CN116589493A - Fluorescent probe based on mercapto naphthalimide and preparation method and application thereof - Google Patents

Fluorescent probe based on mercapto naphthalimide and preparation method and application thereof Download PDF

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CN116589493A
CN116589493A CN202310570270.5A CN202310570270A CN116589493A CN 116589493 A CN116589493 A CN 116589493A CN 202310570270 A CN202310570270 A CN 202310570270A CN 116589493 A CN116589493 A CN 116589493A
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reaction
fluorescent probe
stirring
naphthalimide
compound
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赵宏伟
郭靖荣
见亚洲
王银秀
张艺华
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Shanxi University
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    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
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    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks

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Abstract

The invention belongs to the technical field of fluorescent probes, and particularly relates to a fluorescent probe based on mercapto naphthalimide, and a preparation method and application thereof. R is commonly used at present 1 The part is hydroxyl or amino, and the introduction of sulfhydryl is little. Based on the design, the quick detection method for H based on ICT mechanism is synthesized 2 O 2 4-mercapto naphthalimide is selected as fluorescent group, phenylborate with high hydrogen peroxide selectivity is selected as recognition group, and the probe is matched with H 2 O 2 After the reaction, the phenylborate is cracked, and the mercapto group is exposed, so that the green fluorescence of the 4-mercapto naphthalimide is recovered.

Description

Fluorescent probe based on mercapto naphthalimide and preparation method and application thereof
Technical Field
The invention belongs to the technical field of fluorescent probes, and particularly relates to a fluorescent probe based on mercapto naphthalimide, and a preparation method and application thereof.
Background
Reactive Oxygen Species (ROS) are chemical reactive species generated in organisms. Research has shown that ROS play a vital role in the physiological and pathological processes of the living system, and can exert toxic effects on biological molecules, and thus are considered as the culprit for causing various diseases, such as cardiovascular diseases, neurodegenerative diseases, and even cancers. Hydrogen peroxide (H) 2 O 2 ) Is a more specific class of small molecules in ROS. H as a biological Signal molecule 2 O 2 Takes part in a plurality of important physiological processes such as cell proliferation, intracellular transmission, cytopathy and the like, and when H 2 O 2 Is responsible for oxidative stress and irritation to cells when abnormal levels are present. Due to H 2 O 2 Has a critical role in physiological processes and pathological activities of lesions, thus accurately and quantitatively detecting H 2 O 2 Distribution and concentration in cells, helping to reveal H 2 O 2 Associated disease pathogenesis, and provides a reliable treatment scheme for early diagnosis and treatment of diseases.
Many assays have been developed for H 2 O 2 Is a common method for chemo-selective bioluminescence signal, electron spin resonance mass spectrometry and electrochemistry. However, the above methods have certain drawbacks. In contrast, the fluorescent probe has the advantages of good selectivity, high sensitivity, convenient preparation, real-time monitoring and the like, and is suitable for H 2 O 2 Has wide application prospect in detection and research. Thus, novel fluorescent probes are designed and synthesized for achieving H in vivo 2 O 2 Is a significant task.
The 1, 8-naphthalimide is a fluorescent dye which is widely developed, and has higher electron affinity, stable oxidability and good thermal stability due to a special structure. The 1, 8-naphthalimide dye and the derivative thereof have important roles in the fields of dye and fluorescence, the application and development attention of the dye and the derivative thereof in recent years are very high, the fluorescent dye is simple to synthesize, the molecular stability is high, and the water solubility is superior to that of common fluorescent dye naphthalimide and perylene diimide. The structural core of the 1, 8-naphthalimide is a naphthalene ring containing pi bridge,wherein the imide moiety acts as an electron accepting group, R 1 The electron mechanism of the framework of the D-pi-A system is well verified through theoretical calculation. Thus when R 1 The introduction of different groups excites the ICT effect or PET effect of the whole molecule, resulting in a blue or red shift of the fluorescence emission peak, and quenching or enhancement of fluorescence.
Disclosure of Invention
R is commonly used at present 1 The part is hydroxyl or amino, and the introduction of sulfhydryl is little. Based on the design, the quick detection method for H based on ICT mechanism is synthesized 2 O 2 4-mercapto naphthalimide is selected as fluorescent group, phenylborate with high hydrogen peroxide selectivity is selected as recognition group, and the probe is matched with H 2 O 2 After the reaction, the phenylborate is cracked, and the mercapto group is exposed, so that the green fluorescence of the 4-mercapto naphthalimide is recovered.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the structure of the thiol-naphthalimide-based fluorescent probe is as follows:
a preparation method of a fluorescent probe based on mercapto naphthalimide comprises the following steps:
step 1, dissolving 4-bromo-1, 8-naphthalene dicarboxylic anhydride and N-butylamine in ethanol, stirring, heating, refluxing for reaction, cooling the reaction liquid to room temperature after the reaction is finished, pouring the reaction liquid into distilled water, obtaining a large amount of yellow solid, filtering, collecting the solid, washing to obtain a yellow compound N-1, and directly using the compound N-1 in the next reaction;
step 2, compounds N-1 and Na 2 SO 4 ﹒9H 2 O is dissolved in N, N-dimethylformamide, stirred at room temperature for reaction, the reaction solution is dark purple, poured into cold water, diluted hydrochloric acid is slowly added dropwise under stirring, the pH of the solution is regulated, the solution changes from dark purple to orange until a large amount of yellow solid is precipitated when the solution changes to colorless, the solid is collected by filtration, a crude product is obtained, and the crude product is separated and purified by column chromatography to obtain a pale yellow solid compound N-2;
and 3, dissolving 2- (4- (bromomethyl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolane and anhydrous potassium carbonate in N, N-dimethylformamide, stirring at room temperature for reaction, adding the compound N-2, stirring for heating for reaction, and distilling under reduced pressure to remove a solvent after the reaction is finished to obtain a crude yellow solid, and separating and purifying the crude yellow solid by column chromatography to obtain a yellow solid probe.
Further, the molar ratio of 4-bromo-1, 8-naphthalic anhydride to n-butylamine in the step 1 is 1:2.
Further, in the step 1, stirring and heating are carried out to 70-80 ℃, the reflux reaction time is 6.5h, and the washing is carried out twice by using ethanol.
Further, the compound N-1 and Na in the step 2 2 SO 4 ﹒9H 2 The molar ratio of O is 1:5.
Further, the reaction time at room temperature in the step 2 is 6 hours, the pH of the solution is adjusted to 1, and the eluent for separation and purification by column chromatography is petroleum ether/ethyl acetate=3:1 (V/V).
Further, the molar ratio of 2- (4- (bromomethyl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan, anhydrous potassium carbonate to compound 2 in step 3 was 1.5:2:1.
Further, in the step 3, the reaction is stirred at room temperature for 0.5h, the temperature of stirring and heating is 50 ℃ for 7h, and the eluent for separation and purification by column chromatography is petroleum ether/ethyl acetate=5:1 (V/V).
Application of fluorescent probe based on mercapto naphthalimide for detecting H 2 O 2 。
Compared with the prior art, the invention has the following advantages:
the optical performance test of the fluorescent probe shows that the fluorescent intensity is increased by 21 times in the concentration range of 0-600 mu m of hydrogen peroxide, the detection limit for detecting the hydrogen peroxide is extremely low, and compared with a series of published fluorescent probes for detecting the hydrogen peroxide based on boric acid esters, the fluorescent probe has wider detection range in a linear interval.
The fluorescence probe of the invention changes the fluorescence of the solution under the irradiation of 365nm ultraviolet light within the range of 0-400 mu M of hydrogen peroxide concentration, and the brightness is gradually enhanced along with the increase of the hydrogen peroxide concentration through naked eyes.
The fluorescent probe has the advantages of extremely high response speed, strong anti-interference capability, capability of specifically recognizing hydrogen peroxide and excellent selectivity.
The fluorescent probe has simple synthesis process and stable chemical molecular structure, can normally detect hydrogen peroxide in a pH range with proper biology, has good biocompatibility and low biological toxicity, and is expected to provide help for physiological and pathological research of hydrogen peroxide in biological systems.
Drawings
FIG. 1 is an HRMS (ESI) spectrum of probe Nap-B;
FIG. 2 is a HRMS (ESI) spectrum of probe Nap-B after reaction with hydrogen peroxide;
FIG. 3 shows 20. Mu.M probe and 20. Mu.M probe plus 400. Mu. M H 2 O 2 An ultraviolet-visible absorption spectrum of (a);
FIG. 4 shows 20. Mu.M probe and 20. Mu.M probe plus 400. Mu. M H 2 O 2 Is a fluorescent emission spectrum of (2);
FIG. 5 shows the addition of increasing concentrations of H to a test solution containing 20. Mu.M probe Nap-B 2 O 2 Fluorescence emission spectrum of (ph=7.00);
FIG. 6 shows a Nap-B solution containing 20. Mu.M probeAbsence and presence of 400. Mu.M H in the liquid 2 O 2 The analyte ions (400. Mu.M) were then added to the PBS buffer (pH 7.00).
Detailed Description
Example 1
A fluorescent probe based on mercapto naphthalimide has the following structure:
the preparation method of the probe comprises the following steps:
(1) Synthesis of Compound N-1
4-bromo-1, 8-naphthalene dicarboxylic anhydride (14 mmol,1 eq) and N-butylamine (28 mmol,2 eq) are sequentially added into a round-bottom flask, dissolved in 70mL of ethanol solvent, a reflux device is connected, the mixture is heated to 75 ℃ under stirring, the reflux reaction is carried out for 6.5h, after the reaction is finished, the reaction liquid is cooled to room temperature, then the reaction liquid is poured into distilled water, a large amount of yellow solid appears, the solid is collected by filtration, and the solid is washed twice with ethanol to obtain a yellow compound N-1 which is directly used for the next reaction.
(2) Synthesis of Compound N-2
To a round bottom flask was added in sequence the compound N-1 (2 mmol,1 eq), na 2 SO 4 ﹒9H 2 O (10 mmol,5 eq) is dissolved in 20mL of N, N-dimethylformamide solvent, stirring is carried out at room temperature for reaction for 6h, after the reaction is finished, the reaction solution is dark purple, then the reaction solution is poured into 50mL of cold water, dilute hydrochloric acid is slowly added dropwise under stirring, the pH of the solution is regulated to be about 1, the solution changes from dark purple to orange until a large amount of yellow solid is precipitated when the solution becomes colorless, the solid is collected by filtration, a crude product is obtained, and the crude product is separated and purified by column chromatography to obtain a pale yellow solid compound N-2 (eluent ratio: petroleum ether/ethyl acetate=3:1, silica gel 200-300 meshes).
(3) Synthesis of probe Nap-B
To a round bottom flask was added 2- (4- (bromomethyl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (0.9 mmol,1.5 eq) and anhydrous potassium carbonate (1.2 mmol,2 eq) dissolved in N, N-dimethylformamide solvent, followed by stirring at room temperature for 0.5h, then the above-mentioned compound N-2 (0.6 mmol,1 eq) was added, and the mixture was heated to 50℃with stirring for 7h. After the reaction is finished, the solvent is distilled off under reduced pressure to obtain crude yellow solid, and the crude yellow solid is separated and purified by column chromatography (eluent ratio: petroleum ether/ethyl acetate=5:1, silica gel 200-300 meshes) to obtain yellow solid probe Nap-B.
1H NMR(600MHz,Chloroform-d)δ8.61(d,J＝7.2Hz,1H)，8.56(d,J＝8.4Hz,1H)，8.41(d,J＝7.8Hz,1H)，7.77(d,J＝8.0Hz,2H)，7.72(d,J＝7.9Hz,1H)，7.56(d,J＝7.9Hz,1H)，7.40(d,J＝7.9Hz,2H)，4.36(s,2H)，4.19–4.14(m,2H)，1.71(s,2H)，1.43(s,2H)，1.34(s,12H)，0.97(s,3H)；
13C NMR(150MHz,Chloroform-d)δ164.05，144.12，138.50，135.26，131.48，130.71，130.16，129.76，128.25，126.75，124.37，123.2，119.82，83.93，40.25，37.62，30.23，29.72，26.92，24.88，20.41，13.88；[M] + :calcd for 501.2034，Found 501.2044.
Example 2
Optical Properties of Probe Nap-B
(1) And scanning 20 mu M Nap-B by using an ultraviolet-visible absorption spectrometer to obtain an ultraviolet absorption curve spectrogram of the probe Nap-B. Then continuously dripping 400 mu M hydrogen peroxide into the cuvette, and scanning by using an ultraviolet-visible absorption spectrometer to obtain Nap-B and H in a short time 2 O 2 Ultraviolet absorption spectrum after reaction. As shown in FIG. 3, when the detection system is only probe Nap-B, the maximum absorption peak of the ultraviolet absorption spectrum is 340nm, and when the detection system is Nap-B and H 2 O 2 When the maximum absorption peak of the ultraviolet absorption spectrum is red shifted, the new ultraviolet absorption peak is 434nm. This indicates that probes Nap-B and H 2 O 2 The reaction is carried out, a new ultraviolet absorption peak appears, and the probe Nap-B is supposed to be capable of successfully detecting H 2 O 2 And it can quickly recognize H 2 O 2 。
(2) Probe Nap-B vs H 2 O 2 Fluorescence spectral response of (2)
Scanning 20 μm Nap-B with fluorescence spectrometer, and excitingThe emission wavelength is 410nm, the excitation slit is 5nm, the emission slit is 5nm, the voltage is 480V, and the collection wavelength is 425-750 nm. Obtaining the fluorescence emission spectrum curve of the probe Nap-B. Continue to drop 400. Mu.M H into the cuvette 2 O 2 Scanning by using a fluorescence spectrometer to obtain Nap-B and H 2 O 2 The fluorescence emission spectrum after the reaction does not change the fluorescence excitation condition. As shown in FIG. 4, when the detection system only has probe Nap-B, the fluorescence emission wavelength intensity of 500nm is only 342 under the excitation of 410nm, and when the detection system simultaneously has probes Nap-B and H 2 O 2 When the fluorescent light is excited at 410nm, the fluorescence emission wavelength intensity at 500nm reaches 4415, and the fluorescence intensity is that H is not added dropwise 2 O 2 13 times of (3).
(3) Probe Nap-B along with H 2 O 2 Fluorescence spectral response to concentration variation
To a probe Nap-B solution having a concentration of 20. Mu.M, different volumes of H were added, respectively 2 O 2 So that H in the detection system 2 O 2 The final concentration of (2) is 0-600 mu M, and fluorescence spectrum scanning is carried out, and the test conditions are consistent with the fluorescence emission spectrum. Integrating the obtained different fluorescence emission spectra, selecting fluorescence emission intensity (F) at 500nm in each fluorescence emission spectrum, and then combining with H 2 O 2 Fluorescence emission intensity at 500nm at a concentration of 0 (F 0 ) The ratio is calculated to obtain F/F 0 The data were linearly fitted to obtain their slope. As shown in FIG. 5, the fluorescence emission peak of the probe Nap-B was 500nm, but its intensity was lower. When H is 2 O 2 After addition, the fluorescence emission intensity at 500nm was increased with H 2 O 2 The increasing intensity of the concentration gradually increases.
(4) Probe pair H 2 O 2 Specific recognition of (C)
To investigate the anti-interference ability of the probe Nap-B, the specific recognition performance was evaluated. The biologically relevant substance is selected as interfering ion, cation (K + 、Ca 2+ 、Fe 3+ 、Mg 2+ ) Anions (Cl) - 、F - 、Br - 、SO 4 2- -、ClO - (III),) oxides (TBHP, O 2- ) Biological amino acid (Cys, GSH, hcy) and OH. The concentration of interfering ions was 400. Mu.M and the test conditions for the fluorescence emission spectrum were identical to those described above. The fluorescence emission intensity at 500nm was compared. As can be seen from FIG. 6, the probe Nap-B detects H in the presence of interfering ions 2 O 2 The fluorescence intensity is not greatly changed and is not influenced by interfering ions. This indicates that the probe Nap-B has excellent specificity and can specifically recognize H 2 O 2 。

Claims (9)

1. A fluorescent probe based on mercapto naphthalimide, characterized in that the structure of the fluorescent probe is as follows:
2. a method for preparing the thiol-naphthalimide-based fluorescent probe of claim 1, comprising the steps of:
step 1, dissolving 4-bromo-1, 8-naphthalene dicarboxylic anhydride and N-butylamine in ethanol, stirring, heating, refluxing for reaction, cooling the reaction liquid to room temperature after the reaction is finished, pouring the reaction liquid into distilled water, obtaining a large amount of yellow solid, filtering, collecting the solid, washing to obtain a yellow compound N-1, and directly using the compound N-1 in the next reaction;
step 2, compounds N-1 and Na 2 SO 4 ﹒9H 2 O is dissolved in N, N-dimethylformamide, stirred at room temperature for reaction, the reaction solution is dark purple, poured into cold water, diluted hydrochloric acid is slowly added dropwise under stirring, the pH of the solution is regulated, the solution changes from dark purple to orange until a large amount of yellow solid is precipitated when the solution changes to colorless, the solid is collected by filtration, a crude product is obtained, and the crude product is separated and purified by column chromatography to obtain a pale yellow solid compound N-2;
and 3, dissolving 2- (4- (bromomethyl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolane and anhydrous potassium carbonate in N, N-dimethylformamide, stirring at room temperature for reaction, adding the compound N-2, stirring for heating for reaction, and distilling under reduced pressure to remove a solvent after the reaction is finished to obtain a crude yellow solid, and separating and purifying the crude yellow solid by column chromatography to obtain a yellow solid probe.
3. The method for preparing a fluorescent probe based on mercaptonaphthalimide according to claim 2, wherein the molar ratio of 4-bromo-1, 8-naphthalic anhydride to n-butylamine in step 1 is 1:2.
4. The method for preparing a fluorescent probe based on mercaptonaphthalimide according to claim 2, wherein the stirring and heating in the step 1 are carried out to 70-80 ℃, the reflux reaction time is 6.5h, and the washing is carried out twice by using ethanol.
5. The method for preparing a fluorescent probe based on mercaptonaphthalimide according to claim 2, wherein the compound N-1 and Na in the step 2 2 SO 4 ﹒9H 2 The molar ratio of O is 1:5.
6. The method for preparing the fluorescent probe based on the mercaptonaphthalimide according to claim 2, wherein the stirring reaction time at room temperature in the step 2 is 6 hours, the pH of the solution is adjusted to 1, and the eluent for column chromatography separation and purification is petroleum ether/ethyl acetate=3:1 (V/V).
7. The method for preparing a fluorescent probe based on mercaptonaphthalimide according to claim 2, wherein the molar ratio of 2- (4- (bromomethyl) phenyl) -4, 5-tetramethyl-1, 3, 2-dioxaborolane, anhydrous potassium carbonate to compound 2 in step 3 is 1.5:2:1.
8. The method for preparing a fluorescent probe based on mercaptonaphthalimide according to claim 2, wherein in the step 3, the stirring reaction time at room temperature is 0.5h, the stirring heating temperature is 50 ℃, the stirring heating time is 7h, and the eluent for column chromatography separation and purification is petroleum ether/ethyl acetate=5:1 (V/V).
9. Use of a thiol-naphthalimide based fluorescent probe according to claim 1, for the detection of H 2 O 2 。
CN202310570270.5A 2023-05-19 2023-05-19 Fluorescent probe based on mercapto naphthalimide and preparation method and application thereof Pending CN116589493A (en)

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