A kind of near-infrared fluorescent probe with extremely acidic pH response and its preparation method and application
A fluorescent probe and near-infrared technology, applied in the field of bioluminescent analysis, can solve problems such as large overlap between ultraviolet absorption spectrum and fluorescence spectrum, inability to avoid tissue self-absorption and autofluorescence, and inability to detect pH in cells and living bodies. Achieve the effect of obvious color change, convenient naked eye recognition, and little damage to cells and living bodies
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Embodiment 1
[0070] A preparation method of a near-infrared fluorescent probe with an extremely acidic pH response, comprising the following steps:
[0071] (1) Preparation
[0072] 25.8mg (0.3mmol) of and 63.8 mg (0.1 mmol, molecular weight 638.19) of the compound Dissolve in 2ml of anhydrous DMF solvent, react at 80°C for 1h under argon gas atmosphere, remove the solvent by rotary evaporation, dry in vacuum for 12h, pass through a silica gel column, and carry out gradient elution with a mixed solution of dichloromethane and methanol , the volume ratio of eluent dichloromethane and methyl alcohol is changed from 40:1 to 20:1, remove solvent, obtain blue solid product 55mg, productive rate 80%, the structural formula of this blue solid product is
[0073] (2) Preparation of near-infrared fluorescent probes with extremely acidic pH response:
[0074] The chemical formula will be 68.8mg (0.1mmol) and 68.4mg (0.4mmol) of Put it into a three-necked flask, add 3mL of anhydrous DMF ...
Embodiment 2
[0078] A preparation method of a near-infrared fluorescent probe with an extremely acidic pH response, comprising the following steps:
[0079] (1) Preparation
[0080] The chemical formula will be Dissolve 1.02g (5mmol) of the compound in 15ml of 1,4-dioxane, add 1.05g of Fmoc-Cl, and then add 10% aqueous sodium carbonate solution to control the pH value of the reaction solution between 8.0-9.0 in real time room temperature, stirring overnight. Then add 10mL of distilled water, extract with ethyl acetate several times, collect the organic phase, spin off the solvent, and dry in vacuum for 12h to obtain the chemical formula: white flocculent product.
[0081] (2) The preparation is with embodiment 1;
[0082](3) The chemical formula is 34.4mg (0.05mmol) and 41mg (0.2mmol) of Put it into a three-necked flask, add 2 mL of anhydrous DMF as a solvent, and add 14 μL of triethylamine (0.1 mmol) as an acid-binding agent. Under the protection of argon, react at a tempera...
Embodiment 3
[0085] A preparation method of a near-infrared fluorescent probe with an extremely acidic pH response, comprising the following steps:
[0086] (1) Preparation
[0087] 52mg (0.6mmol) of and 63.8 mg (0.1 mmol) of the compound Dissolve in 3ml of anhydrous DMF solvent, react at 70°C for 1.5h under an argon gas atmosphere, remove the solvent by rotary evaporation, dry in vacuum for 12h, pass through a silica gel column, and carry out gradient washing with a mixed solution of dichloromethane and methanol Remove, the volume ratio of eluent dichloromethane and methanol is changed from 40:1 to 20:1, remove solvent, obtain blue solid product 55mg, productive rate 80%, the structural formula of this blue solid product is
[0088] (2) Preparation of near-infrared fluorescent probes with extremely acidic pH response:
[0089] The chemical formula will be 68.8mg (0.1mmol) and 102mg (0.6mmol) Put it into a three-necked flask, add 3mL of anhydrous DMF as a solvent, and add 35μL...
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