A ratiometric fluorescent probe for peroxynitrite prepared by de novo synthesis and its application in assessing the mitochondrial oxidative stress status in cells and in vivo

Abstract

A ratiometric fluorescent probe Cy-NEt2 for detecting ONOO- is designed and prepared by de novo synthesis, which is a reliable, cheap and flexible route. The probe is applied for monitoring the level of mitochondrial ONOO- and assessing the lipopolysaccharide (LPS)-induced mitochondrial oxidative stress status in living cells and in vivo successfully.

Fluorescent probe for the imaging of superoxide and peroxynitrite during drug-induced liver injury

“…in water) were found to be consistent with the mechanism proposed above, with detection of the mass ion for LW-XTD ([M+H] + , m/z = 229.0860) as well as the indoline byproduct confirming oxidative cleavage of LW-OH by ONOO − (Figure S9 and S10). 38,47 HRMS was also used to prove the alternate activation pathway, with direct addition of ONOO − (5 equiv. in water) to LW−OTf (in MeOH) generating a mass ion for LW-XTD-OTf ([M+H] + , m/z = 361.0537, Figure S12).…”

“…36,37 In the presence of O 2 •− triflate deprotection occurs, which leads to an increased NIRF signal by generation of fluorophore LW−OH. Subsequent reaction with ONOO − results in oxidative cleavage of the alkene linker of LW−OH to generate xanthene derivative LW-XTD, [38][39][40] capable of two-photon fluorescence (see ESI for further discussion hemicyanine-xanthene fluorescent turn-on mechanism and selectivity). An alternative fluorescence activation pathway can also occur, in which LW-OTf is first cleaved by ONOO − to produce non-fluorescent LW-XTD-OTf, which can subsequently react with superoxide to produce the same final xanthene derivative LW-XTD.…”

Application of a Colorimetric and Near-Infrared Fluorescent Probe in Peroxynitrite Detection and Imaging in Living Cells

“…To date, many fluorescent probes for ONOO – detection have been constructed based on hydrazides, 29 − 32 arylboronic esters, 33 , 34 tellurium or selenium, 35 , 36 and C=C double bonds. 37 , 38 However, for some probes, it is difficult to discriminate ONOO – from other relative species including HClO and H 2 O 2 , 39 , 40 which remains a challenge for selective detection of ONOO – . Additionally, most of the reported fluorescent probes had a short emission wavelength (300–650 nm) resulting in photodamage and excitation interference, which limits their biological applications.…”

“…Near-infrared (> 650 nm) fluorescence probes can avoid the abovementioned problems because of their unique, superior low autofluorescence interference, deeper tissue penetration, and minimum photodamage. 37 , 41 , 42 Therefore, it is wise to construct novel near-infrared fluorescent probes with high specificity for the detection of ONOO – in vitro and in vivo.…”

A ruthenium(ii) complex–cyanine energy transfer scaffold based luminescence probe for ratiometric detection and imaging of mitochondrial peroxynitrite

“…[4][5][6][7] In the past few years, a number of probes have been engineered, allowing ONOOdetection to be performed by recording their emission intensity changes during the sensing process. [8][9][10][11][12][13][14][15][16] In comparison with the intensity on/off approach, [17][18][19][20] ratiometric probes that have a self-calibration of external interference on emission intensity are desirable for effective detection of ONOOin mitochondria of live cells. [21][22][23] The ratiometric changes in luminescence intensities at two emission wavelengths mainly arise from the factor of Förster resonance energy transfer (FRET) where generally organic dyes act as energy donors and acceptors.…”