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Fluorescent probe for detecting hypochlorous acid as well as preparation method and application thereof

A technology for detecting hypochlorous acid and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of inability to have both sensitivity and rapid response to two-photon, no two-photon and ratio properties, long reaction time, etc. Simple, easy-to-synthesize effects

Active Publication Date: 2016-08-24
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In recent years, several representative fluorescent probes used to detect hypochlorous acid include: a fluorescent probe synthesized by introducing methylthio in the parent structure of BODIPY (T.I.Kim, S.Park, Y.Choi et al, A BODIPY-based probe for the selective detection of hypochlorous acid in living cells[J].Chemistry-An Asian Journal, 2011,6,1358-1361), but the reaction time of the probe with hypochlorous acid is very long; Fluorescence turn-on detection of hypochlorous acid via HClO-promoted dihydrofluorescein-ether oxidation and its application in vivo[J].Chemical Communications ,2012,48,4677-4679), the probe is not ratiometric
In addition, a fluorescent probe with PET effect reported in the literature (H.Zhu, J.L.Fan, J.Y.Wang, H.Y.Mu et al.An "Enhanced PET"-based Fluorescent Probe with Ultrasensitivity for imaging Basal and Elesclomol-Induced HClO in Cancer Cells.J.Am.Chem.Soc.2014,136(37),12820-12823) has high sensitivity, but does not have two-photon and ratio properties
Generally speaking, none of the above probes can combine high sensitivity, fast response, ratio, and two-photon properties

Method used

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  • Fluorescent probe for detecting hypochlorous acid as well as preparation method and application thereof
  • Fluorescent probe for detecting hypochlorous acid as well as preparation method and application thereof
  • Fluorescent probe for detecting hypochlorous acid as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] (1) 3-Hydroxy-9H-xanthen-9-one (182mg) and Lawson’s reagent (200mg) were dissolved in anhydrous toluene (4mL), refluxed at 75°C for 1.5h, filtered, spin-dried, and carried out on a chromatographic column Separation (eluent V 二氯甲烷 :V 甲醇 =25:1), spin-dried to obtain a reddish-brown solid (P).

[0044] NMR and mass spectrometry characterization:

[0045] 1 HNMR(400MHz,DMSO):δ=6.70(s,1H),6.89-6.91(d,J=8Hz,1H),7.43(s,1H),7.57-7.59(d,J=8Hz,1H),7.81 (s, 1H), 8.50-8.52 (d, J=8Hz, 1H), 8.64-8.65 (d, J=4Hz, 1H).

[0046] HRMS (ESI - ): m / z calcd for [M-H] = 227.0161,, Found 227.0153.

Embodiment 2

[0048](1) 3-Hydroxy-9H-xanthen-9-one (190mg) and Lawson’s reagent (200mg) were dissolved in anhydrous toluene (5mL), refluxed at 75°C for 1.5h, filtered, spin-dried, and carried out on a chromatographic column Separation (eluent V 二氯甲烷 :V 甲醇 =25:1), spin-dried to obtain a reddish-brown solid (P).

[0049] NMR and mass spectrometry characterization:

[0050] 1 HNMR(400MHz,DMSO):δ=6.70(s,1H),6.89-6.91(d,J=8Hz,1H),7.43(s,1H),7.57-7.59(d,J=8Hz,1H),7.81 (s, 1H), 8.50-8.52 (d, J=8Hz, 1H), 8.64-8.65 (d, J=4Hz, 1H).

[0051] HRMS (ESI - ): m / z calcd for [M-H] = 227.0161,, Found 227.0153.

Embodiment 3

[0053] This example is the same as Example 1, except that 3-hydroxy-9H-xanthen-9-one is changed to xanthenone.

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Abstract

The invention discloses a fluorescent probe for detecting hypochlorous acid as well as a preparation method and application thereof. The structural formula of the fluorescent probe is described in the specification, wherein R is H or hydroxyl. The fluorescent probe disclosed by the invention has high detection sensitivity to hypochlorous acid, small damage to tissues and strong penetrating power and can be clearly applied to in vivo imaging. According to he preparation method of the fluorescent probe, oxoxanthone or an oxoxanthone derivative reacts with a Lawson reagent to obtain a target product, namely the fluorescent probe used for detecting hypochlorous acid. The fluorescent probe disclosed by the invention is simple in synthesis method and is applicable to industrial production.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a ratio-type two-photon fluorescent probe with high sensitivity and rapid response. The synthesis method and its application in detecting intracellular hypochlorous acid belong to the technical field of detection. Background technique [0002] As the most important active oxygen in living organisms, hypochlorous acid is an unstable weak acid, which can be ionized into hypochlorite and hydrogen ions in aqueous solution. In daily life, it is often used as bleaching agent and disinfectant and deodorant etc. [0003] In biological cells, hypochlorous acid is usually produced by the reaction of hydrogen peroxide and chloride ions under the catalysis of myeloperoxidase (MPO). Molecules react, participate in many physiological and pathological processes, and play a vital role in maintaining the redox balance in cells. Hypochlorous acid plays an important role in innate host defense and inflammat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/84C09K11/06G01N21/64
CPCC07D311/84C09K11/06C09K2211/1088G01N21/6428G01N21/643G01N21/6486
Inventor 唐波王栩杨婕焦晓云解希雷牛金叶
Owner SHANDONG NORMAL UNIV
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