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Fluorescent probe for double detection on nitric oxide and hydrogen sulfide and preparation method and application of fluorescent probe

A technology of nitric oxide and fluorescent probes, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., to achieve simultaneous detection, high yield, and simple synthesis methods

Inactive Publication Date: 2020-01-17
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among these methods, the fluorescence method has broad application prospects because of its high sensitivity, high selectivity, non-invasive detection and simplicity, but there is no one that can be used to detect NO and H at the same time. 2 Fluorescent probes for S, therefore developing a simultaneous detection of NO and H 2 The fluorescent probe of S is very important

Method used

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  • Fluorescent probe for double detection on nitric oxide and hydrogen sulfide and preparation method and application of fluorescent probe
  • Fluorescent probe for double detection on nitric oxide and hydrogen sulfide and preparation method and application of fluorescent probe
  • Fluorescent probe for double detection on nitric oxide and hydrogen sulfide and preparation method and application of fluorescent probe

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Embodiment 1

[0032] The preparation of fluorescent probe compound of the present invention comprises the following steps:

[0033] (1) Weigh amino silicone oil (4.4g, 20mmol) and dissolve it in ethanol, then add Cy-7 (0.64g, 10mmol), heat and reflux at 68°C and stir for 12h, then remove the ethanol in the reaction solution, and use silica gel chromatography Compound 1 was further purified by column using dichloromethane and methanol at a volume ratio of 20:1 as the eluent. The structural formula of compound 1 is as follows:

[0034]

[0035] (2) Dissolve 4-bromo-1,8-naphthoic anhydride (1.2g, 5mmol) in 15ml DMF, then add NaN 3 (0.4g, 6mmol), adding a catalytic amount of K 2 CO 3 , at N 2 Protected from light, heated to reflux at 45°C and stirred for 2 hours; then poured the reaction solution into ice water, a yellow solid precipitated, then filtered with suction and air-dried to obtain compound 2. Before using compound 2, it can be purified by silica gel chromatography column. Dich...

Embodiment 2

[0040] Test the ultraviolet spectrum titration spectrum of fluorescent probe of the present invention

[0041] Use ethanol as a solvent to prepare a 1mM fluorescent probe solution, take 10ul and dissolve it in a mixed solution of 3ml PBS and ethanol (25μM PBS buff, pH=7.4, 10% ethanol), and then take 0-15μM H 2 S was added to the fluorescent probe, and after a sufficient reaction, the ultraviolet spectrum was tested, and the results are shown in image 3 . It can be seen from the figure that when adding H 2 After S, the probe had an obvious new peak at 430nm and the peak intensity in the ultraviolet spectrum gradually increased, and the color of the solution was gradually deepened by naked eyes and finally turned green, indicating that the probe could be combined with H 2 S response. Take another probe, add 0-20 μM NO to the probe solution and test the UV spectrum. As the solubility of NO gradually increased, the color of the probe gradually became lighter, and the peak in...

Embodiment 3

[0043] Fluorescence Spectrum Test of Fluorescent Probe Ion Selectivity of the Present Invention

[0044] Use ethanol as solvent to make 1mM mother solution, take 10ul of mother solution and dissolve in 3ml PBS and ethanol mixed solution (25μM PBS buff, pH=7.4, 10% ethanol), take 20 equivalents of various metal ions (1Probe 2FeCl 3 3AgNO 3 4CuCl 2 5NiSO 4 6CoCl 2 7SnCl 2 8CdCl 2 9AlCl 3 10NaNO 3 11NaNO 2 12NaCNS 13NaF 14CaCl 2 15BaCl 2 16Na 2 SO 4 17H 2 o 2 18Na2S 2 o 4 19 Na 2 SO 3 20Na 2 S 2 o 3 21Na 2 CO 3 22Cys 23H 2 S) After being added to the mixed solution for a full reaction, use 405nm excitation to find that when other ions are added, the fluorescence intensity does not change significantly, but adding H 2 The fluorescence intensity at 550nm increases obviously at S time. Description probe pair H 2 S has a good response. Excite the probe with a wavelength of 640nm and find that adding other ions (1Probe 2FeCl 3 3AgNO 3 4CuC...

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Abstract

The invention discloses a fluorescent probe for double detection on nitric oxide and hydrogen sulfide and a preparation method and application of the fluorescent probe. The fluorescent probe has a general chemical= structure formula shown in the description. According to the fluorescent probe, naphthalimides and Cy-7 fluorescence groups are introduced into a siloxane-based system, so that on one hand, good physical and chemical properties of a siloxane material can be maintained, and on the other hand, the siloxane material are endowed with properties that raw materials do not have. The organic siloxane fluorescent probe disclosed by the invention is easy to prepare and has good fluorescence performance, achieves specific and rapid detection on NO and H2S in an aqueous solution and a biological environment, and has a broad application prospect in detection on H2S and NO.

Description

technical field [0001] The invention relates to a polymer organosilicon fluorescent probe, in particular to a fluorescent probe for dual detection of nitric oxide and hydrogen sulfide, a preparation method and application thereof. Background technique [0002] Nitric oxide (NO), despite being a simple molecule, has been recognized as an important gas signaling molecule that plays an important role in a variety of physiological and pathological processes. For example, participate in vital activities such as angiogenesis, regulation of vascular functions such as vascular permeability and platelet aggregation. Although NO plays an important role in life activities, excess NO is also a causative factor of various vascular diseases, including arteriosclerosis, ischemia-reperfusion and heart failure, and its pathogenic mechanism remains elusive Yes, medicine has not completely solved this problem. Therefore, it is extremely important to find a suitable method or tool that can mo...

Claims

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Application Information

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IPC IPC(8): C07F7/08C09K11/06G01N21/64
CPCC07F7/0838C07F7/0889C09K11/06C09K2211/1007C09K2211/1029G01N21/6402G01N21/6428
Inventor 林伟英左育静王小妮张宇杨婷新
Owner UNIV OF JINAN
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