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Preparation of basic blue-3 based near-infrared fluorescent probe molecule for hypochlorous acid detection

A technology for detecting hypochlorous acid and fluorescent probes, which is applied in the fields of fluorescence/phosphorescence, luminescent materials, material excitation analysis, etc. It can solve the problems of low sensitivity, complex synthesis and slow response speed of hypochlorous acid detection probes, and achieve rapid The effect of hypochlorous acid response, high sensitivity and short response time

Active Publication Date: 2019-06-25
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the currently reported hypochlorous acid detection probes have disadvantages such as low sensitivity, slow response speed, and complex synthesis.
In recent years, some organic small molecule fluorescent probes have been used in the detection of hypochlorous acid, which can be roughly divided into: marin, BODIPY, cyanine dyes, etc. according to the different luminescent nuclei. -3) There is no relevant report on the near-infrared hypochlorous acid detection probe synthesized as a raw material

Method used

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  • Preparation of basic blue-3 based near-infrared fluorescent probe molecule for hypochlorous acid detection
  • Preparation of basic blue-3 based near-infrared fluorescent probe molecule for hypochlorous acid detection
  • Preparation of basic blue-3 based near-infrared fluorescent probe molecule for hypochlorous acid detection

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The near-infrared fluorescent probe molecule provided in this embodiment is a near-infrared fluorescent probe molecule for detecting hypochlorous acid based on basic blue-3, and its structural formula is:

[0045]

[0046] In the above structural formula: X is different electron-withdrawing groups and electron-donating groups, hydrogen atoms, alkyl or cycloalkyl, substituted alkyl or cycloalkyl.

[0047] The near-infrared fluorescent probe molecule can use an alkyl or cycloalkyl group with less than 6 carbons.

[0048] The near-infrared fluorescent probe molecule is used for preparing rapid response and non-invasive specific detection hypochlorous acid probe, especially for specific detection of hypochlorous acid.

[0049] In the following examples, two compounds BC-2 and BC-3 are prepared and described in detail by taking them as examples.

[0050]

[0051] In the above figure, BB-3 is the basic blue-3 molecule, BC is the product of BB-3 acid chloride, 3 is p-cy...

Embodiment 2

[0055] Embodiment 2 (BC-2):

[0056] The preparation of compound BC-2: add compound BC (50mg, 0.13mmol) in the schlenk tube of 100mL, Na 2 CO 3 (55.4mg, 0.52mmol), p-cymeniline (70.3mg, 0.52mmol), and the solvent dichloromethane (5.0mL) was added. The reaction solution was reacted at 40° C. for 8 h until the reaction was complete. After the reaction, the reaction liquid was cooled to room temperature, concentrated under reduced pressure, separated and purified by column chromatography to obtain compound BC-2 (light blue solid, 64.8%; ethyl acetate:petroleum ether=1:10).

[0057] 1 H NMR (400MHz, CDCl 3 )δ=7.43–7.37(m,2H),7.35(d,J=8.5Hz,2H),7.23(s,1H),7.15(d,J=8.4Hz,2H),6.44(s,4H), 3.36(q, J=7.0Hz, 8H), 2.87(dt, J=13.8, 6.9Hz, 1H), 1.26–1.16(m, 18H).

[0058] 13 C NMR: (100MHz, CDCl 3 )δ=153.25, 152.50, 146.81, 143.86, 136.22, 126.77, 125.04, 119.73, 117.60, 106.74, 100.07, 44.65, 33.54, 24.13, 12.58.

[0059] HR-MS(ESI,m / z):calcd for C 30 h 38 N 4 o 2 [M+H] + ,48...

Embodiment 3

[0060] Embodiment 3 (BC-3):

[0061] The preparation of compound BC-3: add compound BC (50mg, 0.13mmol) in the schlenk tube of 100mL, Na 2 CO 3 (55.4mg, 0.52mmol), p-methoxyaniline (64.0mg, 0.52mmol), added solvent dichloromethane (5.0mL). The reaction solution was reacted at 40° C. for 8 h until the reaction was complete. After the reaction, the reaction solution was cooled to room temperature, concentrated under reduced pressure, separated and purified by column chromatography to obtain compound BC-3 (off-white solid, 65.3%; ethyl acetate:petroleum ether=1:5).

[0062] 1 H NMR (400MHz, CDCl 3 )δ=7.40–7.35(m,2H),7.32(d,J=9.0Hz,2H),7.15(s,1H),6.82(d,J=9.0Hz,2H),6.43(d,J=2.7 Hz,4H),3.77(s,3H),3.34(q,J=7.0Hz,8H),1.16(t,J=7.0Hz,12H).

[0063] 13 C NMR (100MHz, CDCl 3 )δ=155.82, 153.60, 152.49, 146.80, 131.59, 125.06, 121.69, 117.58, 114.04, 106.72, 100.04, 55.50, 44.64, 12.57.

[0064] HR-MS(ESI,m / z):calcd for C 28 h 34 N 4 o 3 [M+H] + ,475.2664,found 475.2735.

[...

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Abstract

The invention relates to preparation of a basic blue-3 based near-infrared fluorescent probe molecule for hypochlorous acid detection. The near-infrared fluorescent probe molecule is a hypochlorous acid-responsive fluorescent probe molecule based on a derivative of basic blue-3, has the advantages of short response time, high sensitivity and the like, thus providing possibility for detecting tracehypochlorous acid in some lesion tissues. The invention has the advantages that: the synthesized probe molecule has fast hypochlorous acid response, good specificity and low detection limit, thus providing possibility for detecting trace hypochlorous acid in lesion tissues; and by adjusting the substituent group of an aniline para-position functional group, a series of hypochlorous acid-responsive probe molecules can be designed and synthesized.

Description

technical field [0001] The invention relates to fluorescent probe molecules based on basic blue-3 (BB-3) compounds as hypochlorous acid responses. The hypochlorous acid provides the possibility. Background technique [0002] Reactive oxygen species (ROS) are a series of reactive oxygen species produced by aerobic cells during metabolism, including: O 2- 、H 2 o 2 And HClO etc. Hypochlorous acid is one of the most important ROS. It is produced by hydrogen peroxide and chloride ions under the catalysis of myeloperoxidase (MPO), and plays roles in maintaining redox balance and resisting pathogens in organisms. However, overexpressed hypochlorous acid can cause oxidative stress, which contributes to various diseases, including cardiovascular disease, neurodegenerative disease, atherosclerosis, etc. Therefore, it is crucial to develop an analytical method that is reliable, accurate and capable of detecting hypochlorous acid at physiological levels. So far, the main methods f...

Claims

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Application Information

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IPC IPC(8): C07D265/38C09K11/06G01N21/64
Inventor 吕光磊郑武斌杨佳佳沈扬李春霞
Owner ZHEJIANG NORMAL UNIVERSITY
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