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  • Title: Sequential detection of hypochlorous acid and sulfur dioxide derivatives by a red-emitting fluorescent probe and bioimaging applications in vitro and in vivo.
    Author: Liu J, Yin H, Shang Z, Gu P, He G, Meng Q, Zhang R, Zhang Z.
    Journal: RSC Adv; 2022 May 23; 12(25):15861-15869. PubMed ID: 35733666.
    Abstract:
    Hypochlorous acid (HOCl) and sulfur dioxide derivatives (SO3 2-/HSO3 -) play critical roles in complex signal transduction and oxidation pathways. Therefore, it is meaningful and valuable to detect both HOCl and SO2 derivatives in biosystems by a fluorescence imaging assay. In this work, we developed a red-emitting fluorescent probe (DP) by the condensation of malononitrile and phenothiazine derivatives through a C[double bond, length as m-dash]C double bond. DP was designed with a donor-π-acceptor (D-π-A) structure, which enables absorption and emission in the long wavelength region. In the presence of HOCl, specific oxidation of the thioether of phenothiazine in DP to a sulfoxide derivative (DP[double bond, length as m-dash]O) occurs, resulting in a hypochromic shift (572 nm to 482 nm) of the absorption spectra and "OFF-ON" response of the maximum emission at 608 nm. After the activation of the C[double bond, length as m-dash]C double bond by oxidation, DP[double bond, length as m-dash]O reacts specifically with SO3 2-/HSO3 - via a 1,4-nucleophilic addition reaction leading to a decrease in the intensity of the absorption and emission spectra, which enabled the realization of sequential detection of HOCl and SO3 2-/HSO3 - by a single fluorescent probe. The detection limits of DP for HOCl and SO3 2-/HSO3 - were calculated to be 81.3 nM and 70.8 nM/65.1 nm, respectively. The results of fluorescence microscopic imaging indicated that DP shows potential for the detection of intracellular HOCl and SO3 2-/HSO3 -. Using adult zebrafish and nude mice as live animal models, DP was successfully used for the fluorescence imaging of HOCl and SO3 2-/HSO3 - in vivo.
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