Fluorescent sensors for Zn(2+) based on a fluorescein platform: synthesis, properties and intracellular distribution.
J Am Chem Soc
; 123(32): 7831-41, 2001 Aug 15.
Article
en En
| MEDLINE
| ID: mdl-11493056
ABSTRACT
Two new fluorescent sensors for Zn(2+) that utilize fluorescein as a reporting group, Zinpyr-1 and Zinpyr-2, have been synthesized and characterized. Zinpyr-1 is prepared in one step via a Mannich reaction, and Zinpyr-2 is obtained in a multistep synthesis that utilizes 4',5'-fluorescein dicarboxaldehyde as a key intermediate. Both Zinpyr sensors have excitation and emission wavelengths in the visible range ( approximately 500 nm), dissociation constants (K(d1)) for Zn(2+) of <1 nM, quantum yields approaching unity (Phi = approximately 0.9), and cell permeability, making them well-suited for intracellular applications. A 3- to 5-fold fluorescent enhancement is observed under simulated physiological conditions corresponding to the binding of the Zn(2+) cation to the sensor, which inhibits a photoinduced electron transfer (PET) quenching pathway. The X-ray crystal structure of a 21 Zn(2+)Zinpyr-1 complex has also been solved, and is the first structurally characterized example of a complex of fluorescein substituted with metal binding ligands.
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Base de datos:
MEDLINE
Asunto principal:
Zinc
/
Fluoresceínas
/
Colorantes Fluorescentes
Idioma:
En
Revista:
J Am Chem Soc
Año:
2001
Tipo del documento:
Article