title: Influence of the oxazole ring connection on the fluorescence of oxazoyl-triphenylamine biphotonic DNA probes.
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.
authors.affiliation: Institut Curie, PSL Research University, CNRS, INSERM, UMR9187/U1196, F-91405, Orsay, France. florence.mahuteau@curie.fr mp.teulade-fichou@curie.fr.
authors.forename: Blaise
authors.initials: B
authors.lastname: Dumat
authors.forename: Elodie
authors.initials: E
authors.lastname: Faurel-Paul
authors.forename: Pauline
authors.initials: P
authors.lastname: Fornarelli
authors.forename: Nicolas
authors.initials: N
authors.lastname: Saettel
authors.forename: Germain
authors.initials: G
authors.lastname: Metgé
authors.forename: Céline
authors.initials: C
authors.lastname: Fiorini-Debuisschert
authors.forename: Fabrice
authors.initials: F
authors.lastname: Charra
authors.forename: Florence
authors.initials: F
authors.lastname: Mahuteau-Betzer
authors.forename: Marie-Paule
authors.initials: MP
authors.lastname: Teulade-Fichou
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D015342:DNA Probes / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D017785:Photons
chemical_list: D000814:Aniline Compounds; D015342:DNA Probes; D005456:Fluorescent Dyes; D010080:Oxazoles; D004247:DNA