Naphthalimide-based double-signal turn-on formaldehyde fluorescent nano probe intermediate compound, and preparation method and application thereof

A technology of naphthalimide and p-hydroxybenzaldehyde, which is applied in fluorescence/phosphorescence, organic chemistry, material excitation analysis, etc., can solve problems such as inability to obtain accurate detection results, and achieve self-assembly, mild reaction conditions, and formaldehyde. specific effect

Active Publication Date: 2018-01-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 2. Nowadays, most fluorescent probes only have the characteristics of single-signal turn-on output when detecting analytes. However, the single-signal turn-on output is easily affected by the external environment and cannot obtain accurate detection results.

Method used

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  • Naphthalimide-based double-signal turn-on formaldehyde fluorescent nano probe intermediate compound, and preparation method and application thereof
  • Naphthalimide-based double-signal turn-on formaldehyde fluorescent nano probe intermediate compound, and preparation method and application thereof
  • Naphthalimide-based double-signal turn-on formaldehyde fluorescent nano probe intermediate compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The preparation of embodiment 1 (1) compound (II)

[0060] Dissolve 1.22g of p-hydroxybenzaldehyde (10mmol) in 50mL of acetone solution, then add 2.07g (15mmol) of potassium carbonate, and after half an hour at 60-70°C, add 2.37g of 3-bromopropyne (20mmol), 60- The reaction was stopped after 2 hours at 70°C, and the solvent was distilled off under reduced pressure. Add water to the mixture, extract with ethyl acetate, combine the organic phases, wash with water and saturated brine several times, dry over anhydrous sodium sulfate, filter, spin to dry the solvent, and separate by column chromatography (ethyl acetate:petroleum ether=1: 10 is the eluent) to obtain white solid compound (II) (1.53 g, 95% yield). 1 H NMR (500MHz, CDCl 3 )δ9.88(s,1H),7.95–7.75(m,2H),7.18–6.98(m,2H),4.77(d,J=2.4Hz,2H),2.58(t,J=2.4Hz,1H ). 13 C NMR (126MHz, CDCl 3 )δ190.69,162.30,131.81,130.51,115.11,77.51,76.35,55.87.ESI calcd.forC 10 h 8 o 2 [M+H] + 161.05, found 161.18.

[0061] (2) ...

Embodiment 2

[0072] Example 2 The nanoprobe nano-MTDF was tested for particle size by dynamic light diffraction under the condition of DMSO / water buffer (pH=7.4, v / v=1 / 99) and nanoparticle imaging by transmission electron microscope.

[0073] Accurately weigh a certain amount of compound (I) prepared in Example 1, prepare a probe mother solution with a concentration of 0.1mM with DMSO, pipette 0.02mL into 1.98mL water, ultrasonicate for several minutes, and then shake vigorously to obtain nano Probe nano-MTDF, and then use nano-zs90particle analyzer to measure the particle size of nano-MTDF in water. At the same time, take the above mixed liquid droplet on the copper grid, and dry it at 37°C for transmission electron microscope imaging. The results are shown in image 3 .

[0074] see image 3 (a) It can be found that the result obtained by the dynamic light diffraction test is that the average particle diameter of the particles is 161.9 nm, and the polydispersity coefficient PDI index is...

Embodiment 3

[0075] Example 3 Fluorescence spectrum detection of nanoprobe nano-MTDF (1 μM) at different DMSO / water ratios.

[0076] Accurately weigh a certain amount of compound (I) prepared in Example 1, use dimethyl sulfoxide to prepare a probe mother solution with a concentration of 0.1mM, pipette 0.02mL and add to 1.98mL different DMSO / water ratios (DMSO 1%, 5%, 10%, 20%, 40%, 60%, 70%, 80%, 90%), ultrasonic for several minutes, then violently shake, and then measure the fluorescence spectrum of compound (I).

[0077] The experimental results show that as the ratio of DMSO increases, the fluorescence of compound (I) increases, which proves that with the reduction of the ratio of DMSO, the aggregation effect of compound (I) is enhanced, and the fluorescence at different excitation wavelengths is weakened, indicating that Rodan Bright B fluorescence is quenched due to aggregation. At the same time, it can also be observed that regardless of the ratio of DMSO, the probe has only one emi...

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Abstract

The invention discloses a preparation method and application of a mitochondrion-targeted double-signal turn-on formaldehyde fluorescent nano probe intermediate compound (V). The method comprises the following steps: activating p-hydroxybenzaldehyde used as an initial raw material in the presence of an acid-binding agent at 60-70 DEG C, and performing a nucleophilic substitution reaction in an acetone solvent by using 3-bromopropyne as a nucleophilic reagent to obtain a compound (II); performing ammonification on the compound (II) at 0 DEG C by means of an ammonia methanol solution, adding allylboronic acid pinacol ester, performing mixing, and performing a reaction while the temperature is controlled at 25-35 DEG C to obtain a compound (III); and performing a Schiff base reaction on 3-formyl-4-hydroxyl-1,8-naphthalimide and the compound (III) under the action of Lewis acid and a reducer, and performing a reduction reaction to obtain the compound (V). The compound (V) can be used as theintermediate compound for preparing a double-signal turn-on formaldehyde fluorescent nano probe. The nano probe reacts with formaldehyde to obtain two free fluorescent substances, thereby achieving adouble turn-on effect, and improving the detection accuracy. The compound (II), the compound (III) and the compound (V) are as shown in the specification.

Description

technical field [0001] The invention relates to a naphthalimide-based dual-signal turn-on formaldehyde fluorescent nano-probe intermediate and a preparation method and application thereof. Background technique [0002] 1. Due to the advantages of sensitivity, specificity, easy operation, and real-time detection of living cells or tissues, fluorescent probes have attracted the attention of researchers. Formaldehyde, as a volatile and difficult to eliminate gas, can easily cause human cancer and other malignant diseases, causing great troubles to human beings. Today, there is an urgent need to develop new detection technologies to detect formaldehyde in cells or tissues, so as to discover more pathogenic mechanisms of formaldehyde. [0003] 2. Nowadays, most fluorescent probes only have the characteristics of single-signal turn-on output when detecting analytes. However, the single-signal turn-on output is easily affected by the external environment and cannot obtain accurate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07D405/14G01N21/64
Inventor 朱勍谢振达应莎莎朱伸赵成艳
Owner ZHEJIANG UNIV OF TECH
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