Preparation and application of a bodipy-based cysteine fluorescent probe compound
A cysteine and fluorescent probe technology, applied in the field of fluorescent probes, can solve the problems of cell damage, low detection limit, short probe excitation wavelength, etc., and achieves less cell damage, easy storage, good sensitivity and selection. sexual effect
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Embodiment 1
[0044] Take 6.24 g (32 mmol) of cyanobiphenol and 4.56 g (48 mmol) of anhydrous MgCl 2 In a three-neck flask, under nitrogen protection, add 16.3 mL (122 mmol) of triethylamine, then add 80 mL of anhydrous acetonitrile, and finally add 12.32 g (440 mmol) of dry paraformaldehyde. Heat to reflux for 8 hours. After the reaction was completed, it was cooled to room temperature, then quenched with a small amount of water, acidified by adding a large amount of 6 M hydrochloric acid, extracted with dichloromethane, and separated on a silica gel column to obtain 3.51 g of white solid II with a yield of about 50%. H NMR spectrum: 1 H NMR (400 MHz, CDCl 3 ) δ ppm: 11.11 (s, 1H), 9.99 (s,1H), 7.73-7.78 (m, 4H), 7.66 (dt, J = 8.59 Hz, 2.12, 2H), 7.12 (d, J = 8.37Hz, 1H).
Embodiment 2
[0046] Take 2.00 g (8.96 mmol) of compound II into a 150 mL three-necked flask, protect it with nitrogen, add 50 mL of dry dichloromethane, and stir at room temperature. After dissolving, slowly add 12.0 mL (174.4 mmol) of newly distilled pyrrole, and then add 0.03 mL of trifluoroacetic acid as a catalyst, and stir at room temperature for 1 hour. After the reaction stopped, the crude product was washed once with saturated sodium carbonate solution, extracted with dichloromethane, and separated on a silica gel column to obtain 1.42 g of off-white solid III with a yield of 46%. H NMR spectrum: 1 H NMR (400 MHz, CDCl 3 ) δ ppm: 7.34 (d, J = 2.27 Hz, 1H), 6.99 (d, J = 8.32 Hz, 1H), 6.76 (m, 2H), 6.19 (dd, J = 5.93, 3.03 Hz, 3H), 6.05 (m, 2H), 5.62 (s, 1H), 5.45 (s, 1H), 4.12 (dd, J = 14.48,7.30 Hz, 1H), 2.05 (s, 1H).
Embodiment 3
[0048] Add 0.71 g (2.06 mmol) of compound III into a 150 mL three-neck flask, protect it with nitrogen, add 50 mL of dry dichloromethane, then add 0.51 g (2.24 mmol) DDQ, and stir the reaction at room temperature for 1.5 h. Then 2.9 mL (20.61 mmol) of triethylamine was added, and finally 3.9 mL (30.86 mmol) of boron trifluoride ether was slowly added, and the reaction was stirred at room temperature for 22 h. After the reaction, the above crude product was washed three times with 50 mL of distilled water, then extracted with dichloromethane, and purified on a silica gel column to obtain 0.3 g of compound IV as an orange-red solid with a yield of about 42%. H NMR spectrum: 1 H NMR (400 MHz, CDCl 3 )δ ppm: 7.98 (s, 2H), 7.69 (m, 5H), 7.55 (d, J = 2.41 Hz,1H), 7.17 (d, J =8.67 Hz,1H), 6.96 (d, J = 4.33 Hz,2H), 6.57 (d, J = 3.69 Hz,2H), 5.43 (s,1H).
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