Fluorescent probe for detecting nitrogen monoxide and preparation method thereof
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A nitric oxide, fluorescent probe technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., to achieve the effect of reducing interference
Inactive Publication Date: 2012-06-27
XIAMEN UNIV
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[0005] 4-Amino-1,8 naphthalimide fluorophore has the advantages of long-wave emission and large Stokes shift (J.Am.Chem.Soc.; 1981; 103:7615-7620.), which can significantly reduce scattering in fluorescence analysis The interference
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Embodiment 1
[0036] Example 1: Probes 1 preparation method
[0037] Step 1. In a 25mL round bottom flask, add 0.5g of 4-amino-1,8-naphthoic anhydride (1.0eq) and 6.0mL of N,N-dimethylformamide, and add 2-(2-amino Ethoxy)ethanol (1.2eq) totaled 0.282mL, heated and stirred at 90°C for 8h; cooled to room temperature, solids precipitated after adding saturated brine, centrifuged and dried to obtain the intermediate with the following structure:
[0038]
[0039] Step 2: Dissolve 0.1 g of the above intermediate in 2 mL of pyridine, add 0.040 mL of acetic anhydride, stir at room temperature and react overnight, and dry the organic solvent pyridine by rotary evaporation; then add 10 mL of water, and extract twice with 10 mL of ethyl acetate; The organic phase was dried with anhydrous sodium sulfate for 1 h, the organic solvent was dried by rotary evaporation, and then separated by column chromatography (ethyl acetate / dichloromethane=1 / 10) to obtain an orange-red solid with the following struc...
Embodiment 2
[0047] Example 2: Probes 1 chemical properties
[0048] (1) Preparation steps of the test solution:
[0049] In a 10mL colorimetric tube, add 1.0mL 3,3-dimethylglutaric acid-sodium hydroxide buffer solution (pH 7.40), and then add different volumes of 1.0×10 -3 M's NOC13 standard solution (prepared nitric oxide carrier NOC13, see literature: Hrabie J.A., Klose J.R.J.Org.Chem.1993, 58, 1472-1476.), diluted to the mark with deionized water 3 times, shaken; Add 0.1mL 1.0×10 -3 m 1 The acetonitrile stock solution was shaken again, placed in a water bath at 37°C for 40 minutes, then excited at 438nm, and measured the fluorescence intensity at 540nm. Operate as above, but do not add nitric oxide or other active oxygen probes 1 Solution, for the preparation of blank test solution.
[0050] (2) Probe in aqueous solution 1 Spectral characteristics and detection performance.
[0051] figure 1 is the probe 1 Fluorescence response to nitric oxide in aqueous solution under neutra...
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Abstract
The invention relates to a fluorescent probe and in particular relates to a fluorescent probe for detecting nitrogen monoxide and a preparation method thereof. The probe uses 4-amino-1,8-naphthalimide as a basic molecular structure and carbamided o-phenylenediamine as a compound with nitrogen monoxide recognition groups. The preparation method comprises the following steps: adding 4-amino-1,8-naphthoic anhydride and an organic solvent into a container, then adding 2-(2-aminoethoxyl)ethanol, heating for reaction, and cooling; adding a saline solution, centrifuging to obtain an intermediate A, then dissolving the intermediate A in pyridine, and adding acetic anhydride to react; performing rotary evaporation, and adding water for extraction; performing rotary evaporation to separate out an intermediate B; adding the intermediate B, diisopropylethylamine and toluene into a container to obtain a mixed solution, then adding the mixed solution in a solution containing triphosgene and toluene, heating for refluxing, and cooling; adding dichloromethane, carrying out centrifugal separation to obtain a supernatant, and then adding the supernatant into a solution containing o-phenylenediamine and dichloromethane to react; performing rotary evaporation, and adding water for extraction; and drying the obtained ethyl acetate, and performing rotary evaporation to separate out the product.
Description
technical field [0001] The invention relates to a fluorescent probe for nitric oxide, in particular to a fluorescent probe for detecting nitric oxide and a preparation method thereof. Background technique [0002] Nitric oxide (NO) is a gas that is first discovered by humans to act as a signal molecule in the body. As an important member of physiological reactive oxygen species (ROS), it is an important cell messenger molecule in organisms and is Known as "information molecule, effect molecule, star molecule". Studies in recent years have shown that nitric oxide, as a new type of intracellular messenger molecule, is widely involved in the physiological and pathological regulation of the cardiovascular, nervous and immune systems of the body. It can dilate blood vessels, lower blood pressure, inhibit the proliferation of vascular smooth muscle cells and platelet adhesion, and as a neurotransmitter, it plays an important role in the information transmission of neurons. Curre...
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