A mitochondria-targeted fluorescent probe for imaging of endogenous carbon monoxide in living cells.

Carbon monoxide (CO), a vital gasotransmitter, plays critical functions in many physiological processes. Mitochondrial CO is closely related to mitochondrial respiration, thus the detection and imaging of mitochondrial CO in living cells is very important and has attracted much attention recently. In this paper, we developed a hemicyanine-based off-on fluorescent probe, CO-H1, which was used for monitoring endogenous mitochondrial CO levels in living cells. After reacted with CO in the presence of PdCl2, the fluorescence of CO-H1 was enhanced notably, accompanied by a significant red shift of absorption. CO-H1 exhibits low cytotoxicity, high sensitivity (detection limit of 0.048 µM), and good selectivity for CO. When incubated with living cells, probe CO-H1 mainly entered the mitochondria. CO-H1 was successfully applied to imaging the exogenous/endogenous mitochondrial CO in living cells, suggesting its potential application for further studying the biological functions of mitochondrial CO in living cells.

A photo-activated aptamer-drug conjugate for targeted drug delivery.

A photo-activated aptamer-drug conjugate, HG1-9-DNP, was developed based on an aptamer HG1-9 and a photolabile naphthalimide derivative DNP. HG1-9-DNP could be internalized into cells mediated by TfR, then photocleaved, and released a promising cytotoxic agent, DNNH, which arrested the cell cycle at the G2/M phase, resulting in high photo-induced cytotoxicity.

A mitochondria-targeted near-infrared fluorescent probe for detection and imaging of HSO3- in living cells.

Sulfur dioxide, an essential gas signaling molecule mainly produced in mitochondria, plays important roles in many physiological and pathological processes. Herein, a near-infrared fluorescent probe, A1, with good mitochondria targeting ability was developed for colorimetric and fluorescence detection of HSO3-. Probe A1 has a conjugated cyanine structure that can selectively react with HSO3- through the nucleophilic addition. The reaction with HSO3- destroys the conjugated structure of probe A1, resulting in fluorescence quenching, and accompaniedby color change of probe A1 solution from purple-red to colorless. Probe A1 showed high selectivity and good sensitivity to HSO3- in PBS. And the limit of detection was calculated to be 1.28 and 0.037 µM for colorimetry and fluorescence spectrophotometry respectively. In addition, probe A1 mainly entered the mitochondria in living cells, and was successfully used for imaging the exogenous/endogenous HSO3- in cells. These results suggest the potential applications of probe A1 in biological systems.

p-Aminostyryl thiazole orange derivatives for monitoring mitochondrial viscosity in live cells.

Viscosity of cell microenvironment plays a significant role in maintaining the normal life activities of cells. Particularly, the abnormal viscosity in mitochondria is closely associated with lots of diseases and cellular dysfunctions. Herein, we developed a group of p-aminostyryl thiazole orange derivatives with different amino side chains. These probes showed good fluorescence response to viscosity with twisted intramolecular charge transfer mechanism, among them, the probes with diethylamino (TOB), dibutylamino (TOC) and pyrrolidin (TOE) side chains showed better response to the viscosity with 78-fold, 55-fold, and 88-fold fluorescence enhancement in 95% glycerol solution respectively. TOB, TOC, and TOE could enter live cells and mainly located in mitochondria. Treatment HeLa cells with nystatin, lipopolysaccharide or oleic acid caused significant fluorescence enhancement of these probes, suggesting the good potential for monitoring the variation of mitochondrial viscosity, as well as for investigating the related physiological process of inflammation and lipid metabolism.

A 4-aminonaphthalimide-based fluorescent traceable prodrug with excellent photoinduced cytotoxicity.

A blue light activated anti-cancer prodrug, NST, was designed based on a photoactive 4-aminonaphthalimide derivative and an anticancer drug, 10-hydroxycamptothecin. NST was hard to be taken up by living cells and showed negligible dark cytotoxicity. The irradiation caused photocleavage of NST and resulted in high cytotoxicity.