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

Blaise Dumat 1 Elodie Faurel-Paul 1 Pauline Fornarelli 1 Nicolas Saettel 1 Germain Metgé 2 Céline Fiorini-Debuisschert 3 Fabrice Charra 3 Florence Mahuteau-Betzer 1 Marie-Paule Teulade-Fichou 1
1 CSVB - Conception, synthèse et vectorisation de biomolécules.
2 SPCSI - Service de Physique et de Chimie des Surfaces et Interfaces
3 LEPO - Laboratoire d'Electronique et nanoPhotonique Organique
SPEC - UMR3680 - Service de physique de l'état condensé, IRAMIS - Institut Rayonnement Matière de Saclay
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.
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Article dans une revue
Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2015, 14 (1), pp.358 - 370. 〈10.1039/C5OB02225H〉
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Soumis le : lundi 6 mars 2017 - 14:48:33
Dernière modification le : jeudi 15 mars 2018 - 15:06:42

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CEA | CURIE | DSM-IRAMIS | FNCLCC | IRAMIS-SPEC | SPCSI | PSL | UNIV-PARIS-SACLAY | CEA-DRF | CEA-UPSAY

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Blaise Dumat, Elodie Faurel-Paul, Pauline Fornarelli, Nicolas Saettel, Germain Metgé, et al.. Influence of the oxazole ring connection on the fluorescence of oxazoyl-triphenylamine biphotonic DNA probes. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2015, 14 (1), pp.358 - 370. 〈10.1039/C5OB02225H〉. 〈cea-01483796〉

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