Synthesis and Application of a Novel Fluorescent Probe for Recognizing Cysteine and Homocysteine
A technology for homocysteine and cysteine, which is applied in the field of detection of cysteine and homocysteine in vitro and inside living cells, and achieves large Stokes shift, good selectivity, and synthetic The effect of a simple route
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0026] Embodiment 1: the synthesis of intermediate product 3-hydroxyphthalonitrile
[0027] In a 50ml round bottom flask, 3-nitrophthalonitrile (2.0g, 11.6mmol), K 2 CO 3 (1.8g, 12.7mmol) and NaNO 2 (0.8g, 11.6mmol) was dissolved in dimethyl sulfoxide (30mL), stirred and refluxed in an oil bath at 130°C for 30 minutes, and the reaction was completed. Cool to room temperature, add 90ml of distilled water to dilute the reaction solution, acidify to PH=3 with 2M hydrochloric acid, produce a precipitate, filter with suction, wash the filter cake with distilled water and methanol, dry in vacuo, recrystallize with glacial acetic acid for further purification to obtain brown crystals. Yield: 0.9 g. Yield 54%.
Embodiment 2
[0028] Embodiment 2: the synthesis of intermediate product dye 4
[0029] In a 25ml round bottom flask, the product 3-hydroxyphthalonitrile (288mg, 2mmol), 2-aminopyridine (385mg, 4.1mmol) and CaCl 2 (46 mg, 0.41 mmol) was dissolved in n-butanol (6 mL). Protected by argon, heated and refluxed in an oil bath at 110°C for 5 days, the reaction was complete, cooled to room temperature, removed n-butanol by vacuum rotary evaporation, washed with water, filtered at normal pressure, vacuum dried the filter cake, purified by column chromatography to obtain the product, and dried overnight in vacuum , to obtain orange powder. Yield: 141.6 mg. Yield 25%. The structural representation is as follows: 1 H NMR (400MHz, CDCl 3 )δ H 13.70(s, 1H), 8.62(m, 2H), 7.78(t, J=7.9Hz, 2H), 7.60(s, 1H), 7.52(d, J=7.3Hz, 2H), 7.38(d, J =8.0Hz, 1H), 7.19-7.09(m, 3H). 13 C NMR (101MHz, CDCl 3 )δ c 160.10, 159.34, 155.81, 155.59, 153.70, 147.98, 147.76, 138.12, 138.08, 135.66, 133.58, 123.43, 1...
Embodiment 3
[0030] Embodiment 3: the synthesis of probe molecule
[0031] Dissolve the product obtained in the previous step (79.25mg, 0.25mmol) in 10mL of anhydrous dichloromethane, then add triethylamine (0.07mL, 0.5mmol), and add acryloyl chloride dissolved in 4ml of anhydrous dichloromethane under ice cooling (58.16mg, 0.31mmol), protected by argon, reacted under stirring at room temperature for 10 minutes, the reaction was complete, the methylene chloride was removed by rotary evaporation in an ice bath, and a yellow powder was obtained by flash column chromatography. Yield: 75.31 mg. Yield: 81.2%. The characterization of the probe molecules is as follows: 1 HNMR (400MHz, DMSO)δ H 14.02(s, 1H), 8.74(d, J=4.6Hz, 2H), 8.02–7.95(m, 2H), 7.91(dd, J=14.1, 7.2Hz, 1H), 7.82(t, J=7.7Hz , 1H), 7.56(d, J=7.9Hz, 1H), 7.48(d, J=7.8Hz, 1H), 7.29(dd, J=12.1, 6.9Hz, 2H), 7.19(d, J=7.8Hz , 1H), 6.63 (d, J=8.0Hz, 2H), 6.29 (dd, J=7.8, 3.0Hz, 1H).
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More