Preparation and application of cysteine fluorescent probe compound based on BODIPY
A cysteine and fluorescent probe technology, applied in the field of fluorescent probes, can solve the problems of short excitation wavelength, low detection limit, cell damage, etc., and achieve good sensitivity and selectivity, easy storage, and cell damage. small effect
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Embodiment 1
[0044] Take 6.24g (32mmol) of cyanobiphenol and 4.56g (48mmol) of anhydrous MgCl 2 In a three-neck flask, under nitrogen protection, add 16.3mL (122mmol) of triethylamine, then add 80mL of anhydrous acetonitrile, and finally add 12.32g (440mmol) 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 6M 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 HNMR (400MHz, CDCl 3 )δppm: 11.11(s,1H), 9.99(s,1H), 7.73-7.78(m,4H), 7.66(dt, J =8.59Hz,2.12,2H),7.12(d, J =8.37Hz, 1H).
Embodiment 2
[0046] Take 2.00g (8.96mmol) of compound II and add it into a 150mL three-necked flask, protect it with nitrogen, add 50mL 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 HNMR (400MHz, CDCl 3 ) δppm: 7.34 (d, J =2.27Hz,1H),6.99(d, J =8.32Hz,1H),6.76(m,2H),6.19(dd, J =5.93,3.03Hz,3H),6.05(m,2H),5.62(s,1H),5.45(s,1H),4.12(dd, J =14.48,7.30Hz,1H),2.05(s,1H).
Embodiment 3
[0048] Take 0.71g (2.06mmol) of compound III into a 150mL three-necked flask, protect it with nitrogen, add 50mL of dry dichloromethane, then add 0.51g (2.24mmol) of DDQ, and stir at room temperature for 1.5h. Then add 2.9mL (20.61mmol) triethylamine, and finally slowly add 3.9mL (30.86mmol) boron trifluoride diethyl ether, and stir the reaction at room temperature for 22h. 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 HNMR (400MHz, CDCl 3 )δppm: 7.98(s,2H),7.69(m,5H),7.55(d, J =2.41Hz,1H),7.17(d, J =8.67Hz,1H),6.96(d, J =4.33Hz,2H),6.57(d, J =3.69Hz, 2H), 5.43(s, 1H).
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