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Molecules 2015, 20(7), 12652-12669; doi:10.3390/molecules200712652

Non-Nucleosidic Analogues of Polyaminonucleosides and Their Influence on Thermodynamic Properties of Derived Oligonucleotides

Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland
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Academic Editors: Mahesh K. Lakshman and Fumi Nagatsugi
Received: 17 March 2015 / Revised: 8 July 2015 / Accepted: 9 July 2015 / Published: 13 July 2015
(This article belongs to the Special Issue Nucleoside Modifications)
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Abstract

The rationale for the synthesis of cationic modified nucleosides is higher expected nuclease resistance and potentially better cellular uptake due to an overall reduced negative charge based on internal charge compensation. Due to the ideal distance between cationic groups, polyamines are perfect counterions for oligodeoxyribonucleotides. We have synthesized non-nucleosidic analogues built from units that carry different diol structures instead of sugar residues and functionalized with polyamines. The non-nucleosidic analogues were attached as internal or 5′-terminal modifications in oligodeoxyribonucleotide strands. The thermodynamic studies of these polyaminooligonucleotide analogues revealed stabilizing or destabilizing effects that depend on the linker or polyamine used. View Full-Text
Keywords: polyaminonucleoside analogue; non-nucleosidic analogue; spermine; putrescine; oligonucleotide; duplex DNA; thermodynamic stability polyaminonucleoside analogue; non-nucleosidic analogue; spermine; putrescine; oligonucleotide; duplex DNA; thermodynamic stability
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Brzezinska, J.; Markiewicz, W.T. Non-Nucleosidic Analogues of Polyaminonucleosides and Their Influence on Thermodynamic Properties of Derived Oligonucleotides. Molecules 2015, 20, 12652-12669.

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