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Issue 1, 2016
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Influence of the oxazole ring connection on the fluorescence of oxazoyl-triphenylamine biphotonic DNA probes

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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

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The article was received on 28 Oct 2015, accepted on 18 Nov 2015 and first published on 18 Nov 2015


Article type: Paper
DOI: 10.1039/C5OB02225H
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Citation: Org. Biomol. Chem., 2016,14, 358-370
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    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

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