Fluorescent small-molecule probe for detecting enzyme activity, its preparation method and application
A technology of small molecule probes and detection methods, applied in the biological field, can solve the problems of poor stability, low sensitivity and high cost
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[0041] The invention provides a method for preparing a small molecule probe for detecting enzyme activity, comprising the steps of:
[0042] Step 1: Dissolve perylene anhydride in alkaline solution, filter, adjust the pH value of the filtrate to 8-9, add tetra-n-octyl ammonium bromide and 1,4-dibromobutane, and reflux reaction at 100°C-120°C for 1 ~3h, after extraction, distillation and purification, the compound 3,4,9,10-tetrakis-(4-bromobutyl-ester)-perylene was obtained; the perylene anhydride, tetra-n-octylamine bromide and 1 , the molar ratio of 4-dibromobutane is 1: 0.1: 10;
[0043] Step 2: Dissolve the compound 3,4,9,10-tetrakis-(4-bromobutyl-ester)-perylene obtained in Step 1 in the mixed solution of tetrahydrofuran and water, and add trimethylamine to the mixed solution, Reflux at 60°C-70°C for 48-96h, obtain 3,4,9,10-tetrakis-(4-trimethylaminobutyloxy-carbonyl)-perylene after distillation, extraction and drying, the 3, The molar ratio of 4,9,10-tetrakis-(4-bromobu...
Embodiment 13
[0064] Synthesis of Example 13,4,9,10-tetra-(4-trimethylaminobutyloxy-carbonyl)-perylene
[0065] 1. Dissolve 2mmol of perylene anhydride (PTCDA) in 30mL of 5% KOH aqueous solution, filter, adjust the pH value of the filtrate to 8-9 with dilute hydrochloric acid, add 0.02mmol of tetra-n-octyl ammonium bromide and 20mmol of 1,4-bis Butyl bromide was reacted under reflux at 100°C for 2 hours, added chloroform for extraction, the separated organic phase was washed 3 times with 15% NaCl aqueous solution, the solvent was distilled off, and the obtained crude product was purified by chromatographic column to obtain pure compound compound 3, 4,9,10-Tetrakis-(4-bromobutyl-esteryl)-perylene;
[0066] 2. Dissolve 2 mmol of compound 3,4,9,10-tetrakis-(4-bromobutyl-ester)-perylene in a mixture of 30 mL of tetrahydrofuran and water (mixed at a volume ratio of 5:1), and add 40 mmol of Trimethylamine, refluxed at 66°C for 72h, distilled off the solvent, dissolved the obtained crude product ...
Embodiment 2
[0068] Example 2 Synthesis of 3,4,9,10-tetra-(4-trimethylaminobutyloxy-carbonyl)-perylene
[0069] 1. Dissolve 4mmol of perylene anhydride (PTCDA) in 60mL of 5% KOH aqueous solution, filter, adjust the pH value of the filtrate to 8-9 with dilute hydrochloric acid, add 0.04mmol of tetra-n-octyl ammonium bromide and 40mmol of 1,4-bis Bromobutane, reflux at 100°C for 2 hours, add chloroform for extraction, wash the separated organic phase 3 times with 15% NaCl aqueous solution, distill off the solvent, and purify the obtained crude product through chromatographic column to obtain pure compound compound 3, 4,9,10-Tetrakis-(4-bromobutyl-esteryl)-perylene;
[0070] 2. Dissolve 4 mmol of compound 3,4,9,10-tetrakis-(4-bromobutyl-ester)-perylene in a mixture of 60 mL of tetrahydrofuran and water (mixed by volume ratio 5:1), and add 80 mmol of Trimethylamine, refluxed at 66°C for 72h, distilled off the solvent, dissolved the obtained crude product in water, extracted 3 times with chlor...
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