A Fluorescent Probe for Carbonic Anhydrase with High Brightness and High Photostability
A technology of carbonic anhydrase and fluorescent probe, which is applied in the field of fluorescence imaging, can solve the problems of small change in lifespan and short lifespan, and achieve the effects of increased fluorescence lifespan, low price of synthetic raw materials, high brightness and photostability
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Embodiment 1
[0030] Synthesis SML-Aze probe enzyme carbonic anhydrase.
[0031] Scheme structure intermediate product and SML-Br are as follows:
[0032]
[0033] 50mL of ethanol were added to 4-bromo-1,8-naphthalic anhydride (2.0g, 7.2mmol), 4- (aminomethyl) benzenesulfonamide hydrochloride (3.2g, 14.4mmol) and triethylamine (6.8 g, 36mmol), and the reaction was heated to 80 ℃. After 8h, the reaction was cooled to room temperature and suction filtered to give an off-white solid turbid solution SML-Br2.94g, 92% yield.
[0034] NMR spectrum which hydrogen spectrum is as follows figure 1 , The following specific data:
[0035] 1 H NMR (400MHz, DMSO-d 6 ) Δ8.50 (tdd, J = 13.0,7.9,5.1Hz, 2H), 8.32-8.24 (m, 1H), 8.20-8.10 (m, 1H), 7.96 (dd, J = 8.4,7.4Hz, 1H) , 7.77 (d, J = 8.1Hz, 2H), 7.56 (d, J = 8.3Hz, 2H), 7.33 (s, 2H), 5.29 (s, 2H).
[0036] Carbon NMR spectrum which spectrum is as follows figure 2 , The following specific data:
[0037] 13 C NMR (101MHz, DMSO-d 6 ) Δ163.45,163.41,143.35,141...
Embodiment 2
[0057] Synthesis of SML-AZE of carbonated anhydrase probe.
[0058] The synthetic route and product structure of intermediate SML-BR is as follows:
[0059]
[0060] 4-bromo-1,8-naphthamine (1.0 g, 3.6 mmol), 4- (amine methyl) benzenesulfonamide hydrochloride (0.9 g, 3.6 mmol) and triethylamine (1.0) were added to 30 ml ethanol. G, 10.2 mmol) and heat the reaction solution to 60 ° C. After 10 h, the reaction solution was cooled to room temperature and the turbid liquid was sued into a gray-white solid SML-BR0.8G, and the yield was 85%.
[0061] Its nuclear magnetic spectrum hydrogen spectrum is as follows figure 1 As shown, the specific data is as follows:
[0062] 1 H NMR (400MHz, DMSO-D 6 Δ8.50 (TDD, J = 13.0, 7.9, 5.1 Hz, 2H), 8.32-8.24 (M, 1H), 8.20-8.10 (m, 1H), 7.96 (DD, J = 8.4, 7.4 Hz, 1H) 7.77 (D, J = 8.1 Hz, 2H), 7.56 (D, J = 8.3Hz, 2H), 7.33 (S, 2H), 5.29 (S, 2H).
[0063] Its nuclear magnetic spectrogram carbon spectrum is as follows figure 2 As shown, the specific d...
Embodiment 3
[0079] Synthesis of SML-AZE of carbonated anhydrase probe.
[0080] The synthetic route and product structure of intermediate SML-BR is as follows:
[0081]
[0082] 4-bromo-1,8-naphthamine (3.0 g, 10.8 mmol), 4- (amine) benzenesulfonamide hydrochloride (7.2 g, 32.4 mmol) and triethylamine (13.6) were added to 50 ml of ethanol. G, 72 mmol) and heated the reaction liquid to 80 ° C. After 6 h, the reaction solution was cooled to room temperature and the turbid liquid was filtered to suck the gray-white solid SML-BR3.97 g, and the yield was 81%.
[0083] Its nuclear magnetic spectrum hydrogen spectrum is as follows figure 1 As shown, the specific data is as follows:
[0084] 1 H NMR (400MHz, DMSO-D 6 Δ8.50 (TDD, J = 13.0, 7.9, 5.1 Hz, 2H), 8.32-8.24 (M, 1H), 8.20-8.10 (m, 1H), 7.96 (DD, J = 8.4, 7.4 Hz, 1H) 7.77 (D, J = 8.1 Hz, 2H), 7.56 (D, J = 8.3Hz, 2H), 7.33 (S, 2H), 5.29 (S, 2H).
[0085] Its nuclear magnetic spectrogram carbon spectrum is as follows figure 2 As shown, the spe...
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