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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

Active Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

However, the lifetime of organic small molecule fluorescent dyes is usually short (about 10 -9 seconds), the lifetime change before and after binding the target molecule is small
Therefore, how to make the dye not only have high brightness and high photostability to meet high-resolution fluorescence imaging through simple structural modification, but also produce obvious lifetime changes before and after binding with carbonic anhydrase to achieve high-resolution fluorescence lifetime imaging has become a problem. huge challenge

Method used

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  • Carbonic anhydrase fluorescent probe with high brightness and high light stability
  • Carbonic anhydrase fluorescent probe with high brightness and high light stability
  • Carbonic anhydrase fluorescent probe with high brightness and high light stability

Examples

Experimental program
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Effect test

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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Abstract

The invention provides a carbonic anhydrase fluorescent probe with high brightness and high light stability. The structural formula of the probe is shown as (1), the probe is 4-substituted naphthalimide dye which can be used for carbonic anhydrase detection and fluorescence imaging, and the dye has the advantages of cheap synthetic raw materials, simple method, easiness in derivation and the like.Researches show that a benzenesulfonamide structure contained in the compound can be combined with carbonic anhydrase in cells in a high-selectivity manner; azetidine is introduced to the 4-site of the naphthalimide dye, so that the TICT process can be inhibited, and the brightness and the light stability of the dye are improved. The molar extinction coefficient of the dye in ethanol reaches 15382 M<-1>cm<-1>, and the quantum yield reaches 0.52. The dye shows short fluorescence lifetime in a water environment and shows long fluorescence lifetime in a weak polarity environment after being combined with carbonic anhydrase, and the fluorescence lifetime is increased from 4.27 ns to 10.6 ns. The carbonic anhydrase dye has very high brightness and light stability, can quickly mark carbonic anhydrase and is applied to the fields of carbonic anhydrase detection, fluorescence imaging, fluorescence lifetime imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescence imaging, in particular to a carbonic anhydrase fluorescent probe with high brightness and high photostability. Background technique [0002] Fluorescence imaging technology is an optical microscopic imaging technology with high sensitivity and good selectivity, which is widely used in related research in the fields of biotechnology, cell imaging, and drug metabolism. In recent years, the emerging super-resolution fluorescence microscopy technology has further improved the resolution of optical microscopy to tens of nanometers or even several nanometers. Carbonic anhydrase is a Zn-containing 2+ Studies have shown that it undertakes a variety of physiological functions in vivo and is closely related to the occurrence of various cancers. Using fluorescent dyes to label carbonic anhydrase and then perform fluorescence imaging can understand the amount of carbonic anhydrase and its distribution i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/08C09K11/06G01N21/64
CPCC09B57/08C09K11/06C09K2211/1007C09K2211/1029G01N21/6428
Inventor 徐兆超刘文娟乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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