RESUMEN
A new benzobisimidazolium derivative (1) bearing four naphthalene moieties was synthesized and demonstrated as an F- ion-selective fluorescent chemosensor. The fluorescence of 1 in acetonitrile (CH3CN) is significantly stronger with F- and acetate (CH3CO2-), but not with other anions (Cl-, Br-, I-, HSO4-, and H2PO4-). The fluorescence of 1 is enhanced selectively with F- in the presence of a small amount of water. Our DFT calculations indicate that the electrostatic interactions between the positively charged benzobisimidazolium moieties and F- play an important role in the formation of stable aggregates. The formation of stable aggregates of 1 with F- in CH3CN is a key step for the selective sensing of F-, and the fluorescence of the aggregates is further enhanced in a mixture of 95 % CH3CN and 5 % water, which can be attributed to the aggregation-induced emission.
RESUMEN
Glutathione (GSH), cysteine (Cys), and homocysteine (Hcy) are three major biothiols, which play key roles in various biological systems. Accordingly, the development of imaging probes has been actively studied. We report a new pyrene derivative 1, which showed large fluorescence quenching with Cu(2+) at pH 7.4. The ensemble 1-Cu(2+) was applied to detect biothiols. Among the various amino acids, GSH, Cys, and Hcy induced distinct turn-on fluorescence changes. The 1-Cu(2+) ensemble was further applied for GSH detection in living cells.
Asunto(s)
Cobre/química , Glutatión/metabolismo , Microscopía de Fluorescencia por Excitación Multifotónica/métodos , Imagen Molecular/métodos , Compuestos Organometálicos/química , Pirenos/química , Compuestos de Sulfhidrilo/metabolismo , Animales , Colorantes Fluorescentes/química , Glutatión/química , Células HeLa , Humanos , Ratas , Compuestos de Sulfhidrilo/químicaRESUMEN
A new tetranaphthoimidazolium receptor was synthesized and reported to be a selective fluorescent chemosensor for phytate, myo-inositol hexakisphosphate (IP6). In a 100% aqueous solution at pH 7.4, chemosensor 1 showed a selective fluorescence enhancement for IP6 over IP3, phosphates, pyrophosphates, AMP, ADP and ATP. An excimer emission at 465 nm linearly increases in the range of 300 nM to 1 µM with a detection limit of 2.28 × 10(-7) M. In addition, first live cell imaging of IP6 has been demonstrated by using a synthetic receptor.
Asunto(s)
Colorantes Fluorescentes/química , Imidazoles/química , Ácido Fítico/análisis , Espectroscopía de Resonancia Magnética con Carbono-13 , Células HeLa , Humanos , Espectroscopía de Protones por Resonancia Magnética , Espectrometría de Fluorescencia , Espectrometría de Masa Bombardeada por Átomos VelocesRESUMEN
A novel bispyrene compound was synthesized to selectively detect RNA through excimer emission "turn-on" in aqueous solution at physiological pH (7.4). The compound was used to successfully image RNA in HeLa cells.
Asunto(s)
Colorantes Fluorescentes/farmacología , Pirenos/farmacología , ARN/análisis , Colorantes Fluorescentes/química , Células HeLa , Humanos , Pirenos/química , ARN/metabolismoRESUMEN
A new sensor for the fluorescent and colorimetric detection of CO(2) is described. The system utilizes fluoride to activate a tetrapropyl benzobisimidazolium salt and operates in the absence of an exogenous base. On the basis of spectroscopic and theoretical analyses, the mode of action of the present system is ascribed to the fluoride-induced formation of an N-heterocyclic carbene intermediate that reacts with CO(2) to form an imidazolium carboxylate.
Asunto(s)
Dióxido de Carbono/análisis , Colorantes Fluorescentes/química , Imidazoles/química , Colorimetría , Colorantes Fluorescentes/síntesis química , Imidazoles/síntesis química , Estructura Molecular , Teoría CuánticaRESUMEN
The first example of an imidazolium-based fluorescent receptor for D-myo-inositol 1,4,5-trisphosphate (IP(3)) is reported in this study. The fluorescent receptor 1 bearing four imidazolium and pyrene groups displayed a large fluorescent quenching effect with myo-IP(3) compared to fluorescent changes with various IP series, pyrophosphate, and ATP.
Asunto(s)
Colorantes Fluorescentes/química , Imidazoles/química , Inositol 1,4,5-Trifosfato/química , Colorantes Fluorescentes/síntesis química , Imidazoles/síntesis química , Estructura Molecular , Espectrometría de FluorescenciaRESUMEN
[structure: see text] Quinoxaline derivatives (1-4) bearing two imidazolium moieties are found to strongly bind anions and show unique charge-transfer fluorescent responses to pyrophosphate and acetate, whereas they show excimer formation with other anions. Anion-binding studies are investigated with fluorescence and 1H NMR analysis, single-crystal X-ray analysis, and theoretical calculations.
Asunto(s)
Acetatos/química , Técnicas Biosensibles/métodos , Difosfatos/química , Colorantes Fluorescentes/química , Imidazoles/química , Quinoxalinas/química , Aniones , Sitios de Unión , Cristalografía por Rayos X , Transporte de Electrón , Fluorescencia , Espectroscopía de Resonancia Magnética , Espectrometría de Fluorescencia , Rayos XRESUMEN
New 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives (1 and 2) were synthesized as an "off-on" fluorescent chemosensor and fluorescent chemodosimeter for Cu2+ and Pb2+. Compound 1 displayed selective and large chelation enhanced fluorescence effects with Pb2+ and Cu2+ among the metal ions examined. On the other hand, compound 2, a fluorescent chemodosimeter, effectively recognized Cu2+ via a selective hydrolysis of the acetyl group.
Asunto(s)
Compuestos de Boro/síntesis química , Cobre/química , Colorantes Fluorescentes/química , Mediciones Luminiscentes/métodos , Compuestos Organometálicos/síntesis química , Compuestos de Boro/química , Plomo/química , Modelos Moleculares , Estructura Molecular , Compuestos Organometálicos/química , Sensibilidad y Especificidad , Espectrometría de Fluorescencia/métodos , Espectrofotometría Ultravioleta/métodosRESUMEN
[Structure: see text]. This study demonstrated that Zinpyr-1*Zn2+ acts as a fluorescent and colorimetric sensor for pyrophosphate at pH 7.4. In addition, Zinpyr-1*Cu2+ and DIARB-1*Cu2+ complexes were found to act as selective fluorescent sensors for pyrophosphate. Furthermore, the chemosensors Zinpyr-1*Zn2+ and Zinpyr-1*Cu2+ show highly selective and ratiometric fluorescence changes for pyrophosphate compared with H2PO4-.