A sensitive zinc probe operating via enhancement of excited-state intramolecular charge transfer.
Org Biomol Chem
; 20(37): 7439-7447, 2022 09 28.
Article
em En
| MEDLINE
| ID: mdl-36102673
ABSTRACT
Novel highly sensitive fluorescent probes for zinc cations based on the diketopyrrolopyrrole scaffold were designed and synthesized. Large bathochromic shifts (≈80 nm) of fluorescence are observed when the Zn2+-recognition unit (di-(2-picolyl)amine) is bridged with the fluorophore possessing an additional pyridine unit able to participate in the coordination process. This effect originates from the dipolar architecture and the increasing electron-withdrawing properties of the diketopyrrolopyrrole core upon addition of the cation. The new, greenish-yellow emitting probes, which operate via modulation of intramolecular charge transfer, are very sensitive to the presence of Zn2+. Introduction of a morpholine unit in the diketopyrrolopyrrole structure induces a selective six-fold increase of the emission intensity upon zinc coordination. Importantly, the presence of other divalent biologically relevant metal cations has negligible effects and typically even at a 100-fold higher concentration of Mg2+/Zn2+, the effect is comparable. Computational studies rationalize the strong bathochromic shift upon Zn2+-complexation. Decorating the probes with the triphenylphosphonium cation and morpholine unit enables selective localization in the mitochondria and the lysosome of cardiac H9C2 cells, respectively.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Zinco
/
Corantes Fluorescentes
Tipo de estudo:
Diagnostic_studies
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article