Photodynamic therapy probe for detecting cyclooxygenase 2 and preparation thereof
A photodynamic therapy, oxygenase technology
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Embodiment 1
[0023] A method for preparing a photodynamic therapy probe for detecting cyclooxygenase 2, the steps comprising:
[0024] 1) Synthesis of Compound 1:
[0025] 4-Bromo-1,8-naphthalene anhydride (0.97 g, 3.5 mmol) and 1,4-butanediamine (1.02 g, 11.6 mmol) were dissolved in anhydrous dioxane solution (100 mL), and the mixture was washed with Argon was purged and triethylamine (10 mL) was added, refluxed under argon for 11 hours, cooled and then stirred at room temperature for 10 hours, the product was precipitated with cold water and vacuum filtered to obtain solid compound 1 in 80% yield.
[0026] Synthesis of compound 2:
[0027] Compound 1 (0.16 g, 0.45 mmol) was dissolved in DMF (15 mL) solution, to which was added indomethacin (0.19 g, 0.54 mmol), EDCl (0.08 g, 0.4 mmol), HOBt (0.12 g, 0.8 mmol) and DMAP (0.07 g, 0.6 mmol), the mixed solution was stirred at room temperature under nitrogen for 22 hours, the solvent was evaporated under reduced pressure, and column purificat...
Embodiment 2
[0033] Fluorescence response of Npco-Ce6 in different concentrations of cyclooxygenase 2
[0034] The Npco-Ce6 (50 μM) synthesized in Example 1 was dissolved in Tris-HCl buffer solution (100 mM) to prepare a stock solution. Measurements of two-photon fluorescence spectral changes were performed using a confocal multiphoton microscope in spectral scanning mode. The tunable filter is automatically stepped from 400 to 700 nm in 1 nm increments. Using a mode-locked titanium:sapphire laser source (CoherentChameleon, 90 MHz, 200 fs) with an excitation wavelength of 800 nm and an output power of 1230 mW, two-photon fluorescence spectra were sequentially captured at each wavelength interval, and the fluorescence intensity (I 575 nm / I 450 nm) to obtain a ratiometric fluorescence spectrum. At low concentrations of COX2 (575 nm / I 450 nm) had a good linear relationship at the concentration of COX2 in the range of 0.5-3.5 μg / mL, and the results indicated that Npco-Ce6 exhibited a h...
Embodiment 3
[0036] Evaluation of the ability of Npco-Ce6 to generate singlet oxygen
[0037]In order to obtain effective photodynamic therapy, the Npco-Ce6 stock solution (10 μM) in Example 2 was taken to efficiently generate singlet oxygen by laser. The two-photon fluorescent compound of unmodified Ce6 cannot generate singlet oxygen, and free Ce6 shows a low singlet oxygen generation rate, which is not affected by laser irradiation, which is due to the aggregation effect caused by the hydrophobicity of Ce6. When laser irradiated, Npco-Ce6 produced 2.67 times more singlet oxygen than free Ce6, which indicated that Npco-Ce6 well dispersed in water could actively generate ROS under laser irradiation.
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