CN108530459B - Preparation method of fluorescent probe - Google Patents

Preparation method of fluorescent probe Download PDF

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CN108530459B
CN108530459B CN201810543446.7A CN201810543446A CN108530459B CN 108530459 B CN108530459 B CN 108530459B CN 201810543446 A CN201810543446 A CN 201810543446A CN 108530459 B CN108530459 B CN 108530459B
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peroxynitrite
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fluorescent probe
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CN108530459A (en
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傅罗琴
刘豫
王瑞康
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Hangzhou Baimaibei Biotechnology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • 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"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Abstract

The invention relates to a preparation method of a fluorescent probe. Specifically, the probe is a benzothiazole-rhodamine compound, and can be used as a peroxynitrite ratiometric fluorescent probe for detecting peroxynitrite. The preparation method adopts a one-step synthesis method, and has simple preparation and high yield.

Description

Preparation method of fluorescent probe
Technical Field
The invention relates to a benzothiazole-rhodamine compound as a peroxynitrite ratiometric fluorescent probe, which can perform high-selection ultrasensitive analysis on peroxynitrite or can determine the concentration of the peroxynitrite in a sample.
Background
Reactive oxygen and nitrogen species are involved in a variety of physiological processes in living systems, including signal transduction, inflammation, and antioxidant injury. Peroxynitrite, a strongly oxidizing substance of active oxygen and active nitrogen, is produced by the reaction of nitric oxide and superoxide radical, has high reactivity and instability, and plays an important role in signal transduction and bacteriostasis in living systems. Peroxynitrite is also considered harmful due to its nitration damage to proteins, nucleic acids, lipids, etc., and abnormal accumulation of peroxynitrite in cells will lead to many diseases, including ischemia reperfusion injury, inflammatory diseases, neurodegenerative diseases, and even cancer. The mechanism of action of peroxynitrite has not been fully elucidated due to the lack of reliable techniques for detecting physiological levels of peroxynitrite. Therefore, it is crucial to find a specific and sensitive technique for detecting peroxynitrite in a living organism.
In recent years, methods for detecting peroxynitrite have been reported, such as spectrophotometry, high performance liquid chromatography, chemiluminescence analysis, and fluorescent probe analysis, wherein fluorescent probes have been the focus of attention of researchers due to their unique advantages of high selectivity, ultrasensitiveness, and simple synthesis. The currently reported fluorescent probe analysis methods still have certain defects, such as low sensitivity, poor selectivity, poor water solubility, complex synthesis and the like. Other active oxygen and active nitrogen in a living body have similar properties with peroxynitrite, and can potentially interfere the detection of peroxynitrite, and the content of peroxynitrite in a physiological environment is low, so that the development of a high-selectivity and high-sensitivity fluorescent probe is an urgent problem to be solved. In addition, the ratiometric fluorescent probe can eliminate interference from environmental factors, and thus has received much attention. In conclusion, the development of highly selective, highly sensitive, synthetically simple, water-soluble ratiometric fluorescent probes is an urgent problem to be solved by those skilled in the art
Disclosure of Invention
There is an urgent need in the art to prepare a simple high-selectivity ultrasensitive peroxynitrite ratiometric fluorescent probe, so as to be able to effectively detect peroxynitrite. Therefore, the invention synthesizes a novel peroxynitrite ratiometric fluorescent probe which is simple to synthesize, has good selectivity and high sensitivity and can identify peroxynitrite. Specifically, the invention provides a peroxynitrite ratiometric fluorescent probe, which is a benzothiazole-rhodamine compound and has the following structure:
Figure BDA0001678654470000021
preferably, the fluorescent probe of the present invention is:
Figure BDA0001678654470000031
the invention also provides a preparation method of the peroxynitrite fluorescent probe, which is synthesized by refluxing the corresponding benzothiazole-rhodamine compound and hydrazine hydrate corresponding to the probe in an absolute ethanol solution for 6 hours.
The invention also provides a detection preparation for detecting the concentration of peroxynitrite in a sample, which comprises the probe of the invention. Preferably, the test formulations of the present invention further comprise instructions for use of the product. Also preferably, the test formulation of the present invention further comprises a buffer for determining the concentration of peroxynitrite in the sample.
The peroxynitrite ratiometric fluorescent probe can act with peroxynitrite to generate the change of a fluorescence spectrum, thereby realizing the quantitative detection of the peroxynitrite.
Specifically, the peroxynitrite ratiometric fluorescent probe disclosed by the invention does not react with potassium ions, calcium ions, sodium ions, magnesium ions, zinc ions, ferric ions, ferrous ions, nitrate radicals, nitrite radicals, chloride ions, sulfate radicals, hydrogen peroxide, potassium superoxide and the like, so that the selective recognition of peroxynitrite is realized.
The peroxynitrite ratiometric fluorescent probe provided by the invention reacts with peroxynitrite very sensitively, so that the peroxynitrite can be detected favorably.
Optionally, the peroxynitrite fluorescent probe has good stability, and can be stored and used for a long time.
Furthermore, the peroxynitrite ratiometric fluorescent probe is a high-selectivity and ultrasensitive peroxynitrite ratiometric fluorescent probe, is simple to synthesize, and is beneficial to commercial popularization and application.
Drawings
FIG. 1a is a fluorescence spectrum of a probe (5. mu.M) before and after addition of peroxynitrite (0-60. mu.M);
FIG. 1b is a graph showing the working curves of probe (5. mu.M) for quantitative analysis of peroxynitrite (0-20. mu.M) at different concentrations;
FIG. 2 is a graph of the spectrum over time after addition of the probe (5. mu.M) to peroxynitrite (50. mu.M);
FIG. 3 is a graph showing the effect of substances commonly found in the human body on the fluorescence intensity of a probe (5. mu.M). Wherein numbers 1-24 are blank, potassium ion, calcium ion, sodium ion, magnesium ion, zinc ion, ferric ion, ferrous ion, nitrate, nitrite, chloride ion, sulfate, cysteine (500. mu.M), homocysteine (500. mu.M), glutathione (5mM), tert-butyl alcohol peroxide, hydroxyl radical, tert-butyl alcohol peroxide free radical, hydrogen peroxide, potassium superoxide, nitric oxide, singlet oxygen, sodium hypochlorite, nitrite peroxide (50. mu.M), respectively (except for special indication, the concentration of other analytes is 100. mu.M). The histogram represents the ratio of fluorescence intensity at 581nm to 454nm for probes in the presence of different analytes.
The specific implementation mode is as follows:
the invention provides a synthetic route, a method and spectral performance of the high-selectivity and high-sensitivity peroxynitrite fluorescent probe.
The peroxynitrite ratiometric fluorescent probe is a benzothiazole-rhodamine compound and has the following structural general formula
Figure BDA0001678654470000051
In the above formula: r1，R2，R3，R4，R5，R6，R7，R8，R9，R10Is hydrogen atom, straight chain or branched chain alkyl, straight chain or branched chain alkoxy, sulfonic group, ester group, carboxyl; r1，R2，R3，R4，R5，R6，R7，R8，R9And R10May be the same or different.
The synthetic route and the method of the peroxynitrite ratiometric fluorescent probe are as follows:
Figure BDA0001678654470000052
specifically, the ratiometric fluorescent probe of the invention can be prepared by dissolving a certain molar ratio (for example, 1: 1-1: 20) of the benzothiazole-rhodamine compound and hydrazine hydrate (for example, 1: 1-1: 20) in absolute ethyl alcohol for cooling, then refluxing for a period of time (for example, 6h), and spin-drying the solvent under reduced pressure. If a purer product is to be obtained, the crude product can be subjected to column chromatography using a mixed system of methylene chloride and methanol (e.g., v/v, 100: 1) to obtain a pure product.
Therefore, the invention also provides the use of hydrazine hydrate in the preparation of ratiometric fluorescent probes for detecting peroxynitrite.
The invention also provides application of the benzothiazole-rhodamine compounds in preparing ratiometric fluorescent probes for detecting peroxynitrite.
The peroxynitrite ratiometric fluorescent probe disclosed by the invention has the remarkable characteristics that the peroxynitrite can be identified with high selectivity and ultra-sensitivity, and the peroxynitrite can be accurately and quantitatively analyzed in the presence of other ions in a human body.
The invention will be explained in more detail below by means of the following examples. The following examples are illustrative only, and it should be understood that the present invention is not limited by the following examples.
Example 1
Figure BDA0001678654470000061
(scheme 1) 200mg (0.38mmol) of benzothiazole-rhodamine compound is dissolved in 15mL of absolute ethanol, 57mg (1.14mmol) of hydrazine hydrate is added for refluxing for 6h, and the solvent is evaporated under reduced pressure. The crude product was subjected to column chromatography using a mixed system of methylene chloride and methanol (v/v, 100: 1) to give a pure product, 110mg of a pale yellow pure product, in 54% yield.
(scheme 2) 200mg (0.38mmol) of benzothiazole-rhodamine compound is dissolved in 15mL of absolute ethanol, 95mg (1.9mmol) of hydrazine hydrate is added for refluxing for 6h, and the solvent is evaporated under reduced pressure. The crude product was subjected to column chromatography using a mixed system of methylene chloride and methanol (v/v, 100: 1) to give a pure product, 130mg of a pale yellow pure product, 64% yield.
(scheme 3) 200mg (0.38mmol) of benzothiazole-rhodamine compound is put in 15mL of absolute ethyl alcohol, 190mg (3.8mmol) of hydrazine hydrate is added for refluxing for 6h, and the solvent is evaporated under reduced pressure. The crude product was purified by column chromatography using a mixed system of dichloromethane and methanol (v/v, 100: 1) to give 140mg of a pale yellow pure product with a yield of 69%.
(scheme 4) 200mg (0.38mmol) of benzothiazole-rhodamine compound is dissolved in 15mL of absolute ethanol, 380mg (7.6mmol) of hydrazine hydrate is added for refluxing for 6h, and the solvent is evaporated under reduced pressure. The crude product was subjected to column chromatography using a mixed system of dichloromethane and methanol (v/v, 100: 1) to give a pure product, 180mg of a pale yellow pure product, in 89% yield.
(scheme 5) 200mg (0.38mmol) of benzothiazole-rhodamine compound is dissolved in 15mL of absolute ethanol, 190mg (10mmol) of hydrazine hydrate is added for refluxing for 2h, and the solvent is evaporated under reduced pressure. The crude product was subjected to column chromatography using a mixed system of methylene chloride and methanol (v/v, 100: 1) to give a pure product in the form of pale yellow pure 105mg with a yield of 52%.
1The correctness of the product structure was confirmed by H NMR.
Example 2
FIG. 1a is the fluorescence spectra of the probe (5. mu.M) before and after addition of peroxynitrite (0-60. mu.M). FIG. 1b is a graph of the linear relationship of various concentrations of peroxynitrite (0-20. mu.M) versus probe (5. mu.M).
A plurality of parallel samples with the probe concentration of 5 mu M are arranged in a 10mL colorimetric tube, peroxynitrite with different concentrations is added into the test system, and the test system is shaken uniformly and then stands. The above measurements were carried out in a dimethylsulfoxide/water 3: 7(20 mpbs, pH7.4) system, the probe used was the probe prepared in example 1, and all spectroscopic measurements were carried out at 25 ℃.
The fluorescence intensity change was measured by fluorescence spectroscopy, and it is clear from FIG. 1a that the fluorescence intensity at 454nm decreased and the fluorescence intensity at 581nm gradually increased with increasing peroxynitrite concentration. Furthermore, it can be seen from FIG. 1b that the ratio of the fluorescence intensity at two wavelengths of the fluorescent probe (5 μ M) after adding peroxynitrite (0-20 μ M) has a good linear relationship with the concentration of peroxynitrite, which proves that the fluorescent probe can be used for quantitative ratiometric analysis of peroxynitrite.
Example 3
FIG. 2 is the response time of the probe (5. mu.M) after addition of peroxynitrite (50. mu.M). 50 mu L of the probe mother liquor is taken out and placed in a 10mL test system, 50 mu M of peroxynitrite is added into the test system, and the change of fluorescence intensity is tested by a fluorescence spectrometer immediately after the probe mother liquor is uniformly shaken. The above assay was performed in a dimethylsulfoxide/water 3: 7(20mM PBS, ph7.4) system, the probe used was the probe prepared in example 1, and all spectroscopic measurements were performed at 25 ℃.
As can be clearly seen from the figure, when peroxynitrite is added, the fluorescence intensity reaches the maximum value after about 6min of detection and keeps unchanged, which shows that the probe reacts with peroxynitrite rapidly, and can provide a rapid analysis method for determining peroxynitrite.
Example 4
FIG. 3 is a graph showing the effect of different analytes on the fluorescence spectrum of a probe (5. mu.M).
The analytes are blank, potassium ion, calcium ion, sodium ion, magnesium ion, zinc ion, ferric ion, ferrous ion, nitrate, nitrite, chloride ion, sulfate radical, cysteine (500 μ M), homocysteine (500 μ M), glutathione (5mM), tert-butyl alcohol peroxide, hydroxyl radical, tert-butyl alcohol peroxide free radical, hydrogen peroxide, potassium superoxide, nitric oxide, singlet oxygen, sodium hypochlorite, nitrite peroxide (50 μ M), and the concentration of other analytes is 100 μ M except for special indication. The histogram represents the ratio of fluorescence intensity at 581nm and 454nm for probes in the presence of different analytes. The above assay was performed in a dimethylsulfoxide: water 3: 7(20mM PBS, pH7.4) system, the probe used was the probe prepared in example 1, and all spectroscopic measurements were performed at 25 ℃. Specifically, a plurality of parallel samples with a probe concentration of 5 μ M were placed in a 10mL cuvette, and then a certain amount of analyte was added, shaken up, and measured after 10 minutes. As is clear from FIG. 3, the probe has high selectivity for peroxynitrite.
Although the present invention has been described in the above-mentioned embodiments, it is to be understood that the present invention may be further modified and changed without departing from the spirit of the present invention, and that such modifications and changes are within the scope of the present invention.

Claims (1)

1. Use of a compound of the structure:
Figure FDA0002611612810000011
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