions chemistry.chemical_compound Monomer Drug Discovery Nucleic acid Chirality (chemistry) Selectivity Spectroscopy DNA |
| Zdroj: | Chirality. 22:E161-E172 |
| ISSN: | 0899-0042 |
| DOI: | 10.1002/chir.20865 |
| Popis: | Two peptide nucleic acids (PNAs) containing three adjacent modified chiral monomers (chiral box) were synthesized. The chiral monomers contained either a C2- or a C5-modified backbone, synthesized starting from D- and L-arginine, respectively (2D- and 5L-PNA). The C2-modified chiral PNA was synthesized using a submonomeric strategy to avoid epimerization during solid-phase synthesis, whereas for the C5-derivative, the monomers were first obtained and then used in solid-phase synthesis. The melting temperature of these PNA duplexes formed with the full-match or with single-mismatch DNA were measured both by UV and by CD spectroscopy and compared with the unmodified PNA. The 5L-chiral-box-PNA showed the highest Tm with full-match DNA, whereas the 2D-chiral-box-PNA showed the highest sequence selectivity. The PNA were spotted on microarray slides and then hybridized with Cy5-labeled full match and mismatched oligonucleotides. The results obtained showed a signal intensity in the order achiral >2D-chiral box >5L-chiral box, whereas the full-match/mismatch selectivity was higher for the 2D chiral box PNA. Chirality, 2010. © 2010 Wiley-Liss, Inc. |
| Databáze: | OpenAIRE |
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