Comparison between properties of 2'-O,4'-C-ethylene-bridged nucleic acid (ENA) phosphorothioate oligonucleotides and N3'-P5' thiophosphoramidate oligonucleotides

Nucleosides, Nucleotides & Nucleic Acids
Makiko HorieShinya Tsutsumi

Abstract

Synthesis and properties of an oligonucleotide uniformly modified with 2'-O,4-C-ethylene-bridged nucleic acid (ENA) units were compared with those of GRN163, which is modified with N3'-P5' thiophosphoramidates, with the sequence targeting human telomerase RNA subunit. Although an ENA phosphorothioate oligonucleotide, ENA-13, could be synthesized using ENA phosphoramidites on a 100-mg scale, synthesis of GRN163 was very hard even on a 1-micomol scale. In view of both stability of the duplex formation with complementary RNA and the efficiency of cellular uptake by endocytosis, ENA-13 was superior to GRN163. These findings suggest that ENA-13 has useful properties for antisense therapeutic application.

References

Aug 11, 1992·Nucleic Acids Research·P BalagurumoorthyV Sasisekharan
Aug 1, 1996·Nucleic Acids Research·R G Schultz, S M Gryaznov
Apr 1, 1997·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·J W Shay, S Bacchetti
Feb 3, 1998·Nature Biotechnology·A Marshall, J Hodgson
Dec 10, 1999·Proceedings of the National Academy of Sciences of the United States of America·B HerbertD R Corey
Oct 18, 2000·Advanced Drug Delivery Reviews·S Dokka, Y Rojanasakul
May 17, 2001·Bioorganic & Medicinal Chemistry·S ObikaT Imanishi
Sep 21, 2001·Nucleosides, Nucleotides & Nucleic Acids·S GryaznovY Yamashita
Oct 24, 2001·The Journal of Organic Chemistry·Jeffrey S. NelsonBernard L. Hirschbein
Apr 16, 2003·European Journal of Biochemistry·Jens Kurreck
Apr 2, 2004·Biological & Pharmaceutical Bulletin·Makoto Koizumi
Apr 7, 2004·Advanced Drug Delivery Reviews·Sérgio SimõesMaria C Pedroso de Lima
Jun 8, 2004·Nucleic Acids Research·Antonio RandazzoLuciano Mayola

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Citations

Sep 15, 2007·Oligonucleotides·Miho Takagi-SatoMakoto Koizumi
Jun 9, 2007·Expert Opinion on Biological Therapy·Toshifumi YokotaKanneboyina Nagaraju
Sep 17, 2011·Chemistry & Biodiversity·Thazha P Prakash

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Methods Mentioned

BETA
Circular Dichroism
flow cytometry

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