Allyl Fluorescein Ethers as Promising Fluorescent Probes for Carbon Monoxide Imaging in Living Cells

Abstract

Recently, the fluorescent detection of carbon monoxide (CO) in living cells has attracted great attention. However, due to the lack of effective ways to construct fluorescent CO probes, fluorescent detection of CO in living cells is still in its infancy. In this paper, we report for the first time the use of allyl ether as a reaction site for construction of fluorescent CO probes. By this way, two readily available allyl fluorescein ethers were prepared, which were found to be highly selective and sensitive probes for CO in the presence of PdCl. These probes have the merits of good stability, good water-solubility, and rapid and distinct colorimetric and remarkable fluorescent turn-on signal changes. Moreover, a very low dose of these two probes can be used to detect and track CO in living cells, indicating that these two probes could be very promising biological tools for CO detection in living systems. Overall, this work provided not only two new promising fluorescent CO probes but also a new way to devise fluorescent CO probes.

Metal-free carbon monoxide-releasing micelles undergo tandem photochemical reactions for cutaneous wound healing

“…Thus, the selective uorescence increase at 515 nm should be solely ascribed to the photo-mediated CO release that, in turn, activated the allyl-Flu probe through the COmediated Tsuji-Trost reaction. 58 Building on the above results, we can safely conclude that CO could be released from OM micelles under visible light irradiation.…”

“…2f). 58 In contrast, no uorescence was detected in the absence of OM micelles under otherwise identical conditions (Fig. S16a †).…”

Recent Advances in Fluorescence Light‐Up Endogenous and Exogenous Carbon Monoxide Detection in Biology

“…Fluorescence confocal microscopic images of endogenous CO detection due to heme stimulation in HeLa cells were also reported. [44] In continuation of these works they have also reported a naphthalimide based CO probe 1 and a coumarin based probe BTHC-CO ( Figure 5B) which showed similar but sensitive responses toward CO. [45,46] Tang and co-workers reported two probes ACP-1 and ACP-2 for the detection of CO in aqueous buffer, while the more efficient ACP-2 can sense endogenous CO inside cell in hypoxia condition. The azobenzene-BODIPY based cyclopalladated com-plex undergoes protonolysis of the PdÀ C bond and subsequently shows fluorescence due to the generation of highly emissive BODIPY-derivative ( Figure 6A).…”

Small-molecule fluorescent probes for imaging gaseous signaling molecules: current progress and future implications

“…Subsequently, by using allyl ether instead of allylcarbonate as the protective unit and recognition site, Feng et al reported a second generation uorescein-based COresponsive uorescent probe (probe 40). 58 This probes exhibited superior stability compared to probe 39 and excellent sensing performance for CO. It is worth noting that this was the rst uorescent probe that utilized allyl ether as the reaction site for CO, which will provide more options for developing effective CO-detecting uorescent probes.…”

“…In the next few years, Feng's group reported various uorescent probes based on the Pd(0)-mediated Tsuji-Trost reaction. [57][58][59][60] In 2016, they reported a readily available uorescent probe 39 (ref. 57) based on the allyl chloroformate functionalized uorescein for the detection of CO.…”