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Molecular Diversity

, Volume 15, Issue 3, pp 677–686 | Cite as

Synthesis and properties of small interfering RNA duplexes carrying 5-ethyluridine residues

  • Montserrat Terrazas
  • Ramon Eritja
Full-Length Paper

Abstract

Oligoribonucleotides carrying 5-ethyluridine units were prepared using solid-phase phosphoramidite chemistry. The introduction of the tert-butyldimethylsilyl group at the 2′-OH position proceeded in good yield and very high 2′-regioselectivity. RNA duplexes carrying 5-ethyluridine either at the sense or the guide strands display RNAi activity comparable to or slightly better than that of unmodified RNA duplexes. Gene suppression experiments using luciferase targets in SH-SY5Y cells show that the ethyl group is generally well accepted at all positions although a small decrease in RNA interference activity is observed when one 5-ethylU residue is incorporated in the 3′ overhangs.

Keywords

SiRNA RNA interference 5-Ethyluridine Dual luciferase assay Oligonucleotide synthesis Solid-phase 

Abbreviations

as

Guide (antisense) strand

ACN

Acetonitrile

DIPEA

N,N-diisopropylethylamine

DMAP

N,N-dimethylaminopyridine

DMEM

Dulbecco’s modified Eagle medium

DMT

4,4′-Dimethoxytrityl

EtOAc

Ethyl acetate

FBS

Fetal bovine serum

HEPES

4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid

MeOH

Methanol

siRNA

Small interfering RNA

ss

Sense strand

TBAF

Tetrabutylammonium fluoride

TBDMS

tert-Butyldimethylsilyl

TEAA

Triethylammonium acetate

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Supplementary material

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Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  1. 1.Institute for Research in Biomedicine (IRB Barcelona)Institute for Advanced Chemistry of Catalonia (IQAC-CSIC), Networking Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN)BarcelonaSpain

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