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Coumarin and styrenepyridinium based hypochlorous acidfluorescent probe and application thereof

A styrene pyridinium, ratio fluorescent probe technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry and other directions, to achieve the effect of broad application prospects

Active Publication Date: 2019-06-21
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Coumarin and styrenepyridinium based hypochlorous acidfluorescent probe and application thereof
  • Coumarin and styrenepyridinium based hypochlorous acidfluorescent probe and application thereof
  • Coumarin and styrenepyridinium based hypochlorous acidfluorescent probe and application thereof

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Embodiment 1

[0022] Embodiment 1 Preparation of the ratio fluorescent probe for detecting hypochlorous acid according to the present invention

[0023] 1-(2-(4-(7-(Diethylamino)-2-oxo-2H-chromene-3-carbonyl)piperazin-1-yl)-2-oxoethyl)-4-methanol Pyridinium chloride (499mg, 1mmol) and 4-(dimethylamino)-benzaldehyde (193mg, 1mmol) and piperidine 0.5mL were refluxed in ethanol for 8h to obtain a mixture. The probe was separated and purified by column chromatography (methanol:dichloromethane=1:15) as a maroon solid with a yield of 53%.

[0024] Structure Confirmation Spectral Data:

[0025] IR(KBr)ν / cm: 3442.41, 2926.99, 1709.53, 1619.54, 1585.55, 1524.27, 1473.39, 1421.85, 1359.92, 1330.28, 1227.02, 1167.83, 1132.17, 821.60;

[0026] 1 H NMR (300MHz, d 6 -DMSO),δ(ppm):1.136(t,6H,J=6.9Hz),3.030(s,6H),3.388-3.614(m,12H),5.602(s,2H),6.570(s,1H) ,6.752-6.815(m,3H),7.200(d,1H,J=15.9Hz),7.528(d,1H,J=8.7Hz),7.616(d,2H,J=9.0Hz),7.921(d, 1H, J=15.9Hz), 8.037-8.097(m, 4H), 8.590(d, 2H, J=6.9Hz); ...

Embodiment 2

[0032] Add 20 equivalents of Ca 2+ , SO 2- 3 ,Cu 2+ , Fe 2+ , Fe 3+ ,GSH,H 2 o 2 ,HO . ,Mg 2+ ,NO - 2 , 1 o 2 ,S 2- , t-BuOOH, t-BuOO. and HOCl. After acting for 1 h, the samples were tested for fluorescence.

[0033] The results showed that this probe exhibited good selectivity only for HClO. See figure 2 .

Embodiment 3

[0035] Into the 10ml volumetric flask containing the 5 μM hypochlorous acid probe, add different equivalents of HClO with a micro-injector, and perform a fluorescence test after acting for 1 hour.

[0036] The results show that the ratio of the fluorescence intensity at 472nm to the fluorescence intensity at 600nm has a linear relationship with the concentration of hypochlorous acid within a certain range. See image 3 .

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Abstract

The invention discloses a coumarin and styrenepyridinium based ratiometricfluorescent probefor detecting hypochlorous acid. The coumarin and styrenepyridinium based ratiometricfluorescent probe comprises an energydonorcoumarinfluorophore, an energy receptor (E)-4-(4-(diethylamine)-styryl)-1-methylpyridiniumchloride, and a link group acetylpiperazine, and the chemical structural formula is shown inthe formula (I). The probe can detect the hypochlorous acid at high selectivity and high sensitivity, the fluorescence emission intensity is gradually reinforced at 472 nm with the increase of the concentration of the hypochlorous acid, and the emission intensity gradually decreases at 600 nm; the ratio of the two (I472 / I600) and the concentration of the hypochlorous acid keep a linear relation at certain degree. The ratiometric imaging is implemented in a cultured cell, and the fluorescent probe is expected to play a role in industrial production and clinical medicine, and has a broad application prospect.

Description

technical field [0001] The invention relates to a ratio fluorescent probe for detecting hypochlorous acid based on a fluorescence resonance energy transfer mechanism and its application, in particular to a ratio fluorescent probe for detecting hypochlorous acid based on coumarin and styrene pyridinium and its application. Application; belongs to the field of small organic molecule fluorescent probes. Background technique [0002] Hypochlorous acid is an important reactive oxygen species in organisms, which is generated by chloride ions and hydrogen peroxide under the catalysis of peroxidase. As an endogenous bactericide, it can sterilize and anti-virus, and plays a vital role in organisms. effect. On the other hand, the imbalance of hypochlorous acid production is closely related to certain diseases, such as: arthritis, kidney disease, lung injury, arteriosclerosis and tumors and other diseases. In order to study the physiological and pathological effects of hypochlorous a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C09K11/06G01N21/64
Inventor 赵宝祥苗俊英闫业浩和晓莹
Owner SHANDONG UNIV