Click conjugation of 4'-C-modified oligonucleotides

2011 ◽  
Author(s):  
Anu Kiviniemi ◽  
Pasi Virta ◽  
Harri Lönnberg
Keyword(s):  
Modified Oligonucleotides

scholarly journals Triazole-Modified Nucleic Acids for the Application in Bioorganic and Medicinal Chemistry

Biomedicines ◽  
2021 ◽  
Vol 9 (6) ◽  
pp. 628
Author(s):  
Dagmara Baraniak ◽  
Jerzy Boryski
Keyword(s):  
Nucleic Acids ◽  
State Of The Art ◽  
Modified Oligonucleotides ◽  
Synthetic Genes ◽  
Chemically Modified ◽  
Amide Linkage ◽  
Dna And Rna ◽  
Modified Dna ◽  
Modified Nucleic Acids ◽  
Non Coding Rnas

This review covers studies which exploit triazole-modified nucleic acids in the range of chemistry and biology to medicine. The 1,2,3-triazole unit, which is obtained via click chemistry approach, shows valuable and unique properties. For example, it does not occur in nature, constitutes an additional pharmacophore with attractive properties being resistant to hydrolysis and other reactions at physiological pH, exhibits biological activity (i.e., antibacterial, antitumor, and antiviral), and can be considered as a rigid mimetic of amide linkage. Herein, it is presented a whole area of useful artificial compounds, from the clickable monomers and dimers to modified oligonucleotides, in the field of nucleic acids sciences. Such modifications of internucleotide linkages are designed to increase the hybridization binding affinity toward native DNA or RNA, to enhance resistance to nucleases, and to improve ability to penetrate cell membranes. The insertion of an artificial backbone is used for understanding effects of chemically modified oligonucleotides, and their potential usefulness in therapeutic applications. We describe the state-of-the-art knowledge on their implications for synthetic genes and other large modified DNA and RNA constructs including non-coding RNAs.

Binding of Chemically-Modified Oligonucleotides to the Double-Stranded Stem of an RNA Hairpin

1999 ◽  
Vol 18 (6-7) ◽  
pp. 1647-1650
Author(s):  
Karine Aupeix ◽  
Jean-Jacques Toulmé
Keyword(s):  
Modified Oligonucleotides ◽  
Chemically Modified ◽  
Rna Hairpin

Cholesterol-Modified Oligonucleotides as Internal Reaction Controls during DNA-Encoded Chemical Library Synthesis

2021 ◽  
Vol 32 (4) ◽  
pp. 667-671
Author(s):  
Guanyu Yang ◽  
Dou He ◽  
Yijun Zhu ◽  
Weiwei Zhu ◽  
Yang Tan ◽  
...  
Keyword(s):  
Modified Oligonucleotides ◽  
Library Synthesis ◽  
Chemical Library ◽  
Internal Reaction

Synthesis and Selective Radical Cleavage of C-4′-Modified Oligonucleotides

1994 ◽  
Vol 33 (18) ◽  
pp. 1861-1863 ◽  
Author(s):  
Bernd Giese ◽  
Adrian Dussy ◽  
Cornelius Elie ◽  
Peter Erdmann ◽  
Urs Schwitter
Keyword(s):  
Modified Oligonucleotides ◽  
Radical Cleavage

N,N′-Bis-(2-(cyano)ethoxycarbonyl)-2-methyl-2-thiopseudourea: A Guanylating Reagent for Synthesis of 2′-O-[2-(Guanidinium)ethyl]-Modified Oligonucleotides

2007 ◽  
Vol 26 (2) ◽  
pp. 149-159 ◽  
Author(s):  
Thazha P. Prakash ◽  
Ask Püschl ◽  
Muthiah Manoharan
Keyword(s):  
Modified Oligonucleotides

Reaction of S-geranyl-2-thiouracil modified oligonucleotides with alkyl amines leads to the N2-alkyl isocytosine derivatives

2017 ◽  
Vol 15 (25) ◽  
pp. 5332-5336 ◽  
Author(s):  
Grazyna Leszczynska ◽  
Klaudia Sadowska ◽  
Malgorzata Sierant ◽  
Milena Sobczak ◽  
Barbara Nawrot ◽  
...  
Keyword(s):  
Modified Oligonucleotides ◽  
Alkyl Amine ◽  
Alkyl Amines ◽  
Alkaline Conditions

The yield of the synthesis ofS-geranylated oligomers depends on the alkaline conditions of oligomer deprotection; a routinely used alkyl amine protocol deliversN2-alkylisocytosine-modified side products.

scholarly journals Correlating In Vitro Splice Switching Activity With Systemic In Vivo Delivery Using Novel ZEN-modified Oligonucleotides

2014 ◽  
Vol 3 ◽  
pp. e212 ◽  
Author(s):  
Suzan M Hammond ◽  
Graham McClorey ◽  
Joel Z Nordin ◽  
Caroline Godfrey ◽  
Sofia Stenler ◽  
...  
Keyword(s):  
Modified Oligonucleotides ◽  
Switching Activity ◽  
In Vivo Delivery

Manufacturing and Analytical Processes for 2'-O-(2-Methoxyethyl)-Modified Oligonucleotides

2007 ◽  
pp. 401-434 ◽  
Author(s):  
Daniel Capaldi ◽  
Anthony Scozzari
Keyword(s):  
Modified Oligonucleotides

Synthesis and properties of GuNA purine/pyrimidine nucleosides and oligonucleotides

2020 ◽  
Vol 18 (46) ◽  
pp. 9461-9472
Author(s):  
Shinji Kumagai ◽  
Hiroaki Sawamoto ◽  
Tomo Takegawa-Araki ◽  
Yuuki Arai ◽  
Shuhei Yamakoshi ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Modified Oligonucleotides ◽  
Robust Method ◽  
Facile Synthesis ◽  
Pyrimidine Nucleosides ◽  
Thymine Adenine ◽  
Purine Pyrimidine

Facile synthesis of GuNA (guanidine-bridged nucleic acid) phosphoramidites bearing thymine, adenine, guanine, and 5-methylcytosine nucleobases and a robust method for the preparation of GuNA-modified oligonucleotides are described.

scholarly journals Synthesis and properties of oligonucleotides modified with an N-methylguanidine-bridged nucleic acid (GuNA[Me]) bearing adenine, guanine, or 5-methylcytosine nucleobases

2021 ◽  
Vol 17 ◽  
pp. 622-629
Author(s):  
Naohiro Horie ◽  
Takao Yamaguchi ◽  
Shinji Kumagai ◽  
Satoshi Obika
Keyword(s):  
Nucleic Acid ◽  
Binding Affinity ◽  
Antisense Oligonucleotides ◽  
Modified Oligonucleotides ◽  
Biophysical Properties ◽  
Chemical Modifications ◽  
Antisense Technology ◽  
Strong Affinity ◽  
The Stability

Chemical modifications have been extensively used for therapeutic oligonucleotides because they strongly enhance the stability against nucleases, binding affinity to the targets, and efficacy. We previously reported that oligonucleotides modified with an N-methylguanidine-bridged nucleic acid (GuNA[Me]) bearing the thymine (T) nucleobase show excellent biophysical properties for applications in antisense technology. In this paper, we describe the synthesis of GuNA[Me] phosphoramidites bearing other typical nucleobases including adenine (A), guanine (G), and 5-methylcytosine (mC). The phosphoramidites were successfully incorporated into oligonucleotides following the method previously developed for the GuNA[Me]-T-modified oligonucleotides. The binding affinity of the oligonucleotides modified with GuNA[Me]-A, -G, or -mC toward the complementary single-stranded DNAs or RNAs was systematically evaluated. All of the GuNA[Me]-modified oligonucleotides were found to have a strong affinity for RNAs. These data indicate that GuNA[Me] could be a useful modification for therapeutic antisense oligonucleotides.

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