A novel multifunctionally labelled DNA probe bearing an intercalator and a fluorophore

Abstract

A 15-mer DNA labelled with a novel multifunctional fluorescent agent bearing acridine and fluorescein moieties is synthesized and the intensity of fluorescein-based fluorescence detected by the excitation of acridine is shown to be strongly affected by the DNA's secondary structure.

Fluorescence based strategies for genetic analysis

“…16). 99 The acridine is a donor in a FRET system, exciting the reporter, fluorescein. Upon hybridisation, the acridine becomes less efficient in energy transfer and the fluorescence of fluorescein is reduced (Fig.…”

Synthesis, spectroscopic studies and biological evaluation of acridine derivatives: The role of aggregation on the photodynamic efficiency

“…3 An abundant collection of acridine-based antiproliferative compounds can be found in the literature, with plethora of structural variants designed to enhance not only their binding abilities at the site of action but also the membrane crossing features and transportation properties of the molecules through the cellular millieu. 4 For example, Delcros et al have described a series of 9-substituted aminoacridines and amidoacridines linked to polyamine chains capable to inhibit the growth of L1210 and CHO cells with IC50 values in the micromolar range. 5 One strategy followed to enhance the DNA binding efficiency is the introduction of a second acridine moiety in the structure, which improves the stacking to the nucleic acids hence potentiates the biological effect.…”

Engineering of an electronically decoupled difluoroindacene-pyrene dyad possessing high affinity for DNA

“…For example, oligonucleotide probes carrying a fluorophore and an intercalating unit have been prepared that signal the presence of their target sequence by modulation of the fluorescence yield because intercalation curtails intramolecular excitation energy transfer. 3 Likewise, homogeneous fluorescence assay methods have been successfully applied to the detection of a specific sequence of oligopeptides and single base alterations. 4 Many different fluorescence markers for specific DNA sequences are now known, including cationic dyes 5 and aromatic polycycles such as benzopyrene, anthracene and pyrene.…”