Quest for novel fluorogenic xanthene dyes: Synthesis, spectral properties and stability of 3-imino-3H-xanthen-6-amine (pyronin) and its silicon analog - Université de Bourgogne Accéder directement au contenu
Article Dans Une Revue Tetrahedron Letters Année : 2018

Quest for novel fluorogenic xanthene dyes: Synthesis, spectral properties and stability of 3-imino-3H-xanthen-6-amine (pyronin) and its silicon analog

Résumé

To expand the range of primary aniline fluorophores available and suitable for the design of fluorogenic protease probes, the synthesis of 3-imino-3H-xanthen-6-amine (known as pyronin) and its silicon analog (Si-pyronin) was explored and presented here. A comprehensive photophysical study of these two fluorescent anilines, confirms the effectiveness of the heteroatom-substitution approach (O®SiMe2) to yield dramatic red-shiftsin absorption and fluorescence maxima of the xanthene scaffold (+85nm). However, it also revealed its adverse effect on the hydrolytic stability of the Si-pyronin, especially at physiological pH.The pro-fluorescent character and utility of these two fluorogenic (hetero) xanthene dyes are also proved by the preparation and in vitro validation of activatable fluorescence "turn-on" probes for penicillin G acylase (PGA).
Fichier principal
Vignette du fichier
Publication-TL-O-vs-Si-pyronin-body-text-revised-07112018.pdf (1.06 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)
Loading...

Dates et versions

hal-02168864 , version 1 (29-06-2019)

Identifiants

Citer

Anthony Romieu, Garance Dejouy, Ibai Valverde. Quest for novel fluorogenic xanthene dyes: Synthesis, spectral properties and stability of 3-imino-3H-xanthen-6-amine (pyronin) and its silicon analog. Tetrahedron Letters, 2018, 59 (52), pp.4574-4581. ⟨10.1016/j.tetlet.2018.11.031⟩. ⟨hal-02168864⟩
55 Consultations
155 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More