A novel fast-response and highly selective AIEgen fluorescent probe for visualizing peroxynitrite in living cells, C. elegans and inflammatory mice

Abstract

Most of ONOO− fluorescent probes have been restricted their further applications because of their aggregation-caused quenching (ACQ) effect, long response time and low fluorescence enhancement. Herein, we developed a novel...

Noncancerous disease-targeting AIEgens

“…On the contrary, AIEgens do not have photobleaching thresholds, show stable fluorescence without ''blinking'' and provide low cytotoxicity and the additional property of a ''fluorescence turn-on mode'', which makes them perfect for the evaluation of inflammatory diseases at a high resolution with long-term bioimaging. [212][213][214][215][216][217] Some inflammatory diseases are characterized and caused by the elevated generation of ONOO À . 218 17A).…”

A Fluorescent Probe with Zwitterionic ESIPT Feature for Ratiometric Monitoring of Peroxynitrite In Vitro and In Vivo

“…The simultaneous introduction of phenothiazine-based coumarin and benzyl boronic ester moieties (BnB) into ABT rendered the probe to detect ClO – and ONOO – through two distinct emission channels with fast responses . James and other groups presented a series of HBT-derived fluorescent probes realizing the ratiometric sensing of ONOO – in vitro and in vivo. − Despite these achievements, only few reports with emission wavelengths for the keto forms of π-delocalized ESIPT chromophores were longer than 550 nm. , In sharp contrast, fluorescent probes featuring the zwitterionic ESIPT mechanism are not reported currently, though it might endow probe molecules with emission at long wavelengths …”

“…26−36 Despite these achievements, only few reports with emission wavelengths for the keto forms of π-delocalized ESIPT chromophores were longer than 550 nm. 30,32 In sharp contrast, fluorescent probes featuring the zwitterionic ESIPT mechanism are not reported currently, though it might endow probe molecules with emission at long wavelengths. 37 In this sense, the zwitterionic ESIPT mechanism is quite different from the conventional π-delocalized one.…”

“…Until now, small molecular fluorescent probes are emerging as the most powerful tool for imaging ONOO – in vitro/in vivo due to their unique characteristics of high sensitivity, specificity, noninvasiveness, and great temporal and spatial resolutions. − Among them, excited-state intramolecular proton-transfer (ESIPT)-based probes reveal a promising applicability featuring with good photostability, large Stokes shift, and ratiometric capability. − Among them, functionalized 2-phenylbenzothiazole including 2-(2′-aminophenyl)­benzothiazole (ABT) − and 2-(2′-hydroxyphenyl)­benzothiazole (HBT), − as the classical ESIPT chromophores, were well developed, which would advance the phototautomerization switching between the enol and keto forms (named as π-delocalized ESIPT) after the release of the sensing moiety for ONOO – . For instance, Hu and co-workers developed a fluorescent switch-on probe by incorporating the p -hydroxyaniline moiety into the ABT skeleton, and the oxidative cleavage of p -hydroxyaniline exerted by ONOO – released the fluorescent ABT core, realizing the monitoring of ONOO – in vitro and in vivo .…”

Regulating the activity of boronate moiety to construct fluorescent probes for the detection of ONOO−in vitroandin vivo

“…, ONOO − , H 2 O 2 )-recognizing portion, with some developed fluorescent probes listed in Schemes S1–S3 (ESI†), the substituent effect has not been studied in the reported publications. 32–67 Resorufin dye possesses several advantages, including bright red emission, excellent stability, high fluorescence quantum yield, and good photostability. 68,69 Several boronate-containing resorufin probes have been reported to be able to detect tyrosinase, benzoyl peroxide (BPO), or hydrogen peroxide (H 2 O 2 ); however, the response rates were slow (10 min to 10 h, Table S1, ESI†).…”