Red-to-Near-Infrared Emitting PyrrolylBODIPY Dyes: Synthesis, Photophysical Properties and Bioimaging Application.
Chemistry
; 29(14): e202203832, 2023 Mar 07.
Article
en En
| MEDLINE
| ID: mdl-36650103
ABSTRACT
Near-infrared (NIR) fluorophores with characteristics such as deep tissue penetration, minimal damage to the biological samples, and low background interference, are highly sought-after materials for inâ
vivo and deep-tissue fluorescence imaging. Herein, series of 3-pyrrolylBODIPY derivatives and 3,5-dipyrrolylBODIPY derivatives have been prepared by a facile regioselective nucleophilic aromatic substitution reaction (SN Ar) on 3,5-halogenated BODIPY derivatives (3,5-dibromo or 2,3,5,6-tetrachloroBODIPYs) with pyrroles. The installation of a pyrrolic unit onto the 3-position of the BODIPY chromophore leads to a dramatic red shift of both the absorption (up to 160â
nm) and the emission (up to 260â
nm) in these resultant 3-pyrrolylBODIPYs with respect to that of the BODIPY chromophore. Their further 5-positional functionalization provides a facile way to fine tune their photophysical properties, and these resulting dipyrrolylBODIPYs and functionalized pyrrolylBODIPYs show strong absorption in the deep red-to-NIR regions (595-684â
nm) and intense NIR fluorescence emission (650-715â
nm) in dichloromethane. To demonstrate the applicability of these functionalized pyrrolylBODIPYs as NIR fluorescent probes for cell imaging, pyrrolylBODIPY 6 a containing mitochondrion-targeting butyltriphenylphosphonium cationic species was also prepared. It selectively localized in mitochondria of HeLa cells, with low cytotoxicity and intense deep red fluorescence emission.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Compuestos de Boro
/
Colorantes Fluorescentes
Límite:
Humans
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2023
Tipo del documento:
Article