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Literature DB >> 23212868

Targeting loop adenines in G-quadruplex by a selective oxirane.

Filippo Doria¹, Matteo Nadai², Marco Folini³, Matteo Scalabrin⁴, Luca Germani¹, Giovanna Sattin², Mariella Mella¹, Manlio Palumbo⁵, Nadia Zaffaroni³, Daniele Fabris⁴, Mauro Freccero¹, Sara N Richter².

Abstract

Caught in the oxirane: Naphthalene diimides conjugated to a quinone methide and an oxirane have been synthesized and investigated as selective DNA G-quadruplex alkylating agents. The oxirane derivative generates a stable adduct with a G-quadruplex and shows selective alkylation of the loop adenines, as illustrated.

Entities: Chemical Disease Gene Mutation Species

Mesh：

Substances：
DNA
Adenine
Ethylene Oxide

Year: 2012 PMID： 23212868 PMCID： PMC3863998 DOI： 10.1002/chem.201203097

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

23 in total

1. Telomere end-binding proteins control the formation of G-quadruplex DNA structures in vivo.

Authors: Katrin Paeschke; Tomas Simonsson; Jan Postberg; Daniela Rhodes; Hans Joachim Lipps
Journal: Nat Struct Mol Biol Date: 2005-09-04 Impact factor: 15.369

Review 2. Fluorescence-based melting assays for studying quadruplex ligands.

Authors: Anne De Cian; Lionel Guittat; Markus Kaiser; Barbara Saccà; Samir Amrane; Anne Bourdoncle; Patrizia Alberti; Marie-Paule Teulade-Fichou; Laurent Lacroix; Jean-Louis Mergny
Journal: Methods Date: 2007-06 Impact factor: 3.608

Review 3. Making sense of G-quadruplex and i-motif functions in oncogene promoters.

Authors: Tracy A Brooks; Samantha Kendrick; Laurence Hurley
Journal: FEBS J Date: 2010-07-29 Impact factor: 5.542

4. Top-down characterization of nucleic acids modified by structural probes using high-resolution tandem mass spectrometry and automated data interpretation.

Authors: Katherine A Kellersberger; Eizadora Yu; Gary H Kruppa; Malin M Young; Daniele Fabris
Journal: Anal Chem Date: 2004-05-01 Impact factor: 6.986

5. Quinone methides tethered to naphthalene diimides as selective G-quadruplex alkylating agents.

Authors: Marco Di Antonio; Filippo Doria; Sara N Richter; Carolina Bertipaglia; Mariella Mella; Claudia Sissi; Manlio Palumbo; Mauro Freccero
Journal: J Am Chem Soc Date: 2009-09-16 Impact factor: 15.419

6. Substituted heterocyclic naphthalene diimides with unexpected acidity. Synthesis, properties, and reactivity.

Authors: Filippo Doria; Marco di Antonio; Michele Benotti; Daniela Verga; Mauro Freccero
Journal: J Org Chem Date: 2009-11-20 Impact factor: 4.354

7. Plasmodium telomeric sequences: structure, stability and quadruplex targeting by small compounds.

Authors: Anne De Cian; Philippe Grellier; Elisabeth Mouray; Delphine Depoix; Hélène Bertrand; David Monchaud; Marie-Paule Teulade-Fichou; Jean-Louis Mergny; Patrizia Alberti
Journal: Chembiochem Date: 2008-11-03 Impact factor: 3.164

8. Exclusive platination of loop adenines in the human telomeric G-quadruplex.

Authors: Hélène Bertrand; Sophie Bombard; David Monchaud; Eric Talbot; Aurore Guédin; Jean-Louis Mergny; Renate Grünert; Patrick J Bednarski; Marie-Paule Teulade-Fichou
Journal: Org Biomol Chem Date: 2009-06-01 Impact factor: 3.876

9. Prevalence of quadruplexes in the human genome.

Authors: Julian L Huppert; Shankar Balasubramanian
Journal: Nucleic Acids Res Date: 2005-05-24 Impact factor: 16.971

10. G-quadruplexes in promoters throughout the human genome.

Authors: Julian L Huppert; Shankar Balasubramanian
Journal: Nucleic Acids Res Date: 2006-12-14 Impact factor: 16.971

14 in total

1. Photoswitchable formation of a DNA interstrand cross-link by a coumarin-modified nucleotide.

Authors: Mohammad Mojibul Haque; Huabing Sun; Shuo Liu; Yinsheng Wang; Xiaohua Peng
Journal: Angew Chem Int Ed Engl Date: 2014-05-19 Impact factor: 15.336

2. Bifunctional cross-linking approaches for mass spectrometry-based investigation of nucleic acids and protein-nucleic acid assemblies.

Authors: M Scalabrin; S M Dixit; M M Makshood; C E Krzemien; Daniele Fabris
Journal: Methods Date: 2018-05-10 Impact factor: 3.608

Targeting loop adenines in G-quadruplex by a selective oxirane.

1. Telomere end-binding proteins control the formation of G-quadruplex DNA structures in vivo.

Review 2. Fluorescence-based melting assays for studying quadruplex ligands.

Review 3. Making sense of G-quadruplex and i-motif functions in oncogene promoters.

4. Top-down characterization of nucleic acids modified by structural probes using high-resolution tandem mass spectrometry and automated data interpretation.

5. Quinone methides tethered to naphthalene diimides as selective G-quadruplex alkylating agents.

6. Substituted heterocyclic naphthalene diimides with unexpected acidity. Synthesis, properties, and reactivity.

7. Plasmodium telomeric sequences: structure, stability and quadruplex targeting by small compounds.

8. Exclusive platination of loop adenines in the human telomeric G-quadruplex.

9. Prevalence of quadruplexes in the human genome.

10. G-quadruplexes in promoters throughout the human genome.

1. Photoswitchable formation of a DNA interstrand cross-link by a coumarin-modified nucleotide.

2. Bifunctional cross-linking approaches for mass spectrometry-based investigation of nucleic acids and protein-nucleic acid assemblies.

3. A dynamic G-quadruplex region regulates the HIV-1 long terminal repeat promoter.

4. Divalent Naphthalene Diimide Ligands Display High Selectivity for the Human Telomeric G-quadruplex in K⁺ Buffer.

5. Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity.

Review 6. May the Best Molecule Win: Competition ESI Mass Spectrometry.

7. A red-NIR fluorescent dye detecting nuclear DNA G-quadruplexes: in vitro analysis and cell imaging.

Review 8. G-quadruplexes and G-quadruplex ligands: targets and tools in antiviral therapy.

9. Probing of G-Quadruplex Structures via Ligand-Sensitized Photochemical Reactions in ^BrU-Substituted DNA.

10. Reprogramming the mechanism of action of chlorambucil by coupling to a G-quadruplex ligand.