Literature DB >> 18972052

Selectivity and affinity of DNA triplex forming oligonucleotides containing the nucleoside analogues 2'-O-methyl-5-(3-amino-1-propynyl)uridine and 2'-O-methyl-5-propynyluridine.

Hong Li1, Paul S Miller, Michael M Seidman.   

Abstract

Triplex forming oligonucleotides (TFOs) containing the nucleoside analogues 2'-O-methyl-5-propynyluridine (1) and 2'-O-methyl-5-(3-amino-1-propynyl)uridine (2) were synthesized. The affinity and selectivity of triplex formation by these TFOs were studied by gel shift analysis, T(m) value measurement, and association rate assays. The results show that the introduction of 1 and 2 into TFOs can improve the stability of the triplexes under physiological conditions. Optimized distribution of 1 or 2 in the TFOs combined with a cluster of contiguous nucleosides with 2'-aminoethoxy sugars resulted in formation of triplexes with further enhanced stability and improved selectivity.

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Year:  2008        PMID: 18972052      PMCID: PMC2603134          DOI: 10.1039/b810709b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  25 in total

1.  2'-O,4'-C-Methylene bridged nucleic acid (2',4'-BNA): synthesis and triplex-forming properties.

Authors:  S Obika; T Uneda; T Sugimoto; D Nanbu; T Minami; T Doi; T Imanishi
Journal:  Bioorg Med Chem       Date:  2001-04       Impact factor: 3.641

2.  2'-O-[2-(guanidinium)ethyl]-modified oligonucleotides: stabilizing effect on duplex and triplex structures.

Authors:  Thazha P Prakash; Ask Püschl; Elena Lesnik; Venkatraman Mohan; Valentina Tereshko; Martin Egli; Muthiah Manoharan
Journal:  Org Lett       Date:  2004-06-10       Impact factor: 6.005

3.  Stability and properties of double and triple helices: dramatic effects of RNA or DNA backbone composition.

Authors:  R W Roberts; D M Crothers
Journal:  Science       Date:  1992-11-27       Impact factor: 47.728

4.  Targeted gene knockout by 2'-O-aminoethyl modified triplex forming oligonucleotides.

Authors:  N Puri; A Majumdar; B Cuenoud; F Natt; P Martin; A Boyd; P S Miller; M M Seidman
Journal:  J Biol Chem       Date:  2001-06-01       Impact factor: 5.157

5.  Selectivity and affinity of triplex-forming oligonucleotides containing 2'-aminoethoxy-5-(3-aminoprop-1-ynyl)uridine for recognizing AT base pairs in duplex DNA.

Authors:  Sadie D Osborne; Vicki E C Powers; David A Rusling; Oliver Lack; Keith R Fox; Tom Brown
Journal:  Nucleic Acids Res       Date:  2004-08-18       Impact factor: 16.971

6.  Minimum number of 2'-O-(2-aminoethyl) residues required for gene knockout activity by triple helix forming oligonucleotides.

Authors:  Nitin Puri; Alokes Majumdar; Bernard Cuenoud; Francois Natt; Pierre Martin; Andre Boyd; Paul S Miller; Michael M Seidman
Journal:  Biochemistry       Date:  2002-06-18       Impact factor: 3.162

7.  Importance of clustered 2'-O-(2-aminoethyl) residues for the gene targeting activity of triple helix-forming oligonucleotides.

Authors:  Nitin Puri; Alokes Majumdar; Bernard Cuenoud; Paul S Miller; Michael M Seidman
Journal:  Biochemistry       Date:  2004-02-10       Impact factor: 3.162

Review 8.  The potential for gene repair via triple helix formation.

Authors:  Michael M Seidman; Peter M Glazer
Journal:  J Clin Invest       Date:  2003-08       Impact factor: 14.808

9.  Sequence and pH effects of LNA-containing triple helix-forming oligonucleotides: physical chemistry, biochemistry, and modeling studies.

Authors:  Bei-Wen Sun; B Ravindra Babu; Mads D Sørensen; Krystyna Zakrzewska; Jesper Wengel; Jian-Sheng Sun
Journal:  Biochemistry       Date:  2004-04-13       Impact factor: 3.162

10.  Poly(pyrimidine) . poly(purine) synthetic DNAs containing 5-methylcytosine form stable triplexes at neutral pH.

Authors:  J S Lee; M L Woodsworth; L J Latimer; A R Morgan
Journal:  Nucleic Acids Res       Date:  1984-08-24       Impact factor: 16.971

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  4 in total

1.  Optimized DNA-targeting using triplex forming C5-alkynyl functionalized LNA.

Authors:  Sujay P Sau; Pawan Kumar; Brooke A Anderson; Michael E Østergaard; Lee Deobald; Andrzej Paszczynski; Pawan K Sharma; Patrick J Hrdlicka
Journal:  Chem Commun (Camb)       Date:  2009-10-12       Impact factor: 6.222

2.  Targeting of an interrupted polypurine:polypyrimidine sequence in mammalian cells by a triplex-forming oligonucleotide containing a novel base analogue.

Authors:  A Semenyuk; E Darian; J Liu; A Majumdar; B Cuenoud; P S Miller; A D Mackerell; M M Seidman
Journal:  Biochemistry       Date:  2010-09-14       Impact factor: 3.162

3.  Invader LNA: efficient targeting of short double stranded DNA.

Authors:  Sujay P Sau; T Santhosh Kumar; Patrick J Hrdlicka
Journal:  Org Biomol Chem       Date:  2010-03-04       Impact factor: 3.876

4.  Fluorescent intercalator displacement replacement (FIDR) assay: determination of relative thermodynamic and kinetic parameters in triplex formation--a case study using triplex-forming LNAs.

Authors:  Sujay P Sau; Pawan Kumar; Pawan K Sharma; Patrick J Hrdlicka
Journal:  Nucleic Acids Res       Date:  2012-08-01       Impact factor: 16.971

  4 in total

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