A kind of high-brightness, high-stability fluorescent dye excited by 405nm and its synthesis method

A fluorescent dye, high-stability technology, applied in the field of fluorescent dyes, can solve the problems of reduced fluorescence signal accuracy, lack of fluorescent dyes, lack of fluorescent dyes, etc.

Active Publication Date: 2021-12-21
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Application Information

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Problems solved by technology

However, due to the formation of pyrene excimer associations, Alexa 405 has a strong sensitivity to microenvironments such as polarity, resulting in a decrease in the accuracy of fluorescent signals
The strong fluorescence state of 7-hydroxycoumarin compounds is an oxygen anion, which leads to poor stability of these compounds. At the same time, pH has a significant impact on fluorescence, and fluorescence quenching occurs under weakly acidic conditions.
Therefore, 405nm fluorescent dyes are still extremely scarce, and there is a lack of fluorescent dyes suitable for super-resolution imaging and single-molecule detection that require higher fluorescence stability and more accurate fluorescence signals.

Method used

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  • A kind of high-brightness, high-stability fluorescent dye excited by 405nm and its synthesis method
  • A kind of high-brightness, high-stability fluorescent dye excited by 405nm and its synthesis method
  • A kind of high-brightness, high-stability fluorescent dye excited by 405nm and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Synthesis of intermediate N-butyl-4-(3-chloro)propionamido-1,8-naphthoimide (ClPAm):

[0053]

[0054] 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 60mL 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:

[0055] 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,2H),1.69(dt,J=7.7,6.6Hz,2H),1...

Embodiment 2

[0065] Synthesis of intermediate N-butyl-4-(4-chloro)butyramide-1,8-naphthalimide (ClBAm):

[0066]

[0067] N-butyl-4-amino-1,8-naphthalimide (400 mg, 1.49 mmol) was dissolved in 16 mL of tetrahydrofuran, and 1.6 mL of 4-chlorobutyryl 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 8 mL of water, filter with suction to obtain a white filter cake, wash the filter cake with 16 mL of methanol, and dry in vacuo to obtain N-butyl-4-(4-chloro)butanylamino-1,8-naphthalene Imide 340 mg, yield 61%. Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0068] 1 H NMR (400MHz, CDCl 3 )δ8.64(d, J=7.2Hz, 1H), 8.61(d, J=8.2Hz, 1H), 8.42(d, J=6.8Hz, 1H), 8.20(d, J=8.5Hz, 1H) ,7.88(s,1H),7.84–7.75(m,1H),4.28–4.11(m,2H),3.81–3.67(m,2H),2.80(t,J=6.6Hz,2H),2.31(dt ,J=13.0,6.5Hz,2H),1.72(dt,J=14.9,7....

Embodiment 3

[0075] Synthesis of N-butyl-4-bromo-5-nitro-1,8-naphthalimide (BuAN-NBr):

[0076]

[0077] 4-Bromo-5-nitro-1,8-naphthalimide (1.0 g, 3.11 mmol) was dissolved in 50 mL of ethanol, and n-butylamine (250 mg, 3.43 mmol) was added dropwise thereto. After 12 hours at 40°C, 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 620 mg of off-white solid with a yield of 53%. Its nuclear magnetic spectrum hydrogen spectrum data are as follows:

[0078] 1 H NMR (400MHz, CDCl 3 )δ8.72(d, J=7.8Hz, 1H), 8.52(d, J=7.9Hz, 1H), 8.21(d, J=7.9Hz, 1H), 7.95(d, J=7.8Hz, 1H) ,3.66(t,J=6.5Hz,2H),1.68(m,2H),1.40(m,J=7.8Hz,2H),0.94(t,J=7.9Hz,3H).

[0079] Synthesis of DOAN:

[0080]

[0081] Dissolve ethylene glycol (20mg, 0.33mmol) in 10mL of dry tetrahydrofuran, add Na block (20mg, 0.89mmol) under nitrogen, and add N-butyl-4-bromo-5-nitrate to the reaction solution after 0.5h 1...

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Abstract

The invention provides a fluorescent dye with high brightness and high stability excited by 405nm and a synthesis method thereof. The fluorescent dye is a series of high-brightness and high-stability fluorescent dyes that match 405nm lasers and are designed and synthesized based on naphthalimide through the regulation of the power supply group. This series of dyes contains two types of DF 405 fluorescent dyes, the first type is 4‑position monosubstituted naphthalimide dyes; the second type is 4,5‑position disubstituted naphthalimide dyes. Among them, the fluorescent Stokes shift of the first type of dye is large (>80nm), the fluorescent quantum yield in water is greater than 0.80, and it is due to derivatization and functionalization. The half-peak width of the second type of dye is less than 50nm, and the water fluorescence quantum yield is greater than 0.6. In addition, the photostability of this series of dyes has been greatly improved, and it is extremely insensitive to microenvironmental changes such as pH (3‑11), viscosity, and temperature, and can provide reliable fluorescent signals in complex environments in vivo. The field has good application prospects.

Description

technical field [0001] The invention belongs to the field of fluorescent dyes, and in particular relates to a fluorescent dye with high brightness and high stability excited at 405 nm and a synthesis method thereof. Background technique [0002] Due to the wide range of fluorescence emission spectra, small size, and easy modification of organic small molecule fluorescent dyes, they have become important tools for optical microscopy imaging and optical detection. However, the innovation of optical microscopy imaging technology also puts forward higher requirements for the fluorescence brightness and stability of organic small molecule fluorescent dyes; the accuracy of single molecule detection also largely depends on the authenticity of the signal of dye molecules. Therefore, the improvement of fluorescent dyes and the enhancement of their fluorescent properties are imminent. [0003] Alexa 405 and Pacific Blue are the most widely used fluorescent dyes under 405nm excitation...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09B57/08C09B57/00C09K11/06G01N21/64
CPCC09B57/08C09B57/00C09K11/06G01N21/6428C09K2211/1029C09K2211/1088
Inventor 徐兆超乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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