CN110105405B - Preparation method and application of Schiff base complex containing rare earth element europium - Google Patents

Preparation method and application of Schiff base complex containing rare earth element europium Download PDF

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CN110105405B
CN110105405B CN201910433591.4A CN201910433591A CN110105405B CN 110105405 B CN110105405 B CN 110105405B CN 201910433591 A CN201910433591 A CN 201910433591A CN 110105405 B CN110105405 B CN 110105405B
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葛红光
唐小波
史娟
庞海霞
卢久富
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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a preparation method and application of a Schiff base complex containing rare earth element europium. The molecular formula of the complex is as follows: c19H25CuN5EuO16. Under the condition of constant stirring, dissolving copper salt and rare earth metal europium in a mixed solvent to obtain a solution 1; dissolving a Schiff base ligand compound in a mixed solvent, adding the solution 1 into the solution 2, constantly stirring for 0.5-1.0 h, and filtering to obtain a solution 3; and then placing the solution 3 in a high-pressure reaction kettle, and obtaining the rare earth Schiff base complex of light blue blocky crystals after temperature rise and temperature drop are controlled by programs. The rare earth Schiff base complex has good crystal form stability, and the preparation method and the post-treatment mode are relatively simple. In the test of the activity (inhibition rate) of the superoxide dismutase, the activity of the Schiff base complex is obviously enhanced compared with that before coordination, and a practical basis is provided for designing and synthesizing the rare earth Schiff base complex later and simulating the biological activity of the superoxide dismutase.

Description

Preparation method and application of Schiff base complex containing rare earth element europium
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a preparation method and application of a Schiff base complex containing rare earth element europium.
Background
Superoxide dismutase (SOD) widely exists in organisms, is an important metalloenzyme for eliminating superoxide anion free radicals by organisms, plays an important role in the balance of oxidation resistance in the organisms, reduces the amount of SOD in the human bodies along with the increase of the ages, so the SOD needs to be supplemented in time, and researches show that the SOD has biological and pharmacological effects of aging resistance, inflammation resistance, cancer resistance and the like, and can also be used for treating a plurality of diseases related to active oxygen damage. At present, researchers synthesize and characterize a series of micromolecular complexes containing metal ions such as copper, manganese, iron and the like to simulate SOD, and expect that the micromolecular simulated compounds can be used for replacing SOD to be applied clinically in the future. The most studied copper-containing complex is copper 3, 5-diisopropylsalicylate, which is a lipophilic complex with low molecular weight, has natural Cu, Zn-SOD-like activity, and has anti-inflammatory and antioxidant effects. Schiff base and metal chelate thereof formed by condensing salicylaldehyde and derivatives thereof with certain primary amine compounds have special activities of resisting cancer, inflammation, sterilization, oxidation and the like, and researches in the field have been reported in a large number, for example, in recent years, salicylidenedimine Schiff base rare earth samarium complexes such as Liujing, Zhengheptui and the like and salicylidenedimine Schiff base rare earth complexes such as Zhang-Ying and the like all have very good biological activities. The process for synthesizing the complex is complex and the preparation period is long.
Disclosure of Invention
The invention aims to provide a preparation method and application of a Schiff base complex containing rare earth element europium.
In order to achieve the purpose, the invention adopts the technical scheme that:
a Schiff base complex containing rare earth element europium has a molecular formula as follows: c19H25CuN5EuO16。
A method for preparing a Schiff base complex containing rare earth element europium,
the synthesis process of the complex is shown as the following formula (I):
Figure BDA0002069809310000011
(1) dissolving copper salt and metal salt of rare earth element europium in a mixed solvent under the stirring condition to obtain a solution 1; wherein the molar volume ratio of the copper salt, the metal salt of the rare earth element europium and the mixed solvent is 0.1-1mmol, 5-10ml
(2) Dissolving Schiff base ligand in a mixed solvent to obtain a solution 2, mixing the obtained solution 1 and the solution 2, stirring for 0.5-1h, and filtering to obtain a solution 3; wherein the molar volume ratio of the Schiff base ligand solution to the solvent is 0.1mmol:8-10 ml; the molar ratio of the copper salt to the Schiff base ligand compound is 1-10: 1; .
(3) And (3) constantly stirring the solution 3 at room temperature for 0.5-1.0 h, heating the filtered solution to 100 ℃ for 2-4h, continuously heating to 180 ℃ and 200 ℃ for 4-6h, then continuously and gradually heating to 200 ℃ and 240 ℃ for 12-16h, then cooling to 120 ℃ and keeping for 4-6h, and finally cooling to room temperature to obtain the light blue blocky crystal rare earth Schiff base complex.
The copper salt is copper acetate monohydrate, copper nitrate, copper chloride, copper bromide or copper perchlorate; the rare earth element metal europium is europium nitrate hexahydrate; the mixed solvent in the step (1) and the step (2) can be the same or different and is selected from two or more of methanol, acetonitrile, ethanol and dichloromethane.
The mixed solvent in the step (1) and the step (2) can be the same or different and is selected from two mixed solvents of methanol, acetonitrile, ethanol and dichloromethane.
The mixed solvent in the step (1) and the step (2) can be the same or different and is selected from (1-4): 1 of methanol and acetonitrile; the volume ratio is (1-3): 1 acetonitrile and dichloromethane; or, the volume ratio is 1: (1-3) methanol and water.
The Schiff base ligand compound is obtained by dissolving 5-methoxysalicylaldehyde and 1, 3-propanediamine in a mixed solvent for aldol condensation reaction; wherein the molar volume ratio of the 5-methoxysalicylaldehyde to the 1, 3-propanediamine to the mixed solvent is 1mmol: 1mmol: (5-10) mL. The mixed solvent is identical to steps 1 and 2.
The molar volume ratio of the 5-methoxysalicylaldehyde to the 1, 3-propanediamine to the mixed solvent is 1mmol: 1mmol: 10 mL.
The application of Schiff base complex containing rare earth element europium as a mimic of the activity center of superoxide dismutase is disclosed.
The invention has the advantages that:
the Schiff base complex is obtained by combining Schiff base ligands containing biological activity, Cu-SOD with natural activity and rare earth elements. Compared with the traditional preparation method for preparing the complex, the preparation method has the advantages of relatively simple preparation process, short preparation period and high yield. In SOD activity (inhibition rate) tests, the Schiff base complex activity is obviously enhanced compared with that before coordination, and a practical basis is provided for designing and synthesizing rare earth Schiff base complexes in the future and simulating the biological activity of SOD samples.
The rare earth Schiff base complex has the advantages of good crystal form stability, relatively simple preparation method and post-treatment mode, obvious simulated SOD sample activity and the like.
Drawings
FIG. 1 is a crystal structure diagram of a rare earth Schiff base complex 3 according to the present invention.
FIG. 2 is a crystal stacking diagram of rare earth Schiff base complex 3 according to the present invention.
FIG. 3 is a graph showing inhibition rate-concentration of Schiff base ligand of SOD model compound according to the present invention.
FIG. 4 is a graph of the inhibition rate-concentration of the rare earth Schiff base complex as a SOD model complex in accordance with the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Under the condition of constant stirring, dissolving copper salt and rare earth metal europium in a mixed solvent to obtain a solution 1; dissolving a Schiff base ligand compound in a mixed solvent, adding the solution 1 into the solution 2, constantly stirring for 0.5-1.0 h, and filtering to obtain a solution 3; and then placing the solution 3 in a high-pressure reaction kettle, and obtaining the rare earth Schiff base complex of light blue blocky crystals after temperature rise and temperature drop are controlled by programs. The rare earth Schiff base complex has good crystal form stability, and the preparation method and the post-treatment mode are relatively simple. In the test of the activity (inhibition rate) of the superoxide dismutase, the activity of the Schiff base complex is obviously enhanced compared with that before coordination, and a practical basis is provided for designing and synthesizing the rare earth Schiff base complex later and simulating the biological activity of the superoxide dismutase.
Example 1
Methanol and acetonitrile are mixed according to a volume ratio of 2: 1, mixing to obtain a mixed solvent 1;
acetonitrile and dichloromethane are mixed according to the volume ratio of 1: 1 to obtain a mixed solvent 2.
Methanol and water are mixed according to the volume ratio of 1: 1 to obtain a mixed solvent 3.
Example 2
Dissolving 1mmol of 5-methoxysalicylaldehyde and 1mmol of 1, 3-propanediamine in 4mL of mixed solvent 1, and carrying out aldol condensation reaction at room temperature to obtain Schiff base ligand compound 1.
Example 3
Dissolving 1mmol of 5-methoxysalicylaldehyde and 1mmol of 1, 3-propanediamine in 5mL of mixed solvent 2, and carrying out aldol condensation reaction at room temperature to obtain Schiff base ligand compound 2.
Example 4
Dissolving 1mmol of 5-methoxysalicylaldehyde and 1mmol of 1, 3-propanediamine in 10mL of mixed solvent 3, and carrying out aldol condensation reaction at room temperature to obtain Schiff base ligand compound 3.
Example 5
Preparation of Complex 1 by obtaining various solutions and complexes as described in the above examples:
(1) under the stirring state, 199.6mg of copper acetate monohydrate and 446mg of europium nitrate hexahydrate are dissolved in 4mL of mixed solvent 1 to obtain solution 1;
(2) 342.4mg of Schiff base ligand compound 1 is dissolved in 3mL of mixed solvent 1 to obtain solution 2, the solution 1 obtained in the step (1) is added into the solution 2, the stirring is carried out for about 0.5 to 1 hour, and the solution 3 is obtained after the filtration;
(3) and (3) continuously stirring the solution 3 obtained in the step (2) at room temperature for 0.5h, then placing the solution in a high-pressure reaction kettle, raising the temperature to 120 ℃ by program control, keeping the temperature for 4h, continuing raising the temperature to 180 ℃ and keeping the temperature for 14-16 h, then gradually cooling, keeping the temperature for 4h after cooling to 120 ℃, and finally cooling to room temperature. Obtaining a light blue powdery Schiff base complex 1; the obtained light blue massive crystal rare earth Schiff base complex 1 is filtered, the crystal is washed for 3 times by a small amount of mixed solvent 1, and then is dried in vacuum, and the calculated yield is 36.4%.
Example 6
Preparation of Complex 2 by obtaining various solutions and complexes as described in the above examples:
(1) under the stirring state, 199.6mg of copper acetate monohydrate and 446mg of europium nitrate hexahydrate are dissolved in 5mL of mixed solvent 2 to obtain solution 1;
(2) 342.4mg of Schiff base ligand compound 1 is dissolved in 6mL of mixed solvent 1 to obtain solution 2, the solution 1 obtained in the step (1) is added into the solution 2, the stirring is carried out for about 0.5 to 1 hour, and the solution 3 is obtained after the filtration;
(3) continuously stirring the solution 3 obtained in the step (2) at room temperature for 1.0h, then placing the solution in a high-pressure reaction kettle, raising the temperature to 80 ℃ by program control, keeping the temperature for 1h, continuing to raise the temperature to 120 ℃ for 6-8 h, gradually raising the temperature to 180 ℃ for 10-12h, then slowly lowering the temperature to 120 ℃ for 4-6h, lowering the temperature to 80 ℃ for 1h, and finally lowering the temperature to room temperature. Obtaining a needle crystal rare earth Schiff base complex 2; the obtained light blue massive crystal rare earth Schiff base complex 2 was filtered, and the crystal was washed with a small amount of mixed solvent 1 for 3 times and then vacuum-dried, with a calculated yield of 39.2%. Explanation: the mixed solution used in the washing needs to be the same as that in example 1.
Example 7
Preparation of Complex 3 by obtaining various solutions and complexes as described in the above examples:
(1) under the stirring state, 199.6mg of copper acetate monohydrate and 446mg of europium nitrate hexahydrate are dissolved in 5mL of mixed solvent 3 to obtain solution 1;
(2) 342.4mg of Schiff base ligand compound 3 is dissolved in 10mL of mixed solvent 3 to obtain solution 2, the solution 1 obtained in the step (1) is added into the solution 2, the stirring is carried out for about 0.5 to 1 hour, and the solution 3 is obtained after the filtration;
(3) and (3) continuously stirring the solution 3 obtained in the step (2) at room temperature for 0.8h, then placing the solution in a high-pressure reaction kettle, raising the temperature to 100 ℃ by program control, keeping the temperature for 2h, continuing raising the temperature to 180 ℃ for 4h, raising the temperature to 200 ℃ for 12-16h, then slowly reducing the temperature to 120 ℃, and finally reducing the temperature to room temperature. Obtaining the light blue blocky crystal rare earth Schiff base complex. Obtaining a light blue blocky crystal rare earth Schiff base complex 3 (see figures 1 and 2 and tables 1 and 2); the obtained light blue massive crystal rare earth Schiff base complex 3 was filtered, and the crystal was washed with a small amount of mixed solvent 3 for 3 times and then vacuum-dried, and the calculated yield was 43.8%.
Elemental analysis was performed on the obtained rare earth Schiff base complex 3, and the result was: c19H25CuN5EuO16(calcd) C, 28.93; h, 3.32; n, 8.89%; (test value) C, 28.92; h, 3.35; and N, 8.91. Infrared characterization: IR (KBr, cm)-1)：νOH(3404)，νC＝N(1542)，νC-O(1309)。
The single crystal structure of the rare earth Schiff base complex 3 is tested by using a Bruker SMART 1000CCD surface-detecting diffractometer with the wavelength of
Figure BDA0002069809310000054
MoK α rays, ω scan mode. The collected diffraction points were subjected to data reduction using the SAINT program, and data correction was performed using the SADABS program. Based on the method of full-angle least squares, the coordinates of all non-hydrogen atoms are found out on a difference Fourier map by using a SHELXTL 5.1 program package through a direct method, and then all the non-hydrogen atoms are refined in an anisotropic mode. The crystallographic data of the rare earth Schiff base complex 3 are shown in the following table 1, and the partial bond lengths and bond angles are shown in the following table 2:
TABLE 1 rare earth Schiff Complex 3 crystallography data
Figure BDA0002069809310000051
R1＝∑||Fo|-|Fc||/∑|Fo|，wR2＝[∑w(Fo 2-Fc 2)2/∑w(Fo 2)2]1/2.
TABLE 2 partial bond length of rare earth Schiff base complex 3
Figure BDA0002069809310000052
And key angle (°) data
Figure BDA0002069809310000053
Figure BDA0002069809310000061
Application example
The light blue bulk crystalline rare earth Schiff base complex 3 obtained in example 7 and the Schiff base ligand compound were subjected to a simulated SOD activity test.
The experimental principle is as follows: nitrogen Blue Tetrazolium (NBT) illumination method
Method for measuring SOD-like activity (inhibition ratio): the experiment used an improved riboflavin photoreduction NBT method to detect the SOD-like activity of the simulant. Under illumination with riboflavin (VB)2) With tetramethylethylenediamine to give O2-.，O2-Can reduce NBT into blue-violet compound formazan; and SOD or mimetics compete with NBT for O2-Thereby inhibiting the rate of reduction of NBT to a blue-violet compound. The simple reaction is as follows:
VB2+(CH3)2N(CH2)2N(CH3)2→O2-.a detection system: o is2-..+ NBT → formazan (F) (blue-violet) competitive system: o is2-+ SOD or simulant → product (P) formazan has maximum light absorption at 560nm, and absorbance A560Is in direct proportion to the concentration of the formazan. So that the absorbance A at different times is detected by tracking560Plotting the time t to obtain the timeThe line and the slope of the straight line reflect the speed of the generation speed of the formazan. In the presence of SOD or a mimic, the rate of generation of formazan is reduced, and therefore the slope of the straight line is reduced. The analog or SOD to O can be obtained according to the formula2-Inhibition ratio (ln h):
lnh＝(1-k′/k)×100％
wherein: k' is the slope of the line after addition of the mimic or SOD; k is the slope of the straight line in the absence of the mimetic or SOD (blank reaction solution). A higher inhibition indicates a higher mimetic SOD activity.
The experimental method comprises the following steps: the mixture was dissolved in 0.05mol/L phosphoric acid buffer solution at pH 7.8 to give a solution containing 6.8X 10-6mol/L riboflavin, and then mixing with 1.0X 10-4mol/L tetramethylethylenediamine, 0.01mol/L methionine, 9.32X 10-5mixing mol/L NBT (nitrotetrazolium chloride blue) and 0.1mmol/L complex, irradiating with fluorescent light, measuring absorbance at 560nm wavelength every half minute at room temperature for 6 times, and calculating the average value.
The experimental results are as follows: by plotting the absorbance at different times against time by tracking, a straight line can be obtained, and from this, the slope k of the straight line can be obtained, and then the inhibition ratio of the complex can be obtained by applying the formula lnh ═ 1-k'/k) × 100%. Inhibition was plotted against Schiff base ligand and Schiff base complex concentrations (fig. 3-4).
From fig. 3 and 4, it can be seen that the inhibition rate of the Schiff base complex is greatly improved compared with that of the ligand. At the same time, the concentration of SOD enzyme and its mimic compound required at lnh ═ 50% is nowadays taken as an active unit, i.e. the IC of the complex50The value is obtained. The IC of each complex can be obtained by plotting the inhibition rate against the concentration50Value, pI50＝-lgIC50. As shown in table 3 below.
TABLE 3 IC of Schiff base ligand with rare earth Schiff base complexes50And pI50Value of
Figure BDA0002069809310000071
As can be seen from the results of activity measurement, the synthesized ligands and complexes have certain activities as a whole, and they are called mimics of the activity center of superoxide dismutase. The rare earth complex synthesized by the invention is similar to the activity center of natural superoxide dismutase, the activity of the rare earth Schiff base complex is higher than that of a Schiff base ligand, and probably the rare earth element participates in coordination to be the main reason of improving the activity, which is also related to the self property of the ligand and the degree of the complex simulating the microenvironment of a natural enzyme structure.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.

Claims (7)

1. A preparation method of a Schiff base complex containing rare earth element europium is characterized in that the molecular formula of the complex is as follows: c19H25CuN5EuO16·H2O；
The preparation method of the complex comprises the following steps of,
the synthesis process of the complex is shown as the following formula (I):
Figure FDA0003080301230000011
(1) dissolving copper salt and metal salt of rare earth element europium in a mixed solvent under the stirring condition to obtain a solution 1; wherein the molar volume ratio of the copper salt, the metal salt of the rare earth element europium and the mixed solvent is 0.1-1mmol, 5-10ml
(2) Dissolving Schiff base ligand in a mixed solvent to obtain a solution 2, mixing the obtained solution 1 and the solution 2, stirring for 0.5-1h, and filtering to obtain a solution 3; wherein the molar volume ratio of the Schiff base ligand solution to the solvent is 0.1mmol:8-10 ml; the molar ratio of the copper salt to the Schiff base ligand compound is 1-10: 1; .
(3) And (3) constantly stirring the solution 3 at room temperature for 0.5-1.0 h, heating the filtered solution to 100 ℃ for 2-4h, continuously heating to 180 ℃ and 200 ℃ for 4-6h, then continuously and gradually heating to 200 ℃ and 240 ℃ for 12-16h, then cooling to 120 ℃ and keeping for 4-6h, and finally cooling to room temperature to obtain the light blue blocky crystal rare earth Schiff base complex.
2. The process for preparing a Schiff base complex containing europium as a rare earth element according to claim 1,
the copper salt is copper acetate monohydrate, copper nitrate, copper chloride, copper bromide or copper perchlorate; the rare earth element metal europium is europium nitrate hexahydrate; the mixed solvent in the step (1) and the step (2) can be the same or different and is selected from two or more of methanol, acetonitrile, ethanol and dichloromethane.
3. The process for preparing a Schiff base complex containing europium as a rare earth element according to claim 2,
the mixed solvent in the step (1) and the step (2) can be the same or different and is selected from two mixed solvents of methanol, acetonitrile, ethanol and dichloromethane.
4. A process for preparing a Schiff base complex containing europium as a rare earth element according to claim 3,
the mixed solvent in the step (1) and the step (2) can be the same or different and is selected from (1-4): 1 of methanol and acetonitrile; the volume ratio is (1-3): 1 acetonitrile and dichloromethane; or, the volume ratio is 1: (1-3) methanol and water.
5. The process for preparing a Schiff base complex containing europium as a rare earth element according to claim 1,
the Schiff base ligand compound is obtained by dissolving 5-methoxysalicylaldehyde and 1, 3-propanediamine in a mixed solvent for aldol condensation reaction; wherein the molar volume ratio of the 5-methoxysalicylaldehyde to the 1, 3-propanediamine to the mixed solvent is 1mmol: 1mmol: (5-10) mL; explanation: the mixed solvent is identical to the steps (1) and (2).
6. The process of claim 5, wherein the Schiff base complex comprises europium as a rare earth element,
the molar volume ratio of the 5-methoxysalicylaldehyde to the 1, 3-propanediamine to the mixed solvent is 1mmol: 1mmol: 10 mL.
7. Use of a Schiff base complex containing europium as a rare earth element according to claim 1, wherein: the application of the complex in preparing a mimic of the activity center of superoxide dismutase.
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CN108218924A (en) * 2018-03-15 2018-06-29 陕西理工大学 A kind of Schiff base complex of ruthenium and preparation method and application

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Publication number Priority date Publication date Assignee Title
CN108218924A (en) * 2018-03-15 2018-06-29 陕西理工大学 A kind of Schiff base complex of ruthenium and preparation method and application

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{μ-6,6’-Dimethoxy-2,2’-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato}-trinitratocopper(II)europium(III);Jing-Chun Xing等;《Acta Crystallographica Section E》;20081231;第E64卷;第m1206和S1-S8页 *
Six new dinuclear Schiff base complexes of Cu(II)/Ln(III) system：Synthesis, characterization and magnetic studies;Tehseen Fatima等;《Journal of Molecular Structure》;20190219;第1184卷;第462-467页 *
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