Literature DB >> 8464037

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

A M Kawasaki1, M D Casper, S M Freier, E A Lesnik, M C Zounes, L L Cummins, C Gonzalez, P D Cook.   

Abstract

"Uniformly" modified phosphodiester or phosphorothioate oligonucleotides incorporating 2'-deoxy-2'-fluoroadenosine, -guanosine, -uridine, and -cytidine, reported herein for the first time, when hybridized with RNA afforded consistent additive enhancement of duplex stability without compromising base-pair specificity. CD spectra of the 2'-deoxy-2'-fluoro-modified oligonucleotides hybridized with RNA indicated that the duplex adopts a fully A-form conformation. The 2'-deoxy-2'-fluoro-modified oligonucleotides in phosphodiester form were not resistant to nucleases; however, the modified phosphorothioate oligonucleotides were highly nuclease resistant and retained exceptional binding affinity to the RNA targets. The stabilizing effects of the 2'-deoxy-2'-fluoro modifications on RNA-DNA duplexes were shown to be superior to those of the 2'-O-methylribo substitutions. RNA hybrid duplexes with uniformly 2'-deoxy-2'-fluoro-modified oligonucleotides did not support HeLa RNase H activity; however, incorporation of the modifications into "chimeric" oligonucleotides has been shown to activate mammalian RNase H. "Uniformly" modified 2'-deoxy-2'-fluoro phosphorothioate oligonucleotides afforded antisense molecules with (1) high binding affinity and selectivity for the RNA target and (2) stability toward nucleases.

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Year:  1993        PMID: 8464037     DOI: 10.1021/jm00059a007

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  106 in total

1.  Solution structure of a DNA duplex with a chiral alkyl phosphonate moiety.

Authors:  R Soliva; V Monaco; I Gómez-Pinto; N J Meeuwenoord; G A Marel; J H Boom; C González; M Orozco
Journal:  Nucleic Acids Res       Date:  2001-07-15       Impact factor: 16.971

2.  2'-Deoxy-2'-fluoro-beta-D-arabinonucleosides and oligonucleotides (2'F-ANA): synthesis and physicochemical studies.

Authors:  C J Wilds; M J Damha
Journal:  Nucleic Acids Res       Date:  2000-09-15       Impact factor: 16.971

Review 3.  Preclinical and clinical pharmacology of antisense oligonucleotides.

Authors:  E G Marcusson; B R Yacyshyn; W R Shanahan; N M Dean
Journal:  Mol Biotechnol       Date:  1999-08       Impact factor: 2.695

4.  Hybridization of 2'-ribose modified mixed-sequence oligonucleotides: thermodynamic and kinetic studies.

Authors:  A Sabahi; J Guidry; G B Inamati; M Manoharan; P Wittung-Stafshede
Journal:  Nucleic Acids Res       Date:  2001-05-15       Impact factor: 16.971

5.  Molecular requirements for degradation of a modified sense RNA strand by Escherichia coli ribonuclease H1.

Authors:  Daniel R Yazbeck; Kyung-Lyum Min; Masad J Damha
Journal:  Nucleic Acids Res       Date:  2002-07-15       Impact factor: 16.971

6.  NMR structure of an alpha-L-LNA:RNA hybrid: structural implications for RNase H recognition.

Authors:  Jakob T Nielsen; Paul C Stein; Michael Petersen
Journal:  Nucleic Acids Res       Date:  2003-10-15       Impact factor: 16.971

7.  Structural basis for the RNA binding selectivity of oligonucleotide analogues containing alkylsulfide internucleoside linkages and 2'-substituted 3'-deoxyribonucleosides.

Authors:  M J Damha; B Meng; D Wang; C G Yannopoulos; G Just
Journal:  Nucleic Acids Res       Date:  1995-10-11       Impact factor: 16.971

Review 8.  DNA and RNA derivatives to optimize distribution and delivery.

Authors:  Eric Wickstrom
Journal:  Adv Drug Deliv Rev       Date:  2015-04-22       Impact factor: 15.470

9.  Translation of 2'-modified mRNA in vitro and in vivo.

Authors:  H Aurup; A Siebert; F Benseler; D Williams; F Eckstein
Journal:  Nucleic Acids Res       Date:  1994-11-25       Impact factor: 16.971

10.  Characterization of fully 2'-modified oligoribonucleotide hetero- and homoduplex hybridization and nuclease sensitivity.

Authors:  L L Cummins; S R Owens; L M Risen; E A Lesnik; S M Freier; D McGee; C J Guinosso; P D Cook
Journal:  Nucleic Acids Res       Date:  1995-06-11       Impact factor: 16.971

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