Nitryl hydrogen fluorescence probe with two photon and near infrared luminescence characteristics and preparation method and application thereof
A technology of nitrosyl hydrogen and fluorescent probes, applied in chemical instruments and methods, luminescent materials, fluorescence/phosphorescence, etc., can solve the problems of poor cell penetration, limited application, and cell photodamage, and increase tissue penetration. Penetration depth and imaging depth, high imaging resolution, and the effect of reducing light damage
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[0042] The present invention also provides the preparation method of the nitrosyl hydrogen fluorescent probe described in the above scheme, comprising the following steps:
[0043](1) Mixing a compound having a structure shown in formula II, a compound having a structure shown in formula III, a first organic base, an organic acid and a first organic solvent for Knoevenagel reaction to obtain a compound having a structure shown in formula IV;
[0044]
[0045] In formula III and formula IV, R 1 , R 2 , R 3 and R 4 is hydrogen, amino, alkyl, alkoxy, alkylamino, haloalkyl, aryl, aryloxy or arylamino;
[0046] (2) The compound having the structure shown in formula IV is mixed with 2-(diphenylphosphino)benzoic acid, a second organic base, a condensation reagent and a second organic solvent, and the condensation reaction is carried out under a protective atmosphere to obtain A nitrosyl hydrogen fluorescent probe having the structure shown in formula I.
[0047] In the presen...
Embodiment 1
[0064] The nitrosyl hydrogen fluorescent probe was prepared according to the following reaction scheme:
[0065]
[0066] (1) Compound 1 (400mg, 1.92mmol), p-hydroxybenzaldehyde (300mg, 2.47mmol), piperidine (0.6ml, 0.006mmol), acetic acid (0.6ml, 0.01mmol) and toluene were mixed, under the protection of nitrogen Reflux at 130°C for 17 h, monitor the reaction progress with a TCL board until compound 1 completely disappears; wash the obtained product with saturated brine, extract three times with ethyl acetate, dry the obtained organic phase with anhydrous sodium sulfate, concentrate to a solid by rotary evaporation, and use Silica gel column chromatography was used for purification, and the eluents used were ethyl acetate and dichloromethane (the volume ratio of ethyl acetate and dichloromethane was 1:20) to obtain 250 mg of a red solid.
[0067] The calculated yield is 42%;
[0068] The resulting red solid is characterized, and the specific data are as follows:
[0069] ...
Embodiment 2
[0077] Carry out performance test to the nitrosyl hydrogen probe prepared in embodiment 1, concrete steps are as follows:
[0078] (1) Determination of the sensitivity of the nitrosyl hydrogen probe to pH: in 2mL PBS / DMF mixed solution (pH values are 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0, the volume ratio of PBS and DMF 10 μL DCMHNO DMF solution (1 mM) was added to 1:1) to obtain a 5 μM DCMHNO solution, and then 50 μM Angeli’s salt solution was added, and the resulting mixed solution was incubated at 37° C. for 5 min, and the fluorescence intensity of the mixed solution was measured as a function of Changes in the pH value of the PBS buffer solution.
[0079] figure 1 It is the change figure of the fluorescence intensity of DCMHNO in the PBS / DMF mixed solution of different pH values, by figure 1 It can be seen that the response of DCMHNO to nitrosyl hydrogen is not sensitive to pH.
[0080] (2) Determination of the response time of the nitrosyl hydrogen probe: Add 10 μL...
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