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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 problems such as poor water solubility and inability to truly apply biological systems, and achieve the effects of rapid action, high sensitivity and strong specificity

Inactive Publication Date: 2013-07-24
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] Example 1: Preparation method of fluorescent probe for detecting hypochlorous acid

[0032] In a 25mL round bottom flask, add dimethylaminothioformyl chloride (1.26g, 10.0mmol), dissolve in 6.0mL dry DMF, and add 7-hydroxyphenoxazinon sodium salt (0.6g, 2.5mmol). ) And potassium carbonate (0.52g, 3.8mmol), stirred at room temperature under nitrogen atmosphere for 30h. The resulting brown-yellow slurry was diluted with 350-400 mL saturated sodium chloride solution, and a red precipitate was salted out. After vacuum drying, it is separated by silica gel column (CH 2 Cl 2 Used as eluent) to obtain 0.375 g of red powder (target product, 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 = 1.2 Hz, 1H, ArH), 6.866 (q, J = 6.0 Hz, 1H, ArH), 7.093 (q, J = 3.4 Hz, 1H, ArH), 7.120 (d, J = 2.4 Hz, 1H, ArH), 7.442 (d, J=10.0 Hz, 1...

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:

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

[0039] In a 10mL graduated test tube, add 5.0mL of 0.2mol / L pH 7.40 phosphate buffer, a certain amount of standard NaClO solution (previously calibrated accurately by spectrophotometry, see literature: M.Mazda and DWMargerum.Inorg .Chem. 1994, 33, 118.), diluted to the mark with three times distilled water. Shake well. Add 0.1mL to a concentration of 1.0×10 -3 mol / L methanol stock solution of fluorescent probe for detecting hypochlorous acid, shake well. Perform relevant measurements immediately. Operate as above, but do not add hypochlorous acid or other active oxygen detection hypochlorous acid fluorescent probe solution, it is the preparation of blank te...

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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 a dimethylaminothioformyl group as a phenolic hydroxyl protecting group and a phenoxazinon as a fluorophore and the same Preparation. Background technique [0002] Hypochlorous acid (HClO) is an important reactive oxygen species mediated by myeloperoxidase (MPO), and it plays an important role in a variety of physiological and pathological processes. Design and synthesize a highly sensitive and specific HClO fluorescent probe, establish a fluorescence microscopy imaging method for intracellular HClO, realize real-time, in-situ tracking of target molecules, and study HClO-related molecules in organisms It provides reliable information for drug screening and evaluation of cell events and related diseases, which has important scientific significance and application prospects. This field has become one of the hotspots of research [0003] In ...

Claims

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Application Information

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