Hypochlorite ion fluorescence probe, and synthetic method and application thereof
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A fluorescent probe and hypochlorite technology, applied in the field of chemical analysis, can solve the problems of low hypochlorite content, single action mechanism, and high reactivity, and achieve low detection limit, simple operation process, and high reaction yield.
Inactive Publication Date: 2013-06-26
CENT SOUTH UNIV
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It is currently reported that the fluorescent probes used to detect hypochlorite have a single mechanism of action with hypochlorite ions, and the content of hypochlorite in organisms is low, the reactivity is high and the life is short. Existing fluorescent probes have certain advantages in its detection. difficulty
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Embodiment 1
[0027] In 20 mL of toluene and n-butanol solvent (1:1 volume ratio), add 3,4-dihydroxy-3-cyclobutene-1,2-dione (1 mmol), 3-N,N-dimethyl Aminophenol (2 mmol) was heated under reflux for 8 hours; after filtration, the precipitate was washed with methanol and dried to obtain 315 mg of intermediate product dimethylamino squaraine dye, with a yield of 81%.
Embodiment 2
[0029] Under the protection of nitrogen, in 20mL of toluene, add the dimethylamino squaraine dye (0.26mmol) and Lawesson (0.4mmol) reagent prepared in step 1), heat to reflux, and react for 10 hours; the solvent was distilled off under reduced pressure, Using silica gel column chromatography (dichloromethane as the mobile phase) to separate and obtain 40 mg of tetramethyl hypochlorite fluorescent probe, the yield is 39%
Embodiment 3
[0031] Add 3,4-dihydroxy-3-cyclobutene-1,2-dione (1.17 mmol), 3-N,N-diethylaminophenol (2.34 mmol) in a molar ratio of 1:2 to 20 mL of toluene and n-butanol (volume ratio: 1:1), stirred and heated to reflux, and reacted for 8 hours; the precipitate was washed three times with methanol, and dried to obtain 0.4088 g of intermediate product, with a yield of 85.5%. 1 H NMR (400MHz, CDCl 3 )δ12.15(s, 1H), 7.94(d, 1H, J=3.2Hz), 7.52(d, 1H, J=2.4Hz), 7.26(d, 1H, J=3.2Hz), 7.00(d, 1H, J=2.4Hz), 6.19(s, 1H), 3.83(s, 1H), 3.50(q, 4H, J=2.4Hz), 1.57(q, 4H, J=2.4Hz), 1.26(t, 6H, J=4.8Hz), 1.10(t, 6H, J=4.8Hz); MS(EI): m / z 408(M + ); HRMS: Cacld.forC 24 h 28 N 2 o 4 [M + ], 408.38; found, 408.391.
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Abstract
The invention discloses a hypochlorite ion fluorescence probe, and a synthetic method and an application thereof. The synthetic method comprises the following steps: 1, adding 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid) and 3-N,N-diethylamino phenol to a solvent which is a mixed solution comprising toluene and n-butanol, carrying out a heating reflux reaction for 8-12h, filtering, washing the obtained reaction precipitate with methanol, and drying to obtain an intermediate squaric acid dye, wherein the molar ratio of 3,4-dihydroxy-3-cyclobutene-1,2-dione (squaric acid) to 3-N,N-diethylamino phenol is 1:1.8-2.2; and 2, carrying out the heating reflux reaction of the squaric acid dye and a Lawesson reagent in a solvent toluene under the protection of nitrogen for 6-24h, carrying out reduced pressure distillation to remove the solvent, and carrying out silica gel column chromatography to obtain the fluorescence probe. The probe has a simple synthetic process, has a very high selectivity and a very high sensitivity to hypochlorite ions, and has a good application prospect.
Description
technical field [0001] The invention relates to the fields of chemical analysis and biological analysis, in particular to a hypochlorite ion fluorescent probe and its synthesis method and application. Background technique [0002] Hypochlorite is not only widely used in daily life such as bleaching, disinfection, cooling water treatment and cyanide treatment, but also one of the important reactive oxygen species (ROS) in living organisms, which plays a vital role in many physiological processes. Due to its interaction with many biomacromolecules such as DNA, RNA, fatty acids, proteins and cholesterol, hypochlorous acid is considered to be the cause of damage to mammalian cells. Therefore, abnormal production of hypochlorous acid tends to cause tissue damage and diseases such as lung injury, arthritis, atherosclerosis, liver ischemia-reperfusion injury, periodontal disease and cancer (C.J.Venglarik, J.Giron-Calle, A.F. Wigley, E. Malle, N. Watanabe, H.J. Forman, Journal of A...
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