Near-infrared aza-BODIPY fluorescent probe for selective Cu²⁺detection and its potential in living cell imaging

Abstract

A near-infrared (NIR) fluorescent sensor 1 composed of an aza-boron-dipyrromethene (aza-BODIPY) core covalently bound to two di-2-picolylamine moieties was conceived for Cu detection in aqueous solutions. Spectroscopic properties and binding abilities with several metal ions were investigated in phosphate buffered saline (pH 7.4): acetonitrile (95 : 5 v/v) with Triton X-100 via fluorometric titrations. The fluorescence of sensor 1 was quenched selectively by cupric ions in the presence of alkali- and transition-metal-ions. A detection limit of 13 ppb was measured for this system, and this is significantly lower than permissible levels of Cu in drinking water according to the guidelines described by the U.S. Environmental Protection Agency (EPA) and by the World Health Organization (WHO). Application of the sensor in detecting Cu in HepG2 cells was demonstrated.

Stable J‐Aggregation of an aza‐BODIPY‐Lipid in a Liposome for Optical Cancer Imaging

“…Aza‐boron dipyrromethenes (aza‐BODIPYs) are a rapidly emerging class of near‐infrared (NIR) fluorophores with NIR emission, high fluorescence quantum yields, and excellent photostability, which are attractive properties for cancer imaging applications . Recent developments of aza‐BODIPY synthetic derivatives have allowed tailored design for specific moieties to promote their use as photoacoustic probes, targeting conjugates, optical sensors, and off/on switch systems . While the in vitro applications for small molecule aza‐BODIPYs grow, hydrophobicity remains a major challenge hindering their in vivo applications .…”

A reversible and highly selective two-photon fluorescent “on–off–on” probe for biological Cu2+ detection

“…So far, many Cu 2+ fluorescent probes have attracted great concern because of their high sensitivity and selectivity [12][13][14][15][16][17][18][19][20][21][22][23] . However, most of the designed probes are only available for one-photon fluorescence microscopy (1PM) with short excitation wavelengths and suffering from background interference.…”

“…Then, the probe L in ethanol. The probe L was characterized using 1 H NMR,13 C NMR spectroscopy and mass spectrometry. The molecular structure of probe L was also confirmed by single-crystal X-ray diffraction analysis.…”

Stable J‐Aggregation of an aza‐BODIPY‐Lipid in a Liposome for Optical Cancer Imaging

“…[9] Recent developments of aza-BODIPY synthetic derivatives have allowed tailored design for specific moieties to promote their use as photoacoustic probes, [10] targeting conjugates, [11] optical sensors, [12] and off/ on switch systems. [9] Recent developments of aza-BODIPY synthetic derivatives have allowed tailored design for specific moieties to promote their use as photoacoustic probes, [10] targeting conjugates, [11] optical sensors, [12] and off/ on switch systems.…”

“…Aza-boron dipyrromethenes (aza-BODIPYs) are ar apidly emerging class of near-infrared (NIR) fluorophores with NIR emission, high fluorescence quantum yields,a nd excellent photostability,which are attractive properties for cancer imaging applications. [9] Recent developments of aza-BODIPY synthetic derivatives have allowed tailored design for specific moieties to promote their use as photoacoustic probes, [10] targeting conjugates, [11] optical sensors, [12] and off/ on switch systems. [13] While the in vitro applications for small molecule aza-BODIPYs grow,h ydrophobicity remains am ajor challenge hindering their in vivo applications.…”