Iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as preparation method and application thereof
A technology of pyrrolidone and diagnostic reagent, which is applied in the field of iridium-coated azapyrrolidone photodiagnostic reagent and preparation thereof, can solve the problems of unfavorable in vivo application, short absorption wavelength, low penetration depth, etc., and achieves good photothermal and photodynamic effects, The effect of reducing damage and simple process
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Embodiment 1
[0040] Embodiment 1: Preparation of azapyrrolidone auxiliary ligand
[0041]
[0042] Preparation of Compound 2: Compound 1 (26mmol) and benzaldehyde (26mmol) were dissolved in methanol solution, then 50% NaOH aqueous solution was added, and after stirring and reacting at room temperature for 22 hours, the pH was adjusted to neutrality, and the methanol solvent was removed by filtration to obtain Pale yellow solid powder, then washed three times with water to remove the salt to give the white product 2. Yield: 91%.
[0043] 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.01 (d, J = 8.4Hz, 2H), 7.78 (d, J = 16.4Hz, 1H), 7.53 (d, J = 8.4Hz, 2H), 7.35 (d, J = 16.4Hz ,2H),6.98(d,J=8.4Hz,2H),6.69(d,J=8.4Hz,2H),3.77-3.65(s,6H). 13 C NMR (100MHz, CDCl 3 )δ (ppm): 188.85, 169.10, 162.20, 151.91, 144.95, 131.97, 130.49, 130.27, 122.82, 116.63, 114.27.
[0044] The preparation of compound 3: in the methanol solution of compound 2 (5mmol), add 10mL diethylamine and 15mL nitromethane, after ...
Embodiment 2
[0049] Embodiment 2: Preparation of iridium coordination azapyrrolidone complex
[0050]
[0051] The preparation of compound 7: compound 6 (0.14mmol) and iridium trichloride trihydrate are dissolved in the mixed solution of ethylene glycol ether and water, under N 2 Stir overnight at 110°C under atmosphere, then add water to the reaction solution, at this time, a large amount of yellow solid precipitates, the solution is removed by suction filtration, and then washed repeatedly with ethanol to obtain a yellow solid 7.
[0052] Preparation of Compound 8: Compound 7 (0.10 mmol) and silver trifluoromethanesulfonate were dissolved in an aqueous ethanol solution, and refluxed at 100° C. for 24 h. Subsequently, the reaction solution was removed, the obtained solid was dissolved in dichloromethane, the filter residue was removed by filtration, and the filtrate was spin-dried to obtain a yellow solid 8.
[0053] Preparation of compound IrDipy-7: Compound 5 was dissolved in tetrah...
Embodiment 3
[0055] Embodiment 3: Absorption and emission spectrum test of iridium complex IrDipy-7
[0056] The spectrum test concentration used is 10μM, and the test solvent is CH 2 Cl 2 solution, when measuring the emission spectrum, the excitation wavelength is 690nm.
[0057] The absorption and emission spectra of IrDipy-7 as image 3 and Figure 4 shown. The complex shows strong absorption at 400-500nm in the ultraviolet region and 600-800nm in the near-infrared region. In particular, the complex can be excited by near-infrared light, which greatly reduces the impact of the excitation light source on the cells when doing cell imaging experiments. damage.
[0058] Its emission is wide, and the emission peak is located at 730nm. Red light emission increases the penetration depth of biological tissue, making it more suitable for biological imaging.
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