Abstract
Peptide nucleic acids (PNAs) are polyamidic oligonucleotide analogs which have been described for the first time fifteen years ago and were immediately found to be excellent tools in binding DNA and RNA for diagnostics and gene regulation. Their use as therapeutic agents have been proposed since early studies and recent advancements in cellular delivery systems, and in the so called antigene strategy, makes them good candidates for drug development. The search for new chemical modification of PNAs is a very active field of research and new structures are continuously proposed. This review focuses on the recent advancements obtained by the modification of the PNA backbone, and their possible use in medicinal chemistry. In particular two classes of structurally biased PNAs are described in details: i) PNAs with acyclic structures and their helical preference, which is regulated by stereochemistry and ii) cyclic PNAs with preorganized structures, whose performances depend both on stereochemistry and on conformational constraints. The properties of these compounds are discussed in terms of affinity for nucleic acids, and several recent examples of their use in cellular or animal systems are presented.
Keywords: DNA binding ability, PNA-DNA duplex, Unmodified aminoethylglycine PNAs, mismatch discrimination, scrambled (SC) sequences
Current Topics in Medicinal Chemistry
Title: Peptide Nucleic Acids with a Structurally Biased Backbone: Effects of Conformational Constraints and Stereochemistry
Volume: 7 Issue: 7
Author(s): Roberto Corradini, Stefano Sforza, Tullia Tedeschi, Filbert Totsingan and Rosangela Marchelli
Affiliation:
Keywords: DNA binding ability, PNA-DNA duplex, Unmodified aminoethylglycine PNAs, mismatch discrimination, scrambled (SC) sequences
Abstract: Peptide nucleic acids (PNAs) are polyamidic oligonucleotide analogs which have been described for the first time fifteen years ago and were immediately found to be excellent tools in binding DNA and RNA for diagnostics and gene regulation. Their use as therapeutic agents have been proposed since early studies and recent advancements in cellular delivery systems, and in the so called antigene strategy, makes them good candidates for drug development. The search for new chemical modification of PNAs is a very active field of research and new structures are continuously proposed. This review focuses on the recent advancements obtained by the modification of the PNA backbone, and their possible use in medicinal chemistry. In particular two classes of structurally biased PNAs are described in details: i) PNAs with acyclic structures and their helical preference, which is regulated by stereochemistry and ii) cyclic PNAs with preorganized structures, whose performances depend both on stereochemistry and on conformational constraints. The properties of these compounds are discussed in terms of affinity for nucleic acids, and several recent examples of their use in cellular or animal systems are presented.
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Cite this article as:
Corradini Roberto, Sforza Stefano, Tedeschi Tullia, Totsingan Filbert and Marchelli Rosangela, Peptide Nucleic Acids with a Structurally Biased Backbone: Effects of Conformational Constraints and Stereochemistry, Current Topics in Medicinal Chemistry 2007; 7 (7) . https://dx.doi.org/10.2174/156802607780487759
DOI https://dx.doi.org/10.2174/156802607780487759 |
Print ISSN 1568-0266 |
Publisher Name Bentham Science Publisher |
Online ISSN 1873-4294 |
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