A nitric oxide two-photon lipid droplet locking fluorescent probe and its preparation method and application in detecting neuroinflammation
A nitric oxide, reaction technology, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve the problems of poor ability to cross the blood-brain barrier, difficult to enter brain tissue, lack of targeting, etc., and achieve maximum fluorescence. The effect of high response multiples, improved targeting, and improved clarity
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Embodiment 1
[0120] like figure 1 As shown, a method for synthesizing a nitric oxide two-photon lipid droplet-locked fluorescent probe (SUN-TAN) for detecting neuroinflammation includes the following steps:
[0121] S1. Synthesis of compound 1: 3g (14.71mmol) of 1-fluoro-4-nitrobenzene and 2g (12.26mmol) of aminotriethylene glycol monomethyl ether were dissolved in 20mL of DMSO, and the temperature was raised to 100°C to react for 6h. After the reaction was completed, the mixture was cooled to room temperature, extracted with dichloromethane and water, the lower organic phase was collected, and the crude product was obtained by distillation under reduced pressure. : DCM=2:1 (v / v), 2.8 g of compound 1 were obtained in 80% yield.
[0122] S2, the synthesis of compound 2: 2.8 g (9.854 mmol) of compound 1 prepared in step S1, 100 mg of Pd / C powder and 20 mL of hydrazine hydrate were successively added to a three-necked flask filled with 80 mL of ethanol, and the temperature was raised to 80° ...
Embodiment 2
[0129] The fluorescence response experiment between fluorescent probe molecules and NO includes the following steps:
[0130] (1) Weigh 3.5 mg of the probe (SUN-TAN) prepared in Example 1, dissolve it in 1 mL of DMSO, sonicate, mix well, then take 0.2 mL of the above solution into a 1 mL centrifuge tube, add 0.8 mL of DMSO to prepare 1 mM probe Needle stock solution.
[0131] (2) Preparation of NO saturated solution (1.9 mM): at room temperature, nitrogen was passed through the 10 mM PBS solution for 30 min to remove O in the solution 2 , and then quickly introduce the NO gas generated by the reaction of sodium nitrite and concentrated sulfuric acid into the above solution, and the time of introducing NO is about 40min to prepare a saturated solution of NO, and store it in a 4°C refrigerator. When used, the NO saturated solution was diluted to 1 mM.
[0132] (3) Take 10 μL of the probe stock solution obtained in step (1), add an appropriate amount of a mixed solution of PBS / ...
Embodiment 3
[0136] Anti-interference performance is one of the important indicators to measure the practicality of fluorescent probes. In order to investigate the specific recognition performance of the probe (SUN-TAN) prepared by the present invention to NO, the experimental method is as follows:
[0137] In the 10 μM probe solution prepared in Example 1, 100 μM metal ions ( Figure 7 2-7 in the respectively represent Zn 2+ , Mn 2+ , Ba 2+ , Mg 2+ , Ca 2+ , Fe 2+ ), 1.0 mM biothiol ( Figure 7 8-14 in the respectively represent H 2 S, Cys, Hcy, GSH, AA, DHA, MGO); 50 μM reactive oxygen species ( Figure 7 15-17 in the respectively represent H 2 O 2 , OH, ClO - ) and 50 μM reactive nitrogen ( Figure 7 The 18-19 in the represent HNO, ONOO respectively - ) and 20μM NO ( Figure 7 20) in the solution, and then quickly put the test solution into a constant temperature oscillator with a temperature of 37° C. and a rotation speed of 200 r, and shake the reaction for 3 min. Final...
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