CN110357810A - 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe and its preparation method and application - Google Patents
2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe and its preparation method and application Download PDFInfo
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- CN110357810A CN110357810A CN201910776870.0A CN201910776870A CN110357810A CN 110357810 A CN110357810 A CN 110357810A CN 201910776870 A CN201910776870 A CN 201910776870A CN 110357810 A CN110357810 A CN 110357810A
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- pyridinecarboxylic
- hypochlorous acid
- pyrene
- diazanyl
- fluorescence probe
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- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000000523 sample Substances 0.000 title claims abstract description 25
- 239000002262 Schiff base Substances 0.000 title claims abstract description 18
- 150000004753 Schiff bases Chemical class 0.000 title claims abstract description 15
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 title claims abstract description 14
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 24
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000001514 detection method Methods 0.000 claims abstract description 10
- QULAJXAYTLPVCP-UHFFFAOYSA-N hydrazine;pyridine-2-carboxylic acid Chemical compound NN.OC(=O)C1=CC=CC=N1 QULAJXAYTLPVCP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims 1
- 229910001753 sapphirine Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- -1 2- pyridinecarboxylic diazanyl Schiff base Chemical class 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000003139 buffering effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008557 oxygen metabolism Effects 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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"
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
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- Pyridine Compounds (AREA)
Abstract
The invention discloses a kind of 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probes and its preparation method and application.The present invention is raw material using 2- pyridinecarboxylic hydrazine, condensation reaction is carried out with 1- pyrene formaldehyde, 2- pyridinecarboxylic diazanyl Schiff base derivatives N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine is made, the compound at room temperature can be in specific manner by hypochlorous acid oxidization, and solution colour is converted into bright blue fluorescence by yellow-green fluorescence under 365nm ultraviolet light.The compound can be used as detection hypochlorous acid fluorescence probe, have a good application prospect.
Description
Technical field
The invention belongs to Minute Organic Synthesis technical fields, are related to 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe
And its preparation method and application.
Background technique
HOCI/CIO-As a kind of active oxygen (ROS) known to us, it has very strong chemical reactivity, is
The by-product of normal oxygen metabolism, plays important role in a variety of pathological processes in organism vital movement.Normally
The lower hypochlorous acid of level is to maintaining intracellular redox equilibrium important role, but more and more evidence shows
The diseases such as the content of hypochlorite and tissue damage, neuronal degeneration, cancer, cardiovascular disease and arthritis have weight in organism
It is related to.Therefore, develop a high sensitivity, it is highly selective, can specificity detection method come detect hypochlorous acid for study time
The relationship of chloric acid and related disease has very important significance.
In recent years, there are many study on the synthesis about small organic molecule fluorescence probe and detected for hypochlorous acid
Report, but they have the shortcomings that more or less, such as sensitivity is not high, poor selectivity.This greatly limits them
Application prospect and range.Therefore, the good novel C lO of high sensitivity, selectivity is developed-Ion fluorescence probe has important meaning
Justice.
Summary of the invention
For the deficiencies in the prior art, of the invention the technical problem to be solved is that provide a kind of 2- pyridine first
Hydrazide group Schiff bases hypochlorous acid fluorescence probe, the compound at room temperature can be in specific manner by hypochlorous acid oxidizations, and solution is by Huang
Green fluorescence is converted into bright blue fluorescence, which can be used as detection hypochlorous acid fluorescence probe.Of the invention to be solved
Another technical problem be to provide the preparation method of 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe a kind of.The present invention
Also technical problems to be solved be to provide the purposes of 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe a kind of.
In order to solve the above technical problems, the technical solution adopted by the present invention are as follows:
2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe, the fluorescence probe are N '-(pyrene -1- methylene) -2-
Pyridinecarboxylic hydrazine, structural formula are as follows:
The preparation method of the 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe: with acetic acid catalyst, 2-
Pyridinecarboxylic hydrazine is condensed with 1- pyrene formaldehyde, obtains N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine.
The preparation method of the 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe, which is characterized in that including
Following steps:
(1) by 0.10mol 2- pyridinecarboxylic hydrazine, 0.10~0.12mol 1- pyrene formaldehyde, 0.10~0.15mol acetic acid and
0.2~0.5L ethyl alcohol sequentially adds in the three-necked flask equipped with blender, thermometer and reflux condenser, heating reflux reaction 8
~12h is reacted using LC-MS tracing detection；
(2) after reaction, reaction solution is concentrated into 0.1~0.2L, be cooled to room temperature, flaxen N '-(pyrene-is precipitated
1- methylene) -2- pyridinecarboxylic hydrazine crude product；
(3) N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine crude product is recrystallized with 95% ethyl alcohol, obtains N ' -
(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine sterling.
Application of the 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe in detection hypochlorous acid.N′-
(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine at room temperature can be in specific manner by hypochlorous acid oxidization, the solution under 365nm ultraviolet light
Color is converted into bright blue fluorescence by yellow-green fluorescence.It can be used as the hypochlorous fluorescence probe of detection.
The utility model has the advantages that the present invention is 2- pyrrole made from raw material using 2- pyridinecarboxylic hydrazine compared with existing research achievement
Pyridine formohydrazide group Schiff bases compound；The compound at room temperature can be in specific manner by hypochlorous acid oxidization, in 365nm ultraviolet light
Lower solution colour is converted into bright blue fluorescence by yellow-green fluorescence, which can be used as detection hypochlorous acid fluorescence probe.
Detailed description of the invention
Fig. 1 is the fluorescence spectrum result figure of N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine and different analytes；Analyte
It include: S2-、HSO3 -、SO3 2-、CO3 2-、SO4 2-、HCO3 -、Cl-、PO4 3-、CH3COO-、F、N2H4、H2O2、NH3、Hg2+、Pb2+、Cd2+、
Ag+。
Fig. 2 is the fluorescence spectrum knot that N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine is acted on from the hypochlorous acid of different solubility
Fruit figure.
Specific embodiment
The present invention is described further combined with specific embodiments below.
Embodiment 1
2- pyridinecarboxylic diazanyl Schiff bases compound prepares reaction equation are as follows:
Concrete operations are as follows:
By 1.0mmol 2- pyridinecarboxylic hydrazine, 1.1mmol 1- pyrene formaldehyde, 1.3mmol acetic acid and 35mL ethyl alcohol, successively plus
Enter in the three-necked flask equipped with blender, thermometer and reflux condenser, heating reflux reaction 10h, with LC-MS tracing detection,
After reaction, reaction solution is concentrated into 10mL, be cooled to room temperature, flaxen N '-(pyrene -1- methylene) -2- pyridine is precipitated
Formylhydrazine crude product, then recrystallized with 95% ethyl alcohol, N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine sterling is obtained,
Yield is 84%.1H NMR (400MHz, DMSO-d6) δ: 8.82 (d, J=8Hz, 1H), 8.76 (d, J=4Hz, 1H), 8.63 (d,
J=8Hz, 1H), 8.31 (d, J=12Hz, 4H), 8.16-8.23 (m, 3H), 8.08 (t, J=8Hz, 2H), 7.68 (t, J=
8Hz, 1H)13C NMR (400MHz, DMSO-d6) δ: 160.23,149.50,148.46,147.74,138.02,131.94,
130.78,130.10,128.92,128.59,128.33,127.33,127.06,127.02,126.48,125.99,125.69,
125.16,124.48,124.07,123.72,122.67,122.39,40.13,39.92,39.71,39.50,39.30,
39.09,38.88.HRMS (m/z): [M+H]+calculated for C23H15N3O+H+, 350.1293；Found,
350.1302。
Embodiment 2
N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine is configured to 1 × 10-5The PBS/CH of M3CN (v/v=4/6) buffering
All kinds of metal ions and anion are equally dissolved in PBS/CH by solution3Be made into CN (v/v=4/6) buffer concentration be 1 ×
10-4The solution of M measures influence of the different analytes to the fluorescence emission spectrum of N '-(pyrene -1- methylene) pyridinecarboxylic hydrazine, such as
Shown in Fig. 1.The result shows that hypochlorous acid is added the fluorescence intensity of system is remarkably reinforced, and by the way that other chaff interferents are added, such as
S2-、HSO3 -、SO3 2-、CO3 2-、SO4 2-、HCO3 -、Cl-、PO4 3-、CH3COO-、F-、N2H4、H2O2、NH3、Hg2+、pb2+、Cd2+、Ag+
Thus equal paired observations, the fluorescence spectrum of solution illustrate, which can be used as specificity there is no apparent change occurs
Identify hypochlorous fluorescence probe.
Embodiment 3
N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine is configured to 1 × 10-5The PBS/CH of M3CN (v/v=4/6) buffering
Hypochlorous acid is dissolved in PBS/CH by solution3It is 0,5,10,15,20,25,30,35 that concentration is made into CN (v/v=4/6) buffer,
40,45,50 μM of solution determines fluorescence of the hypochlorous acid to N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine of various concentration
The influence of emission spectrum, as a result as shown in Figure 2.The result shows that in system hypochlorous acid concentration be continuously increased, compound
Fluorescence intensity enhances therewith.Thus illustrate, which can be used as sensitivity and detect hypochlorous fluorescence probe.
Claims (4)
1.2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe, which is characterized in that the fluorescence probe is that (pyrene -1- is sub- by N ' -
Methyl) -2- pyridinecarboxylic hydrazine, structural formula are as follows:
2. the preparation method of 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe described in claim 1, feature exist
In: with acetic acid catalyst, 2- pyridinecarboxylic hydrazine is condensed with 1- pyrene formaldehyde, obtains N '-(pyrene -1- methylene) -2- pyridine first
Hydrazides.
3. the preparation method of 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe according to claim 2, special
Sign is that specific preparation method includes:
(1) by 0.10mol 2- pyridinecarboxylic hydrazine, 0.10~0.12mol 1- pyrene formaldehyde, 0.10~0.15mol acetic acid and 0.2~
0.5L ethyl alcohol sequentially adds in the three-necked flask equipped with blender, thermometer and reflux condenser, 8~12h of heating reflux reaction,
It is reacted using LC-MS tracing detection；
(2) after reaction, reaction solution is concentrated into 0.1~0.2L, be cooled to room temperature, flaxen N '-is precipitated, and (pyrene -1- is sub-
Methyl) -2- pyridinecarboxylic hydrazine crude product；
(3) N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine crude product is recrystallized with 95% ethyl alcohol, obtains N '-(pyrene -
1- methylene) -2- pyridinecarboxylic hydrazine sterling.
4. 2- pyridinecarboxylic diazanyl Schiff bases hypochlorous acid fluorescence probe described in claim 1 answering in detection hypochlorous acid
With.N '-(pyrene -1- methylene) -2- pyridinecarboxylic hydrazine at room temperature can be in specific manner by hypochlorous acid oxidization, in 365nm ultraviolet light
The fluorescence color of lower solution is converted into sapphirine by yellow green.
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| CN113845516B (en) * | 2021-11-08 | 2022-05-31 | 齐鲁工业大学 | Hypochlorous acid fluorescent probe based on Schiff base and preparation method thereof |
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