Liproxstatin-1A potent ferroptosis inhibitor CAS# 950455-15-9 |
- Ferrostatin-1 (Fer-1)
Catalog No.:BCC2323
CAS No.:347174-05-4
Quality Control & MSDS
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| Cas No. | 950455-15-9 | SDF | Download SDF |
| PubChem ID | 20931416 | Appearance | Powder |
| Formula | C19H21ClN4 | M.Wt | 340.85 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 31 mg/mL (90.95 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | N-[(3-chlorophenyl)methyl]spiro[4H-quinoxaline-3,4'-piperidine]-2-amine | ||
| SMILES | C1CNCCC12C(=NC3=CC=CC=C3N2)NCC4=CC(=CC=C4)Cl | ||
| Standard InChIKey | YAFQFNOUYXZVPZ-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C19H21ClN4/c20-15-5-3-4-14(12-15)13-22-18-19(8-10-21-11-9-19)24-17-7-2-1-6-16(17)23-18/h1-7,12,21,24H,8-11,13H2,(H,22,23) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Liproxstatin-1 is a potent ferroptosis inhibitor, with IC50 of appr 38 nM.In Vitro:Liproxstatin-1 prevents BODIPY 581/591 C11 oxidation in Gpx4−/− cells. Moreover, Liproxstatin-1 does not interfere with other classical types of cell death, such as TNFα-induced apoptosis and H2O2-induced necrosis, and in the bona fide L929 model of TNFα/zvad-induced necroptosis[1]. Liproxstatin-1 has great antiferroptotic activity with EC50 of appr 38 nM. Fer-1 and Liproxstatin-1 are inherently good, but not great, radical-trapping antioxidants, but they are excellent in phospholipid bilayers. Fer-1 (10 μM) and Liproxstatin-1 (10 μM) do not exhibit significant inhibitory activity in the 15-LOX-1 overexpressing cells, and the concentration is almost 1000-fold higher than their EC50s for subverting RSL3-induced ferroptosis in these cells (15 and 27 nM, respectively)[2].In Vivo:Liproxstatin-1 (10 mg/kg, i.p.) suppresses ferroptosis in human cells, Gpx4−/− kidney and in an ischaemia/reperfusion-induced tissue injury model[1]. References: | |||||
Liproxstatin-1 Dilution Calculator
Liproxstatin-1 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9338 mL | 14.6692 mL | 29.3384 mL | 58.6768 mL | 73.346 mL |
| 5 mM | 0.5868 mL | 2.9338 mL | 5.8677 mL | 11.7354 mL | 14.6692 mL |
| 10 mM | 0.2934 mL | 1.4669 mL | 2.9338 mL | 5.8677 mL | 7.3346 mL |
| 50 mM | 0.0587 mL | 0.2934 mL | 0.5868 mL | 1.1735 mL | 1.4669 mL |
| 100 mM | 0.0293 mL | 0.1467 mL | 0.2934 mL | 0.5868 mL | 0.7335 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Liproxstatin-1 is a potent ferroptosis inhibitor.
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Theoretical insights into the mechanism of ferroptosis suppression via inactivation of a lipid peroxide radical by liproxstatin-1.[Pubmed:28489094]
Phys Chem Chem Phys. 2017 May 24;19(20):13153-13159.
Ferroptosis is a recently discovered iron-dependent form of non-apoptotic cell death caused by the accumulation of membrane lipid peroxidation products, which is involved in various pathological conditions of the brain, kidney, liver and heart. A potent spiroquinoxalinamine derivative named Liproxstatin-1 is discovered by high-throughput screening, which is able to suppress ferroptosis via lipid peroxide scavenging in vivo. Thus, molecular simulations, density functional theory (DFT) and variational transition-state theory with a small-curvature tunneling (SCT) coefficient are utilized to elucidate the detailed mechanisms of inactivation of a lipid peroxide radical by Liproxstatin-1. H-atom abstracted from Liproxstatin-1 by a CH3OO radical occurs preferentially at the aromatic amine site (1'-NH) under thermodynamic and frontier molecular orbital analysis. The value of a calculated rate constant at 300 K is up to 6.38 x 10(3) M(-1) S(-1), indicating that the quantum tunneling effect is responsible for making a free radical trapping reaction more efficient by Liproxstatin-1. The production of a Liproxstatin-1 radical is easily regenerated to the active reduced form by ubiquinol in the body to avoid secondary damage by free radicals. A benzene ring and the higher HOMO energy are beneficial to enhance the lipid radical scavenging activity based on the structure-activity relationship study. Overall, the present results provide theoretical insights into the exploration of novel ferroptosis inhibitors.
On the Mechanism of Cytoprotection by Ferrostatin-1 and Liproxstatin-1 and the Role of Lipid Peroxidation in Ferroptotic Cell Death.[Pubmed:28386601]
ACS Cent Sci. 2017 Mar 22;3(3):232-243.
Ferroptosis is a form of regulated necrosis associated with the iron-dependent accumulation of lipid hydroperoxides that may play a key role in the pathogenesis of degenerative diseases in which lipid peroxidation has been implicated. High-throughput screening efforts have identified ferrostatin-1 (Fer-1) and Liproxstatin-1 (Lip-1) as potent inhibitors of ferroptosis - an activity that has been ascribed to their ability to slow the accumulation of lipid hydroperoxides. Herein we demonstrate that this activity likely derives from their reactivity as radical-trapping antioxidants (RTAs) rather than their potency as inhibitors of lipoxygenases. Although inhibited autoxidations of styrene revealed that Fer-1 and Lip-1 react roughly 10-fold more slowly with peroxyl radicals than reactions of alpha-tocopherol (alpha-TOH), they were significantly more reactive than alpha-TOH in phosphatidylcholine lipid bilayers - consistent with the greater potency of Fer-1 and Lip-1 relative to alpha-TOH as inhibitors of ferroptosis. None of Fer-1, Lip-1, and alpha-TOH inhibited human 15-lipoxygenase-1 (15-LOX-1) overexpressed in HEK-293 cells when assayed at concentrations where they inhibited ferroptosis. These results stand in stark contrast to those obtained with a known 15-LOX-1 inhibitor (PD146176), which was able to inhibit the enzyme at concentrations where it was effective in inhibiting ferroptosis. Given the likelihood that Fer-1 and Lip-1 subvert ferroptosis by inhibiting lipid peroxidation as RTAs, we evaluated the antiferroptotic potential of 1,8-tetrahydronaphthyridinols (hereafter THNs): rationally designed radical-trapping antioxidants of unparalleled reactivity. We show for the first time that the inherent reactivity of the THNs translates to cell culture, where lipophilic THNs were similarly effective to Fer-1 and Lip-1 at subverting ferroptosis induced by either pharmacological or genetic inhibition of the hydroperoxide-detoxifying enzyme Gpx4 in mouse fibroblasts, and glutamate-induced death of mouse hippocampal cells. These results demonstrate that potent RTAs subvert ferroptosis and suggest that lipid peroxidation (autoxidation) may play a central role in the process.
