CN110759833B - Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide - Google Patents
Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide Download PDFInfo
- Publication number
- CN110759833B CN110759833B CN201911029928.1A CN201911029928A CN110759833B CN 110759833 B CN110759833 B CN 110759833B CN 201911029928 A CN201911029928 A CN 201911029928A CN 110759833 B CN110759833 B CN 110759833B
- Authority
- CN
- China
- Prior art keywords
- hydroxy
- benzylidene
- benzyl
- hydrazide
- zinc ions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
-
- 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
-
- 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"
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The invention discloses a preparation method and application of 4-hydroxy-benzyl (2 '-hydroxy-benzylidene) -hydrazide, wherein the structural formula of the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide is as follows:
4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide which is a fluorescence enhanced zinc ion fluorescent probe and can be used for detecting zinc ions in bamboo shoots and the like and realizing the quantitative detection of the zinc ions; 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide + Zn2+Fluorescent system can realize S2‑The quantitative detection method can also be used for cell fluorescence imaging. The preparation method of the compound is simple, and the product has high yield and high purity.
Description
Technical Field
The invention relates to a preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide, belonging to the field of ion detection.
Background
Zinc is the second most abundant transition metal element in human body, has very important biological action, and is closely related to the processes of DNA synthesis, gene expression, apoptosis, nerve transmission, signal transduction, ion channel regulation and the like. Zinc in human body is mainly from daily food, but bamboo shoots and the like contain abundant zinc element.
At present, methods such as atomic absorption spectrometry, an electrochemical method, a spectrophotometric method, an organic fluorescence probe method and the like are mainly used for detecting zinc. Wherein, the organic fluorescence probe method has high sensitivity, good selectivity, fast reaction time and capability of carrying out real-time regional ion measurementTest is to detect Zn2+The ideal method of (1). Therefore, synthesizing and searching a new zinc ion organic fluorescence enhanced probe for detecting the zinc content in the bamboo shoots and carrying out cell fluorescence imaging have very important practical significance.
Disclosure of Invention
The invention provides a preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide, which can realize quantitative detection of zinc ions and can also realize S by combining with the zinc ions2-The quantitative detection of (3); can also be combined with zinc ions for cell fluorescence imaging; the preparation method is simple, and the product has high yield and high purity.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
the application of 4-hydroxy-benzyl (2 '-hydroxy-benzylidene) -hydrazide for a fluorescent probe, wherein the structural formula of the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide is as follows:
further, 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide can be used for detection of zinc ions. The inventor finds that 4-hydroxy-benzyl (2 '-hydroxy-benzylidene) -hydrazide has highly selective fluorescence enhancement performance on zinc ions, and other ions hardly interfere with the zinc ions, so that the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide serving as a specific fluorescent probe molecule can be applied to detection of the zinc ions in bamboo shoots and the like.
When the fluorescent probe is used for detecting zinc ions, 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide and zinc ions form a complex in a solution or a solvent, the solution is changed from colorless to light green, fluorescence is enhanced under a 365nm ultraviolet lamp and blue fluorescence is emitted, the solution is a buffer solution, and the solvent is ethanol, toluene, chlorobenzene or acetone.
The inventor has found that 4-hydroxyethyl piperazine ethanesulfonic acid (HEPES) buffer solution (20mM, pH 7.2, 50% (v/v) CH3CH2OH) as a solvent in (0.1-1.1) x 10-5In the range of M, the fluorescence intensity and the concentration of zinc ions present a linear relationship, y is 840.01x +180.84, R20.98914. That is, with Zn2+The fluorescence intensity gradually increases with the stepwise increase in concentration.
The inventor also found that the combination of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide and zinc ions is used for detecting S by fluorescence quenching2-Wherein the molar ratio of the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide to the zinc ions is 1: (1. + -. 0.2).
Further, the fluorescence intensity and S2-The concentration satisfies the linear relationship: -1685.3x +1062.8, R20.9975. Thus, S can be realized2-The rapid quantitative detection of the method.
The inventors have also found that a combination of 4-hydroxy-benzyl (2 '-hydroxy-benzylidene) -hydrazide and zinc ions can be used for cellular fluorescence imaging, wherein the molar ratio of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide to zinc ions is 1: (0.5-2).
The preparation method of the 4-hydroxy-benzyl (2 '-hydroxy-benzylidene) -hydrazide comprises the following steps of carrying out condensation reaction on salicylaldehyde and 4-hydroxybenzoyl hydrazine to prepare the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide, wherein the reaction equation is as follows:
in order to increase the product yield, a preferred preparation method of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide comprises the following steps:
(1) carrying out reflux reaction on 4-hydroxybenzoyl hydrazine, salicylaldehyde and absolute ethyl alcohol for 0.5-7h, wherein the molar ratio of the 4-hydroxybenzoyl hydrazine to the salicylaldehyde is 1: (1-1.3), wherein the amount of the absolute ethyl alcohol is 1-20 ml per millimole of the 4-hydroxybenzoyl hydrazine;
(2) concentrating the material obtained in the step (1) under reduced pressure to obtain a light yellow crude product;
(3) and (3) purifying the material obtained in the step (2) to obtain the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide.
In order to improve the purity of the product, the purification in the step (3) is to use absolute ethyl alcohol for recrystallization, the purity of the obtained 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide crystal is more than 98.0 percent, and the yield is more than 90 percent.
The prior art is referred to in the art for techniques not mentioned in the present invention.
The 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide of the invention is a fluorescence enhanced zinc ion fluorescent probe, can be used for quantitatively detecting zinc ions in bamboo shoots and the like, and can also be combined with the zinc ions to realize S2-The quantitative detection of (3); can also be combined with zinc ions for cell fluorescence imaging; the preparation method is simple, and the product has high yield and high purity.
Drawings
FIG. 1 is a graph of the results of fluorescence enhancement selectivity experiments with 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide reacting with different ions;
FIG. 2 is a linear relationship between fluorescence intensity and zinc ion concentration when 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide is used as a fluorescent probe;
FIG. 3 shows fluorescence intensity and S of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide zinc ion fluorescent probe used as a fluorescence quenching probe2-A linear relationship of concentration;
FIG. 4 is 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide + Zn2+Imaging Ln229 cell fluorescence;
FIG. 5 is a photograph showing fluorescence imaging of Ln229 cells by an enzyme Red fluorescent probe (Lyso Tracker Red).
Detailed Description
In order to better understand the present invention, the following examples are further provided to illustrate the present invention, but the present invention is not limited to the following examples.
Example 1
Preparation of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide:
in a 100mL three-necked flask equipped with a thermometer, a stirrer and a condenser, 1.52g (10mmol) of 4-hydroxybenzoyl hydrazine, 1.22g (10mmol) of salicylaldehyde and 120mL of anhydrous ethanol were sequentially added, and the mixture was heated toReacting for 1.5h at the reflux temperature; the reactant is concentrated to 30mL, then cooled to room temperature, light yellow crystals are separated out, and then 25mL of absolute ethyl alcohol is used for recrystallization, so that light yellow crystals of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide is obtained, the yield is 91.2%, the purity is 98.7%, and the product characterization result is as follows: FT-IR (KBr) v (cm)-1):3317,3159,1641,1605,1585,1541,1485,1446,1352,1280,1235,1174,1155,875,841,747,730；1H NMR(DMSO-d6,600MHz):6.90-6.94(m,4H),7.27-7.29(t,1H),7.49-7.50(d,1H),7.85-7.87(d,2H),8.62(s,1H),10.19(s,1H),11.46(s,1H),11.95(s,1H)；13C NMR(DMSO-d6,150MHz),δ(ppm):115.68,116.94,119.21,119.80,123.73,130.20,130.28,131.66,148.24,158.01,161.49,163.04；HRMS(m/z):[M+H]+C14H12N2O3+H+The calculation result is 257.0920, and the detection result is 257.0927; HRMS (M/z): [ M + Na]+C14H12N2O3+Na+The calculation result was 279.0746, and the detection result was 279.0746.
Example 2
The selectivity of the compound 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide fluorescent probe for zinc ions:
4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide compound (1X 10)-5M) and other ions (15 species, 1X 10)-5M) was dissolved in 4-hydroxyethylpiperazine ethanesulfonic acid (HEPES) buffer (20mM, pH 7.2, 50% (v/v) CH3CH2OH), preparing a solution. The change of fluorescence intensity in the presence of different ions was measured at an excitation wavelength of 380nm, as shown in FIG. 1, and the results showed that 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide p-Zn2+Has strong fluorescence enhancement effect, and indicates that the compound has Zn resistance2+Has better selectivity.
Example 3
The 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide fluorescent probe is used for detecting zinc in bamboo shoots:
line of fluorescence intensity of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide + zinc ion and concentration of zinc ionThe relationship is shown in FIG. 2. 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide HEPES buffer system (1X 10)-5M) adding Zn with different concentrations respectively2+(0.1-1.1×10-5M) to obtain the change of fluorescence intensity under 380nm excitation light, the fluorescence intensity and Zn2+The concentration shows a linear relationship, y is 840.01x +180.84, R20.9891, limit of detection (LOD) 1.13 × 10-6mM。
The water content of the fresh bamboo shoots purchased in the vegetable market is 90.5 percent; peeling fresh bamboo shoots, slicing, drying at 45 ℃ for 24h to remove water, crushing to obtain bamboo shoot powder, putting a crucible containing 100.0g of bamboo shoot powder into a muffle furnace for combustion for 4h, cooling, adding 20mL of 20% (mass concentration) hydrochloric acid, stirring for 12h, filtering to obtain a filtrate, washing a filter cake for 2 times by using a HEPES (high efficiency particulate ES) buffer solution, filtering, combining the filtrates, and fixing the volume to 1000mL by using the HEPES buffer solution to obtain the zinc ion measuring solution. 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide HEPES buffer solution (1X 10)-4M) and the obtained zinc ion measuring solution are respectively added into a 10ml volumetric flask with 1ml, the volume is fixed and shaken up by HEPES buffer solution, the fluorescence intensity of the filtrate is measured for 3 times and respectively is 776.41, 771.37 and 773.05, and Zn is detected by adopting the equation of y being 840.01x +180.842+The concentration is 0.709 × 10 respectively-5M、0.703×10-5M、0.705×10-5M, calculating the zinc content of 100.0g of bamboo shoot powder, and comparing the zinc content with the detection result of ICP-MS, wherein the result is shown in table 1, and the measurement results of the two are highly consistent. The result shows that the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide fluorescent probe can be used for detecting the zinc content in bamboo shoots.
TABLE 1 detection of Zinc content in bamboo shoots
Example 4
4-hydroxy-benzyl (2'-hydroxyl-benzylidene) -hydrazide + zinc ion fluorescent probe for detecting S2-Concentration:
fluorescence intensity and S of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide + zinc ion fluorescent probe2-The linear relationship of the concentrations is shown in FIG. 3. 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide (1X 10)-5M) + Zinc ion (1X 10)-5M) adding S with different concentrations into fluorescent HEPES buffer system2-(0.1-0.6×10-5M), obtaining the change of fluorescence intensity under 380nm excitation light, the fluorescence intensity and S2-The concentration has a good linear relationship, y is-1685.3 x +1062.8, R20.9975, limit of detection (LOD) 1.66X 10-7mM。
Example 5
Human glioma cells (LN229) were routinely cultured in DMEM medium containing 10% fetal bovine serum, cultured for 24h and then adherent culture for 5h, and the cells were washed three times with phosphate buffered saline (PBS, pH 7.4). Respectively adding Zn into the culture dish2+(1×10-5M) in 1.00mL of DMEM medium, incubated at 37 ℃ for 1 hour. After completion, the solution is reused by containing 1 × 10-5M4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide 1.00mL DMEM medium was incubated at 37 ℃ for 3h, and after washing the cells 3 times with PBS buffer, images of the cells were recorded using confocal laser scanning microscopy, as shown in FIG. 4. Meanwhile, LN229 cells were treated with lysosomal Red fluorescent probe (Lyso Tracker Red, 1X 10) under the same conditions-5M) and images of the cells were recorded by confocal laser scanning microscopy as shown in FIG. 5. The results show that the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide + zinc ion fluorescent probe can be used for Ln229 cell fluorescence imaging, and the imaging result is the same as that of the Lyso Tracker Red.
Claims (8)
1. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide which is characterized in that: the structural formula of the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide is as follows:
4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide for detection of zinc ions: in a solution or a solvent, 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide reacts with zinc ions to generate coordination reaction, the solution is rapidly changed from colorless to light green, fluorescence is enhanced under a 365nm ultraviolet lamp and blue fluorescence is emitted, the solution is a buffer solution, and the solvent is ethanol, toluene, chlorobenzene or acetone.
2. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide according to claim 1, wherein: the method is used for quantitative detection of zinc ions in bamboo shoots.
3. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide according to claim 2, wherein: when Zn2+The concentration of (1) is (0.1 to 1.1) × 10-5M, fluorescence intensity and Zn2+The concentration satisfies the linear relationship: 840.01x +180.84, R2＝0.9891。
4. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide according to any one of claims 1 to 3, wherein: combination of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide and zinc ion for fluorescence quenching detection of S2-Wherein the molar ratio of the 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide to the zinc ions is 1: (1. + -. 0.2).
5. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide according to claim 4, wherein: when S is2-The concentration of (1) is 0.1 to 0.6) x 10-5Fluorescence intensity at M and S2-The concentration satisfies the linear relationship: -1685.3x +1062.8, R2＝0.9975。
6. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide according to any one of claims 1 to 3, wherein: a combination of 4-hydroxy-benzyl (2 '-hydroxy-benzylidene) -hydrazide and zinc ions for cellular fluorescence imaging, wherein the molar ratio of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide to zinc ions is 1: (0.5-2).
7. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide according to any one of claims 1 to 3, wherein: a method for preparing 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide comprising the steps of:
(1) carrying out reflux reaction on 4-hydroxybenzoyl hydrazine, salicylaldehyde and absolute ethyl alcohol for 0.5-7h, wherein the molar ratio of the 4-hydroxybenzoyl hydrazine to the salicylaldehyde is 1: (1-1.3), wherein the amount of the absolute ethyl alcohol is 1-20 ml per millimole of the 4-hydroxybenzoyl hydrazine;
(2) concentrating the material obtained in the step (1) under reduced pressure to obtain a light yellow crude product;
(3) and (3) purifying the material obtained in the step (2) to obtain 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide crystals.
8. Use of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide according to claim 7, wherein: the purification in the step (3) is to use absolute ethyl alcohol for recrystallization, the purity of the obtained 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide crystal is more than 98.0 percent, and the yield is more than 90 percent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911029928.1A CN110759833B (en) | 2019-10-25 | 2019-10-25 | Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911029928.1A CN110759833B (en) | 2019-10-25 | 2019-10-25 | Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110759833A CN110759833A (en) | 2020-02-07 |
| CN110759833B true CN110759833B (en) | 2022-06-14 |
Family
ID=69334013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911029928.1A Active CN110759833B (en) | 2019-10-25 | 2019-10-25 | Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110759833B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111440089A (en) * | 2020-03-31 | 2020-07-24 | 西安医学院 | Fluorescent material applied to zinc ion content detection and preparation method thereof |
| CN111689973A (en) * | 2020-07-28 | 2020-09-22 | 朱翠萍 | Dibenzocaprolactam pyrazolidine compound, preparation method and application |
| CN112028790B (en) * | 2020-09-17 | 2022-06-24 | 浙江工业大学温州科学技术研究院 | Cinnamic aldehyde derivative fluorescent probe compound, and preparation method and application thereof |
| CN115650876B (en) * | 2022-10-31 | 2023-12-12 | 国家林业和草原局竹子研究开发中心 | 2- (fluoranthene-3-iminomethyl) -phenol, preparation method thereof, bamboo shoot and bamboo fiber detection test paper prepared from same and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB762187A (en) * | 1952-10-09 | 1956-11-28 | Bayer Ag | Metal complexes of hydrazide-hydrazones and process for producing the same |
| CN106562946A (en) * | 2016-10-31 | 2017-04-19 | 北京大学 | Benzoyl hydrazine allosteric inhibitor for D-3-phosphoglycerate dehydrogenase and applications of benzoyl hydrazine allosteric inhibitor |
| CN107056779A (en) * | 2017-04-25 | 2017-08-18 | 三峡大学 | A kind of schiff bases fluorescence probe QCS and preparation method thereof |
| CN107151220A (en) * | 2015-10-19 | 2017-09-12 | 中国医学科学院药物研究所 | Phenolic compound, preparation method and the usage containing benzyloxy-phenyl |
| CN109942509A (en) * | 2019-05-08 | 2019-06-28 | 东北农业大学 | The fluorescence probe and its preparation method and application of copper ion is identified under a kind of alkaline condition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002089745A2 (en) * | 2001-05-10 | 2002-11-14 | Cytovia, Inc. | Substituted n'-(arylcarbonyl)-benzhydrazides, n'-(arylcarbonyl)-benzylidene-hydrazides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
-
2019
- 2019-10-25 CN CN201911029928.1A patent/CN110759833B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB762187A (en) * | 1952-10-09 | 1956-11-28 | Bayer Ag | Metal complexes of hydrazide-hydrazones and process for producing the same |
| CN107151220A (en) * | 2015-10-19 | 2017-09-12 | 中国医学科学院药物研究所 | Phenolic compound, preparation method and the usage containing benzyloxy-phenyl |
| CN106562946A (en) * | 2016-10-31 | 2017-04-19 | 北京大学 | Benzoyl hydrazine allosteric inhibitor for D-3-phosphoglycerate dehydrogenase and applications of benzoyl hydrazine allosteric inhibitor |
| CN107056779A (en) * | 2017-04-25 | 2017-08-18 | 三峡大学 | A kind of schiff bases fluorescence probe QCS and preparation method thereof |
| CN109942509A (en) * | 2019-05-08 | 2019-06-28 | 东北农业大学 | The fluorescence probe and its preparation method and application of copper ion is identified under a kind of alkaline condition |
Non-Patent Citations (2)
| Title |
|---|
| Crystal structures of transition metal complexes with an asymmetrical tridentate Schiff-base ligand;Bei-bei Tang等;《Journal of Molecular Structure》;20100918;第984卷;第111-116页 * |
| 水杨醛缩对羟基苯甲酰肼及其配合物的荧光研究;丁瑜等;《化学试剂》;20080715;第30卷;第489-492页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110759833A (en) | 2020-02-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110759833B (en) | Preparation method and application of 4-hydroxy-benzyl (2' -hydroxy-benzylidene) -hydrazide | |
| Das et al. | Ratiometric fluorescence sensing and intracellular imaging of Al 3+ ions driven by an intramolecular excimer formation of a pyrimidine–pyrene scaffold | |
| Huang et al. | Selective off–on fluorescent chemosensor for detection of Fe 3+ ions in aqueous media | |
| CN108752331A (en) | Synthesis and application a kind of while that distinguish detection Cys, Hcy and GSH Multifunction fluorescent molecular probe | |
| CN109970751B (en) | Double-site high-sensitivity pH fluorescent probe and synthesis and application thereof | |
| CN109232626B (en) | SO based on difluoro boro coumarin2Ratiometric fluorescent probes | |
| CN110511245B (en) | Near-infrared fluorescent probe SHCy-P based on thiohemicyanine dye and preparation method and application thereof | |
| CN110746321B (en) | Malononitrile Schiff base hypochlorous acid fluorescent probe and preparation method thereof | |
| CN107311977B (en) | Indole ethylene compound and preparation method and application thereof | |
| CN110092773B (en) | Xanthene derivative and preparation method and application thereof | |
| CN108383774B (en) | Cysteine fluorescent probe based on terminal alkynone and preparation and application thereof | |
| CN111675632B (en) | Fluorescent molecular probe for detecting genotoxin Colibactin through visual imaging as well as preparation method and application of fluorescent molecular probe | |
| CN105623647A (en) | Fluorescent probe for detecting CO (carbon monoxide) in cells and preparation method and application of fluorescent probe | |
| CN113788821B (en) | Near-infrared hydrazine compound, preparation method, formaldehyde detection kit and application | |
| CN113637048A (en) | Two-photon fluorescent probe of gamma-glutamyl transpeptidase, and preparation method and application thereof | |
| CN110386898B (en) | Quinoline ring derivative fluorescent probe and preparation method and application thereof | |
| CN114634497B (en) | Cysteine/homocysteine response AIE fluorescent probe and preparation method and application thereof | |
| Zhou et al. | An effective biocompatible fluorescent probe for bisulfite detection in aqueous solution, living cells, and mice | |
| CN110776458B (en) | Fluorescent probe for detecting mitochondrial membrane potential and preparation method and application thereof | |
| CN116239518A (en) | Preparation and application of near infrared fluorescent molecular probe with ESIPT+AIE effect | |
| CN112480909B (en) | Fluorescent probe for detecting glutathione in cells and preparation method and application thereof | |
| CN109369565A (en) | A kind of benzothiazole derivant and its preparation method and application | |
| CN108840818B (en) | Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide | |
| CN109180694B (en) | Rhodamine derivative fluorescent probe for cell imaging and preparation method thereof | |
| CN109020988B (en) | Application of rhodamine fluorescent probe of triazole compound in Hela cell imaging |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |