ArticleThe Journal of organic chemistry2009
Functionalized 2'-amino-alpha-L-LNA: directed positioning of intercalators for DNA targeting.
Article in The Journal of organic chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Hybridization Probes Featuring a Pyrenylpyridine C-Nucleoside or Its Palladacycle as a Fluorescent Sensor Moiety.Chembiochem : a European journal of chemical biology · 2025Article
- Alpha-l-Locked Nucleic Acid-Modified Antisense Oligonucleotides Induce Efficient Splice Modulation In Vitro.International journal of molecular sciences · 2020Article
- Recent Advances in Nucleic Acid Targeting Probes and Supramolecular Constructs Based on Pyrene-Modified Oligonucleotides.Molecules (Basel, Switzerland) · 2017Review
- Synthesis and characterization of oligodeoxyribonucleotides modified with 2'-thio-2'-deoxy-2'-S-(pyren-1-yl)methyluridine.Bioorganic & medicinal chemistry letters · 2015Article
- Recognition of double-stranded DNA using energetically activated duplexes with interstrand zippers of 1-, 2- or 4-pyrenyl-functionalized O2'-alkylated RNA monomers.Organic & biomolecular chemistry · 2014Article
- C5-alkynyl-functionalized α-L-LNA: synthesis, thermal denaturation experiments and enzymatic stability.The Journal of organic chemistry · 2014Article
- Synthesis and biophysical properties of C5-functionalized LNA (locked nucleic acid).The Journal of organic chemistry · 2014Article
- Synthesis and characterization of oligodeoxyribonucleotides modified with 2'-amino-α-L-LNA adenine monomers: high-affinity targeting of single-stranded DNA.The Journal of organic chemistry · 2013Article
- Sandwich assay for mixed-sequence recognition of double-stranded DNA: invader-based detection of targets specific to foodborne pathogens.Chemical communications (Cambridge, England) · 2013Article
- Identification and characterization of second-generation invader locked nucleic acids (LNAs) for mixed-sequence recognition of double-stranded DNA.The Journal of organic chemistry · 2013Article
- Invaders: Recognition of Double-Stranded DNA by Using Duplexes Modified with Interstrand Zippers of 2'-O-(Pyren-1-yl)methyl-ribonucleotides.Chembiochem : a European journal of chemical biology · 2013Article
- Structure Activity Relationships of α-L-LNA Modified Phosphorothioate Gapmer Antisense Oligonucleotides in Animals.Molecular therapy. Nucleic acids · 2012Article
- C2'-pyrene-functionalized triazole-linked DNA: universal DNA/RNA hybridization probes.The Journal of organic chemistry · 2012Article
- Pyrene-functionalized oligonucleotides and locked nucleic acids (LNAs): tools for fundamental research, diagnostics, and nanotechnology.Chemical Society reviews · 2011Review
- High-affinity DNA targeting using readily accessible mimics of N2'-functionalized 2'-amino-α-L-LNA.The Journal of organic chemistry · 2011Article
- A pyrenyl-PNA probe for DNA and RNA recognition: Fluorescence and UV absorption studies.Artificial DNA, PNA & XNA · 2010Article
- Invader LNA: efficient targeting of short double stranded DNA.Organic & biomolecular chemistry · 2010Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Chemically modified oligonucleotides are increasingly applied in nucleic acid based therapeutics and diagnostics. LNA (locked nucleic acid) and its diastereomer alpha-L-LNA are two promising examples thereof that exhibit increased thermal and enzymatic stability. Herein, the synthesis, biophysical characterization, and molecular modeling of N2'-functionalized 2'-amino-alpha-L-LNA is described. Chemoselective N2'-functionalization of protected amino alcohol 1 followed by phosphitylation afforded a structurally varied set of target phosphoramidites, which were incorporated into oligodeoxyribonucleotides. Incorporation of pyrene-functionalized building blocks such as 2'-N-(pyren-1-yl)carbonyl-2'-amino-alpha-L-LNA (monomer X) led to extraordinary increases in thermal affinity of up to +19.5 degrees C per modification against DNA targets in particular. In contrast, incorporation of building blocks with small nonaromatic N2'-functionalities such as 2'-N-acetyl-2'-amino-alpha-L-LNA (monomer V) had detrimental effects on thermal affinity toward DNA/RNA complements with decreases of as much as -16.5 degrees C per modification. Extensive thermal DNA selectivity, favorable entropic contributions upon duplex formation, hybridization-induced bathochromic shifts of pyrene absorption maxima and increases in circular dichroism signal intensity, and molecular modeling studies suggest that pyrene-functionalized 2'-amino-alpha-L-LNA monomers W-Y having short linkers between the bicyclic skeleton and the pyrene moiety allow high-affinity hybridization with DNA complements and precise positioning of intercalators in nucleic acid duplexes. This rigorous positional control has been utilized for the development of probes for emerging therapeutic and diagnostic applications focusing on DNA targeting.
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