19316-85-9Relevant academic research and scientific papers
Lipid-conjugated oligonucleotides via click chemistry efficiently inhibit hepatitis C virus translation
Godeau, Guilhem,Staedel, Cathy,Barthélémy, Phílippe
, p. 4374 - 4376 (2008)
Conjugation of a lipid moiety via click chemistry potentiates the cellular uptake of oligonucleotides and allows their intracellular delivery. These nontoxic lipid conjugates efficiently inhibit hepatitis C virus internal ribosome entry site (IRES)-mediated translation in human hepatic Huh7 cells. The biological activity of the lipid-conjugated oligonucleotides is not affected by the presence of serum.
Glycosyl-nucleoside fluorinated amphiphiles as components of nanostructured hydrogels
Godeau, Guilhem,Brun, Christophe,Arnion, Hélène,Staedel, Cathy,Barthélémy, Philippe
, p. 1012 - 1015 (2010)
The synthesis of two novel glycosyl-nucleoside fluorinated amphiphiles (GNFs) derived from the 2H,2H,3H,3H-perfluoro-undecanoyl hydrophobic chain is described. The GNF amphiphiles, which feature either β-d-glucopyranosyl or β-d-lactopyranosyl moieties linked to a thymine base via a 1,2,3 triazole linker, were prepared using a 'double click' chemistry route. Surface tension measurements, gelation properties, and TEM studies show that GNFs spontaneously assemble into supramolecular structures. Similarly to their hydrocarbon analogues (GNLs), the GNFs have unique gelation properties in water. A minimum hydrogelation concentration of 0.1% (w/w), was determined in the case of the β-d-glucopyranosyl derivative. Cell viability studies indicate that fluorocarbon GNF 5 was not toxic for human cells (Huh7), whereas hydrocarbon analogue GNL is toxic above 100 μm.
Microwave-assisted synthesis of a triazole-linked 3′-5′ dithymidine using click chemistry
Lucas, Romain,Neto, Virginie,Hadj Bouazza, Amel,Zerrouki, Rachida,Granet, Robert,Krausz, Pierre,Champavier, Yves
, p. 1004 - 1007 (2008)
Synthesis of a triazole-linked 3′-5′ thymidine dimer making use of 1,3-dipolar cycloaddition is described. The azido-precursor was obtained by regioselective chlorination of thymidine, followed by azidation. The second precursor, a propargyl derivative, was obtained by selective 3′-O-alkylation of thymidine. Two 'click systems' were compared to obtain the desired dimer. These reactions were performed by microwave irradiation.
Synthesis of bioconjugated sym -pentasubstituted corannulenes: Experimental and theoretical investigations of supramolecular architectures
Mattarella, Martin,Berstis, Laura,Baldridge, Kim K.,Siegel, Jay S.
, p. 115 - 128 (2014)
Applications of supramolecular architectures span a broad range of fields from medicinal chemistry to materials science and gas storage, making the design and synthesis of such structures a goal of high interest. The unique structural and symmetric proper
Synthesis and characterization of ferrocene-labeled oligodeoxynucleotides
Beilstein, Amy E.,Grinstaff, Mark W.
, p. 398 - 406 (2001)
Using a facile on-column derivatization procedure, oligodeoxynucleotides (ODNs) are labeled with a ferrocene derivative at specific sites. A Sonagashira cross-coupling reaction, using Pd(PPh3)4 and CuI, links ferrocene propargylamide
Photodimerisation of glycothymidines in solution and in micelles
Schwekendiek, Kirsten,Kobarg, Hauke,Daumlechner, Lena,Soennichsen, Frank D.,Lindhorst, Thisbe K.
, p. 9399 - 9401 (2011)
Glycothymidines were designed and synthesized as a new class of functional glycomimetics in which a photochemical [2+2] cycloaddition of the thymine moiety induces structural changes of carbohydrate presentation. To test if photodimerisation of these glycothymidines is feasible within an array of molecules, the photochemical reaction was investigated using NMR and NMR diffusion experiments in solution as well as in the supramolecular context of detergent micelles that mimic cellular membranes.
Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues
Batta, Gyula,Bege, Miklós,Bereczki, Ilona,Borbás, Anikó,Debreczeni, Nóra,Herczeg, Mihály,Herczegh, Pál
supporting information, p. 8711 - 8721 (2021/10/22)
The polyanionic phosphodiester backbone of nucleic acids contributes to high nuclease sensitivity and low cellular uptake and is therefore a major obstacle to the biological application of native oligonucleotides. Backbone modifications, particularly charge alterations is a proven strategy to provide artificial oligonucleotides with improved properties. Here, we describe the synthesis of a new type of oligonucleotide analogues consisting of a morpholino and a ribo- or deoxyribonucleoside in which the 5′-amino group of the nucleoside unit provides the nitrogen of the morpholine ring. The synthetic protocol is compatible with trityl and dimethoxytrityl protecting groups and azido functionality, and was extended to the synthesis of higher oligomers. The chimeras are positively charged in aqueous medium, due to theN-alkylated tertiary amine structure of the morpholino unit.
Design, Synthesis and Biological Evaluation of Novel Anthraniloyl-AMP Mimics as PQS Biosynthesis Inhibitors against Pseudomonas aeruginosa Resistance
Black, David StC,Das, Theerthankar,Kumar, Naresh,Rice, Scott A.,Sabir, Shekh,Subramoni, Sujatha
, (2020/07/25)
The Pseudomonas quinolone system (PQS) is one of the three major interconnected quorum sensing signaling systems in Pseudomonas aeruginosa. The virulence factors PQS and HHQ activate the transcription regulator PqsR (MvfR), which controls several activiti
Deoxynucleic Guanidines (DNG)- Modified Oligonucleotides and Methods of Synthesizing Deoxynucleic Guanidine Strands
-
Paragraph 0096; 0099, (2021/01/22)
Disclosed herein are spherical nucleic acids (SNAs) comprising oligonucleotides comprising one or more modified oligonucleotides, and methods of use thereof. Also disclosed are methods of synthesizing modified oligonucleotides for use in therapeutics, inc
Synthesis and biological assay of new 2’-deoxyuridine dimers containing a 1,2,3-triazole linker. Part I
Michalska, Lucyna,Wawrzyniak, Dariusz,Szymańska-Michalak, Agnieszka,Barciszewski, Jan,Boryski, Jerzy,Baraniak, Dagmara
, p. 218 - 235 (2019/01/04)
We describe a simple method for the synthesis of modified dinucleosides containing pyrimidine nucleoside analogues (2’-deoxyuridine, thymidine and 5-fluoro-2’-deoxyuridine). Six different dimers with a 1,2,3-triazole linkage were obtained by azide–alkyne
