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Literature DB >> 18515097

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

Mavurapu Satyanarayana¹, Suzanne G Rzuczek, Edmond J Lavoie, Daniel S Pilch, Angela Liu, Leroy F Liu, Joseph E Rice.

Abstract

The synthesis of a 24-membered macrocyclic hexaoxazole via ring-closing metathesis is described. The target compound selectively stabilizes G-quadruplex DNA with no detectable stabilization of duplex DNA. An MTT cytotoxicity assay indicated that this unsaturated macrocyclic hexaoxazole exhibits significant cytotoxicity toward P388, RPMI 8402, and KB3-1 cell lines with IC50 values of 45, 25, and 38 nM, respectively.

Entities: Chemical Disease

Mesh：

Substances：
Oligonucleotides
DNA

Year: 2008 PMID： 18515097 PMCID： PMC2518403 DOI： 10.1016/j.bmcl.2008.05.032

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

16 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

Review 4. DNA tetraplex-binding drugs: structure-selective targeting is critical for antitumour telomerase inhibition.

Authors: P J Perry; T C Jenkins
Journal: Mini Rev Med Chem Date: 2001-05 Impact factor: 3.862

5. Metathesis reactions in total synthesis.

Authors: K C Nicolaou; Paul G Bulger; David Sarlah
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

6. Structure of the human telomere in K+ solution: an intramolecular (3 + 1) G-quadruplex scaffold.

Authors: Kim Ngoc Luu; Anh Tuân Phan; Vitaly Kuryavyi; Laurent Lacroix; Dinshaw J Patel
Journal: J Am Chem Soc Date: 2006-08-02 Impact factor: 15.419

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

Authors: Gurpreet Singh Minhas; Daniel S Pilch; John E Kerrigan; Edmond J LaVoie; Joseph E Rice
Journal: Bioorg Med Chem Lett Date: 2006-06-02 Impact factor: 2.823

8. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors: M Scholl; S Ding; C W Lee; R H Grubbs
Journal: Org Lett Date: 1999-09-23 Impact factor: 6.005

5. 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

5 in total

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

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

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

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

Review 4. DNA tetraplex-binding drugs: structure-selective targeting is critical for antitumour telomerase inhibition.

5. Metathesis reactions in total synthesis.

6. Structure of the human telomere in K+ solution: an intramolecular (3 + 1) G-quadruplex scaffold.

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

8. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

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

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

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

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

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

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