Literature DB >> 12964158

Pyrenemethyl ara-uridine-2'-carbamate: a strong interstrand excimer in the major groove of a DNA duplex.

Natalia N Dioubankova1, Andrei D Malakhov, Dmitry A Stetsenko, Michael J Gait, Pavel E Volynsky, Roman G Efremov, Vladimir A Korshun.   

Abstract

The synthesis of new nucleoside derivatives, ara-uridine-2'-carbamates, and their incorporation into synthetic DNA oligomers is described. The modification directs ligands into the major groove of duplex DNA and somewhat destabilizes the duplexes of modified oligonucleotides with complementary DNA or RNA. In the case of pyrenemethyl carbamate modification in DNA-DNA duplexes, the destabilization is considerably reduced. The pyrenemethyl derivative also shows remarkable spectral properties: a "reversed" absorbance change for pyrene at 350 nm in the course of denaturation of the DNA duplex, as compared to the change seen in the nucleotide absorbance at 260 nm. This derivatization also causes pronounced sequence-dependent excimer formation in the major groove.

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Year:  2003        PMID: 12964158     DOI: 10.1002/cbic.200300678

Source DB:  PubMed          Journal:  Chembiochem        ISSN: 1439-4227            Impact factor:   3.164


  15 in total

1.  Impact of non-nucleotidic bulges on recognition of mixed-sequence dsDNA by pyrene-functionalized Invader probes.

Authors:  Dale C Guenther; Raymond G Emehiser; Allison Inskeep; Saswata Karmakar; Patrick J Hrdlicka
Journal:  Org Biomol Chem       Date:  2020-06-24       Impact factor: 3.876

Review 2.  DNA-multichromophore systems.

Authors:  Yin Nah Teo; Eric T Kool
Journal:  Chem Rev       Date:  2012-03-16       Impact factor: 60.622

3.  Recognition of double-stranded DNA using energetically activated duplexes with interstrand zippers of 1-, 2- or 4-pyrenyl-functionalized O2'-alkylated RNA monomers.

Authors:  Saswata Karmakar; Andreas S Madsen; Dale C Guenther; Bradley C Gibbons; Patrick J Hrdlicka
Journal:  Org Biomol Chem       Date:  2014-08-21       Impact factor: 3.876

Review 4.  Pyrene-functionalized oligonucleotides and locked nucleic acids (LNAs): tools for fundamental research, diagnostics, and nanotechnology.

Authors:  Michael E Østergaard; Patrick J Hrdlicka
Journal:  Chem Soc Rev       Date:  2011-04-13       Impact factor: 54.564

5.  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

6.  Synthesis and characterization of oligodeoxyribonucleotides modified with 2'-thio-2'-deoxy-2'-S-(pyren-1-yl)methyluridine.

Authors:  Brooke A Anderson; Patrick J Hrdlicka
Journal:  Bioorg Med Chem Lett       Date:  2015-07-07       Impact factor: 2.823

7.  Recognition of mixed-sequence DNA duplexes: design guidelines for invaders based on 2'-O-(pyren-1-yl)methyl-RNA monomers.

Authors:  Saswata Karmakar; Dale C Guenther; Patrick J Hrdlicka
Journal:  J Org Chem       Date:  2013-11-20       Impact factor: 4.354

8.  Functionalized 2'-amino-alpha-L-LNA: directed positioning of intercalators for DNA targeting.

Authors:  T Santhosh Kumar; Andreas S Madsen; Michael E Østergaard; Sujay P Sau; Jesper Wengel; Patrick J Hrdlicka
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

9.  Identification and characterization of second-generation invader locked nucleic acids (LNAs) for mixed-sequence recognition of double-stranded DNA.

Authors:  Sujay P Sau; Andreas S Madsen; Peter Podbevsek; Nicolai K Andersen; T Santhosh Kumar; Sanne Andersen; Rie L Rathje; Brooke A Anderson; Dale C Guenther; Saswata Karmakar; Pawan Kumar; Janez Plavec; Jesper Wengel; Patrick J Hrdlicka
Journal:  J Org Chem       Date:  2013-09-25       Impact factor: 4.354

10.  Nicked Invader probes: multistranded and sequence-unrestricted recognition of double-stranded DNA.

Authors:  Shiva P Adhikari; Saswata Karmakar; Patrick J Hrdlicka
Journal:  Org Biomol Chem       Date:  2022-02-02       Impact factor: 3.876

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