| Chemical & Physical Properties | |
|---|---|
| CAS Number | 1258-84-0 |
| Catalog No. | 2A-3185587 |
| Chinese Name | 扁塑藤素 |
| Synonyms | Celastrol-methylether; pristimerine |
| Molecular Formula | C30H40O4 |
| Molecular Weight | 464.64 |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 607.7±55.0 °C at 760 mmHg |
| Melting Point | 219.5°C |
| Appearance | orange |
| Water Solubility | DMSO: ≥5mg/mL |
| Storage Condition | Store at -20°C |
| Application | Pristimerin is a highly effective and reversible inhibitor of monoacylglycerol lipase (MGL) with an IC50 value of 93 nM. |
| PubChem ID | 10826 |
| SMILES | COC(=O)C1(C)CCC2(C)CCC3(C)C4=CC=C5C(=CC(=O)C(O)=C5C)C4(C)CCC3(C)C2C1 |
| InChI | InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27-,28+,29-,30+/m1/s1 |
| InChI Key | JFACETXYABVHFD-WXPPGMDDSA-N |
| Hazard Symbols | transportation |
| Bioactivity | Pristimerin is a potent and reversible monoacylglycerol lipase (MGL) inhibitor with an IC50 of 93 nM. Related Catalog Signaling Pathways >> Anti-infection >> Bacterial Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer Target IC50: 93 nM (MGL)[1] In Vitro Pristimerin inhibits the activity of purified MGL with an IC50 of 93±8 nM and that of non-purified MGL (cell lysates of MGL-transfected HeLa cells) with an IC50 of 398±68 nM. Pristimerin inhibits MGL through a mechanism that is rapid, reversible and non-competitive. The binding of pristimerin to MGL might be strengthened by formation of a polar interaction with a regulatory cysteine, possibly Cys208[1]. Pristimerin inhibits HFLS-RA and HUVEC cell viability in a dose- and time-dependent manner. Pristimerin decreases VEGF-induced autophosphorylation of VEGFR2 and attenuates the activation of the VEGF-induced VEGFR2-mediated signaling pathway [2]. In Vivo Pristimerin inhibits inflammation and tumor angiogenesis. Pristimerin significantly reduces vessel density in synovial membrane tissues of inflamed joints and reduces the expression of pro-angiogenic factors in sera, including TNF-α, Ang-1, and MMP-9[2]. Cell Assay HFLS-RA (5 × 103 cells/mL) or HUVECs (1 × 104 cells/well) are seeded in 96-well plates and cultured in normal growth medium for 24 h. The cells are then incubated with different Pristimerin concentrations (0, 0.125, 0.25, 0.5 μM). The effects of Pristimerin on HUVECs viability are determined under VEGF-induced conditions. Cell viability is quantified by MTT assay. At 4 h before the end of the culture period, 30 μL of MTT solution (5.0 mg/mL) is added to each well. Cells without Pristimerin or VEGF served as a vehicle control[2]. Animal Admin Rat: Pristimerin is dissolved in DMSO (0.4%) and intraperitoneally injected daily into Male Sprague-Dawley rats in the experimental group (low-dose group, 0.40 mg/kg of body weight; high-dose group, 0.80 mg/kg of body weight) from day 11 to day 24 of immunization. The model group received vehicle (DMSO, 0.4%), and the normal control group received normal saline (NS). Methotrexate (positive control) is suspended in NS and orally administered in the autoimmune phase at an interval of 5 days[2]. References [1]. King AR, et al. Discovery of potent and reversible monoacylglycerol lipase inhibitors. Chem Biol. 2009 Oct 30;16(10):1045-52. [2]. Deng Q, et al. Pristimerin inhibits angiogenesis in adjuvant-induced arthritic rats by suppressing VEGFR2 signaling pathways. Int Immunopharmacol. 2015 Dec;29(2):302-13. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 607.7±55.0 °C at 760 mmHg Melting Point 219.5°C Molecular Formula C30H40O4 Molecular Weight 464.636 Flash Point 195.1±25.0 °C Exact Mass 464.292664 PSA 63.60000 LogP 7.54 Appearance of Characters orange Vapour Pressure 0.0±3.9 mmHg at 25°C Index of Refraction 1.582 InChIKey JFACETXYABVHFD-WXPPGMDDSA-N SMILES COC(=O)C1(C)CCC2(C)CCC3(C)C4=CC=C5C(=CC(=O)C(O)=C5C)C4(C)CCC3(C)C2C1 Storage condition Store at -20°C Water Solubility DMSO: ≥5mg/mL |
| Use of | Pristimerin is a potent and reversible monoacylglycerol lipase (MGL) inhibitor with an IC50 of 93 nM. Properties Articles19 Name Pristimerin Synonym More Synonyms Pristimerin Biological Activity Description Pristimerin is a potent and reversible monoacylglycerol lipase (MGL) inhibitor with an IC50 of 93 nM. Related Catalog Signaling Pathways >> Anti-infection >> Bacterial Natural Products >> Terpenoids and Glycosides Research Areas >> Cancer IC50: 93 nM (MGL)[1] In Vivo Pristimerin inhibits inflammation and tumor angiogenesis. Pristimerin significantly reduces vessel density in synovial membrane tissues of inflamed joints and reduces the expression of pro-angiogenic factors in sera, including TNF-α, Ang-1, and MMP-9[2]. References [1]. King AR, et al. Discovery of potent and reversible monoacylglycerol lipase inhibitors. Chem Biol. 2009 Oct 30;16(10):1045-52. [2]. Deng Q, et al. Pristimerin inhibits angiogenesis in adjuvant-induced arthritic rats by suppressing VEGFR2 signaling pathways. Int Immunopharmacol. 2015 Dec;29(2):302-13. Chemical & Physical Properties Molecular Formula C30H40O4 Exact Mass 464.292664 PSA 63.60000 Appearance of Characters orange Index of Refraction 1.582 InChIKey JFACETXYABVHFD-WXPPGMDDSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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