6823-69-4
4',4''-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride
CAS: 6823-69-4
Molecular Formula: C30H29N6O3X
6823-69-4 - Names and Identifiers
| Name | 4',4''-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride |
| Synonyms | GW4869 CS-2410 GW69A, GW554869A N-SMase Inhibitor GW4869 dihydrochloride GW 4869 (hydrochloride hydrate) 4',4''-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride |
| CAS | 6823-69-4 |
6823-69-4 - Physico-chemical Properties
| Molecular Formula | C30H29N6O3X |
| Molar Mass | 521.58966 |
| Melting Point | >300 °C |
| Solubility | DMSO: 0.044 mg/mL (Need ultrasonic and warming) |
| Appearance | Morphological powder |
| Color | light yellow to yellow |
| Storage Condition | 2-8°C |
| Physical and Chemical Properties | Bioactive GW4869 (GW69A, GW554869A) is a non-competitive inhibitor of neutral Smase (sphingomyelinase) with an IC50 of 1 μM. It is selective for N-SMase and has no inhibitory effect on acidic SMase at concentrations up to 150 μM. |
| Use | Use GW4869 is a N-SMase inhibitor that can control the biological activity of N-SMase. This small molecule/inhibitor is mainly used for cell signaling. |
| In vitro study | GW4869 was inhibited by N-SMase in an in vitro cell model. GW4869 does not significantly disrupt TNF-induced NF-κB translocation into the nucleus, and therefore, GW4869 does not interfere with other key signaling effects mediated by TNF. By detecting nuclear concentration, caspase activation, PARP degradation and trypan blue uptake, GW4869 was found to protect cells from death in a concentration-dependent manner, at the same time, the release of cytochrome C from mitochondria and the activation of caspase 9 were significantly inhibited, so N-SMase activation should be located upstream of mitochondrial dysfunction. At concentrations as high as 150 μm, GW4869 had no inhibitory effect on the cloned human A- SMase, and had no or only weak inhibitory activity against other hydrolytic enzymes such as bacterial phosphatidylcholine-PLC and bovine PP2A, compared with human lyso-PAF PLC, the activity of this enzyme in rat brain was more significant. |
| In vivo study | Systemic administration (GW4869) did not alter ceramide or sphingomyelin levels in the liver, heart, or skeletal muscle, but decreased ceramide levels and increased sphingomyelin levels in the brain. Inhibition of nSMase2 by GW4869 delayed learning, and after administration of GW4869 to mice, did not reduce the delay in finding the covert platform after repeated training, indicating their learning disability in navigating the application of spatial cues. Intraperitoneal injection of GW4869 in mice reduced the levels of exosomes, ceramide, and Aβ1-42 plaque burden in their brains and serum. GW4869 reduces amyloid plaque formation in vivo by preventing exosomal secretion, and GW4869 is less toxic at concentrations that achieve inhibition of physiological effects caused by nSMase2 (I. E., effective concentrations). |
6823-69-4 - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
6823-69-4 - Reference
| Reference Show more | 1. Chen Tao, Gao Shaoying, Hao Yi, Zhang Feifei, Tang, Xiu, Jun, Wei in rongdali, Qi, Jianping. Exosomes from human amniotic mesenchymal stem cells promote fibroblast migration through micro RNA-135a [J]. Chinese Journal of reparative and reconstructive surgery, 2020, 34(02):234-239. |
6823-69-4 - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 1.732 ml | 8.658 ml | 17.316 ml |
| 5 mM | 0.346 ml | 1.732 ml | 3.463 ml |
| 10 mM | 0.173 ml | 0.866 ml | 1.732 ml |
| 5 mM | 0.035 ml | 0.173 ml | 0.346 ml |
Last Update：2024-01-02 23:10:35
6823-69-4 - Uses and synthesis methods
Target
Target Value
SMase
(Cell-free assay) 1 μM
in vitro studies
GW4869 inhibits N-SMase in an in vitro cell model. GW4869 does not significantly destroy TNF-induced NF-& kappa;B translocation into the nucleus, therefore, GW4869 does not interfere with other key signaling effects mediated by TNF. Through the detection of nuclear staining, caspase activation, PARP degradation and trypan blue absorption, it is found that GW4869 can protect cells from death in a concentration-dependent manner, and at the same time significantly inhibit the release of cytochrome C from mitochondria and the activation of caspase9. Therefore, the activation of N-SMase should be located upstream of mitochondrial dysfunction. When the concentration is as high as 150 μM, GW4869 has no inhibitory effect on cloned human A- SMase, and has no or only weak inhibitory activity on other hydrolase enzymes such as bacterial phosphatidylcholine-PLC and bovine PP2A. Compared with human lyso-PAF PLC, the activity of this enzyme in rat brain is more significant.
In vivo studies
Systemic administration (GW4869) does not change the content of ceramide or sphingomyelin in liver, heart or skeletal muscle, but reduces the content of ceramide in brain and increases the content of sphingomyelin. nSMase2 inhibition by GW4869 can delay learning. After GW4869 is given to mice, the delay in finding hidden platforms after repeated training is not reduced, which indicates their learning disability in navigating spatial clues. Intraperitoneal injection of GW4869 into mice will reduce the levels of external body, brain ceramide and Aβ1-42 plaque load in the brain and serum. GW4869 reduces amyloid plaque formation in vivo by preventing exosome secretion. GW4869 is less toxic at a concentration (I. e. effective concentration) that inhibits nSMase2-induced physiological effects.
Last Update：2024-04-10 22:29:15
6823-69-4 - Introduction
4 ',4'-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride is an organic compound. The following is a description of its nature, use, preparation and safety information:
Nature:
-Appearance: Common as a white crystalline solid
-Solubility: Soluble in water and organic solvents
-Melting Point: about 200-210 degrees Celsius
-Chemical structure: Its chemical structure contains two groups of imidazoline and terephthaloanilide
Use:
- 4 ',4'-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride is commonly used as a reagent in biochemistry, medicinal chemistry and organic synthesis.
-It can be used as a catalyst, ligand or reaction intermediate for catalysis, activation or selective control in organic synthesis reactions.
-It can also be used in the field of drug research and development, for example as an ingredient in anti-cancer drugs.
Preparation Method:
- 4 ',4'-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride has many preparation methods.
-One of the common methods is to react imidazoline with terephthaloanilide, and obtain the desired product through appropriate oxidation and hydrochloric acid treatment.
-The preparation process may require the use of organic solvents and some treatment methods under specific conditions.
Safety Information:
-It has no obvious harm under regular use, but it still needs to pay attention to safe operation.
-Wear appropriate protective equipment during operation, including laboratory gloves, glasses and protective clothing.
-Due to the different properties and uses of this compound, further safety assessment and operational guidance may be required according to the specific situation.
Please note that this is only a general introduction to 4 ',4 ''-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride, and the specific situation should be verified and understood according to actual needs. When using, please refer to the relevant chemical literature and preparation guidelines, follow the correct laboratory safety procedures.
Nature:
-Appearance: Common as a white crystalline solid
-Solubility: Soluble in water and organic solvents
-Melting Point: about 200-210 degrees Celsius
-Chemical structure: Its chemical structure contains two groups of imidazoline and terephthaloanilide
Use:
- 4 ',4'-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride is commonly used as a reagent in biochemistry, medicinal chemistry and organic synthesis.
-It can be used as a catalyst, ligand or reaction intermediate for catalysis, activation or selective control in organic synthesis reactions.
-It can also be used in the field of drug research and development, for example as an ingredient in anti-cancer drugs.
Preparation Method:
- 4 ',4'-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride has many preparation methods.
-One of the common methods is to react imidazoline with terephthaloanilide, and obtain the desired product through appropriate oxidation and hydrochloric acid treatment.
-The preparation process may require the use of organic solvents and some treatment methods under specific conditions.
Safety Information:
-It has no obvious harm under regular use, but it still needs to pay attention to safe operation.
-Wear appropriate protective equipment during operation, including laboratory gloves, glasses and protective clothing.
-Due to the different properties and uses of this compound, further safety assessment and operational guidance may be required according to the specific situation.
Please note that this is only a general introduction to 4 ',4 ''-Di-2-imidazolin-2-yl-p-benzenediacrylanilide dihydrochloride, and the specific situation should be verified and understood according to actual needs. When using, please refer to the relevant chemical literature and preparation guidelines, follow the correct laboratory safety procedures.
Last Update：2024-04-09 19:04:58
Supplier List
Spot supply
Product Name: GW4869 Visit Supplier Webpage Request for quotationCAS: 6823-69-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: GW4869 Visit Supplier Webpage Request for quotationCAS: 6823-69-4
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History