Investigation of thiolysis of 4-substituted SBD derivatives and rational design of a GSH-selective fluorescent probe
| Autor: | Zhen Xi, Lu Sun, Long Yi, Shan Li, Xiuru Ji, Xiaoqiang Tu, Haishun Ye, Chao Yang |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Biocompatibility
010405 organic chemistry Aryl Organic Chemistry Rational design 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Fluorescence 0104 chemical sciences chemistry.chemical_compound chemistry Thiolysis Moiety Reactivity (chemistry) Physical and Theoretical Chemistry Selectivity |
| Zdroj: | Organic & Biomolecular Chemistry. 19:6527-6533 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/d1ob01114f |
| Popis: | In order to evaluate 7-sulfonamide benzoxadiazole (SBD) derivatives for the development of fluorescent probes, herein we investigated the thiolysis reactivity and selectivity of a series of SBD compounds with different atoms (N/O/S/Se) at the 4-position. Both SBD-amine and SBD-ether are stable toward biothiols in buffer (pH 7.4), while SBD-selenoether can react efficiently with biothiols GSH/Hcy, Cys, and H2S to produce SBD-SG/S-Hcy, SBD-NH-Cys, and SBD-SH, respectively, with three different sets of spectral signals. Therefore, the SBD-selenoether compounds should be useful platforms for the differentiation of these biothiols. Though SBD-alkylthioether shows much lower reactivity than SBD-selenoether, SBD-arylthioether is a tunable motif and structural modifications at the aryl moiety enable the rate of thiol-mediated thiolysis to be modified. To this end, an ER-targeted GSH-selective fluorescent probe 7 was rationally designed via thiolysis of SBD-arylthioether. Compared with control probe SBD-Cl, probe 7 exhibits improved GSH selectivity and better biocompatibility. In total, this study highlights that the modification at the 4-position of SBD is an efficient strategy for the development of new fluorescent probes with tunable reactivity and selectivity. |
| Databáze: | OpenAIRE |
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