Application of a class of heptamethine indole cyanine dyes
A technology of heptamethine indole cyanine and dyes, which is applied in the field of medicine and can solve problems such as body damage
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Embodiment 1
[0048] The synthesis of embodiment 1 compound 1-3
[0049] The preparation steps are as follows:
[0050] Preparation of 2-chloro-3-hydroxymethane-1-formylcyclohexene
[0051]
[0052] A solution of 35 mL of dry dichloromethane and 37 mL of phosphorus oxychloride was dropped into a mixture of 80 mL of dry dichloromethane and N,N-dimethylformyl (1:1, v / v) under an ice bath. Maintaining at 0°C, 10 g (0.10 mol) of cyclohexanone was added dropwise to the reaction solution, and then the temperature was slowly raised to reflux for 3 h. Stop the reaction, cool in an ice-water bath, and pour the reaction solution into 200 g of crushed ice in batches. A large amount of red solid precipitated out. Filter under reduced pressure, wash the solid in batches with frozen acetone until yellow, and vacuum-dry to obtain the crude product, which is recrystallized with acetone to obtain 12.86 g of yellow solid, yield: 73%, melting point: 130-132°C. 1 H NMR: 1 H NMR(400MHz,DMSO-d):1.573(m,2...
Embodiment 2
[0062] Embodiment 2 cell proliferation experiment:
[0063] Human umbilical cord-derived mesenchymal stem cells (hUCMSCs) were selected as the cell line, and cultured at 37°C, 5% CO in human umbilical cord-derived mesenchymal stem cell culture medium (Lonza, Switzerland) containing cell growth factors. 2 Under the condition of cultivation, the culture medium was changed once every 2 days. Take cells that grow well and reach 70-80% confluence, digest and inoculate in 96-well plates (1×10 4 / well) overnight. Then add 10 μM small molecule compounds 1-3 to the cells at 37°C, 5% CO 2 Incubate under conditions for 30 minutes. Discard the staining solution, wash three times with PBS, and culture with 100 μL of fresh medium for 72 hours. The relative cell viability was detected by CCK-8 assay. The results showed that, compared with normal cells, the above three small molecular compounds all had obvious pro-proliferation effects on cells ( figure 1 ).
Embodiment 3
[0064] Example 3 Cell Mitochondria Localization:
[0065] Human umbilical cord-derived mesenchymal stem cells (hUCMSCs) were selected as the cell line, and cultured at 37°C, 5% CO in human umbilical cord-derived mesenchymal stem cell culture medium (Lonza, Switzerland) containing cell growth factors. 2 Under the condition of cultivation, the culture medium was changed once every 2 days. Cells that grow well and reach 70-80% confluence are taken, digested and centrifuged, inoculated into laser confocal small dishes, and cultured overnight. Discard the medium the next day, add compound 1 with a concentration of 10 μM and a volume of 1 mL to the culture dish, and store at 37 °C, 5% CO 2 Incubate for 20 minutes under conditions. The staining solution was discarded, washed three times with PBS buffer, and the cells were incubated with 100nM mitochondrial probe Mito-Tracker Green or 10μM rhodamine 123 for 15 minutes. The staining solution was discarded, washed three times with PB...
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