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DNA mimics based on pyrrolidine and hydroxyproline

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Abstract

In recent years, a great number of analogues and mimics of nucleic acids have been developed with the aim of improving the physicochemical and biological properties of native oligonucleotides, in particular, to increase their affinity for nucleic acids, selectivity of action, and biological stability. This review summarizes the data on the synthesis and properties of DNA mimics, the analogues of peptide nucleic acids, which are the derivatives of pyrrolidine and hydroxyproline. Some physicochemical and biological properties of negatively charged mimics of this type are considered, which contain phosphonate residues in the back-bone and exhibit a high affinity for DNA and RNA, the selectivity of binding to nucleic acids, and stability in various biological systems. Examples of using these mimics as tools in molecular biology studies, in particular, functional genomics, are given. The prospects for their application in diagnosis and medicine are discussed.

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Abbreviations

GFP:

green fluorescent protein

Hyp:

trans-4-hydroxy-L-proline

NA:

nucleic acid

PNA:

peptide nucleic acid

pPNA:

phosphonate analogue of PNA

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Authors and Affiliations

  1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia

    V. A. Efimov, A. V. Aralov & O. G. Chakhmakhcheva

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  1. V. A. Efimov
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  2. A. V. Aralov
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  3. O. G. Chakhmakhcheva
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Original Russian Text © V.A. Efimov, A.V. Aralov, O.G. Chakhmakhcheva, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 6, pp. 725–746.

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Efimov, V.A., Aralov, A.V. & Chakhmakhcheva, O.G. DNA mimics based on pyrrolidine and hydroxyproline. Russ J Bioorg Chem 36, 663–683 (2010). https://doi.org/10.1134/S1068162010060014

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