Thiazole orange derivative, preparation and application thereof
A technology of orange derivatives and thiazoles, applied in the field of small molecule photothermal materials, can solve the problem of low photothermal conversion efficiency of mitochondrial photothermal probes
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Embodiment 1
[0081] The embodiment of the present application provides a thiazole orange derivative (I-b), the synthesis method of which comprises:
[0082] (1) Add 2,4-dimethylquinoline and methyl iodide to acetonitrile solvent at a molar ratio of 1:1, react at 60°C for 24 hours, cool to room temperature, add an appropriate amount of ethyl acetate dropwise, and solids precipitate out. Collect solid, purify, obtain product formula (Ⅴ-b);
[0083]
[0084] The NMR data of formula (Ⅴ-b) is: 1 H NMR (DMSO, 400Hz): δ8.13 (d, J = 8.4Hz, 1H), 8.04 (d, J = 8.4Hz, 1H), 7.68 (m, 2H), 6.92 (s, 1H), 4.33 ( s,3H), 2.68(s,3H), 2.59(s,3H); ESI-MS m / z299.02[M-I] + ;
[0085] (2) Dissolve the formula (V-b) and N,N'-diphenylformamidine in ethanol at a molar ratio of 1:2, and heat at reflux at 60°C for 1 hour. After cooling to room temperature, the precipitate was collected by filtration, washed three times with ethanol, and then dried in vacuo to obtain a brown solid product formula (VI-b);
[0086...
Embodiment 2
[0102] The embodiment of the present application provides the photothermal conversion performance test of the compound of the formula I-b structure in Example 1, including:
[0103] The formula (I-b) prepared in Example 1 and commercialized ICG (indocyanine green ICG is a kind of cyanine dye used in medical diagnosis) are diluted to 1mM, 2mM, 3mM, 4mM, 5mM with deionized water Concentration of five gradients, then irradiated with 808nm laser for 5 minutes, irradiation energy is 2J / cm 2 , detect the ambient temperature every 1 minute with a near-infrared temperature detector, and the control group uses deionized water to measure the formula (I-b) and commercial ICG prepared in Example 1 when the irradiation energy is 2J / cm 2 The temperature rise within 5 minutes under the irradiation of the 808nm laser, the results are as follows Figure 4 ~ Figure 5 as shown, Figure 4 The formula (I-b) and ICG provided for the embodiment of the application are 2J / cm at the irradiation energ...
Embodiment 3
[0105] The embodiment of the present application provides the cytotoxicity test of the compound of formula I-b structure in embodiment 1, including:
[0106] Cell culture: Inoculate tumor cells (human prostate cancer PC3, breast cancer MCF7, non-small cell lung cancer A549 and liver cancer HepG2 cell lines) and Hacat epidermal cells in cell culture flasks and place at 37°C, 5% CO 2 The medium is cultured in the environment, and the medium is 1640 medium containing 10% fetal bovine serum and 0.5% double antibody. Cell inoculation: Inoculate the cultured cells in a 96-well plate with a cell density of 8000 cells / mL, and continue to store at 37°C, 5% CO 2 Incubate in the environment for 48 hours. Add gradient compound solution: remove the medium in the 96-well plate, wash with pre-cooled PBS 3 times, add 1640 complete medium containing formula (I-b) of different gradient Example 1, and continue to store at 37°C, 5% CO 2 Incubate in the environment for 24 hours. Add MTT solutio...
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