CN112010879B - Zn functional complex and preparation method and application thereof - Google Patents
Zn functional complex and preparation method and application thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000010668 complexation reaction Methods 0.000 title description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims abstract description 34
- 239000011701 zinc Substances 0.000 claims abstract description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229960004441 tyrosine Drugs 0.000 claims abstract description 18
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims abstract description 15
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZCIFWRHIEBXBOY-UHFFFAOYSA-N 6-aminonicotinic acid Chemical compound NC1=CC=C(C(O)=O)C=N1 ZCIFWRHIEBXBOY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012153 distilled water Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011259 mixed solution Substances 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims abstract description 4
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 238000001514 detection method Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000010413 mother solution Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- 238000002447 crystallographic data Methods 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- -1 hydrogen ions Chemical class 0.000 abstract description 5
- 238000001914 filtration Methods 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000001917 fluorescence detection Methods 0.000 description 7
- 239000003446 ligand Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 102000003425 Tyrosinase Human genes 0.000 description 1
- 108060008724 Tyrosinase Proteins 0.000 description 1
- 229910007379 Zn3N2 Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000009088 enzymatic function Effects 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002361 ketogenic effect Effects 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000001144 powder X-ray diffraction data Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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"
- 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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Abstract
The invention provides a two-dimensional Zn functional complex and a preparation method thereofMethods and uses. The molecular formula of the complex is as follows: [ Zn ]3(L‑)2(HBTC2‑)2]n, wherein L‑6-aminonicotinic acid, HBTC, for dehydrogenation2‑For removing two hydrogen ions of trimesic acid. The preparation method of the complex comprises the following steps: dissolving zinc nitrate hexahydrate, 6-aminonicotinic acid and trimesic acid in a mixed solution of distilled water and acetonitrile in a volume ratio of 1-3: 2-4 according to a molar ratio of 2-4: 3-5: 1-3; and (3) placing the mixture in an oven at the temperature of 130-150 ℃ for reacting for 65-80 hours, naturally cooling, and filtering to obtain a white crystalline solid. The preparation method of the complex is simple. The complex has an obvious characteristic peak between emission wavelengths of 340-360, has high fluorescence intensity, and can be used for detecting L-tyrosine.
Description
Technical Field
The invention relates to a preparation method of a Zn functional complex and application of the complex in L-tyrosine fluorescence detection.
Background
Amino acids are basic substances constituting proteins required for human and animal nutrition, and are organic compounds containing basic amino groups and acidic carboxyl groups. Wherein Tyrosine (Tyr) is an aromatic alpha-amino acid containing phenolic hydroxyl, is an essential amino acid for human body and is a ketogenic amino acid; it is a catalytic substrate of tyrosinase monophenol enzyme function, and is a main raw material for finally forming superior melanin and pheomelanin, so that tyrosine can help leucoderma patients to relieve symptoms, and can also treat poliomyelitis, sexual nuclear encephalitis, hyperthyroidism and other symptoms. Therefore, the detection and analysis of tyrosine have been the hot spots of research in the fields of feed, food, medicine, agriculture and environmental monitoring.
The functional complex is an organic-inorganic hybrid material formed by an organic ligand and metal ions or metal clusters through coordination bonds. Due to the unique porous structure and the various coordination modes, the material has wide attention in the application of energy, catalysis, adsorption, energy storage and other fields.
Disclosure of Invention
Based on the background, the invention aims to provide a Zn functional complex, a preparation method thereof and application of the complex in L-tyrosine fluorescence detection.
The invention provides a Zn functional complex, which has the chemical formula as follows: [ Zn ]3(L-)2(HBTC2-)2]n, wherein L-6-aminonicotinic acid, HBTC, for dehydrogenation2-Trimesic acid ions for removing two hydrogens; the structural formula is as follows:
the invention provides a preparation method of a Zn functional complex, which comprises the following steps:
dissolving zinc nitrate hexahydrate, 6-aminonicotinic acid and trimesic acid in a mixed solution of distilled water and acetonitrile in a volume ratio of 1-3: 2-4 according to a molar ratio of 2-4: 3-5: 1-3; and (3) placing the mixture in an oven at 130-150 ℃ for reacting for 65-80 hours, naturally cooling and filtering to obtain white crystalline solid, namely the target product.
The molar ratio of the zinc nitrate hexahydrate, the 6-amino nicotinic acid and the trimesic acid is preferably 3:4: 2.
The volume ratio of the distilled water to the acetonitrile is preferably 2: 3.
The Zn functional complex can be applied to the fluorescence detection of L-tyrosine.
A fluorescence detection method of Zn functional complex to L-tyrosine comprises the following steps:
uniformly dispersing the Zn functional complex in a methanol solution to obtain a stable turbid liquid, putting 1.8-2.2 ml of the stable turbid liquid in a cuvette, and putting the cuvette in a fluorescence spectrophotometer to detect the L-tyrosine.
Compared with the prior art, the invention has the beneficial effects that: the functional complex [ Zn ] is prepared for the first time3(L-) 2(HBTC2-) 2]n, carrying out structural characterization on the protein simultaneously, and applying the protein to the detection of the L-tyrosine. The complex is simple in preparation method, rapid, visual and reliable in detection of L-tyrosine, has an obvious characteristic peak with an emission wavelength of 340-360 nm, and is high in fluorescence intensity and good in detection effect.
Drawings
FIG. 1 is a diagram showing a coordination structure of a Zn functional complex.
FIG. 2 is a graph of powder X-ray diffraction pattern of a Zn functional complex compared to single crystal simulation data.
FIG. 3 is a fluorescence diagram of a fluorescence detection solution for Zn functional complex for detecting L-tyrosine.
Detailed Description
Example 1: zn functional complex [ Zn)3(L-)2(HBTC2-)2]nSynthesis and characterization of
[Zn3(L-)2(HBTC2-)2]And n is synthesized:
dissolving 22.31mg of zinc nitrate hexahydrate, 13.81mg of 6-aminonicotinic acid and 10.51mg of trimesic acid in a mixed solution of 2mL of distilled water and 3mL of acetonitrile, placing the mixed solution in a polytetrafluoroethylene bottle, plugging the polytetrafluoroethylene bottle into a reaction kettle, placing the reaction kettle in an oven at 140 ℃ for reacting for 65 hours, and naturally cooling to obtain a white crystalline solid, namely the Zn functional complex.
Characterization of the properties of the Zn functional complex:
(1) measurement of Single Crystal Structure
The crystal structure is determined by Supernova X-ray single crystal diffractometer and Mo Kalpha ray monochromatized by graphite
Is a source of incident radiation, in
Diffraction points are collected in a scanning mode, unit cell parameters are obtained through least square method correction, a crystal structure is obtained through direct solution of a difference Fourier electron density diagram by using a SHELXL-97 method, and Lorentz and polarization effect correction are carried out. All H atoms were synthesized by difference Fourier and determined by ideal position calculations. The crystal determination data are shown in table 1.
TABLE 1[ Zn ]3(L-)2(HBTC2-)2]nCrystallographic data of
FIG. 1 is a diagram showing the coordination structure of the functional complex. The compound contains three Zn (II) ions and two L ions in the molecule-(dehydro-6-aminonicotinic acid) and two HBTC2-(trimesic acid ion with both hydrogens removed). Wherein Zn1 and Zn3 have the same coordination mode and are both four-coordination structures, and 3O atoms in the coordination atoms are respectively from two different HBTC2-Ions and an L-Ions; the ligand N originates from another L-Ions. Zn2 is a hexa-coordinated structure with 6O coordinated atoms from four different HBTC2-Ions and two different Ls-Ions. Form a { Zn3N2O10The nodes passing through the ligand L along the a-axis direction-And b-axis direction passes through ligand HBTC2-Extending to form a three-dimensional net structure. Four L in FIG. 1-Ligand and four HBTC2-The ligands are all shared with other building blocks.
(2) Powder X-ray diffraction measurement
Powder X-ray diffraction data were collected on a Rigaku D/Max-2500 diffractometer at an operating voltage of 40kV and a current of 100mA, using graphite monochromated copper target X-rays as the source of incident radiation during the test. Density data collection continuous scans were performed in the range of 5 to 50 using a 2 θ/deg. scan pattern, with a scan speed of 3 of 8/sec and a span of 0.02/pass. Experimental data fitting the program Cerius2 was used and the software Mercury 3.9 was used for powder X-ray diffraction spectrum simulation transformation of single crystal structures. FIG. 2 is a powder X-ray diffraction pattern of the Cu functional complex compared to a simulated single crystal data.
EXAMPLE 2 detection of L-tyrosine by Zn functional complexes
1mg of the Zn functional complex prepared in example 1 was weighed and added to 20mL of methanol solution under ultrasonic conditions to obtain a white suspension. And (3) taking 2ml of the suspension in a clean cuvette, measuring the fluorescence intensity once every 2min at the excitation wavelength of 265nm, and obtaining a fluorescence detection solution when the fluorescence intensity is stable. This fluorescence detection solution was used as a mother solution, 10. mu.L of 1 mmol/L-tyrosine was added thereto, and the fluorescence intensity was detected. Has a distinct characteristic peak between the emission wavelengths of 350nm and high fluorescence intensity. The functional complex has good response to L-tyrosine, and is shown in figure 3.
Claims (6)
1. A Zn functional complex characterized by the chemical formula: [ Zn ]3(L-)2(HBTC2-)2]n, wherein L-6-aminonicotinic acid, HBTC, for dehydrogenation2-Trimesic acid ions for removing two hydrogens;
crystallographic data of the complex: crystal system: monoclinic; space group:P-1; unit cell parameters: a = 7.9473(9) A, b = 9.4439(11) A, c = 11.2652(14) A,α = 94.781(4)°，b = 96.496(4)°，γ = 107.421(4)°。
2. a method of preparing a Zn functional complex according to claim 1, comprising the steps of:
dissolving zinc nitrate hexahydrate, 6-aminonicotinic acid and trimesic acid in a mixed solution of distilled water and acetonitrile in a volume ratio of 1-3: 2-4 according to a molar ratio of 2-4: 3-5: 1-3; and (3) placing the mixture in an oven at 130-150 ℃ for reacting for 65-80 hours, and naturally cooling to obtain white crystalline solid, namely the target product.
3. A method of preparing a functional complex of Zn as claimed in claim 2, wherein the molar ratio of zinc nitrate hexahydrate, 6-aminonicotinic acid and trimesic acid is 3:4: 2.
4. The method of claim 2, wherein the volume ratio of distilled water to acetonitrile is 2: 3.
5. Use of a Zn functional complex as claimed in claim 1 in the preparation of a reagent for the detection of L-tyrosine.
6. A method for detecting L-tyrosine, comprising the steps of: uniformly dispersing the Zn functional complex of claim 1 in a methanol solution to obtain a test mother solution, placing 1.8-2.2 mL of the test mother solution in a cuvette, adding an L-tyrosine solution, uniformly mixing, measuring the fluorescence intensity, and having an obvious enhancement characteristic peak at an emission wavelength of 350 nm.
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