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Full-spectrum optical switch molecule as well as synthesis and application thereof

An optical switching, full-spectrum technology, applied in the field of fluorescence imaging, which can solve the problems of reduced positioning accuracy, poor anti-bleaching performance of fluorescent proteins, and limited applications

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

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Problems solved by technology

However, the anti-bleaching performance of fluorescent proteins is poor, and the number of photons in the same time is significantly less than that of organic molecules, which reduces the accuracy of positioning, which just promotes the application of organic small molecule fluorescent dyes in this field
However, such organic fluorescent dyes are still relatively scarce, and those that can achieve high signal-to-noise ratio bright and dark states are even rarer.
In addition, such dyes usually require strong activating light to switch molecules from a dark state to a bright state, and in stochastic optical reconstruction technology (d-Storm), it is even more necessary to add tens or even hundreds of mM thiol molecules to realize the switch. , which severely limits the application of this technique to living cells

Method used

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  • Full-spectrum optical switch molecule as well as synthesis and application thereof
  • Full-spectrum optical switch molecule as well as synthesis and application thereof
  • Full-spectrum optical switch molecule as well as synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Synthesis of AB-405

[0089] Synthesis of intermediate N-butyl-4-(3-chloro)propionamido-1,8-naphthoimide (ClPAm):

[0090]

[0091] N-butyl-4-amino-1,8-naphthalimide (200 mg, 0.75 mmol) was dissolved in 100 mL of tetrahydrofuran, and 1.25 mL of 3-chloropropionyl chloride was added dropwise to the reaction solution at 0°C. After the dropwise addition, the mixture was transferred to room temperature for 6 h. After removing the solvent under reduced pressure, wash the residue with 63mL of water, filter with suction to obtain a white filter cake, wash the filter cake with 25mL of methanol, and dry in vacuo to obtain N-butyl-4-(3-chloro)propionamido-1,8-naphthalene Imide 180 mg, yield 67%. Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0092] 1 H NMR (400MHz, CD 3 CN)δ8.91(s,1H),8.59(dd,J=7.3,0.9Hz,1H),8.54(d,J=8.1Hz,1H),8.52–8.48(m,1H),8.29(d, J=8.1Hz, 1H), 7.85(dd, J=8.5, 7.3Hz, 1H), 4.15–4.10(m, 2H), 3.98(t, J=6.3Hz, 2H), 3.08(t, J=6.3 Hz...

Embodiment 2

[0099] Synthesis of AB-405

[0100] Synthesis of intermediate N-butyl-4-(3-chloro)propionamido-1,8-naphthoimide (ClPAm):

[0101]

[0102] N-butyl-4-amino-1,8-naphthalimide (200 mg, 0.75 mmol) was dissolved in 8 mL of tetrahydrofuran, and 0.5 mL of 3-chloropropionyl chloride was added dropwise to the reaction solution at 0°C. After the dropwise addition, the mixture was transferred to room temperature for 10 h. After removing the solvent under reduced pressure, wash the residue with 25 mL of water, filter with suction to obtain a white filter cake, wash the filter cake with 10 mL of methanol, and dry in vacuo to obtain N-butyl-4-(3-chloro)propionamido-1,8-naphthalene Imide 142 mg, yield 53%.

[0103] Synthesis of Dye N-Butyl-4-Cyclobutanylamido-1,8 Naphthalimide (PAm):

[0104]

[0105] N-butyl-4-(3-chloro)propionamido-1,8-naphthalimide (100 mg, 0.28 mmol) was dissolved in 20 mL of acetonitrile, and 400 mg of potassium carbonate was added thereto. The temperature of ...

Embodiment 3

[0108] Synthesis of AB-405

[0109] Synthesis of intermediate N-butyl-4-(3-chloro)propionamido-1,8-naphthoimide (ClPAm):

[0110]

[0111] N-butyl-4-amino-1,8-naphthalimide (200 mg, 0.75 mmol) was dissolved in 100 mL of tetrahydrofuran, and 5 mL of 3-chloropropionyl chloride was added dropwise to the reaction solution at 0°C. After the dropwise addition, the mixture was transferred to room temperature for 8 h. After removing the solvent under reduced pressure, wash the residue with 25 mL of water, filter with suction to obtain a white filter cake, wash the filter cake with 60 mL of methanol, and dry in vacuo to obtain N-butyl-4-(3-chloro)propionamido-1,8-naphthalene Imide 161 mg, yield 60%.

[0112] Synthesis of Dye N-Butyl-4-Cyclobutanylamido-1,8 Naphthalimide (PAm):

[0113]

[0114] N-butyl-4-(3-chloro)propionamido-1,8-naphthalimide (100 mg, 0.28 mmol) was dissolved in 15 mL of acetonitrile, and 200 mg of potassium carbonate was added thereto. The reaction solutio...

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Abstract

The invention provides a full-spectrum optical switch molecule as well as synthesis and application thereof. The optical molecular switch is a full-spectrum optical switch molecule designed and synthesized based on fluorescent matrixes such as naphthalimide and rhodamine, and can be used for excitation of 405nm, 450nm, 488nm, 560nm and 640nm. Intramolecular twisting is limited through azetidine, cyclobutylamide and other rigid structures, and the stability and brightness of the dye are greatly improved. The series of optical switch molecules do not need activation light, and only need monochromatic excitation light to realize reciprocating circulation from a dark state to a bright state of the molecules so as to obtain more accurate light spot positioning information. Molecules based on rhodamine dye have switch balance in a ground state, quenching of strong laser is not needed, and super-resolution imaging of cells can be achieved through mild laser. The dye provides full-spectrum novel photoswitch molecules, and has good application prospects in the fields of living cell super-resolution imaging, information storage and the like.

Description

technical field [0001] The invention belongs to the field of fluorescence imaging, and in particular relates to a full-spectrum optical switch molecule and its synthesis and application. Background technique [0002] In recent years, super-resolution microscopy imaging technology has gradually become an indispensable tool in life science research. It can break through the limitation of the diffraction limit, allowing researchers to observe unknown fine structures and improve the entire life system. But as Stefan.W.Hell, the founder of super-resolution technology, said: "In the era of Ernst Abbe, the imaging quality was determined by the objective lens; today, the imaging quality is determined by the fluorophore." As the name suggests, the performance of the fluorescent dye determines The universality of the application of super-resolution microscopy imaging technology, the accuracy of imaging, etc. At present, the most widely used super-resolution techniques above 100nm res...

Claims

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Application Information

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IPC IPC(8): C07D401/04C07D471/06C07D495/20C07F7/08C09B57/08C09K11/06G01N21/64
CPCC07D401/04C07D471/06C07D495/20C07F7/0816C09B57/08C09K11/06G01N21/6428G01N21/6486G01N21/643C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096
Inventor 徐兆超刘晓刚乔庆龙李锦
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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