A membrane-permeable dye with a large two-photon fluorescence active cross-section and its application
A two-photon fluorescence and permeability technology, applied in the direction of luminescent materials, fluorescence/phosphorescence, styrene-based dyes, etc., can solve the problems that restrict two-photon three-dimensional imaging technology for cell biological imaging and observation, and achieve excellent cell membrane permeability , excellent low toxicity, good biocompatibility
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Embodiment 1
[0027] Synthesis of 4,4-2 Formyl Triphenylamine
[0028] 20ml of DMF was added to the single neck flask. Under stirring in an ice-water bath, 20 ml of phosphorus oxychloride was slowly added dropwise to the above solution, and stirred at room temperature for 1 h to obtain a yellow turbid liquid. 5 g (20.4 mmol) of triphenylamine was weighed, dissolved in 10 ml of chloroform, and then gradually added to the above-mentioned stirred solution, and the reaction was heated under reflux for 10 hours. The reaction solution was poured into 1000 mL of water, and CH 2 Cl 2 extraction. The organic layer was washed with saturated sodium chloride solution, anhydrous MgSO 4 Dry, filter and evaporate the solvent. The crude product was separated by column chromatography, and petroleum ether / ethyl acetate (10:1) was used as the eluent to obtain a light yellow solid, which was 4,4-2 formyl triphenylamine. Yield: 55%.
[0029] 1 H NMR (400MHz, d6-DMSO): δ (ppm) 9.88 (s, 2H), 7.85 (d, J=8....
Embodiment 2
[0037] 4-[(E)-2-(1H-benzimidazol-2-yl)vinyl]-N-{4-[(E)-2-(1H-benzimidazol-2-yl)vinyl] Synthesis of Phenyl}-N-phenylaniline
[0038] The synthesis technique is the same as in Example 1, and 4-[(E)-2-(1H-benzimidazol-2-yl)vinyl]-N-{4-[(E)-2-(1H-benzoyl) is obtained by synthesis Imidazol-2-yl)vinyl]phenyl}-N-phenylaniline, yield: 17%.
[0039] 1H NMR (400MHz, d6-DMSO): δ (ppm): 12.55 (s, 2H), 7.65 (m, J=7.67Hz, 6H), 7.55 (d, J=7.64Hz, 4H), 7.41 (t, J=7.84Hz, 2H), 7.16 (t, J=7.76Hz, 5H), 7.11 (d, J=7.68Hz, 4H), 7.07 (d, J=8.24Hz, 4H).
Embodiment 3
[0041] RBL-2H3 and Hela cell culture
[0042] RBL-2H3 or HeLa cell lines were adherently cultured in medium containing 10% fetal bovine serum at 37°C, 5% CO 2 Cultured in a saturated humidity incubator, and the medium was changed every 2 to 3 days for passage. After the cells grow to the logarithmic phase, the slicing culture: ① Soak the coverslip in absolute ethanol for 30 minutes, dry it in an alcohol lamp and put it into a disposable 35mm petri dish; ② Wash the cells in the 100ml cell flask with PBS Three times, digest with 1 ml of 0.25% trypsin for 3-5 minutes, carefully pour out the medium, add a small amount of fresh medium and pipet evenly, after counting the cells, leave the cells of the appropriate density, and add the medium to the desired volume ( Control cells at a final concentration of 1x10 5 ), inoculated into a Petri dish containing a coverslip, placed in CO 2 Cultured in an incubator to allow the cells to grow on the sheet.
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