Application of Oxazine Compounds in the Preparation of Near Infrared Fluorescent Probes
A technology of fluorescent probes and compounds, applied in the application field of oxazine compounds in the preparation of near-infrared fluorescent probes, can solve the problems of high dyeing concentration, high probe cytotoxicity, long incubation time, etc., and achieve photobleaching Low, good cell membrane permeability, good photostability effect
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[0043] The preparation method of the compound of general formula F represented by above-mentioned route comprises the steps:
[0044] (1) In the hydrochloric acid acidification system, p-nitrobenzenediazonium chloride and the compound of formula I were reacted at 25-35° C. for 0.5-2 hours according to the molar ratio of 1:1, to prepare the compound of formula II;
[0045]
[0046] (2) The compound of formula F was prepared by reacting the compound of formula II with 8-hydroxyjuloridin at a molar ratio of 1:1 in acidic DMF at 135-145°C for 2-4 hours.
[0047] The near-infrared fluorescent probe based on oxazine of the present invention has the following advantages:
[0048] The compound has a certain level of water solubility and good cell membrane permeability.
[0049] The compound has specificity and specific recognition for RNA molecules;
[0050] The compound has excellent fluorescence properties, has low biological photobleaching, photodamage and biological toxicity wh...
Embodiment 1
[0057] Embodiment 1: Preparation of probe compound F-1
[0058]
[0059] (1) Synthesis of intermediate 1-II
[0060] In the hydrochloric acid acidification system, the compound of p-nitrodiazonium chloride and 1-I was reacted at 25-35°C for 0.5-2 hours according to the molar ratio of 1:1. After the reaction was completed, a brick red color was obtained after suction filtration and washing. The compound of formula 1-II was obtained from the solid powder crude product with a yield of 95%.
[0061] (2) Synthesis of compound F-1
[0062] The intermediate 1-II and 8-hydroxyjuloridine prepared in the above reaction (1) were added into a round bottom flask containing DMF, and 1 mL of perchloric acid solution was added dropwise. After the dropwise addition was completed, the system was stirred for 2.5 hours to stop the reaction, and purified by column chromatography to obtain the target probe compound F-1 as dark blue needle-like crystals with metallic luster, with a yield of 78....
Embodiment 2
[0064] Embodiment 2: The labeling experiment of probe compound F-1 in breast cancer cell (MCF-7)
[0065] Using the compound F-1 synthesized in Example 1, the F-1-DMSO solution was added to MCF-7 cells containing 2 mL of medium for shaking, and imaged with a laser confocal microscope. Select a representative area, observe with an oil lens (60×), and repeat three times. The result is as figure 2 shown, where: figure 2 (a) F-1 channel; figure 2 (b) is a bright field image of cells; figure 2 (c) is the mixing channel of (a) and (b). It can be seen that F-1 molecules can stain cells.
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