Full-spectrum high-brightness high-stability fluorescent dye as well as synthesis and application thereof

A fluorescent dye, high stability technology, applied in the field of fluorescent dyes, to achieve the effect of high cell permeability, stability improvement, and fluorescence brightness improvement

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, its low molar extinction coefficient results in a brightness of only 6900M -1 cm -1 (ε×Φ)

Method used

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  • Full-spectrum high-brightness high-stability fluorescent dye as well as synthesis and application thereof
  • Full-spectrum high-brightness high-stability fluorescent dye as well as synthesis and application thereof
  • Full-spectrum high-brightness high-stability fluorescent dye as well as synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0221] Synthesis of dye N-butyl-4-cyclobutyramido-1,8 naphthalimide (PAm)

[0222] Synthesis of intermediate N-butyl-4-(3-chloro)propionamido-1,8 naphthimide (ClPAm):

[0223]

[0224] N-butyl-4-amino-1,8-naphthimide (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 addition is complete, the mixed solution is transferred to room temperature and reacted for 6 hours. After the solvent was removed under reduced pressure, the residue was washed with 60 mL of water and filtered with suction to obtain a white filter cake. The filter cake was washed with 25 mL of methanol and dried under vacuum to obtain N-butyl-4-(3-chloro)propionamido-1,8-naphthalene. Imide 180mg, yield 67%. The hydrogen spectrum data of the NMR spectrum are as follows:

[0225] 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 = 8.1 Hz, 1H), ...

Embodiment 2

[0232] Synthesis of dye N-butyl-4-cyclopentanamido-1,8 naphthalimide (BAm)

[0233] Synthesis of intermediate N-butyl-4-(4-chloro)butyramido-1,8 naphthalimide (ClBAm):

[0234]

[0235] N-butyl-4-amino-1,8-naphthimide (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 addition, the mixed solution was transferred to room temperature and reacted for 10 hours. After the solvent was removed under reduced pressure, the residue was washed with 8 mL of water and filtered with suction to obtain a white filter cake. The filter cake was washed with 16 mL of methanol and dried under vacuum to obtain N-butyl-4-(4-chloro)butyramido-1,8-naphthalene. Imide 340mg, yield 61%. The hydrogen spectrum data of the NMR spectrum are as follows:

[0236] 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...

Embodiment 3

[0243] Synthesis of DOAN

[0244] Synthesis of N-butyl-4-bromo-5-nitro-1,8-naphthimide (BuAN-NBr):

[0245]

[0246] 4-Bromo-5-nitro-1,8-naphthimide (1.0 g, 3.11 mmol) was dissolved in 50 mL of ethanol, and n-butylamine (250 mg, 3.43 mmol) was added dropwise. After 12 hours at 40°C, the solvent was distilled off under reduced pressure, and the residue was separated on a silica gel column (petroleum ether: dichloromethane=2:1, V / V) to obtain 620 mg of off-white solid with a yield of 53%. The hydrogen spectrum data of the NMR spectrum are as follows:

[0247] 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).

[0248] Synthesis of DOAN:

[0249]

[0250] Dissolve ethylene glycol (20mg, 0.33mmol) in 10mL dry tetrahydrofuran, add Na block (20mg, 0.89mmol) under nitrogen, add N-butyl-4-bromo-5-nitroto the reaction solution after 0.5h Base-1,8-naphthimide (120mg, 0.31...

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Abstract

The invention provides full-spectrum high-brightness high-stability fluorescent dye. The dye is prepared by mixing one or more selected from 4-acylamino-substituted naphthalimide dye, bialkoxy-substituted naphthalimide fluorescent dye, diamino-substituted naphthalimide fluorescent dye, 9,10-diamino-substituted perylene bisimide dye, six-membered rhodamine dye, five-membered rhodamine dye, and Si-rhodamine dye according to any ratio. Compared with existing commercial dye, the fluorescent dye provided by the invention is higher in light stability, narrower in half-peak width (25 nm) and insensitive to various external environments such as pH, polarity, temperature and the like. Through introduction of Click groups, protein labels, drug molecules and other active groups, the obtained functionalized fluorescent molecules have very high biocompatibility, and can be used for rapid and specific staining of living cells and living bodies. In addition, due to the improvement of light stabilityand fluorescence brightness, the dye realizes super-resolution fluorescence imaging in various modes such as Storm, STED and SIM.

Description

Technical field [0001] The invention belongs to the field of fluorescent dyes, and specifically relates to the synthesis and application of a full-spectrum, high-brightness, high-stability fluorescent dye. Background technique [0002] Organic fluorescent dyes can be divided into resonance (Resonant) dyes and charge transfer (Charge Transfer, CT) dyes from the fluorescence structure-activity relationship. The fluorescence properties are determined by the electron transfer between the ground state and the excited state, which can be achieved through the study of the structure-activity relationship Structural transformation for different light performance requirements, or accurate prediction of luminous performance for known structures. Fluorescein, Rhodamine, Bodipy and most of the cyanine dyes belong to resonance dyes, which have narrow absorption and emission peaks, solvent insensitivity, small Stokes shift, high molar extinction coefficient and high quantum yield. Performance;...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/08C09B57/00C09K11/06G01N21/64
CPCC09B57/00C09B57/08C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1074C09K2211/1088C09K2211/1096G01N21/6428C07D221/14C07D473/18C07K1/13G01N21/64
Inventor 徐兆超乔庆龙周伟
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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