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Fluorescent probe for detecting hypochlorous acid and preparation method thereof

A technology for detecting hypochlorous acid and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of not being able to truly apply to biological systems, poor water solubility, etc., and achieve rapid action, excellent performance, and strong specificity

Inactive Publication Date: 2012-03-21
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the other reported HClO probes, some need to be used under harsh conditions of strong alkalinity (such as pH 12) (see literature: H.M.Ma, et al, Chem.Eur.J.2008, 14, 4719.) , or poor water solubility (see literature: W.Tan et al, Chem.Eur.J.2009, 15, 2305.), cannot really be applied in biological systems

Method used

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  • Fluorescent probe for detecting hypochlorous acid and preparation method thereof
  • Fluorescent probe for detecting hypochlorous acid and preparation method thereof
  • Fluorescent probe for detecting hypochlorous acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation method of the fluorescent probe that detects hypochlorous acid

[0032] In a 25mL round bottom flask, add dimethylaminothioformyl chloride (1.26g, 10.0mmol), dissolve it in 6.0mL of dry DMF, add 7-hydroxyphenoxazinone sodium salt (0.6g, 2.5mmol ) and potassium carbonate (0.52g, 3.8mmol), stirred at room temperature for 30h under nitrogen atmosphere. The obtained brownish-yellow slurry was diluted with 350-400mL saturated sodium chloride solution, and a red precipitate was precipitated by salting out. After vacuum drying, the silica gel column separation (CH 2 Cl 2 as eluting agent) to obtain 0.375 g of red powder (target product, i.e. a fluorescent probe for detecting hypochlorous acid). (Yield 50%).

[0033] ESI-MS: C 15 h 12 N 2 o 3 S, m / z: 301.1 (M+1) + .

[0034] 1 H NMR (CDCl 3 ): δ3.388 (s, 3H, NCH 3 ), 3.477 (s, 3H, NCH 3 ), 6.331(d, J=1.2Hz, 1H, ArH), 6.866(q, J=6.0Hz, 1H, ArH), 7.093(q, J=3.4Hz, 1H, ArH), 7.120(d, J= ...

Embodiment 2

[0036] Example 2: Description of the chemical properties of the fluorescent probe for detecting hypochlorous acid and its application in microscopic fluorescence imaging of endogenous HClO in cells

[0037] 1. Probe in neutral aqueous solution 1 The detection performance test of:

[0038] (1) Preparation steps of the test solution:

[0039] In a 10mL graduated test tube, sequentially add 5.0mL of pH 7.40 phosphate buffer solution with a concentration of 0.2mol / L, a certain amount of standard NaClO solution (accurately calibrated by spectrophotometry in advance, see literature: M.Mazda and D.W.Margerum.Inorg .Chem.1994, 33, 118.), diluted to the mark with three times distilled water. Shake well. Add 0.1 mL to a concentration of 1.0 x 10 -3 mol / L methanol stock solution of the fluorescent probe for detecting hypochlorous acid, shake well. Make relevant measurements immediately. The fluorescent probe solution for detecting hypochlorous acid, which is operated as above, but ...

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Abstract

The invention discloses a fluorescent probe for detecting hypochlorous acid and a preparation method thereof, relating to fluorescent probes. The fluorescent probe for detecting hypochlorous acid, which has higher sensitivity and selectivity and is mainly applied to detecting the hypochlorous acid in an aqueous solution under a neutral condition, as well as the preparation method and the application thereof are provided. The fluorescent probe for the detecting hypochlorous acid is a 7-dimethylamino thiomethoxy-3-phenoxazone compound containing a phenoxazone fluorophore structure and taking dimethylamino thioformyl chloride as phenolichydroxyl protective group. The preparation method comprises the following steps of: adding dimethylamino thioformyl chloride to a container, solving the dimethylamino thioformyl chloride by DMF (Dimethyl Formamide), adding resorufin sodium salt and potassium carbonate and stirring to obtain isabelline slurry, diluting the isabelline slurry by a saturated sodium chloride solution to salt out red sediment, drying the red sediment, and separating by a silicagel column to obtain the fluorescent probe for detecting the hypochlorous acid in red powders. Thefluorescent probe for detecting the hypochlorous acid can be applied to the fluorescence detection of HC1O in the aqueous solution under the neutral condition.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a fluorescent probe for detecting hypochlorous acid with dimethylaminothioformyl as a phenolic hydroxyl protecting group and phenoxazinone as a fluorophore and its Preparation. Background technique [0002] Hypochlorous acid (HClO) is an important reactive oxygen species mediated by myeloperoxidase (MPO) in organisms, and plays an important role in various physiological and pathological processes. Design and synthesize HClO fluorescent probes with high sensitivity and specificity, establish a fluorescence microscopy imaging method for intracellular HClO, realize real-time and in situ tracking of target molecules, and provide a basis for the study of HClO-related molecules in vivo And cell events, as well as drug screening and evaluation of related diseases to provide reliable information, has important scientific significance and application prospects. This field has become one of the hot...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D265/38G01N21/64
CPCY02P20/55
Inventor 郑洪詹心琪王淑萍
Owner XIAMEN UNIV
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