Synthesis and Biophysical Evaluation of 2′,4′-Constrained 2′O-Methoxyethyl and 2′,4′-Constrained 2′O-Ethyl Nucleic Acid Analogues

PP Seth, G Vasquez, CA Allerson… - The Journal of …, 2010 - ACS Publications
We have recently shown that combining the structural elements of 2′ O-methoxyethyl
(MOE) and locked nucleic acid (LNA) nucleosides yielded a series of nucleoside …

Design, synthesis and evaluation of constrained methoxyethyl (cMOE) and constrained ethyl (cEt) nucleoside analogs

PP Seth, A Siwkowski, CR Allerson… - Nucleic Acids …, 2008 - academic.oup.com
Antisense drug discovery technology is a powerful method to modulate gene expression in
animals and represents a novel therapeutic platform. 1 We have previously demonstrated …

Re-engineering RNA molecules into therapeutic agents

M Egli, M Manoharan - Accounts of chemical research, 2019 - ACS Publications
Conspectus Efforts to chemically modify nucleic acids got underway merely a decade after
the discovery of the DNA double helix and initially targeted nucleosides and nucleotides …

2′-O, 4′-C-ethylene-bridged nucleic acids (ENA): highly nuclease-resistant and thermodynamically stable oligonucleotides for antisense drug

K Morita, C Hasegawa, M Kaneko, S Tsutsumi… - Bioorganic & Medicinal …, 2002 - Elsevier
To develop antisense oligonucleotides, novel nucleosides, 2′-O, 4′-C-ethylene
nucleosides and their corresponding phosphoramidites, were synthesized as building …

Correlating Structure and Stability of DNA Duplexes with Incorporated 2'-O-Modified RNA Analogues,

V Tereshko, S Portmann, EC Tay, P Martin, F Natt… - Biochemistry, 1998 - ACS Publications
Chemically modified nucleic acids are currently being evaluated as potential antisense
compounds for therapeutic applications. 2 '-O-Ethylene glycol substituted …

Synthesis of Novel 3'-C-Methylene Thymidine and 5-Methyluridine/Cytidine H-Phosphonates and Phosphonamidites for New Backbone Modification of …

H An, T Wang, MA Maier, M Manoharan… - The Journal of …, 2001 - ACS Publications
Novel 5 '-O-DMT-and MMT-protected 3 '-C-methylene-modified thymidine, 5-methyluridine,
and 5-methylcytidine H-phosphonates 1− 7 with O-methyl, fluoro, hydrogen, and O-(2 …

An LNA-amide modification that enhances the cell uptake and activity of phosphorothioate exon-skipping oligonucleotides

YR Baker, C Thorpe, J Chen, LM Poller, L Cox… - Nature …, 2022 - nature.com
Oligonucleotides that target mRNA have great promise as therapeutic agents for life-
threatening conditions but suffer from poor bioavailability, hence high cost. As currently …

Uniformly modified 2'-deoxy-2'-fluoro-phosphorothioate oligonucleotides as nuclease-resistant antisense compounds with high affinity and specificity for RNA targets

AM Kawasaki, MD Casper, SM Freier… - Journal of medicinal …, 1993 - ACS Publications
“Uniformly” modified phosphodiester or phosphorothioate oligonucleotides incorporating 2'-
deoxy-2'-fluoroadenosine,-guanosine,-uridine, and-cytidine, reported herein for the first time …

Synthesis, improved antisense activity and structural rationale for the divergent RNA affinities of 3′-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified …

M Egli, PS Pallan, CR Allerson… - Journal of the …, 2011 - ACS Publications
The synthesis, biophysical, structural, and biological properties of both isomers of 3′-fluoro
hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides are reported …

Synthesis of phosphate-methylated DNA fragments using 9-fluorenylmethoxycarbonyl as transient base protecting group

LH Koole, HM Moody, NLHL Broeders… - The Journal of …, 1989 - ACS Publications
Synthesis of the phosphate-methylated DNA dinucleotidesd (CpG)(4), d (GpC)(5), d
(ApC)(6), d (ApT)(7), d (ApA)(8), and d (CpC)(9) is described. The 9 …