Literature DB >> 18776540

Hetero-expanded purine nucleosides. Design, synthesis and preliminary biological activity.

Katherine L Seley-Radtke1, Zhibo Zhang, Orrette R Wauchope, Sarah C Zimmermann, Alexander Ivanov, Brent Korba.   

Abstract

Several thieno-expanded purine nucleoside analogues were synthesized for use as tools in ongoing investigations into nucleic acid structure and function in our laboratories. The inclusion of the thiophene ring system in the nucleoside endows the purine scaffold with advantages not previously available in other reported expanded purines. The synthesis and preliminary biological studies are reported herein.

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Year:  2008        PMID： 18776540      PMCID： PMC2785017          DOI： 10.1093/nass/nrn321

Source DB:  PubMed          Journal:  Nucleic Acids Symp Ser (Oxf)        ISSN： 0261-3166


  20 in total

1.  Polymerase recognition of unnatural base pairs.

Authors:  Chengzhi Yu; Allison A Henry; Floyd E Romesberg; Peter G Schultz
Journal:  Angew Chem Int Ed Engl       Date:  2002-10-18       Impact factor: 15.336

Review 2.  Beyond A, C, G and T: augmenting nature's alphabet.

Authors:  Allison A Henry; Floyd E Romesberg
Journal:  Curr Opin Chem Biol       Date:  2003-12       Impact factor: 8.822

3.  Probing minor groove recognition contacts by DNA polymerases and reverse transcriptases using 3-deaza-2'-deoxyadenosine.

Authors:  Cynthia L Hendrickson; Kevin G Devine; Steven A Benner
Journal:  Nucleic Acids Res       Date:  2004-04-23       Impact factor: 16.971

4.  Experimental Measurement of Aromatic Stacking Affinities in the Context of Duplex DNA.

Authors:  Kevin M Guckian; Barbara A Schweitzer; Rex X-F Ren; Charles J Sheils; Pamela L Paris; Deborah C Tahmassebi; Eric T Kool
Journal:  J Am Chem Soc       Date:  1996-08-28       Impact factor: 15.419

5.  Factors Contributing to Aromatic Stacking in Water: Evaluation in the Context of DNA.

Authors:  Kevin M Guckian; Barbara A Schweitzer; Rex X-F Ren; Charles J Sheils; Deborah C Tahmassebi; Eric T Kool
Journal:  J Am Chem Soc       Date:  2000-02-10       Impact factor: 15.419

6.  "Fleximers". Design and synthesis of a new class of novel shape-modified nucleosides(1).

Authors:  Katherine L Seley; Liang Zhang; Asmerom Hagos; Stephen Quirk
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

7.  Synthesis and antiviral activity of some acyclic and C-acyclic pyrrolo[2,3-d]pyrimidine nucleoside analogues.

Authors:  S M Bennett; N Nguyen-Ba; K K Ogilvie
Journal:  J Med Chem       Date:  1990-08       Impact factor: 7.446

8.  Synthesis and antitumor activity of thieno-separated tricyclic purines.

Authors:  K L Seley; P Januszczyk; A Hagos; L Zhang; D T Dransfield
Journal:  J Med Chem       Date:  2000-12-14       Impact factor: 7.446

9.  A new four-base genetic helix, yDNA, composed of widened benzopyrimidine-purine pairs.

Authors:  Alex H F Lee; Eric T Kool
Journal:  J Am Chem Soc       Date:  2005-03-16       Impact factor: 15.419

10.  Carbocyclic isoadenosine analogues of neplanocin A.

Authors:  Katherine L Seley; Sylvester L Mosley; Fanxing Zeng
Journal:  Org Lett       Date:  2003-11-13       Impact factor: 6.005
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  9 in total

1.  Synthesis of 2'-deoxy-9-deaza nucleosides using Heck methodology.

Authors:  Kartik Temburnikar; Kelin Brace; Katherine L Seley-Radtke
Journal:  J Org Chem       Date:  2013-07-05       Impact factor: 4.354

2.  Antiproliferative activities of halogenated thieno[3,2-d]pyrimidines.

Authors:  Kartik W Temburnikar; Sarah C Zimmermann; Nathaniel T Kim; Christina R Ross; Christopher Gelbmann; Christine E Salomon; Gerald M Wilson; Jan Balzarini; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem       Date:  2014-03-03       Impact factor: 3.641

3.  Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines.

Authors:  Kartik W Temburnikar; Christina R Ross; Gerald M Wilson; Jan Balzarini; Brian M Cawrse; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem       Date:  2015-06-16       Impact factor: 3.641

4.  Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2'-deoxy nucleoside analogues.

Authors:  Orrette R Wauchope; Cameron Johnson; Pasupathy Krishnamoorthy; Graciela Andrei; Robert Snoeck; Jan Balzarini; Katherine L Seley-Radtke
Journal:  Bioorg Med Chem       Date:  2012-03-12       Impact factor: 3.641

5.  Tricyclic 2'-C-modified nucleosides as potential anti-HCV therapeutics.

Authors:  Orrette R Wauchope; Matthew J Tomney; Joseph L Pepper; Brent E Korba; Katherine L Seley-Radtke
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

Review 6.  Artificial genetic sets composed of size-expanded base pairs.

Authors:  Malte Winnacker; Eric T Kool
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-07       Impact factor: 15.336

Review 7.  The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold.

Authors:  Katherine L Seley-Radtke; Mary K Yates
Journal:  Antiviral Res       Date:  2018-04-10       Impact factor: 10.103

Review 8.  The evolution of antiviral nucleoside analogues: A review for chemists and non-chemists. Part II: Complex modifications to the nucleoside scaffold.

Authors:  Mary K Yates; Katherine L Seley-Radtke
Journal:  Antiviral Res       Date:  2018-12-08       Impact factor: 10.103

9.  Synthesis and evaluation of Janus type nucleosides as potential HCV NS5B polymerase inhibitors.

Authors:  Longhu Zhou; Franck Amblard; Hongwang Zhang; Tamara R McBrayer; Mervi A Detorio; Tony Whitaker; Steven J Coats; Raymond F Schinazi
Journal:  Bioorg Med Chem Lett       Date:  2013-03-29       Impact factor: 2.823
  9 in total

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