Fluorescent probe for tumor diagnosis and treatment as well as preparation method and application of fluorescent probe
A fluorescent probe and tumor technology, applied in preparations for in vivo experiments, chemical instruments and methods, medical preparations containing active ingredients, etc., can solve the problem of poor tumor targeting effect, reduced application, and metabolism of mesoporous nanomaterials Poor ability and other issues
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Embodiment 1
[0113] Dissolve ethylenediamine (0.67mL, 10mmol) in 10mL ethanol, and heat to reflux;
[0114] 4-(Bromomethyl)pyridinium bromate (1.27 g, 5 mmol) was slowly added to the above solution, heated to reflux for 12 hours, and the solvent was spin-dried, and the obtained solid was dissolved in DMF (20 mL);
[0115] Then, add IR-783 (3.2g, 5mmol), triethylamine (2.77mL, 20mmol), heat to 40°C, and react for 5 hours under nitrogen protection;
[0116] Rotate off the solvent, dry in vacuo for 12 hours, pass through a silica gel column, dichloromethane:methanol=20:1, gradient elution, remove the solvent to obtain 12.06 mg of a dark blue solid product, which is the target product IR-PY, with a yield of 32%.
[0117] The synthetic route of embodiment 1 is referred to as follows:
[0118]
[0119] Example 1 product nuclear magnetic detection collection spectrum is as figure 1 As shown, among them, 1 HNMR (400MHz, CDCl 3 );δ=8.57(d,J=5.5Hz,2H),7.72(d,J=13.1Hz,2H),7.52(d,2H),7.29(s,2H)...
Embodiment 2
[0122] Dissolve ethylenediamine (1.34mL, 20mmol) in 20mL ethanol and heat to reflux;
[0123] 4-(Bromomethyl)pyridinium bromide (2.53 g, 10 mmol) was slowly added to the above solution, heated to reflux for 18 hours, and the solvent was spin-dried, and the obtained solid was dissolved in DMF (40 mL);
[0124] Then, add IR-783 (6.4g, 10mmol), triethylamine (4.54mL, 40mmol), heat to 50°C, and react for 8 hours under nitrogen protection;
[0125] Rotate off the solvent, dry in vacuo for 12 hours, pass through a silica gel column, dichloromethane: methanol = 20:1, gradient elution, remove the solvent, and obtain 20.35 mg of a dark blue solid product with a yield of 27%.
Embodiment 3
[0127] Dissolve ethylenediamine (6.7mL, 100mmol) in 100mL ethanol and heat to reflux;
[0128] 4-(Bromomethyl)pyridinium bromide (12.7 g, 50 mmol) was slowly added to the above solution, heated to reflux for 24 hours, and the solvent was spin-dried, and the obtained solid was dissolved in DMF (100 mL);
[0129] Then, add IR783 (32g, 50mmol), triethylamine (27.7mL, 200mmol), heat to 40°C, and react under nitrogen protection for 24 hours;
[0130] The solvent was spun off, dried in vacuo for 12 hours, passed through a silica gel column, dichloromethane:methanol=20:1, gradient elution, and the solvent was removed to obtain 86.68 mg of a dark blue solid product with a yield of 23%.
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