CN110330511B - Synthesis method and biological detection application of imidazole ligand - Google Patents

Synthesis method and biological detection application of imidazole ligand Download PDF

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CN110330511B
CN110330511B CN201910463257.3A CN201910463257A CN110330511B CN 110330511 B CN110330511 B CN 110330511B CN 201910463257 A CN201910463257 A CN 201910463257A CN 110330511 B CN110330511 B CN 110330511B
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CN110330511A (en
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王峥
范勇玲
张晓凡
彭旭
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Hubei University
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    • C—CHEMISTRY; METALLURGY
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    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • G—PHYSICS
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    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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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
    • 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"
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • 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"
    • G01N2021/6432—Quenching

Abstract

The invention relates to a synthesis method of imidazole ligandA method, comprising: (1) uniformly mixing the compound 1 and the compound 2 according to the molar ratio of 1: 3-1: 3.4, carrying out reflux reaction at the temperature of 150-; (2) diluting the reaction stock solution in the step (1) with deionized water, cooling and filtering to obtain white precipitate, and adding Na into the precipitate2CO3Neutralizing the solution, standing the neutralized solution, cooling and filtering to obtain a crude product; recrystallizing the crude product in methanol solution for three times, filtering, washing and drying in vacuum to obtain a light yellow solid, namely a compound 3: 5- (1H-imidazo [4, 5-c)]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene; the compound 1 is trimesic acid; the compound 2 is 3, 4-diaminopyridine. The compound 3 is simple to synthesize, contains groups such as benzene rings, imidazole and pyridine, and can be applied to the field of biological detection.

Description

Synthesis method and biological detection application of imidazole ligand
Technical Field
The invention relates to a preparation method of an organic matter, in particular to a synthesis method of an organic ligand 5- (1H-imidazo [4,5-c ] pyridine-2-yl) -1, 3-di (3H-imidazo [4,5-c ] pyridine-2-yl) benzene (L for short) and application of the L in biological detection.
Background
The imidazole compound is a polydentate ligand containing N and containing imidazole rings, and has a larger conjugated rigid plane. Because of containing imidazole ring, imidazole compounds are widely applied to the field of biological detection. Meanwhile, the imidazole compound contains a plurality of N coordination atoms, has a plurality of coordination modes, and forms a stable complex by coordinating with metal, thereby forming a novel material with various varieties and excellent structure. After the imidazole compound ligand absorbs ultraviolet light, the singlet state ground state S0 is transited to the excited state S1, the singlet state excited state is transited to the triplet state, and when electrons are transited from the excited state to the ground state, fluorescence is generated. The 5- (1H-imidazo [4,5-c ] pyridine-2-yl) -1, 3-di (3H-imidazo [4,5-c ] pyridine-2-yl) benzene contains benzene rings, pyridyl and imidazole rings, has yellow green fluorescence, large light absorption coefficient, multiple coordination sites and strong coordination capacity, and can be widely applied to the fields of biological detection, fluorescent materials and the like. To date, there has been no research on the synthesis and use of 5- (1H-imidazo [4,5-c ] pyridin-2-yl) -1, 3-bis (3H-imidazo [4,5-c ] pyridin-2-yl) benzene, and it is therefore of great interest to design a rational method for the synthesis and use of this ligand. Bovine Serum Albumin (BSA) and human serum albumin (HAS) are similar in structure and physiological function and are more economical and easy to obtain, so that the BSA is widely used in scientific research, the influence of a substance on the HAS is predicted by exploring the BSA process, and the theoretical basis is laid for subsequent work research.
Disclosure of Invention
In order to overcome the problems in the prior art, the invention aims to provide a preparation method of an organic ligand 5- (1H-imidazo [4,5-c ] pyridine-2-yl) -1, 3-bis (3H-imidazo [4,5-c ] pyridine-2-yl, and the performance of the organic ligand is tested by a series of characterization methods such as solid nuclear magnetism, infrared, ultraviolet, fluorescence and the like, and the fluorescence quenching effect of L on BSA is detected.
In order to achieve the purpose, the invention adopts the technical scheme that:
the method for synthesizing the imidazole ligand is characterized by comprising the following steps of:
(1) uniformly mixing the compound 1 and the compound 2 according to the molar ratio of 1: 3-1: 3.4, carrying out reflux reaction at the temperature of 150-;
(2) by using deionizationDiluting the reaction stock solution in the step (1) with water, cooling and filtering to obtain white precipitate, and adding Na into the precipitate2CO3Neutralizing the solution, standing the neutralized solution, cooling and filtering to obtain a crude product; recrystallizing the crude product in methanol solution for three times, filtering, washing and drying in vacuum to obtain a light yellow solid, namely a compound 3: 5- (1H-imidazo [4, 5-c)]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene;
wherein the compound 1 is trimesic acid, and the structural formula is as follows:
Figure BDA0002078681500000021
the compound 2 is 3, 4-diaminopyridine and has a structural formula:
Figure BDA0002078681500000022
the reaction process of the steps is as follows:
Figure BDA0002078681500000023
further, the mass ratio of the compound 1 and the compound 2 in the step (1) to the polyphosphoric acid in the above technical scheme is (1: 1.56: 23.8) to (1: 1.76: 47.6).
Further, Na used for neutralizing the product in the step (2) in the technical scheme is Na2CO3The mass fraction of the solution is: 10% and the solvent is deionized water.
Further, polyphosphoric acid, deionized water and Na used in steps (1) and (2) in the technical scheme2CO3The volume ratio of the solution is 1: 10: 10.
further, the solvent used for washing the compound 3 in the step (2) in the above technical scheme is water and methanol.
The biological detection application of the imidazole ligand is characterized by further comprising the following steps based on the synthesis method: and (3) respectively testing the fluorescence emission spectra of bovine serum albumin BSA solutions at different temperatures, then gradually dropwise adding the solution of the compound 3 into the BSA solution, testing the fluorescence emission spectra of the mixed solution, and exploring the fluorescence quenching effect of the compound 3 on BSA.
Further, in the above technical solution, in the step (3), the different temperatures are T298K, T K308K, respectively.
Further, the concentration of the BSA solution used in step (3) in the above-mentioned technical solution is 6X 10-6mol/L, the solvent is NaH2PO3-Na2HPO3Buffer solution, pH 7.42.
Further, the concentrations of the compound 3 solution used in the step (3) in the above-mentioned technical method were 0mol/L and 1X 10, respectively- 6mol/L、2×10-6mol/L、4×10-6mol/L、6×10-6mol/L、1×10-5mol/L、1.4×10-5mol/L、1.8×10-5mol/L、2×10-5mol/L、2.4×10-5mol/L、2.8×10-5mol/L, and the solvent is DMSO (dimethyl sulfoxide).
Further, the condition of the fluorescence test in step (3) in the above technical scheme is λex280nm, 5nm slit, test range 300 and 500 nm.
The invention has the beneficial effects that: compared with the prior art, the invention has the advantages that:
(1) the compound 3 is simple to synthesize, contains groups such as benzene rings, imidazole and pyridine, and can be applied to the field of biological detection.
(2) The compound 3 has a large light absorption coefficient and a plurality of coordination sites, can coordinate with metal, and forms a novel material with various varieties and excellent performance.
(3) The compound 3 has yellow green fluorescence, and can be widely applied to other fields as a fluorescent material.
Drawings
FIG. 1 shows the preparation of Compound 3 from examples 1 to 41H NMR spectrum.
FIG. 2 shows the preparation of Compound 3 from examples 1 to 413C NMR spectrum.
FIG. 3 is an IR spectrum of Compound 3 prepared in examples 1 to 4.
FIG. 4 is a graph showing fluorescence excitation and emission spectra of Compound 3 prepared in examples 1 to 4.
Fig. 5 shows uv spectra of compound 3 prepared in examples 1 to 4.
FIG. 6 is a thermogravimetric plot of Compound 3 prepared in examples 1-4.
Fig. 7 is a plot of the fluorescence spectrum of compound 3 of example 5 interacting with BSA, where a is T298K and b is T308K.
FIG. 8 is a graph of the Stern-Volmer equation for quenching BSA for Compound 3 in example 5.
FIG. 9 is a double reciprocal plot of quenching of BSA by Compound 3 of example 5.
FIG. 10 is a spectral overlay of the UV spectrum and BSA fluorescence spectrum of Compound 3 of example 5.
Detailed Description
In order to better understand the present invention, the following examples are further provided to illustrate the present invention, but the present invention is not limited to the following examples. Various changes or modifications may be effected therein by one skilled in the art and such equivalents are intended to be within the scope of the invention as defined by the claims appended hereto. The technical solution of the present invention will be described in detail by the following examples.
Example 1:
step (1): 0.21g of the compound 1 and 0.327g of the compound 2 (molar ratio 1: 3) were uniformly mixed in an agate mortar, and then the mixture was refluxed at 160 ℃ for 12 hours in a 5mL polyphosphoric acid system, and cooled to room temperature after the reaction.
Step (2): diluting the reaction stock solution obtained in the step (1) with 50mL of deionized water, cooling and filtering to obtain a white precipitate, and adding 50mL of 10% Na2CO3Neutralizing the solution, standing the neutralized solution, cooling, and filtering to obtain a crude product. Recrystallizing the crude product in methanol solution for three times, filtering, washing and drying in vacuum to obtain a light yellow solid, namely a compound 3: 5- (1H-imidazo [4, 5-c)]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene.
Example 2:
step (1): 0.21g of compound 1 and 0.3488g of compound 2 (molar ratio 1: 3.2) were uniformly mixed in an agate mortar, and then the mixture was refluxed at 150 ℃ for 15 hours in 8mL of polyphosphoric acid system, and cooled to room temperature after the reaction.
Step (2): diluting the reaction stock solution obtained in the step (1) with 80mL of deionized water, cooling and filtering to obtain a white precipitate, and adding 80mL of 10% Na into the white precipitate2CO3Neutralizing the solution, standing the neutralized solution, cooling, and filtering to obtain a crude product. Recrystallizing the crude product in methanol solution for three times, filtering, washing and drying in vacuum to obtain a light yellow solid, namely a compound 3: 5- (1H-imidazo [4, 5-c)]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene.
Example 3:
step (1): 0.21g of compound 1 and 0.3706g of compound 2 (molar ratio of 1: 3.4) were uniformly mixed in an agate mortar, and then the mixture was refluxed at 170 ℃ for 12 hours in a 5mL polyphosphoric acid system, and cooled to room temperature after the reaction.
Step (2): diluting the reaction stock solution obtained in the step (1) with 50mL of deionized water, cooling and filtering to obtain a white precipitate, and adding 50mL of 10% Na2CO3Neutralizing the solution, standing the neutralized solution, cooling, and filtering to obtain a crude product. Recrystallizing the crude product in methanol solution for three times, filtering, washing and drying in vacuum to obtain a light yellow solid, namely a compound 3: 5- (1H-imidazo [4, 5-c)]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene.
Example 4:
step (1): 0.21g of the compound 1 and 0.327g of the compound 2 (molar ratio 1: 3) were uniformly mixed in an agate mortar, and then the mixture was refluxed at 150 ℃ for 15 hours in a 10mL polyphosphoric acid system, and cooled to room temperature after the reaction.
Step (2): diluting the reaction stock solution obtained in the step (1) with 100mL of deionized water, cooling and filtering to obtain a white precipitate, and adding 100mL of 10% Na2CO3Neutralizing the solution, standing the neutralized solution, cooling, and filtering to obtain a crude product. Recrystallizing the crude product in methanol solution for three times, filtering, washing and drying in vacuum to obtain a light yellow solid, namely a compound 3: 5- (1H)-imidazo [4,5-c]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene.
Compound 3, prepared as described in examples 1-4 above, was used as a solid1H NMR and13the C NMR detection means is characterized, the detection is reported in the attached figures 1 and 2, and can be seen from the attached figure 1:1h NMR. delta.: 6.81(12H), 14.50(3H), as can be seen in FIG. 2:13CNMR δ: 105.56, 112.61, 125.32, 127.79, 139.41, 143.15, 151.10. In accordance with the theoretical situation1H NMR and13c NMR results prove that the compound 3 synthesized by the method is 5- (1H-imidazo [4, 5-C)]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene.
The infrared spectrum of compound 3 is shown in figure 3. As can be seen from fig. 3, the infrared peak of compound 3 is mainly: FT-IR (KBr, cm)-1)：2981、1597、143179、1282、11218、1019、783、703、570。
Compound 3 was characterized using an ultraviolet-visible spectrophotometer and the results are shown in figure 4. As can be seen from FIG. 4, the ultraviolet absorption peaks of Compound 3 are 258nm and 300 nm. Corresponds to the Sigma- π transition of the imidazole ring and the π - π transition of the benzene ring in the compound 3 system.
Compound 3 was characterized using a fluorescence combination spectrometer and the results are shown in FIG. 5. As can be seen from FIG. 5, the excitation peak of compound 3 is 310nm, the emission peak is 372nm, corresponding to the intramolecular π → π transition, indicating that the ligand itself has yellow-green fluorescence.
The compound 3 prepared in the above examples 1-4 was characterized by thermogravimetry-differential thermal analysis, and the results are shown in fig. 6. From FIG. 6, it can be seen that at and before 100 deg.C, the decrease in the curve indicates the loss of residual solvent or water of crystallization of Compound 3, and that Compound 3 starts to decompose around 500 deg.C until 91.74% of the product remains at 600 deg.C, demonstrating that Compound 3 has good thermal stability.
Example 5:
example 5 is based on example 1, and further studies the fluorescence quenching effect of compound 3 on BSA, and is an example of application of compound 3 in biological detection. The method further comprises the following steps (1) and (2) in the embodiment 1:
step (3) of measuring the fluorescence emission spectrum of a Bovine Serum Albumin (BSA) solution at a temperature of 298K and 308K, respectively, under the condition of lambdaex280nm, 5nm slit, test range 300 and 500nm, BSA solution with NaH pH 7.422PO3-Na2HPO3Preparing buffer solution with concentration of 6 × 10-6mol/L. Subsequently, a solution of compound 3 (compound 3 dissolved in DMSO) was gradually added dropwise to the BSA solution, and the concentration of compound 3 in the BSA solution was changed to: 0mol/L, 1X 10-6mol/L,2×10-6mol/L,4×10-6mol/L,6×10-6mol/L,1×10-5mol/L,1.4×10-5mol/L,1.8×10- 5mol/L,2×10-5mol/L,2.4×10-5mol/L,2.8×10-5mol/L. The fluorescence emission spectra of the mixed solutions at different concentrations were then tested to explore the fluorescence quenching effect of compound 3 on BSA.
As can be seen from FIG. 7, the intensity of the BSA fluorescence gradually decreased with the addition of the compound 3 solution, and fluorescence quenching occurred. The process of BSA fluorescence quenching has two mechanisms, one is dynamic quenching, one is static quenching, the process of static quenching, KsvWill decrease with increasing temperature; and dynamic quenching process, KsvWill increase with increasing temperature. Dynamic quenching is the collision of the compound with the protein, resulting in quenching of BSA fluorescence. Static quenching is due to the formation of a complex between the compound and BSA that quenches the fluorescence of the protein. Both the static quenching and dynamic quenching mechanisms follow the following formulas:
F0/F＝1+Ksv[Q]＝1+kqτo[Q] [1]
kq＝Ksv/τo [2]
in the above formula, F0And F represents the fluorescence intensity without addition of quencher and with addition of quencher, KsvIs the Stern-Volmer quenching constant, and it is the slope of the Stern-Volmer equation. [ Q ]]Is the concentration of the quencher, kqIs the rate constant for the bimolecular quenching process. Tau is0Average fluorescence lifetime of biomacromolecules, typically 10-8s。
The Stern-Volmer equation for quenching BSA with Compound 3 is shown in FIG. 8, KsvThe temperature-dependent changes are shown in the attached Table 1.
TABLE 1 quenching constants of Compound 3 for BSA
Figure BDA0002078681500000061
Figure BDA0002078681500000071
As can be seen from Table 1, K is increased with increasing temperaturesvTherefore, the quenching pattern of compound 3 to BSA was static quenching. k is a radical ofqAs the quenching rate constant of the biomolecule, the maximum value of the dynamic quenching constant is 2.0X 1010L·mol-1·s-1. K of Compound 3qAbove the maximum, it is further demonstrated that the quenching mechanism of compound 3 for BSA is static quenching.
The binding constant and binding site for the interaction of organic molecules with BSA can be calculated by equation 3:
log[(F0-F)/F]＝log Ka+n lg[Q] [3]
make log [ (F)0-F)/F]For log [ Q ]]Can be derived from the intercept and slopea) And binding site (n), see FIG. 9. The forces of the complex and the protein are mainly van der waals force, hydrogen bond, electrostatic force and hydrophobic force. It is well known that temperature has a significant effect on thermodynamic parameters. Thermodynamic parameters can be calculated according to the following formula, see attached table 2.
Under the conditions that the delta H is more than 0 and the delta S is more than 0 under certain temperature (T) and pressure (P), the acting force of the substance and the BSA is mainly hydrophobic acting force; when the delta H is less than 0 and the delta S is more than 0, the substance and the BSA are mainly electrostatic acting force; in the case where Δ H < 0 and Δ S < 0, the acting force of the substance to BSA is mainly van der Waals force and hydrogen bond. The positive and negative of Δ G can be used to determine whether the reaction is spontaneously proceeding.
ln Ka＝-△H/RT+△S/R [4]
△G＝△H-T△S [5]
TABLE 2 binding constants, binding site trees and thermodynamic parameter values for Compound 3 with BSA
Figure BDA0002078681500000072
As shown in the attached Table 2, since Δ H < 0 and Δ S < 0 occur in the quenching process of BSA by Compound 3, it was found that the acting force of Compound 3 with BSA was mainly Van der Waals force and hydrogen bond and that Δ G < 0, indicating that the action of Compound 3 with BSA proceeded spontaneously.
The fluorescence energy transfer theory is generally summarized as a radiative energy transfer theory and a non-radiative energy transfer theory, wherein the energy transfer between the organic molecule and the bovine serum albumin belongs to the non-radiative energy transfer theory. The overlap of the ultraviolet spectrum and the BSA fluorescence spectrum of the compound 3 is shown in the attached FIG. 10, and the related data can be calculated by the following formula:
E＝R0 6/(R0 6+r6) [6]
R0 6＝8.79×10-25K2n-4ΦJ [7]
J(λ)＝∑F(λ)ε(λ)λ4△(λ)/∑F(λ)△(λ) [8]
E＝1-F/F0 [9]
wherein R is0Is the critical distance, K, at a transfer efficiency of 50%2Is a dipole spatial orientation factor (K)22/3), n is the refractive index of the medium (n 1.36), Φ is the donor fluorescence quantum yield (Φ 0.11), and J is the overlap integral of the fluorescence emission spectrum of BSA and the uv-vis spectrum of the small organic molecule. r is the distance between the quencher and the protein. F (λ) is the fluorescence intensity of BSA at wavelength λ, and ε (λ) is the molar absorption coefficient of small organic molecules at wavelength λ. After E and J are obtained, r can be obtained by calculation, and the calculation result is shown in an attached table 3.
TABLE 3 binding distance of Compound 3 to BSA and related constants
Figure BDA0002078681500000081
As can be seen from the attached Table 3, the calculated value r<7nm，0.5R0<r<1.5R0Indicating that non-radiative energy transfer can occur. Meanwhile, the R values are all between 0.5 and 1.5R0In the meantime, it was further demonstrated that the quenching mechanism of the interaction of the substance with BSA is static quenching.
Finally, it should be noted that the above-mentioned contents are only used for illustrating the technical solutions of the present invention, and not for limiting the protection scope of the present invention, and that the simple modifications or equivalent substitutions of the technical solutions of the present invention by those of ordinary skill in the art can be made without departing from the spirit and scope of the technical solutions of the present invention.

Claims (5)

1. The method for synthesizing the imidazole ligand is characterized by comprising the following steps of:
(1) uniformly mixing the compound 1 and the compound 2 according to the molar ratio of 1: 3-1: 3.4, carrying out reflux reaction at the temperature of 150-;
(2) diluting the reaction stock solution in the step (1) with deionized water, cooling and filtering to obtain white precipitate, and adding Na into the precipitate2CO3Neutralizing the solution, standing the neutralized solution, cooling and filtering to obtain a crude product; recrystallizing the crude product in methanol solution for three times, filtering, washing and drying in vacuum to obtain a light yellow solid, namely a compound 3: 5- (1H-imidazo [4, 5-c)]Pyridin-2-yl) -1, 3-bis (3H-imidazo [4, 5-c)]Pyridin-2-yl) benzene;
wherein the compound 1 is trimesic acid, and the structural formula is as follows:
Figure FDA0003471982250000011
the compound 2 is 3, 4-diaminopyridine and has a structural formula:
Figure FDA0003471982250000012
the reaction process of the steps is as follows:
Figure FDA0003471982250000013
2. the method for synthesizing imidazole ligands according to claim 1, characterized in that: the mass ratio of the compound 1, the compound 2 and the polyphosphoric acid in the step (1) is (1: 1.56: 23.8) - (1: 1.76: 47.6).
3. The method for synthesizing imidazole ligands according to claim 1, characterized in that: na used for neutralizing products in step (2)2CO3The mass fraction of the solution is: 10% and the solvent is deionized water.
4. The method for synthesizing imidazole ligands according to claim 1, characterized in that: polyphosphoric acid, deionized water and Na used in steps (1) and (2)2CO3The volume ratio of the solution is 1: 10: 10.
5. the method for synthesizing imidazole ligands according to claim 1, characterized in that: the solvent used for washing the compound 3 in the step (2) is water and methanol.
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