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Application of 2,3-dihydrogen-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparing medicaments for inducing embryonic stem cells to differentiate towards vascular endothelial cells

A technology of embryonic stem cells and benzoxazine, applied in the field of benzoxazine derivatives

Inactive Publication Date: 2010-09-22
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] According to the search by authoritative organizations, there is no research on 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in inducing the differentiation of embryonic stem cells into vascular endothelial cells at home and abroad. to report

Method used

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  • Application of 2,3-dihydrogen-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparing medicaments for inducing embryonic stem cells to differentiate towards vascular endothelial cells
  • Application of 2,3-dihydrogen-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparing medicaments for inducing embryonic stem cells to differentiate towards vascular endothelial cells
  • Application of 2,3-dihydrogen-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparing medicaments for inducing embryonic stem cells to differentiate towards vascular endothelial cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1 Preparation of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine

[0067] Addition of 2,4-dinitrophenoxymethyloxirane (0.480 g, 2 mmol) and acetic acid (1 mL, 17.5 mmol) in EtOH / H at reflux temperature 2 Iron powder (0.670 g, 12 mmol) was added to the O (v / v=6:1, 100 mL) solution. The reaction mixture was continued to reflux for 120 minutes. Cool to room temperature to saturate Na 2 CO 3 The solution was adjusted to pH=8, filtered with celite, the ethanol and water in the filtrate were concentrated, and the obtained solid was washed with ethanol (10 mL×4). ethanol phase with anhydrous MgSO 4 Dry and filter to obtain a crude product; the above crude product is separated by silica gel column chromatography (ethanol as a developing solvent) to obtain 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxane Azine (0.149 g, 42%).

Embodiment 2

[0068] Example 2 Detection of the influence of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine on the morphology of embryonic stem cells

[0069] Embryonic stem cells were divided into 2×10 4Cells / well were evenly seeded in a 24-well plate with DMEM containing leukemia inhibitory factor, L-glutamine, penicillin, β-mercaptoethanol, non-essential amino acids, nucleotides, and 15% fetal calf serum. (high glucose) for 24 hours. After the cells adhered to the wall, the waste liquid was discarded and washed with 1×PBS. Set normal group: cultivated under the culture condition of removing leukemia inhibitory factor; solvent control group: add DMSO and culture under the culture condition of removing leukemia inhibitory factor; experimental group: add concentration of 0.5μM, 1 μM, 5 μM, 10 μM, 20 μM, 30 μM and 40 μM of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine were incubated. Culture conditions: 37°C, CO 2 Cultured in an incubator. The medium was changed regularly...

Embodiment 3

[0071] Example 3 Detection of Vascular Endothelial Cell Marker (Flk-1)

[0072] Embryonic stem cells were evenly seeded in 48-well plates, and DMEM (high glucose ) for 24 hours. After the cells adhered to the wall, the waste liquid was discarded and washed with 1×PBS. Set up normal group: cultured under the culture condition of removing leukemia inhibitory factor; solvent control group: added DMSO culture under the culture condition of removing leukemia inhibitory factor; experimental group: added concentrations of 0.5 μM, 1 μM, 5 μM, 10 μM, 20 μM, 30 μM and 40 μM of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine were incubated. 37°C, CO 2 Culture in the incubator, replace the culture medium every day, discard the waste liquid after 10 days, wash with 0.1×PBS three times, fix with 4% paraformaldehyde for 15 minutes, after washing, block with goat serum for 20 minutes, add Flk-1 The primary antibody was incubated overnight at 4°C, washed three times with 0.1×PBS, add...

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Abstract

The invention discloses application of 2,3-dihydrogen-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparing medicaments for inducing embryonic stem cells to differentiate toward vascular endothelial cells. The the concentration of 2,3-dihydrogen-3-hydroxymethyl-6-amino-[1,4]-benzoxazine for effectively inducing mice embryonic stem cells to differentiate towards the vascular endothelial cells is 1-20 mu M. The 2,3-dihydrogen-3-hydroxymethyl-6-amino-[1,4]-benzoxazine provided in the invention establishes the foundation for the research and development of drugs for inducing the embryonic stem cells to differentiate towards the vascular endothelial cells, and also can be used as an effective embryonic stem cell research tool for the differentiation of the embryonic stem cells and the research of vascular neogenesis molecular mechanism.

Description

technical field [0001] The present invention relates to the use of benzoxazine derivatives, in particular to the use of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in the preparation of induced embryonic stem cells to vascular endothelial cells applications in differentiation medicine. Background technique [0002] The structural formula of 2,3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine is: [0003] [0004] Molecular formula: C 9 h 12 N 2 o 2 [0005] Molecular weight: 180.2, properties: light yellow solid, melting point: 154-156°C. [0006] 2,3-Dihydro-[1,4]-benzoxazine derivatives are very important structural units, which are contained in many natural products and synthetic drugs. [0007] It is known that 2,3-dihydro-2-substituted-[1,4]-benzoxazine derivatives have pharmacological activities such as antibacterial, antithrombotic, bradycardia, and anti-central nervous system (CNS) disorders, such as patent The structures of 2,3-dihydro-2-subst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/538A61P9/00
CPCA61K31/538A61P9/00
Inventor 苗俊英赵宝祥张尚立赵静苏乐韩雷
Owner SHANDONG UNIV