CN114230583A - Binuclear copper complex with biological activity, preparation method and application - Google Patents
Binuclear copper complex with biological activity, preparation method and application Download PDFInfo
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- 150000004699 copper complex Chemical class 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 230000004071 biological effect Effects 0.000 title claims abstract description 8
- 239000013078 crystal Substances 0.000 claims abstract description 20
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 244000063299 Bacillus subtilis Species 0.000 claims abstract description 6
- 235000014469 Bacillus subtilis Nutrition 0.000 claims abstract description 6
- 241000588724 Escherichia coli Species 0.000 claims abstract description 6
- 241000191967 Staphylococcus aureus Species 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims description 7
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 abstract description 12
- 230000002401 inhibitory effect Effects 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 description 6
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 5
- -1 DPPH radicals Chemical class 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000002292 Radical scavenging effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229910001431 copper ion Inorganic materials 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- SZDVDUDLIIZMKX-UHFFFAOYSA-N copper;pyridine Chemical compound [Cu].C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 SZDVDUDLIIZMKX-UHFFFAOYSA-N 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention relates to the technical field of crystal materials, in particular to a binuclear copper complex with biological activity, a preparation method and application thereof. The molecular formula of the complex is Cu2(AcO)2(L)2Wherein L represents 2-amino-5-bromopyridine, AcO represents CH3COO-is provided. The complex disclosed by the invention has inhibitory activity on three tested strains, wherein the inhibitory activity on staphylococcus aureus and bacillus subtilis is particularly strong, and the inhibitory activity on escherichia coli is relatively weak. The complex has good activity of eliminating DPPH free radicals.
Description
Technical Field
The invention relates to the technical field of crystal materials, in particular to a binuclear copper complex with biological activity, a preparation method and application thereof.
Background
The complex formed by ligand and metal atom or ion through coordination bond is called metal complex, the metal complex is commonly used in coordination catalytic reaction, such as removing carbon monoxide by copper diammine acetate in ammonia synthesis industry, or the metal complex is used in asymmetric catalytic reaction for preparing medicine, etc. In biology, many biomolecules are also metal complexes, for example, sodium citrate is coordinated with heavy metal ions to be converted into coordination compounds with low toxicity, so that the aim of detoxification is fulfilled.
Copper is an important endogenous metal and is an essential trace element for the human body. Cu2+Easily react with organic matters containing coordination atoms such as N, O to generate mononuclear and polynuclear copper complexes with different structures.
Disclosure of Invention
The invention aims to provide a nitrogen heterocyclic ring binuclear copper complex with biological activity, and provides a preparation method and application of the complex.
In order to achieve the purpose, the technical scheme of the invention is as follows:
the binuclear copper complex with biological activity is characterized in that the molecular formula of the complex is Cu2(AcO)2(L)2Wherein L represents 2-amino-5-bromopyridine, AcO represents CH3COO-。
A binuclear copper complex crystal with biological activity, which is monoclinic system, P2(1)/c space group
Volume of
The preparation method of the complex comprises the steps of respectively dissolving copper acetate and 2-amino-5-bromopyridine in an organic solvent, wherein the mass ratio of the copper acetate to the 2-amino-5-bromopyridine is 1: 0.5-5, stirring and reacting at 40-80 ℃ for 0.5-5 h, cooling to room temperature, and filtering; adding chloroform into the filtrate, standing for 2-5 days to obtain blue-green blocky crystal, i.e. the target product Cu2(AcO)2(L)2And (3) single crystal.
Preferably, the organic solvent is selected from methanol, ethanol or ethyl acetate.
Preferably, the volume ratio of the total volume of the organic solvent solution of the copper acetate and the organic solvent solution of the 2-amino-5-bromopyridine to the chloroform is 20: 1-10.
Use of a complex or crystal according to any preceding claim in the preparation of an antibacterial or bactericidal medicament.
Preferably, the bacteria are selected from staphylococcus aureus, bacillus subtilis or escherichia coli.
Use of a complex or crystal as described in any preceding claim in the preparation of an antioxidant for inhibiting DPPH radicals.
Advantageous effects
We have synthesized an unreported binuclear copper pyridine complex with excellent antibacterial and DPPH free radical scavenging activities. The complex has inhibitory activity on three tested strains, wherein the inhibitory activity on staphylococcus aureus and bacillus subtilis is particularly strong, and the inhibitory activity on escherichia coli is relatively weak. The complex has good activity of eliminating DPPH free radicals.
Drawings
FIG. 1 is a crystal structure diagram of a target complex.
FIG. 2 is a unit cell stacking diagram of a target complex along the a-axis
FIG. 3 is an infrared spectrum of a target complex.
FIG. 4 is a graph showing the determination of the optimal reaction time for the target complex to scavenge DPPH radicals
FIG. 5 is a graph of concentration of DPPH radical scavenging versus clearance rate for a target complex
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to specific embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. The following description of at least one exemplary embodiment is merely illustrative in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1: binuclear copper complex Cu2(AcO)2(L)2Synthesis and single crystal preparation of
A100 mL round-bottom flask was charged with 0.1816g (1mmol) of anhydrous copper acetate and 12mL of methanol, and dissolved by stirring at 70 ℃. Then, adding 5mL of methanol solution of 0.348g (2mmol) of 2-amino-5-bromopyridine, reacting for 2h, cooling to room temperature, filtering, washing filter residue with methanol for 3 times, and drying;
putting the filtrate in a 50mL beaker, adding 3mL of trichloromethane, sealing with a preservative film, pricking holes on the preservative film symmetrically with a needle, placing in a cool and quiet place, obtaining blue-green blocky crystals after 3 days, filtering, washing with methanol to obtain the target binuclear copper complex Cu2(AcO)2(L)2The melting point is greater than 290 ℃. The yield was about 57%.
FIG. 3 shows the infrared spectrum (KBr/pellet, cm) of the target complex-1) The main infrared characteristic peaks are as follows: 3451m,2976w,1631s,1600s,1481w,1433m,1354m,1262w,1138m,1067m,955m,866m,828w,669m,624w,540w,526w (cm)-1)。3451cm-1The medium-strength broad peak is ascribed to amino group, 1600cm-1The strong absorption peak is ascribed to C ═ N on the pyridine ring, since N coordinates with copper (in the ligand, the absorption peak of C ═ N is located at 1624cm-1)；1631、1433cm-1Attribution is carboxylate radical; at 1480-471 cm-1In the range, absorption peaks of functional groups such as pyridine ring and acetate are shown.
Selecting a block of the above size of about 0.18mm by 0.16mm by 0.14mmThe obtained binuclear copper complex Cu2(AcO)2(L)2Single crystals were placed on a BRUKER SMART 1000CCD diffractometer and monochromated Mo-K with graphiteα(λ 0.71073nm) at 2.031 °<θ<In the range of 27.482 ℃ in an omega-2 theta scan at 296(2) K. All intensity data reduction was performed on the Bruker SAINT program. With LpFactor correction data, crystal structure is solved by direct method by adopting SHELESS 97 software, theoretical hydrogenation is carried out, and coordinates and anisotropic thermal parameters of all non-hydrogen atoms are corrected and converged by a full matrix least square method. Detailed crystallographic data are shown in table 1.
TABLE 1 Complex Cu2(AcO)2(L)2Crystallographic data of
Binuclear copper complex Cu2(AcO)2(L)2Is monoclinic system, P2(1)/c space group. The single crystal X-ray diffraction analysis result shows that the complex contains 2 penta-coordinated Cu2+Each of Cu2+Respectively coordinated with 1N atom on pyridine ring from 2-amino-5-bromopyridine and 4O atoms on acetate radical from 2 molecules to form a geometrical configuration of a square cone; 2 oxygen atoms of each acetate ion are respectively coordinated with 2 copper ions, and the 2 copper ions are bridged by 4 acetate ions to form a binuclear copper structure. The ORTEP diagram and atomic number are shown in figure 1, and the unit cell stacking diagram is shown in figure 2.
Example 2 binuclear copper Complex Cu2(AcO)2(L)2Efficiency of DPPH radical scavenging
Determination of the reaction time for scavenging DPPH free radicals:
adding 10mL of 0.3mM DPPH methanol solution into a 25mL plugged brown colorimetric tube, adding 10mL of 1mg/mL of methanol solution of the binuclear copper complex, shaking uniformly, placing in a water bath kettle at 37 ℃, reacting for a certain time (5, 30, 40, 50, 60, 70 and 80min) in a dark place, sampling, taking methanol as a reference, and immediately measuring the absorbance A value at 516nm by using an ultraviolet spectrophotometer. The clearance rate of the binuclear copper complex to DPPH & is calculated according to the following formula:
DPPH clearance/% ([ 1- (Ai-Aj) ] × 100%/a 0)
Wherein: a0 is the absorbance of the blank; ai is absorbance of the sample solution; aj is sample fluid background absorption.
The results of the experiment are shown in FIG. 4. As can be seen from the figure, the binuclear copper complex of the present invention has excellent scavenging effect on DPPH free radicals; and along with the extension of the reaction time, the clearance rate is rapidly increased, the clearance rate reaches 72% at 30min, the clearance rate reaches the maximum (93%) at 60min, and the clearance rate is basically unchanged after the reaction time is prolonged, which indicates that the optimal reaction time for the complex to eliminate DPPH free radicals is 60 min.
The relation curve of the concentration of the complex and the DPPH free radical clearance rate is as follows:
6 10mL of plugged brown colorimetric tubes were taken, 2mL of 0.3mM DPPH-methanol solution and 2mL of binuclear copper complex methanol solutions with different concentrations (0.05, 0.1, 0.2, 0.5, 0.8 and 1mg/mL) were added, and then 1mL of methanol was added to the volume of 5 mL. Shaking, placing in 37 deg.C water bath, and reacting in dark for 60 min. Sampling, taking methanol as reference, and immediately measuring the absorbance A value at 516nm by using an ultraviolet spectrophotometer. The clearance of DPPH was calculated as above.
The results of the experiment are shown in FIG. 5. As can be seen from the figure, the clearance rate of the binuclear copper complex to DPPH free radicals is increased along with the increase of the concentration of the complex, the concentration is in the range of 0.05-1 mg/ml, the clearance rate of the complex to DPPH free radicals is in a good linear relation, and the regression equation is that y is 0.7303x +0.1252, R is2＝0.9968。
Example 3 evaluation of antibacterial Activity of binuclear copper Complex
The bacteriostatic test procedures and methods of the reference (Xu R.B., J.chem.Crystallogr.2012,42(9):928-932) determine the inhibitory effect of the binuclear copper complex on three tested bacteria, namely escherichia coli, staphylococcus aureus and bacillus subtilis. Taking 34g of nutrient agar, adding 1L of distilled water, dissolving, placing in an autoclave, and sterilizing at 120 deg.C for 30 min. Cooling to 50-60 ℃ to prepare a flat plate. 0.1mL of activated bacterium solution is uniformly coated on a flat plate, and 5 Oxford cups are uniformly and vertically placed at equal intervals. Adding 0.1mL of binuclear copper complex solution into an oxford cup, covering a plate, and culturing in a biochemical incubator at 37 ℃ for 24 hours. After removal, the diameter (mm) of the zone of transparent inhibition produced around each oxford cup was measured. The results are shown in Table 2.
TABLE 2 antibacterial test results of binuclear copper complex
As can be seen from table 2, the binuclear copper complex showed inhibitory effects on three strains tested, among which: the activity to staphylococcus aureus and bacillus subtilis is particularly excellent, and the inhibition effect to escherichia coli is general; the inhibitory activity against the three bacteria was also enhanced with increasing concentration of the complex.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention.
Claims (8)
1. The binuclear copper complex with biological activity is characterized in that the molecular formula of the complex is Cu2(AcO)2(L)2Wherein L represents 2-amino-5-bromopyridine, AcO represents CH3COO-。
2. The crystal of the complex of claim 1, wherein the crystal isThe crystal is monoclinic system, P2(1)/c space group
Volume of
3. The preparation method of the crystal according to claim 2, characterized in that copper acetate and 2-amino-5-bromopyridine are respectively dissolved in an organic solvent, the mass ratio of the copper acetate to the 2-amino-5-bromopyridine is 1: 0.5-5, the mixture is stirred and reacted for 0.5-5 h at the temperature of 40-80 ℃, cooled to room temperature and filtered; adding chloroform into the filtrate, standing for 2-5 days to obtain blue-green blocky crystal, i.e. the target product Cu2(AcO)2(L)2And (3) single crystal.
4. The method according to claim 3, wherein the organic solvent is selected from methanol, ethanol, and ethyl acetate.
5. The preparation method according to claim 3, wherein the volume ratio of the total volume of the organic solvent solution of copper acetate and the organic solvent solution of 2-amino-5-bromopyridine to chloroform is 20: 1-10.
6. Use of the complex according to claim 1 or the crystal according to claim 2 for the preparation of an antibacterial or bactericidal medicament.
7. Use according to claim 6, wherein the bacteria are selected from Staphylococcus aureus, Bacillus subtilis or Escherichia coli.
8. Use of the complex of claim 1 or the crystal of claim 2 for the preparation of an antioxidant that inhibits DPPH radicals.
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