Carbonic anhydrase fluorescent probe with high brightness and high light stability
A technology of carbonic anhydrase and fluorescent probe, which is applied in the field of fluorescence imaging, can solve the problems of short lifespan and small change in lifespan, and achieve the effects of low price of synthetic raw materials, increased fluorescence lifespan, high brightness and photostability
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Embodiment 1
[0030] Synthesis of carbonic anhydrase probe SML-Aze.
[0031] The synthetic route and product structure of intermediate SML-Br are as follows:
[0032]
[0033] Add 4-bromo-1,8-naphthalene anhydride (2.0 g, 7.2 mmol), 4-(aminomethyl)benzenesulfonamide hydrochloride (3.2 g, 14.4 mmol) and triethylamine (6.8 g, 36mmol), and the reaction solution was heated to 80°C. After 8 hours, the reaction solution was cooled to room temperature and the turbid solution was suction-filtered to obtain 2.94 g of off-white solid SML-Br, with a yield of 92%.
[0034] Its H NMR spectrum is as follows figure 1 As shown, the specific data are as follows:
[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] Its carbon NMR spectrum is as follows figure 2 As shown, the specific data are as follows:
[0037] 13 C NMR (101MHz, DMSO-d 6 )δ163.45, 163.4...
Embodiment 2
[0057] Synthesis of carbonic anhydrase probe SML-Aze.
[0058] The synthetic route and product structure of intermediate SML-Br are as follows:
[0059]
[0060] Add 4-bromo-1,8-naphthalene anhydride (1.0 g, 3.6 mmol), 4-(aminomethyl)benzenesulfonamide hydrochloride (0.9 g, 3.6 mmol) and triethylamine (1.0 g, 10.2mmol), and the reaction solution was heated to 60°C. After 10 h, the reaction solution was cooled to room temperature and the turbid solution was suction-filtered to obtain 0.8 g of off-white solid SML-Br, with a yield of 85%.
[0061] Its H NMR spectrum is as follows figure 1 As shown, the specific data are as follows:
[0062] 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).
[0063] Its carbon NMR spectrum is as follows figure 2 As shown, the specific data are as follows:
[0064] 13 C NMR (101MHz, DMSO-d 6 )δ163.45, 163.41, ...
Embodiment 3
[0079] Synthesis of carbonic anhydrase probe SML-Aze.
[0080] The synthetic route and product structure of intermediate SML-Br are as follows:
[0081]
[0082] Add 4-bromo-1,8-naphthalene anhydride (3.0 g, 10.8 mmol), 4-(aminomethyl)benzenesulfonamide hydrochloride (7.2 g, 32.4 mmol) and triethylamine (13.6 g, 72mmol), and the reaction solution was heated to 80°C. After 6h, the reaction solution was cooled to room temperature and the turbid solution was suction-filtered to obtain 3.97 g of off-white solid SML-Br, with a yield of 81%.
[0083] Its H NMR spectrum is as follows figure 1 As shown, the specific data are as follows:
[0084] 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).
[0085] Its carbon NMR spectrum is as follows figure 2 As shown, the specific data are as follows:
[0086] 13 C NMR (101MHz, DMSO-d 6)δ163.45, 163.41, 1...
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