Jump to main content
Jump to site search

Issue 1, 2016
Previous Article Next Article

Influence of the oxazole ring connection on the fluorescence of oxazoyl-triphenylamine biphotonic DNA probes

Author affiliations

Abstract

On the basis of our previous work on DNA fluorophores derived from vinylpyridinium-triphenylamine, we explored the structure space around the electron-rich triphenylamine (TP) core by changing the vinyl bond to an oxazole ring. As 2,5-diaryloxazoles are known to be highly fluorescent and efficient two photon absorbers, we synthesized analogues with two different connections of the oxazole to the triphenylamine core: TP-Ox2Py and TP-Ox5Py sets. Since the benzimidazolium group was proven to be more effective in the TP series than the pyridinium, we also synthesized a TP-Ox5Bzim set. The TP-Ox5Py series retains the TP-Py properties: on/off behavior on DNA, good two-photon cross-section and bright staining of nuclear DNA by microscopy under both one or two-photon excitation. On the other hand, the TP-Ox2Py series does not display fluorescence upon binding to DNA. The TP-Ox5Bzim set is fluorescent even in the absence of DNA and displays lower affinity than the corresponding TP-Ox5Py. CD experiments and docking were performed to understand these different behaviors.

Graphical abstract: Influence of the oxazole ring connection on the fluorescence of oxazoyl-triphenylamine biphotonic DNA probes

Back to tab navigation

Supplementary files

Article information


Submitted
28 Oct 2015
Accepted
18 Nov 2015
First published
18 Nov 2015

Org. Biomol. Chem., 2016,14, 358-370
Article type
Paper
Author version available

Influence of the oxazole ring connection on the fluorescence of oxazoyl-triphenylamine biphotonic DNA probes

B. Dumat, E. Faurel-Paul, P. Fornarelli, N. Saettel, G. Metgé, C. Fiorini-Debuisschert, F. Charra, F. Mahuteau-Betzer and M. Teulade-Fichou, Org. Biomol. Chem., 2016, 14, 358
DOI: 10.1039/C5OB02225H

Social activity

Search articles by author

Spotlight

Advertisements