Literature DB >> 8760882

Oligodeoxynucleotides containing C-7 propyne analogs of 7-deaza-2'-deoxyguanosine and 7-deaza-2'-deoxyadenosine.

C A Buhr1, R W Wagner, D Grant, B C Froehler.   

Abstract

The synthesis, hybridization properties and antisense activities of oligodeoxynucleotides (ODNs) containing 7-(1-propynyl)-7-deaza-2'-deoxyguanosine (pdG) and 7-(1-propynyl)-7-deaza-2'-deoxyadenosine (pdA) are described. The suitably protected nucleosides were synthesized and incorporated into ODNs. Thermal denaturation (Tm) of these ODNs hybridized to RNA demonstrates an increased stability relative to 7-unsubstituted deazapurine and unmodified ODN controls. Antisense inhibition by these ODNs was determined in a controlled microinjection assay and the results demonstrate that an ODN containing pdG is approximately 6 times more active than the unmodified ODN. 7-Propyne-7-deaza-2'-deoxyguanosine is a promising lead analog for the development of antisense ODNs with increased potency.

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Year:  1996        PMID： 8760882      PMCID： PMC146038          DOI： 10.1093/nar/24.15.2974

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN： 0305-1048            Impact factor:   16.971


  15 in total

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Authors:  F Seela; A Kehne
Journal:  Biochemistry       Date:  1987-04-21       Impact factor: 3.162

2.  A system for rapid DNA sequencing with fluorescent chain-terminating dideoxynucleotides.

Authors:  J M Prober; G L Trainor; R J Dam; F W Hobbs; C W Robertson; R J Zagursky; A J Cocuzza; M A Jensen; K Baumeister
Journal:  Science       Date:  1987-10-16       Impact factor: 47.728

3.  The structures of di-N-aroyl derivatives of adenosine and 2-aminopyridine.

Authors:  P A Lyon; C B Reese
Journal:  J Chem Soc Perkin 1       Date:  1974

4.  A serum-resistant cytofectin for cellular delivery of antisense oligodeoxynucleotides and plasmid DNA.

Authors:  J G Lewis; K Y Lin; A Kothavale; W M Flanagan; M D Matteucci; R B DePrince; R A Mook; R W Hendren; R W Wagner
Journal:  Proc Natl Acad Sci U S A       Date:  1996-04-16       Impact factor: 11.205

5.  Palindromic oligonucleotides containing 7-deaza-2'-deoxyguanosine: solid-phase synthesis of d[(p)GG*AATTCC] octamers and recognition by the endodeoxyribonuclease EcoRI.

Authors:  F Seela; H Driller
Journal:  Nucleic Acids Res       Date:  1986-03-11       Impact factor: 16.971

6.  Antisense gene inhibition by oligonucleotides containing C-5 propyne pyrimidines.

Authors:  R W Wagner; M D Matteucci; J G Lewis; A J Gutierrez; C Moulds; B C Froehler
Journal:  Science       Date:  1993-06-04       Impact factor: 47.728

7.  Cationic lipids enhance cellular uptake and activity of phosphorothioate antisense oligonucleotides.

Authors:  C F Bennett; M Y Chiang; H Chan; J E Shoemaker; C K Mirabelli
Journal:  Mol Pharmacol       Date:  1992-06       Impact factor: 4.436

8.  Dialkylformamidines: depurination resistant N6-protecting group for deoxyadenosine.

Authors:  B C Froehler; M D Matteucci
Journal:  Nucleic Acids Res       Date:  1983-11-25       Impact factor: 16.971

9.  Use of an antisense oligonucleotide to inhibit expression of a mutated human procollagen gene (COL1A1) in transfected mouse 3T3 cells.

Authors:  A Colige; B P Sokolov; P Nugent; R Baserga; D J Prockop
Journal:  Biochemistry       Date:  1993-01-12       Impact factor: 3.162

10.  An anti-parallel triple helix motif with oligodeoxynucleotides containing 2'-deoxyguanosine and 7-deaza-2'-deoxyxanthosine.

Authors:  J F Milligan; S H Krawczyk; S Wadwani; M D Matteucci
Journal:  Nucleic Acids Res       Date:  1993-01-25       Impact factor: 16.971
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  8 in total

1.  Propynyl groups in duplex DNA: stability of base pairs incorporating 7-substituted 8-aza-7-deazapurines or 5-substituted pyrimidines.

Authors:  Junlin He; Frank Seela
Journal:  Nucleic Acids Res       Date:  2002-12-15       Impact factor: 16.971

2.  Enhancing the catalytic repertoire of nucleic acids. II. Simultaneous incorporation of amino and imidazolyl functionalities by two modified triphosphates during PCR.

Authors:  T Gourlain; A Sidorov; N Mignet; S J Thorpe; S E Lee; J A Grasby; D M Williams
Journal:  Nucleic Acids Res       Date:  2001-05-01       Impact factor: 16.971

3.  The ups and downs of nucleic acid duplex stability: structure-stability studies on chemically-modified DNA:RNA duplexes.

Authors:  S M Freier; K H Altmann
Journal:  Nucleic Acids Res       Date:  1997-11-15       Impact factor: 16.971

4.  A new, but old, nucleoside analog: the first synthesis of 1-deaza-2'-deoxyguanosine and its properties as a nucleoside and as oligodeoxynucleotides.

Authors:  Naoshi Kojima; Kaori Inoue; Rina Nakajima-Shibata; Shun-ichi Kawahara; Eiko Ohtsuka
Journal:  Nucleic Acids Res       Date:  2003-12-15       Impact factor: 16.971

5.  The base pairing properties of 8-aza-7-deaza-2'-deoxyisoguanosine and 7-halogenated derivatives in oligonucleotide duplexes with parallel and antiparallel chain orientation.

Authors:  Frank Seela; Rita Kröschel
Journal:  Nucleic Acids Res       Date:  2003-12-15       Impact factor: 16.971

6.  Generation of DNA interstrand cross-links by post-synthetic reductive amination.

Authors:  Todor Angelov; Angelo Guainazzi; Orlando D Schärer
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

Review 7.  Modified Nucleic Acids: Expanding the Capabilities of Functional Oligonucleotides.

Authors:  Steven Ochoa; Valeria T Milam
Journal:  Molecules       Date:  2020-10-13       Impact factor: 4.411

8.  pH-Dependent mismatch discrimination of oligonucleotide duplexes containing 2'-deoxytubercidin and 2- or 7-substituted derivatives: protonated base pairs formed between 7-deazapurines and cytosine.

Authors:  Xiaohua Peng; Hong Li; Frank Seela
Journal:  Nucleic Acids Res       Date:  2006-10-27       Impact factor: 16.971
  8 in total

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