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Cell membrane fluorescent probe with high brightness, high stability and insensitivity to environment

A high-stability, fluorescent probe technology, applied in the field of fluorescence imaging, can solve the problems of poor photostability, long staining time, weak fluorescence, etc., and achieve high-stability results

Inactive Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the photostability of cyanine dyes is generally extremely poor, which cannot meet the needs of long-term imaging observation; and due to the twisting of the double bond, these dyes are environmentally sensitive dyes, and the fluorescence is very weak in a large polar environment, and in a low polar environment. Environments such as cell membranes have high brightness, but cell membranes are not homogeneous structures, which greatly reduces the imaging accuracy of such environmentally sensitive dyes
In addition, the staining time of these dyes is long (usually more than 30 minutes), which is strictly limited in live cell staining experiments
Existing cell membrane fluorescent dyes are difficult to meet the performance requirements of super-resolution technology for fluorescence stability, fluorescence brightness, and long-term staining. Therefore, it is imminent to develop cell membrane fluorescent dyes with high brightness, high stability, and environmental insensitivity.

Method used

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  • Cell membrane fluorescent probe with high brightness, high stability and insensitivity to environment
  • Cell membrane fluorescent probe with high brightness, high stability and insensitivity to environment
  • Cell membrane fluorescent probe with high brightness, high stability and insensitivity to environment

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of cell membrane probe DDAN-DAC.

[0068] Synthesis of intermediate DDAN-NBr:

[0069]

[0070] 4-Bromo-5-nitro-1,8-naphthalimide (0.50g, 1.56mmol) was dissolved in 30mL of ethanol, and dodecylamine (0.87g, 4.68mmol) was added dropwise thereto, heated to 90 After reacting at ℃ for 24 h, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (petroleum ether / dichloromethane=2 / 1, V / V) to obtain 0.54 g of DDAN-NBr as a yellow-white solid with a yield of 71%.

[0071] Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0072] 1 H NMR (400MHz, CDCl 3 )δ8.71(d, J=7.9Hz, 1H), 8.51(d, J=7.8Hz, 1H), 8.23(d, J=7.8Hz, 1H), 7.94(d, J=7.8Hz, 1H) ,3.66(t,J=6.4Hz,2H),1.1-1.8(m,20H),0.94(t,J=7.9Hz,3H).

[0073] After detection, its structure is shown in the above formula DDAN-NBr.

[0074] Synthesis of cell membrane probe DDAN-DAC:

[0075]

[0076] DDAN-NBr (0.25g, 0.51mmol) was dissolve...

Embodiment 2

[0083] Synthesis of cell membrane probe HexAN-DAC.

[0084] Synthesis of intermediate HexAN-NBr:

[0085]

[0086] Dissolve 4-bromo-5-nitro-1,8-naphthalimide (0.50g, 1.56mmol) in 60mL of ethanol, and add hexadecylamine (0.11g, 4.68mmol) to it, and heat to 90°C After reacting for 24 hours, the solvent was distilled off under reduced pressure, and the residue was separated through a silica gel column (petroleum ether / dichloromethane=2 / 1, V / V) to obtain 0.52 g of a yellow-white solid HexAN-NBr, with a yield of 62%.

[0087] Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0088] 1 H NMR (400MHz, CDCl 3)δ8.71(d, J=7.7Hz, 1H), 8.51(d, J=7.9Hz, 1H), 8.23(d, J=7.8Hz, 1H), 7.94(d, J=7.9Hz, 1H) ,3.63(t,J=6.5Hz,2H),1.1-1.8(m,28H),0.92(t,J=7.8Hz,3H).

[0089] After detection, its structure is shown in the above formula HexAN-NBr.

[0090] Synthesis of cell membrane probe HexAN-DAC:

[0091]

[0092] Dissolve N-hexadecyl-4-bromo-5-nitro-1,8-naphthalimide...

Embodiment 3

[0104] Synthesis of cell membrane probe MBSO3-DAC.

[0105] Synthesis of intermediate MBAN-NBr:

[0106]

[0107] 4-Bromo-5-nitro-1,8-naphthalimide (0.50g, 1.56mmol) was dissolved in 60mL of ethanol, and 1-(N-(3-amino)propyl-N- Methyl)amino-3,7-dimethyloctane (1.07g, 4.68mmol), heated to 70°C for 12h, then distilled off the solvent under reduced pressure, and the residue was passed through a silica gel column (dichloromethane / methanol=80 : 1, V / V) isolated yellow solid MBAN-NBr 0.43g, yield 52%.

[0108] Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0109] 1 H NMR (400MHz, CDCl 3 )δ8.68(d, J=7.6Hz, 1H), 8.48(d, J=7.7Hz, 1H), 8.20(d, J=7.8Hz, 1H), 7.92(d, J=7.6Hz, 1H) ,4.24(t,J=6.5Hz,2H),2.80(s,2H),2.65(s,2H),2.46(s,3H),2.10(s,2H),1.41(s,2H),1.30– 1.03(m,8H),0.86(t,J=6.3Hz,9H).

[0110] Its nuclear magnetic spectrum carbon spectrum data are as follows:

[0111] 13 C NMR (101MHz, CDCl 3 )δ162.87,162.12,151.31,135.98,132.38,131.32,130.52,125....

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Abstract

The invention provides a cell membrane fluorescent probe with high brightness, high stability and insensitivity to environment, particularly a naphthalimide probe which can be used for cell membrane fluorescence imaging. The fluorescent probe has the advantages of being low in synthetic raw material cost, simple in method, easy to derive and the like. Research finds that azetidine, azolidine and other high-rigidity structures are introduced to the 4-position and the 5-position of a naphthalimide parent of the dye, and the rigidity and lipophilicity of the dye are improved. The molar extinctioncoefficient of the dye in ethanol is 35000 M<-1>cm<-1> or above, the highest quantum yield can reach 0.72, and the dye has very high brightness and light stability; the dye also has environmental insensitivity, extremely small spectral property difference in different environments and good imaging accuracy; the dye structurally contains structures such as long aliphatic hydrocarbon chains or cholesterol derivatives or quaternary ammonium salts and can interact with cell membranes, so that the cell membranes can be quickly and accurately positioned, can be quickly labeled and can be applied tothe fields of cell membrane fluorescence imaging and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescence imaging, and in particular relates to a class of cell membrane fluorescent probes with high brightness, high stability and insensitive environment. Background technique [0002] The cell membrane can regulate the entry and exit of substances to ensure the needs of various life activities in the cell, maintain the stability of the intracellular environment, and rely on glycoproteins to identify and transmit information. It has complex functions in cell life activities. With the continuous deepening of research on cell membranes, researchers have continuously improved the properties and functions of cell membrane fluorescent dyes. In particular, the rapid rise of super-resolution fluorescence imaging technology has prompted the development of new high-stability, high-brightness cell membrane fluorescent dyes. application. [0003] Currently commonly used cell membrane fluorescent dyes such as ...

Claims

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Application Information

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IPC IPC(8): C07D471/06C07J43/00C07J9/00C07D401/14C09K11/06G01N21/64
CPCC07D401/14C07D471/06C07J9/00C07J43/003C09K11/06C09K2211/1011C09K2211/1029C09K2211/1044G01N21/6486
Inventor 徐兆超陈婕乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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