Fluorescent dye based on naphthalimide, and preparation method and application thereof

A naphthalimide and fluorophore technology, applied in the field of naphthalimide-based fluorescent dyes, can solve the problems of poor water solubility, weak fluorescence, prolonged emission wavelength, etc., and achieve the effects of good water solubility and high fluorescence intensity

Active Publication Date: 2018-01-19
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although the fluorophores constructed by the first method can greatly extend the emission wavelength and reduce the interference of autofluorescence in vivo, they generally have large molecules and poor water solubility; Cause energy loss, weaker fluorescence, more complex synthesis
These defects also greatly limit the application of this type of fluorophore in biological systems.

Method used

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  • Fluorescent dye based on naphthalimide, and preparation method and application thereof
  • Fluorescent dye based on naphthalimide, and preparation method and application thereof
  • Fluorescent dye based on naphthalimide, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Embodiment 1: the synthesis of compound FM1

[0114]

[0115]M1: Add acenaphthene (3.10g, 20.1mmol) in batches to 20mL of anhydrous DMF, and drop the solution of NBS (3.60g, 20.3mmol) dissolved in 10mL of DMF into the DMF solution of acenaphthene at a constant pressure, keeping the speed at 1 drop / s, the temperature is controlled at room temperature. After stirring overnight, pour into ice water, filter and wash with water to obtain a pale yellow solid. Ethanol was recrystallized to obtain 2.39 g of a light yellow solid, with a yield of 51.0%. Melting point: 55.5-56.6°C.

[0116] 1 H NMR (400MHz, CDCl 3 ): δ7.76(d, J=8.4Hz, 1H), 7.64(d, J=7.6Hz, 1H), 7.53(t, J=7.2Hz, 1H), 7.31(d, J=6.8Hz, 1H ), 7.12 (d, J=7.2Hz, 1H), 3.41 (t, J=7.2Hz, 2H), 3.32 (t, J=7.2Hz, 2H).

[0117] M2: M1 (22.78g, 97.7mmol) was dissolved in 150mL glacial acetic acid in a 500mL two-necked flask, and the temperature was controlled at 10-15°C. Add the mixed solution of 21mL fuming nitric a...

Embodiment 2

[0124] Embodiment 2: the synthesis of compound FM2

[0125]

[0126] M4-2: Dissolve 4-bromo-5-nitro-1,8-naphthalene anhydride (M3, 2.00g, 6.2mmol), 2-(2-aminoethoxy)ethanol (616μL, 6.2mmol) in 20mL In ethanol, reflux 10h, TLC traces until the reaction is complete, and the reaction solution is cooled to room temperature, and the solvent is removed by rotary evaporation, and the silica gel column chromatography (CH 2 Cl 2 / CH 3 OH=200:1, v / v), recrystallized from ethanol to obtain 835 mg of milky white powder solid, yield 33.0%. Melting point: 176.4-176.9°C. 1 H NMR (400MHz, CDCl 3 ): δ8.71(d, J=4.0Hz, 1H), 8.52(d, J=4.0Hz, 1H), 8.21(d, J=4.0Hz, 1H), 7.93(d, J=4.0Hz, 1H ),4.44(t,J=5.6Hz,2H),3.86(t,J=5.6Hz,2H),3.67-3.69(m,2H),3.63-3.65(m,2H),2.08(s,1H) . HRMS (ESI) C 16 h 14 N 2 o 6 Br[M+H] + The theoretical value is 409.0035, and the measured value is 409.0029.

[0127] FM2: Weigh compound M4-2 (200mg, 0.488mmol) and diethanolamine (472μL, 4.88mmol) into a 25mL r...

Embodiment 3

[0128] Embodiment 3: the synthesis of compound FM3

[0129]

[0130] M4-3: Weigh compound M3 (2.00g, 6.21mmol) and 2-aminoethylmorpholine (808mg, 6.21mmol) into a 250mL round bottom flask, add 100mL absolute ethanol to dissolve, heat to 50°C, continue The reaction was stirred for 8h, followed by TLC until the reaction was complete. After the reaction solution was cooled to room temperature, the solvent was removed by rotary evaporation, and silica gel column chromatography (CH 2 Cl 2 / CH 3 OH=200:1, v / v), 1.05 g of milky white powder solid was obtained, and the yield was 38.9%. Melting point: 200.7~201.1℃. 1 H NMR (400MHz, CDCl 3 ): δ8.70(d, J=7.6Hz, 1H), 8.51(d, J=8.0Hz, 1H), 8.22(d, J=8.0Hz, 1H), 7.93(d, J=7.6Hz, 1H ),4.33(t,J=6.2Hz,2H),3.65(br,4H),2.70(t,J=6.2Hz,2H),2.57(br,4H). 13 C NMR (100MHz, CDCl 3): δ162.82, 162.06, 151.28, 135.98, 132.33, 131.23, 130.57, 125.69, 124.17, 123.56, 122.41, 121.21, 66.98, 55.92, 53.79, 37.65. HRMS (ESI) C 18 h 17 N 3 o 5 B...

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Abstract

The invention relates to a fluorescent dye based on naphthalimide, and a preparation method and an application thereof. Specifically, the invention provides a naphthalimide fluorophore which has a structure as shown in a general formula I which is described in the speicification, wherein groups in the formula I are described in the specification. The compound provided by the invention has good water solubility and high fluorescent quantum yield in an aqueous solution, and can be used for two-photon imaging and co-localization imaging to living cells.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a class of fluorescent dyes based on naphthalimide, a preparation method and application thereof. Background technique [0002] Due to the advantages of high sensitivity and convenient operation, fluorescence analysis has gradually replaced radioactive isotopes as detection labels in recent years, and has been widely used in environmental monitoring, fluorescent immunoassay, and cell staining. Fluorescent dyes commonly used in fluorescence analysis techniques include coumarins, cyanine dyes, fluoropyrroles, fused ring aromatic hydrocarbons, xanthenes, naphthalimides, etc. [0003] For dyes used in fluorescence analysis and fluorescence imaging, it is usually required to maintain stable optical properties in aqueous solution, and it is not sensitive to environmental factors such as polarity, pH, temperature, etc. Especially for cell staining dyes, it must have High fluor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C09K11/06C07D471/06G01N21/64
CPCY02P20/55
Inventor 朱维平张静雯余峰张磊吴慧菁徐玉芳钱旭红
Owner EAST CHINA UNIV OF SCI & TECH
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