Application of high-specificity fluorescent probe for detecting human serum albumin
A serum albumin and fluorescent probe technology, applied in the field of fine chemicals, can solve the problems of complex operation, time-consuming, high cost, interference, etc., and achieve the effect of simple synthesis process, high sensitivity, fast and sensitive detection
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Embodiment 1
[0031] Example 1 Synthesis of 1,3-dichloro-7-acetoxy-9,9-dimethyl-2(9H)-acridone (DDAA)
[0032] Add 0.25 mmol of 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone, 0.31 mmol of triethylamine and 10 mL of dichloromethane to a 25 mL two-necked flask , Dissolve 0.3 mmol of acetyl chloride in 5 mL of dichloromethane, gradually drop it into the reaction flask within 30 minutes under nitrogen protection and ice bath, stir at this temperature for 1 h, and then stir overnight at room temperature. The solvent was removed by rotary evaporation under reduced pressure, and the remaining solid was purified by column chromatography. The developing solvent was ethyl acetate: petroleum ether = 1:5 (v:v) to obtain 45.9 mg of orange solid (yield 52.5%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.66 (d, J =8.5 Hz, 1H), 7.63 (s, 1H), 7.24 (d, J = 2.3 Hz, 1H), 7.13 (dd, J = 8.5, 2.3Hz, 1H), 2.34 (s, 3H), 1.88 (s, 6H). 13 C NMR (100 MHz, CDCl 3 ) δ 173.16, 168.81, 153.32, 149.81, 140.33, 139.45, 138.56, 137.3...
Embodiment 2
[0033] Example 2 Synthesis of 1,3-Dichloro-7-(2-thiazolylcarbonyloxy)-9,9-dimethyl-2(9H)-acridone (DDAT)
[0034] Add 0.25 mmol of 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone, 0.31 mmol of triethylamine and 10 mL of dichloromethane to a 25 mL two-necked flask , Dissolve 0.3 mmol of 2-thenoyl chloride in 5 mL of dichloromethane, gradually drip into the reaction flask within 30 minutes under nitrogen protection and ice bath, stir at this temperature for 1 h, and then stir overnight at room temperature . The solvent was removed by rotary evaporation under reduced pressure, and the remaining solid was purified by column chromatography. The developing solvent was ethyl acetate: petroleum ether = 1:5 (v:v) to obtain 26.8 mg of orange solid (yield: 25.6%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.02(d, J = 3.7 Hz, 1H), 7.75 – 7.69 (m, 2H), 7.66 (s, 1H), 7.39 (d, J = 2.4 Hz,1H), 7.29 (d, J = 2.4 Hz, 1H), 7.24 – 7.19 (m, 1H), 1.91 (s, 6H). 13 C NMR (100MHz, CDCl 3 ) δ 173.19, 160.01, 153....
Embodiment 3
[0035] Example 3 Synthesis of 1,3-Dichloro-7-(1-naphthylcarbonyloxy)-9,9-dimethyl-2(9H)-acridone (DDAN)
[0036] Add 0.25 mmol of 1,3-dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone, 0.31 mmol of triethylamine and 10 mL of dichloromethane to a 25 mL two-necked flask , Dissolve 0.3 mmol of 1-naphthoyl chloride in 5 mL of dichloromethane, gradually drip into the reaction flask within 30 minutes under nitrogen protection and ice bath, stir at this temperature for 1 h, and then stir overnight at room temperature . The solvent was removed by rotary evaporation under reduced pressure, and the remaining solid was purified by column chromatography. The developing solvent was ethyl acetate: petroleum ether = 1:5 (v:v) to obtain 33.0 mg of orange solid (yield 28.6%). 1 H NMR (400 MHz, CDCl 3 ) δ 9.04 (d, J = 8.7 Hz, 1H), 8.52 (d, J = 7.3 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.96 (d, J = 8.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.73 – 7.65 (m, 2H), 7.61 (t, J =7.7 Hz, 2H), 7.44 (d, J = 2.3...
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