title: Non-Nucleosidic Analogues of Polyaminonucleosides and Their Influence on Thermodynamic Properties of Derived Oligonucleotides.
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.
authors.affiliation: Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland. jabrzoza@ibch.poznan.pl.
authors.forename: Jolanta
authors.initials: J
authors.lastname: Brzezinska
authors.affiliation: Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland. markwt@ibch.poznan.pl.
authors.forename: Wojciech T
authors.initials: WT
authors.lastname: Markiewicz
mesh_terms: D002412:Cations; D060326:Chemistry Techniques, Synthetic; D004247:DNA / Q000737:chemistry*; D018716:Molecular Mimicry; D009705:Nucleosides / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D011700:Putrescine / Q000737:chemistry*; D013096:Spermine / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D002412:Cations; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D013096:Spermine; D004247:DNA; D011700:Putrescine
keywords: duplex DNA; non-nucleosidic analogue; oligonucleotide; polyaminonucleoside analogue; putrescine; spermine; thermodynamic stability