Literature DB >> 18248989

Lysinyl macrocyclic hexaoxazoles: synthesis and selective G-quadruplex stabilizing properties.

Suzanne G Rzuczek1, Daniel S Pilch, Edmond J LaVoie, Joseph E Rice.   

Abstract

Macrocyclic hexaoxazoles having one or two lysinyl side chains in which the terminal nitrogen is either a primary amine, N,N-dimethylamine, or an acetamide have been synthesized. Sodium ion has been found to be beneficial to the macrocyclization step by acting as a template around which the linear polyoxazole can organize. Each of the targeted compounds selectivity stabilizes G-quadruplex versus duplex DNA. Compounds with one valine and one lysine residue display the best combination of G-quadruplex stabilizing ability with no detectable stabilization of duplex DNA.

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Year:  2008        PMID： 18248989      PMCID： PMC2262165          DOI： 10.1016/j.bmcl.2007.12.048

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  26 in total

Review 1.  G-quadruplexes as targets for drug design.

Authors:  L H Hurley; R T Wheelhouse; D Sun; S M Kerwin; M Salazar; O Y Fedoroff; F X Han; H Han; E Izbicka; D D Von Hoff
Journal:  Pharmacol Ther       Date:  2000-03       Impact factor: 12.310

Review 2.  Secondary DNA structures as molecular targets for cancer therapeutics.

Authors:  L H Hurley
Journal:  Biochem Soc Trans       Date:  2001-11       Impact factor: 5.407

3.  Telomestatin, a novel telomerase inhibitor from Streptomyces anulatus.

Authors:  K Shin-ya; K Wierzba; K Matsuo; T Ohtani; Y Yamada; K Furihata; Y Hayakawa; H Seto
Journal:  J Am Chem Soc       Date:  2001-02-14       Impact factor: 15.419

4.  Senescence induced by altered telomere state, not telomere loss.

Authors:  Jan Karlseder; Agata Smogorzewska; Titia de Lange
Journal:  Science       Date:  2002-03-29       Impact factor: 47.728

5.  Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular g-quadruplex.

Authors:  Mu-Yong Kim; Hariprasad Vankayalapati; Kazuo Shin-Ya; Konstanty Wierzba; Laurence H Hurley
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

6.  Direct evidence for a G-quadruplex in a promoter region and its targeting with a small molecule to repress c-MYC transcription.

Authors:  Adam Siddiqui-Jain; Cory L Grand; David J Bearss; Laurence H Hurley
Journal:  Proc Natl Acad Sci U S A       Date:  2002-08-23       Impact factor: 11.205

7.  Crystal structure of parallel quadruplexes from human telomeric DNA.

Authors:  Gary N Parkinson; Michael P H Lee; Stephen Neidle
Journal:  Nature       Date:  2002-05-26       Impact factor: 49.962

8.  Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor.

Authors:  A J Phillips; Y Uto; P Wipf; M J Reno; D R Williams
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

9.  Defining the mode, energetics and specificity with which a macrocyclic hexaoxazole binds to human telomeric G-quadruplex DNA.

Authors:  Christopher M Barbieri; Annankoil R Srinivasan; Suzanne G Rzuczek; Joseph E Rice; Edmond J LaVoie; Daniel S Pilch
Journal:  Nucleic Acids Res       Date:  2007-04-22       Impact factor: 16.971
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  7 in total

1.  A G-quadruplex stabilizer induces M-phase cell cycle arrest.

Authors:  Yuan-Chin Tsai; Haiyan Qi; Chao-Po Lin; Ren-Kuo Lin; John E Kerrigan; Suzanne G Rzuczek; Edmond J LaVoie; Joseph E Rice; Daniel S Pilch; Yi Lisa Lyu; Leroy F Liu
Journal:  J Biol Chem       Date:  2009-06-16       Impact factor: 5.157

2.  Ring-closing metathesis for the synthesis of a highly G-quadruplex selective macrocyclic hexaoxazole having enhanced cytotoxic potency.

Authors:  Mavurapu Satyanarayana; Suzanne G Rzuczek; Edmond J Lavoie; Daniel S Pilch; Angela Liu; Leroy F Liu; Joseph E Rice
Journal:  Bioorg Med Chem Lett       Date:  2008-05-15       Impact factor: 2.823

3.  Macrocyclic pyridyl polyoxazoles: selective RNA and DNA G-quadruplex ligands as antitumor agents.

Authors:  Suzanne G Rzuczek; Daniel S Pilch; Angela Liu; Leroy Liu; Edmond J LaVoie; Joseph E Rice
Journal:  J Med Chem       Date:  2010-05-13       Impact factor: 7.446

4.  "One ring to bind them all"-part I: the efficiency of the macrocyclic scaffold for g-quadruplex DNA recognition.

Authors:  David Monchaud; Anton Granzhan; Nicolas Saettel; Aurore Guédin; Jean-Louis Mergny; Marie-Paule Teulade-Fichou
Journal:  J Nucleic Acids       Date:  2010-05-24

5.  Targeting human telomeric G-quadruplex DNA with oxazole-containing macrocyclic compounds.

Authors:  Daniel S Pilch; Christopher M Barbieri; Suzanne G Rzuczek; Edmond J Lavoie; Joseph E Rice
Journal:  Biochimie       Date:  2008-04-04       Impact factor: 4.079

6.  Macrocyclic pyridyl polyoxazoles: structure-activity studies of the aminoalkyl side-chain on G-quadruplex stabilization and cytotoxic activity.

Authors:  Gifty Blankson; Suzanne G Rzuczek; Cody Bishop; Daniel S Pilch; Angela Liu; Leroy Liu; Edmond J Lavoie; Joseph E Rice
Journal:  Molecules       Date:  2013-09-26       Impact factor: 4.411

7.  Evaluation of the interaction between long telomeric DNA and macrocyclic hexaoxazole (6OTD) dimer of a G-quadruplex ligand.

Authors:  Keisuke Iida; Satoki Majima; Takahiro Nakamura; Hiroyuki Seimiya; Kazuo Nagasawa
Journal:  Molecules       Date:  2013-04-12       Impact factor: 4.411
  7 in total

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