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Literature DB >> 16735121

Synthesis and G-quadruplex stabilizing properties of a series of oxazole-containing macrocycles.

Gurpreet Singh Minhas¹, Daniel S Pilch, John E Kerrigan, Edmond J LaVoie, Joseph E Rice.

Abstract

The synthesis of 24-membered macrocycles containing four, six, and seven oxazole moieties is described. Selected compounds were evaluated for their ability to specifically bind and stabilize G-quadruplex DNA and for cytotoxic activity. An unexpected oxidative cleavage reaction afforded a macrocyclic imide that was also evaluated for G-quadruplex stabilizing and cytotoxic activity.

Entities: Chemical

Mesh：

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Year: 2006 PMID： 16735121 DOI： 10.1016/j.bmcl.2006.05.038

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

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Cited

15 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. Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties.

Authors: Keisuke Iida; Masayuki Tera; Takatsugu Hirokawa; Kazuo Shin-Ya; Kazuo Nagasawa
Journal: J Nucleic Acids Date: 2010-05-24

Synthesis and G-quadruplex stabilizing properties of a series of oxazole-containing macrocycles.

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

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

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

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

5. Synthesis of Macrocyclic Hexaoxazole (6OTD) Dimers, Containing Guanidine and Amine Functionalized Side Chains, and an Evaluation of Their Telomeric G4 Stabilizing Properties.

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

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

8. Macrocyclic biphenyl tetraoxazoles: synthesis, evaluation as G-quadruplex stabilizers and cytotoxic activity.

9. G-quadruplex preferentially forms at the very 3' end of vertebrate telomeric DNA.

10. G-quadruplex DNA bound by a synthetic ligand is highly dynamic.