CN116617217A - Application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in pharmacy - Google Patents
Application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in pharmacy Download PDFInfo
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- CN116617217A CN116617217A CN202310838723.8A CN202310838723A CN116617217A CN 116617217 A CN116617217 A CN 116617217A CN 202310838723 A CN202310838723 A CN 202310838723A CN 116617217 A CN116617217 A CN 116617217A
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- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 title claims abstract description 19
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 210000002889 endothelial cell Anatomy 0.000 claims abstract description 44
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 23
- 230000032677 cell aging Effects 0.000 claims abstract description 19
- 239000003814 drug Substances 0.000 claims abstract description 9
- 210000003606 umbilical vein Anatomy 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 5
- 210000003556 vascular endothelial cell Anatomy 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000007246 mechanism Effects 0.000 abstract description 3
- 150000003384 small molecules Chemical class 0.000 abstract description 3
- 230000003511 endothelial effect Effects 0.000 abstract description 2
- -1 4-methylbenzo [4,5] imidazo [1, 2-a ] pyridine-3-carbaldehyde Chemical compound 0.000 abstract 2
- 230000032683 aging Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000002792 vascular Effects 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 230000009758 senescence Effects 0.000 description 14
- 101710157927 Translationally-controlled tumor protein Proteins 0.000 description 11
- 102100024180 Transmembrane emp24 domain-containing protein 10 Human genes 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 9
- 210000002966 serum Anatomy 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 description 6
- 108010005774 beta-Galactosidase Proteins 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 4
- 238000007619 statistical method Methods 0.000 description 4
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 3
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 239000012636 effector Substances 0.000 description 3
- 230000037361 pathway Effects 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
- 238000010186 staining Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 235000013878 L-cysteine Nutrition 0.000 description 2
- 239000004201 L-cysteine Substances 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 210000003954 umbilical cord Anatomy 0.000 description 2
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 2
- 238000001262 western blot Methods 0.000 description 2
- HCQLRUAJQLCXJK-REOHCLBHSA-N (2S)-2-amino-1-oxo-3-sulfanylpropane-1-sulfinic acid Chemical compound N[C@@H](CS)C(=O)S(O)=O HCQLRUAJQLCXJK-REOHCLBHSA-N 0.000 description 1
- MMKXZVZBTQSEMU-UHFFFAOYSA-N 2-oxo-3-sulfinylpropanoic acid Chemical compound OC(=O)C(=O)C=S=O MMKXZVZBTQSEMU-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 102000015295 Cysteine Dioxygenase Human genes 0.000 description 1
- 108010039724 Cysteine dioxygenase Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 102100036764 Transmembrane emp24 domain-containing protein 7 Human genes 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000010094 cellular senescence Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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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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- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses an application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in preparing medicaments for inhibiting endothelial cell aging. Also disclosed is an endothelial cell aging-inhibiting agent comprising 4-methylbenzo [4,5] imidazo [1, 2-a ] pyridine-3-carbaldehyde according to claim 1, wherein the concentration of 4-methylbenzo [4,5] imidazo [1, 2-a ] pyridine-3-carbaldehyde effective to inhibit high sugar-induced endothelial cell aging is 5 to 10 μm. The application provided by the invention lays a foundation for developing medicaments related to chemical small molecules for inhibiting vascular endothelial aging, and meanwhile, the compound can be used as an effective chemical tool to provide a powerful means for researching the mechanism of inhibiting vascular endothelial cell aging by the chemical small molecules.
Description
Technical Field
The invention relates to application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde [ 4-methyl lbenzo [4,5] imidozo [1, 2-alpha ] pyridine-3-carbaldehyde ] (ZSO) in pharmacy, in particular to application in preparation of medicaments for inhibiting endothelial cell aging. Belongs to the technical field of biological preparation or pharmacy.
Background
Sulfur-containing amino acids are metabolized by the aspartate aminotransferase pathway to produce sulfur dioxide. The L-cysteine is oxidized to L-cysteinyl sulfinic acid under the action of cysteine oxidase, and the L-cysteine is converted into sulfinyl pyruvic acid by the action of aspartate aminotransferase, and then is spontaneously decomposed into pyruvic acid and sulfur dioxide. Sulfur dioxide is mainly produced in cardiovascular tissue, and aspartate aminotransferase mRNA that produces sulfur dioxide is localized to vascular endothelial cells and vascular smooth muscle cells in the vicinity of the endothelial layer. Sulfur dioxide is considered to be a sulfur-containing gas signaling molecule produced in cells. Recent studies on the physiological and pathological effects of endogenous sulfur dioxide on the cardiovascular system have found that sulfur dioxide can inhibit vascular smooth muscle cell proliferation, inhibit inflammation, reduce hypertension, regulate lipid metabolism, and the like.
Sulfur dioxide is mainly produced in vascular endothelial cells, but the regulation and control of intracellular sulfur dioxide on vascular endothelial cell function and its mechanism are not well known at present. Today, due to the diversity of eating habits, glucose intake by people is increasing. And damage to the cardiovascular system caused by high sugar is also becoming a cause of cardiovascular disease. 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde (ZSO for short) is a compound synthesized previously by the applicant subject group, and research determines that the compound can label endogenous sulfur dioxide in cells, can more intuitively detect dynamic change of sulfur dioxide level, and has the function of a sulfur dioxide probe. However, the application of sulfur dioxide probe 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde as a medicament for inhibiting endothelial cell aging is not reported through the research of authorities.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide the application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in pharmacy, in particular to the application in preparing medicaments for inhibiting endothelial cell aging.
The structural formula of the 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde is as follows:
the molecular formula: c (C) 13 H 10 N 2 O
Molecular weight: 210.24
Traits: yellow powdery solid.
The invention provides an application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in preparing medicaments for inhibiting endothelial cell aging.
In the above application: the endothelial cells are preferably Human Umbilical Vein Endothelial Cells (HUVECs).
The invention provides a preparation for inhibiting endothelial cell aging, which contains the 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde, and is characterized in that: the concentration of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in the preparation is 5-10 mu M, which is effective for inhibiting high sugar-induced endothelial cell aging.
In order to better understand the essence of the present invention, the following pharmacological experiments and results of binding 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-carbaldehyde are used to illustrate the application thereof in the preparation of medicaments for inhibiting endothelial cell aging.
The following experiments were performed using methods of cell biology and molecular biology: wherein the 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-carbaldehyde is abbreviated as ZSO in the following experiments.
1. ZSO inhibiting high sugar-induced endothelial cell senescence
Human umbilical vein endothelial cells from human umbilical cord are taken as model cells for in vitro culture.
Human umbilical vein endothelial cells were seeded into six well plates, and control and experimental groups were set for the following experiments. Control group: 10 mu M dimethyl sulfoxide (DMSO) was added to the medium in a high sugar (30 mM) environment at 15% serum; experimental group: normal environment, 15% serum culture medium treatment and high sugar environment, 15% serum concentration of 0.5 muM, 1. Mu.M, 5. Mu.M, 10. Mu.M of ZSO. 33 ℃,5% CO 2 After 24h of culture in an incubator, beta-gal staining was performed, and observation under a microscope, photographing, and statistical analysis were performed.
The results show that: high sugar can induce senescence of endothelial cells, whereas ZSO treatment can alleviate high sugar-induced senescence of endothelial cells (fig. 1).
2. ZSO inhibits high sugar-induced endothelial cell senescence by inhibiting the p21, p23 pathway
Human umbilical vein endothelial cells were seeded into six well plates, and control and experimental groups were set for the following experiments. Control group: adding 10 mu M dimethyl sulfoxide (DMSO) under high sugar environment and 15% serum condition for culturing; experimental group: in a high sugar environment, ZSO with concentration of 5. Mu.M and 10. Mu.M respectively was added under 15% serum condition for culture. 33 ℃,5% CO 2 After 24h of culture in the incubator, protein levels of p21 and p23, which are key effector factors of cell senescence, were detected by Western blot.
The results show that: ZSO is able to inhibit high sugar-induced endothelial cell senescence by inhibiting p21 as well as p23 (fig. 2).
Statistical treatment of experimental data as described above:
experimental data are expressed as mean ± standard error, t-test: * P <0.05 indicates significant differences; * P <0.01 indicates a very significant difference.
From the above experiments and their results, the following conclusions can be drawn:
it can be seen by β -gal staining that the high sugar treatment induced endothelial cell senescence, whereas ZSO treatment inhibited high sugar induced endothelial cell senescence; and as can be seen from the protein level detection of p21, p23, a key effector of cellular senescence, ZSO is able to inhibit high sugar-induced endothelial cell senescence by inhibiting p21 as well as p 23; wherein the concentration of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-carbaldehyde effective to inhibit high sugar-induced endothelial cell senescence is 5 to 10 mu M.
The application of the 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde provided by the invention lays a foundation for developing medicaments related to inhibiting endothelial cell aging. The ZSO related by the invention can be used as an effective chemical tool to provide a powerful means for further researching the mechanism of inhibiting the endothelial cell aging under high sugar induction by chemical small molecules.
Drawings
Fig. 1: ZSO inhibit the observation of high sugar induced endothelial cell aging
Wherein: a-b: endothelial cells were treated with medium (Nor) without high sugar and ZSO high sugar models at concentrations of 0. Mu.M, 0.5. Mu.M, 1. Mu.M, 5. Mu.M, 10. Mu.M, respectively, for 24h, and then stained with beta-gal, observed under a microscope, photographed, and statistically analyzed.
Fig. 2: ZSO quantitative analysis of endothelial cell aging induced by inhibition of p21 and p23
Wherein: a-b: after 24h treatment of endothelial cells with different concentrations (0. Mu.M, 5. Mu.M, 10. Mu.M) ZSO under high sugar conditions, the p21, p23 protein levels were detected. c-d: statistical analysis was performed on p21, p23 protein levels.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings and specific embodiments. The following examples are only preferred embodiments of the present invention, and it should be noted that the following descriptions are merely for explaining the present invention, and are not limiting in any way, and any simple modification, equivalent variation and modification of the embodiments according to the technical principles of the present invention are within the scope of the technical solutions of the present invention.
In the examples described below, materials, reagents, cells and the like used, unless otherwise specified, were all obtained commercially.
Example 1: ZSO inhibiting high sugar-induced endothelial cell senescence
Human Umbilical Vein Endothelial Cells (HUVECs) derived from human umbilical cord were taken as model cells for in vitro culture.
Human umbilical vein endothelial cells were seeded into six well plates, and control and experimental groups were set for the following experiments.
Control group: 10 mu M dimethyl sulfoxide (DMSO) was added to the medium in a high sugar (30 mM) environment at 15% serum; experimental group: normal environment, 15% serumThe culture medium was treated under the conditions of high sugar (30 mM) and cultured in a medium containing 15% serum at concentrations of 0.5. Mu.M, 1. Mu.M, 5. Mu.M, and 10. Mu.M in ZSO, respectively. 33 ℃,5% CO 2 After culturing for 24 hours in an incubator, absorbing and discarding old culture solution, washing twice with PBS, fixing for 15 minutes at room temperature with 2-formaldehyde-glutaraldehyde which is prepared at present, removing the fixing solution by pipette, washing 2 times with PBS for 5 minutes each time, incubating beta-gal dye solution for 1-2 minutes, removing waste liquid, adding beta-gal dyeing working solution (beta-gal auxiliary solution: dye solution 1:20), sealing in a dark place, incubating for 18-24 hours in a 33 ℃ constant temperature incubator, discarding dye solution, washing 2 times with PBS, observing under a microscope, and counting the positive number of cells.
The results show that: high sugar induced senescence of endothelial cells, whereas ZSO treatment can alleviate high sugar induced senescence of endothelial cells (see FIG. 1, wherein: a-b. Beta. -gal staining was performed after treatment of endothelial cells with medium (Nor) without high sugar and ZSO high sugar models at concentrations of 0. Mu.M, 0.5. Mu.M, 1. Mu.M, 5. Mu.M, 10. Mu.M, respectively, for 24h, microscopic observation, photographing and statistical analysis).
Example 2: ZSO inhibits high sugar-induced endothelial cell senescence by inhibiting the p21, p27 pathway
Human umbilical vein endothelial cells were seeded into six well plates, and control and experimental groups were set for the following experiments.
Control group: 10 mu M dimethyl sulfoxide (DMSO) was added to the medium in a high sugar (30 mM) environment at 15% serum; experimental group: in a high sugar (30 mM) environment, ZSO culture was added at a concentration of 5. Mu.M and 10. Mu.M, respectively, under 15% serum conditions. 33 ℃,5% CO 2 After culturing for 24 hours in an incubator, the cells are lysed, cell lysate is collected, centrifugation is carried out at 12000g for 15min at 4 ℃, the supernatant is taken, and protein levels of p21 and p23 which are key effector factors of cell aging are detected by using Western blot.
The results show that: ZSO by inhibiting p21 and p23, the levels of p21, p23 protein were detected after treatment of endothelial cells with different concentrations (0. Mu.M, 5. Mu.M, 10. Mu.M) ZSO under high sugar conditions (see FIG. 2: a-b: statistical analysis of p21, p23 protein levels).
Claims (3)
- Use of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-carbaldehyde in the preparation of a medicament for inhibiting endothelial cell aging.
- 2. The use according to claim 1, characterized in that: the endothelial cells are human umbilical vein endothelial cells.
- 3. An endothelial cell aging inhibiting formulation comprising 4-methylbenzo [4,5] imidazo [1,2- α ] pyridine-3-carbaldehyde according to claim 1, characterized by: the concentration of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in the preparation is 5-10 mu M, which is effective for inhibiting high sugar-induced endothelial cell aging.
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| CN202310838723.8A CN116617217B (en) | 2023-07-10 | 2023-07-10 | Application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in pharmacy |
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| CN202310838723.8A CN116617217B (en) | 2023-07-10 | 2023-07-10 | Application of 4-methylbenzo [4,5] imidazo [1, 2-alpha ] pyridine-3-formaldehyde in pharmacy |
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| CN116617217A true CN116617217A (en) | 2023-08-22 |
| CN116617217B CN116617217B (en) | 2024-04-02 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030059724A (en) * | 2002-01-04 | 2003-07-10 | 주식회사 코오롱 | Method for preparing of imidazole derivatives |
| CN102274226A (en) * | 2011-06-18 | 2011-12-14 | 山东大学 | Pharmaceutical use of 1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazol-5-carbohydrazide |
| CN107412228A (en) * | 2017-08-31 | 2017-12-01 | 山东大学 | Application of the carboxylic acid of the chlorine imidazo of 3 butyl 1 [1,5 a] pyridine 7 in pharmacy |
| CN112608880A (en) * | 2020-12-03 | 2021-04-06 | 山东大学 | Application of 4-substituted styryl-1-methylpyridine iodide derivative in pharmacy |
-
2023
- 2023-07-10 CN CN202310838723.8A patent/CN116617217B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030059724A (en) * | 2002-01-04 | 2003-07-10 | 주식회사 코오롱 | Method for preparing of imidazole derivatives |
| CN102274226A (en) * | 2011-06-18 | 2011-12-14 | 山东大学 | Pharmaceutical use of 1-(3-(6-chloropyridine)methyl)-3-phenyl-1H-pyrazol-5-carbohydrazide |
| CN107412228A (en) * | 2017-08-31 | 2017-12-01 | 山东大学 | Application of the carboxylic acid of the chlorine imidazo of 3 butyl 1 [1,5 a] pyridine 7 in pharmacy |
| CN112608880A (en) * | 2020-12-03 | 2021-04-06 | 山东大学 | Application of 4-substituted styryl-1-methylpyridine iodide derivative in pharmacy |
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