A fluorescent molecular rotor for the selective detection of the hybrid-conformation 22AG G-Quadruplex

Guralamatta Siddappa Ravi Kumara, Anup Pandtih, Young Jun Seo

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

G-quadruplex (G4) DNA plays a vital role in myriad biological process and is linked to several human diseases, including Alzheimer's disease. Probing G4s with fluorescent probes can provide a better understanding their mechanisms of action and of their roles in Nature. In this study we developed a quinolinium–vinylaniline molecular rotor probe, featuring a diethylaminosalicylaldehyde unit that could discriminate the hybrid-22AG G4 sequence selectively amongst other G4 sequences. This probe underwent a significant red-shift upon binding to the target G4 (broad 575 nm → sharp 630 nm) with enhanced fluorescence (up to 14-fold). We suspect that the vinylaniline unit of the molecular rotor, when bound to the hybrid-22 A G4, experienced restricted rotation, thereby undergoing enhanced intramolecular charge transfer. The presence of the diethylaminosalicylaldehyde moiety appeared to play a major role in the enhanced selectivity toward the 22AG G4.

Original languageEnglish
Article number128462
JournalBioorganic and Medicinal Chemistry Letters
Volume55
DOIs
Publication statusPublished - Jan 2022
Externally publishedYes

Keywords

  • Fluorescent Probe
  • G-quadruplex(G4)
  • Molecular Rotor
  • Quinolinium
  • Selective detection

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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