Z-IETD-FMKCaspase-8 inhibitor CAS# 210344-98-2 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 210344-98-2 | SDF | Download SDF |
| PubChem ID | 25108681 | Appearance | Powder |
| Formula | C30H43FN4O11 | M.Wt | 654.68 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 125 mg/mL (190.93 mM; Need ultrasonic) H2O : < 0.1 mg/mL (insoluble) | ||
| Chemical Name | methyl (4S)-5-[[(2S,3R)-1-[[(3S)-5-fluoro-1-methoxy-1,4-dioxopentan-3-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-[[(2S,3S)-3-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-5-oxopentanoate | ||
| SMILES | CCC(C)C(C(=O)NC(CCC(=O)OC)C(=O)NC(C(C)O)C(=O)NC(CC(=O)OC)C(=O)CF)NC(=O)OCC1=CC=CC=C1 | ||
| Standard InChIKey | PHLCQASLWHYEMX-DEKIMQJDSA-N | ||
| Standard InChI | InChI=1S/C30H43FN4O11/c1-6-17(2)25(35-30(43)46-16-19-10-8-7-9-11-19)28(41)32-20(12-13-23(38)44-4)27(40)34-26(18(3)36)29(42)33-21(22(37)15-31)14-24(39)45-5/h7-11,17-18,20-21,25-26,36H,6,12-16H2,1-5H3,(H,32,41)(H,33,42)(H,34,40)(H,35,43)/t17-,18+,20-,21-,25-,26-/m0/s1 | ||
| 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 | Z-IETD-FMK is a specific inhibitor of caspase 8 | |||||
| Targets | caspase 8 | |||||
| Cell experiment [1]: | |
| Cell lines | Purified CD4+ and CD8+ T cells. |
| Preparation method | Limited solubility. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
| Reacting condition | 24 h |
| Applications | T cell proliferation was assayed using [3H]-thymidine incorporation. z-IETD-FMK (100 μM) inhibits T cell proliferation. About 9% of control activated T cells took up PI after activation and in the presence of 100 μM of z-IETD-FMK cell death increases to 23%. In addition, 100 μM z-IETD-FMK decreases the nuclear translocation of p65 in activated T cells. |
| Animal experiment [2]: | |
| Animal models | SHIP1-/- (CD45.1) mice |
| Dosage form | 5 mg/kg three times each week for 3 weeks |
| Application | There is a significant diminution of anatomical pathology in both the small intestine and lungs of Z-IETD-FMK-treated mice compared with vehicle-administered controls. There is also a prominent recovery of viable CD3+ T-cell numbers in small intestine and lung of the Z-IETD-FMK-treated SHIP1-/- hosts, whereas the vehicle-treated SHIP1-/- hosts exhibit the T-cell paucity. |
| Other notes | Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
| References: 1. Lawrence CP, Chow SC. Suppression of human T cell proliferation by the caspase inhibitors, z-VAD-FMK and z-IETD-FMK is independent of their caspase inhibition properties. Toxicol Appl Pharmacol. 2012 Nov 15;265(1):103-12. 2. Park MY, Srivastava N, Sudan R et al. Impaired T-cell survival promotes mucosal inflammatory disease in SHIP1-deficient mice. Mucosal Immunol. 2014 Nov;7(6):1429-39. | |
Z-IETD-FMK Dilution Calculator
Z-IETD-FMK Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.5275 mL | 7.6373 mL | 15.2746 mL | 30.5493 mL | 38.1866 mL |
| 5 mM | 0.3055 mL | 1.5275 mL | 3.0549 mL | 6.1099 mL | 7.6373 mL |
| 10 mM | 0.1527 mL | 0.7637 mL | 1.5275 mL | 3.0549 mL | 3.8187 mL |
| 50 mM | 0.0305 mL | 0.1527 mL | 0.3055 mL | 0.611 mL | 0.7637 mL |
| 100 mM | 0.0153 mL | 0.0764 mL | 0.1527 mL | 0.3055 mL | 0.3819 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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Z-IETD-FMK is an inhibitor of caspase 8 [1].
Z-IETD-FMK inhibits T cell proliferation induced by PHA or anti-CD3 plus anti-CD28 without toxicity of resting T cells. The mechanism of this inhibition of Z-IETD-FMK has been proved not through the effect on IL-2 secretion or IFN-γ production but the decrease of CD25 expression. Experiments show that Z-IETD-FMK has no effect on normal cell growth when there is no activation signal. Z-IETD-FMK has also been found to significantly inhibit NF-κB activation when the concentration is 100μM [1].
Apart from the ability of inhibiting cell proliferation, Z-IETD-FMK is reported to inhibit TRAIL-mediated killing in cells. It protects the procaspases 9, 2, and 3, and protects PARP to a similar extent in both HCT116 and SW480 cells [2].
References:
[1] C.P. Lawrence, S.C. Chow. Suppression of human T cell proliferation by the caspase inhibitors, z-VAD-FMK and z-IETD-FMK is independent of their caspase inhibition properties. Toxicology and Applied Pharmacology. 2012, 265: 103-112.
[2] Nesrin Özören, Kunhong Kim, Timothy F. Burns, et al. The caspase 9 inhibitor Z-LEHD-FMK protects human liver cells while permitting death of cancer cells exposed to tumor necrosis factor-related apoptosis-inducing ligand. Cancer Research. 2000, 60: 6259-6265.
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Suppression of human T cell proliferation by the caspase inhibitors, z-VAD-FMK and z-IETD-FMK is independent of their caspase inhibition properties.[Pubmed:22982538]
Toxicol Appl Pharmacol. 2012 Nov 15;265(1):103-12.
The caspase inhibitors, benzyloxycarbony (Cbz)-l-Val-Ala-Asp (OMe)-fluoromethylketone (z-VAD-FMK) and benzyloxycarbonyl (Cbz)-Ile-Glu (OMe)-Thr-Asp (OMe)-FMK (Z-IETD-FMK) at non-toxic doses were found to be immunosuppressive and inhibit human T cell proliferation induced by mitogens and IL-2 in vitro. Both caspase inhibitors were shown to block NF-kappaB in activated primary T cells, but have little inhibitory effect on the secretion of IL-2 and IFN-gamma during T cell activation. However, the expression of IL-2 receptor alpha-chain (CD25) in activated T cells was inhibited by both z-VAD-FMK and Z-IETD-FMK, whereas the expression of the early activated T cell marker, CD69 was unaffected. During primary T cell activation via the antigen receptor, both caspase-8 and caspase-3 were activated and processed to their respective subunits, but neither caspase inhibitors had any effect on the processing of these two caspases. In sharp contrast both caspase inhibitors readily blocked apoptosis and the activation of caspases during FasL-induced apoptosis in activated primary T cells and Jurkat T cells. Collectively, the results demonstrate that both z-VAD-FMK and Z-IETD-FMK are immunosuppressive in vitro and inhibit T cell proliferation without blocking the processing of caspase-8 and caspase-3.
