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Z-VAD(OMe)-FMK

Catalog No. T6013   CAS 187389-52-2
Synonyms: Z-VAD-FMK, Z-Val-Ala-Asp(OMe)-FMK

Z-VAD(OMe)-FMK (Z-Val-Ala-Asp(OMe)-FMK) is a cell-permeable and irreversible pan-caspase inhibitor. It inhibits cleavage of PARP, preventing apoptosis when used at 10-50 μM.

All products from TargetMol are for Research Use Only. Not for Human or Veterinary or Therapeutic Use.
Z-VAD(OMe)-FMK Chemical Structure
Z-VAD(OMe)-FMK, CAS 187389-52-2
Pack Size Availability Price/USD Quantity
1 mg In stock
$ 52.00
$ 41.60
2 mg In stock
$ 80.00
$ 64.00
5 mg In stock
$ 147.00
$ 117.60
10 mg In stock
$ 247.00
$ 197.60
25 mg In stock
$ 368.00
$ 294.40
50 mg In stock
$ 497.00
$ 397.60
100 mg In stock
$ 693.00
$ 554.40
200 mg In stock
$ 982.00
$ 785.60
1 mL * 10 mM (in DMSO) In stock
$ 148.00
$ 118.40
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Purity: 99.41%
Purity: 98%
Purity: 95.92%
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Biological Description
Chemical Properties
Storage & Solubility Information
Description Z-VAD(OMe)-FMK (Z-Val-Ala-Asp(OMe)-FMK) is a cell-permeable and irreversible pan-caspase inhibitor. It inhibits cleavage of PARP, preventing apoptosis when used at 10-50 μM.
In vitro Z-VAD.FMK was a poor inhibitor of PARP protease activity in cell lysates. Z-VAD.FMK (10 μM) is a potent inhibitor of Fas-induced apoptosis [1]. CPP32 is activated during camptothecin-induced apoptosis, and Z-VAD-fmk blocks all features of apoptosis. However, Z-VAD-fmk is inactive in a cell-free system reconstituted from nuclei of untreated HL60 cells and cytosol from camptothecin-treated cells [2]. z-VAD-FMK suppressed TUNEL and caspase-3 staining in endothelial cells, decreased caspase-3 activation, reduced BBB permeability, relieved vasospasm, abolished brain edema, and improved neurological outcome [3].
In vivo LPS (30 mg/kg) was administered intravenously to Institute for Cancer Research mice. Z-VAD.fmk was injected before and after the administration of LPS. The injection of Z-VAD.fmk suppressed the caspase-3 activity in lung tissues and significantly decreased the number of terminal dUTP nick-end labeling-positive cells [4]. Treatment with the specific caspase inhibitor Z-VAD-FMK (i.p.) prior to heat-killed group B streptococcus (i.p.) delayed but did not prevent preterm delivery [5].
Cell Research The human monocytic tumour cell line, THP.1 and the leukaemic T-cell line, Jurkat (clone E-6) were maintained in RPMI 1640 supplemented with 10% (v/v) heat-inactivated fetal calf serum, 100 units/ml penicillin and 100 μg/ml streptomycin in an atmosphere of 5% CO2 in air at 37 °C. The cells were maintained in logarithmic growth phase by routine passage every 2–3 days. To induce apoptosis in THP.1 cells, 2×10^6 cells/ml were incubated either alone or in the presence of cycloheximide (25 μM) and TLCK (100 μM) as previously described. In order to assess the possible effects of various ICE-like protease inhibitors, THP.1 cells were also pretreated for 1 h with Z-VAD.FMK (10 μM), Ac-DEVD-CHO (20 μM) and Ac-YVAD-CHO (20 μM) before being exposed to the apoptotic stimulus. To induce apoptosis in Jurkat cells, 2×10^6 cells/ml were stimulated with 200 ng/ml anti-human Fas as described previously [1].
Animal Research Mice used in this study were 5- to 6-week-old (20 to 22 g) ICR males. Mice were injected with 30 mg/kg LPS from E. coli serotype O111:B4 through the tail vein. Z-VAD.fmk was dissolved at 2 mg/ml in 1% dimethyl sulfoxide in sterile saline, and administered to mice by the method of Rodriguez et al. A single intravenous injection of Z-VAD.fmk (0.25 mg) was made 15 minutes before LPS injection, followed by three intravenous injections of Z-VAD.fmk (0.1 mg each) per hour. Control mice were injected with the same volume of 1% DMSO in sterile saline [4].
Synonyms Z-VAD-FMK, Z-Val-Ala-Asp(OMe)-FMK
Molecular Weight 467.49
Formula C22H30FN3O7
CAS No. 187389-52-2

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

H2O: <1 mg/mL

Ethanol: <1 mg/mL

DMSO: 93 mg/mL (198.93 mM)

TargetMolReferences and Literature

1. Slee EA, et al. Benzyloxycarbonyl-Val-Ala-Asp (OMe) fluoromethylketone (Z-VAD.FMK) inhibits apoptosis by blocking the processing of CPP32. Biochem J. 1996 Apr 1;315 ( Pt 1):21-4. 2. Shimizu T, Pommier Y. Camptothecin-induced apoptosis in p53-null human leukemia HL60 cells and their isolated nuclei: effects of the protease inhibitors Z-VAD-fmk and dichloroisocoumarin suggest an involvement of both caspases and serine proteases. Leukemia. 1997 Aug;11(8):1238-44. 3. Park S, et al. Neurovascular protection reduces early brain injury after subarachnoid hemorrhage. Stroke. 2004 Oct;35(10):2412-7. 4. Kawasaki M, et al. Protection from lethal apoptosis in lipopolysaccharide-induced acute lung injury in mice by a caspaseinhibitor. Am J Pathol. 2000 Aug;157(2):597-603. 5. Equils O, et al. Pretreatment with pancaspase inhibitor (Z-VAD-FMK) delays but does not prevent intraperitoneal heat-killed group B Streptococcus-induced preterm delivery in a pregnant mouse model. Infect Dis Obstet Gynecol. 2009;2009:749432. 6. Lu Z, Zhang G, Zhang Y, et al. Isoalantolactone induces apoptosis through reactive oxygen species-dependent upregulation of death receptor 5 in human esophageal cancer cells[J]. Toxicology and applied pharmacology. 2018, 352: 46-58. 7. Shao C S, Zhou X H, Zheng X X, et al. Ganoderic acid D induces synergistic autophagic cell death except for apoptosis in ESCC cells[J]. Journal of Ethnopharmacology. 2020, 262: 113213. 8. Wu X, Luo Q, Zhao P, et al. JOSD1 inhibits mitochondrial apoptotic signalling to drive acquired chemoresistance in gynaecological cancer by stabilizing MCL1[J]. Cell Death & Differentiation. 2020, 27(1): 55-70. 9. Zhu Q, Ding L, Zi Z, et al. Viral-Mediated AURKB Cleavage Promotes Cell Segregation and Tumorigenesis[J]. Cell reports. 2019 Mar 26;26(13):3657-3671.e5. 10. Wang S, Li F, Qiao R, et al. Arginine-Rich Manganese Silicate Nanobubbles as a Ferroptosis-Inducing Agent for Tumor-Targeted Theranostics[J]. ACS nano. 2018 Dec 26;12(12):12380-12392.

TargetMolCitations

1. Bi G, Liang J, Shan G, et al.Retinol saturase mediates retinoid metabolism to impair a ferroptosis defense system in cancer cells.Cancer Research.2023: CAN-22-3977. 2. Li Y, Yang W, Zheng Y, et al.Targeting fatty acid synthase modulates sensitivity of hepatocellular carcinoma to sorafenib via ferroptosis.Journal of Experimental & Clinical Cancer Research.2023, 42(1): 1-19. 3. Quan D, Hou R, Shao H, et al.Structure-Based Design of Novel Alkynyl Thio-Benzoxazepinone Receptor-Interacting Protein Kinase-1 Inhibitors: Extending the Chemical Space from the Allosteric to ATP Binding Pockets.Journal of Medicinal Chemistry.2023 4. Zhang X, Han Q, Hou R, et al.Targeting Receptor-Interacting Protein Kinase 1 by Novel Benzothiazole Derivatives: Treatment of Acute Lung Injury through the Necroptosis Pathway.Journal of Medicinal Chemistry.2023 5. Yang W, Sun X, Liu S, et al.TLR8 agonist Motolimod-induced inflammatory death for treatment of acute myeloid leukemia.Biomedicine & Pharmacotherapy.2023, 163: 114759. 6. Cui N, Li S, Zhang Y, et al.Discovery of Sibiriline derivatives as novel receptor-interacting protein kinase 1 inhibitors.European Journal of Medicinal Chemistry.2023: 115190. 7. Urade R, Chang W T, Ko C C, et al.A fluorene derivative inhibits human hepatocellular carcinoma cells by ROS-mediated apoptosis, anoikis and autophagy.Life Sciences.2023: 121835. 8. Xu Y, Liang C, Zhang W, et al.Profiling of the chemical space on the phenyl group of substituted benzothiazole RIPK3 inhibitors.Bioorganic Chemistry.2022: 106339. 9. Tang J, Wu Y, Zhao W, et al.Scaffold hopping derived novel benzoxazepinone RIPK1 inhibitors as anti-necroptosis agents.Bioorganic & Medicinal Chemistry.2023: 117385. 10. Yang D L, Zhang Y, He L, et al. Demethylzeylasteral (T-96) Initiates Extrinsic Apoptosis Against Prostate Cancer cells by Inducing ROS-Mediated ER Stress and Suppressing Autophagic Flux. Biological Research. 2021, 54(1): 1-14.
11. Zhu Q, Ding L, Zi Z, et al. Viral-Mediated AURKB Cleavage Promotes Cell Segregation and Tumorigenesis. Cell Reports. 2019 Mar 26;26(13):3657-3671.e5 12. Wang S, Li F, Qiao R, et al. Arginine-Rich Manganese Silicate Nanobubbles as a Ferroptosis-Inducing Agent for Tumor-Targeted Theranostics. ACS nano. 2018 Dec 26;12(12):12380-12392. 13. Xia Z, Zhang X, Liu P, et al. GNA13 regulates BCL2 expression and the sensitivity of GCB-DLBCL cells to BCL2 inhibitors in a palmitoylation-dependent manner. Cell Death & Disease. 2021, 12(1): 1-11. 14. Liao X, Fan Y, Hou J, et al. Identification of Chaetocin as a Potent non-ROS-mediated Anticancer Drug Candidate for Gastric Cancer. Journal of Cancer. 2019, 10(16): 3678-3690. 15. Ouyang S, Li H, Lou L, et al. Inhibition of STAT3-ferroptosis negative regulatory axis suppresses tumor growth and alleviates chemoresistance in gastric cancer. Redox Biology. 2022: 102317 16. Wu X, Lu Y, Qin X. Combination of Compound Kushen Injection and cisplatin shows synergistic antitumor activity in p53-R273H/P309S mutant colorectal cancer cells through inducing apoptosis. Journal of Ethnopharmacology. 2021: 114690. 17. Wu Q, Zhang M, Wen Y, et al. Identifying chronic alcoholism drug disulfiram as a potent DJ-1 inhibitor for cancer therapeutics. European Journal of Pharmacology. 2022: 175035 18. Shao C S, Zhou X H, Zheng X X, et al. Ganoderic acid D induces synergistic autophagic cell death except for apoptosis in ESCC cells. Journal of Ethnopharmacology. 2020, 262: 113213. 19. Hussain M, Lu Y, Tariq M, et al. A small-molecule Skp1 inhibitor elicits cell death by p53-dependent mechanism. Iscience. 2022, 25(7): 104591. 20. Wen L, Guo R, You L, et al. Major triterpenoids in Chinese hawthorn “Crataegus pinnatifida” and their effects on cell proliferation and apoptosis induction in MDA-MB-231 cancer cells. Food and chemical toxicology. 2017 Feb;100:149-160. 21. Zhu L, Han Z, He Y, et al. Caspase-1-Dependent Pyroptosis Mediates Adjuvant Activity of Platycodin D as an Adjuvant for Intramuscular Vaccines. Cells. 2022, 11(1): 134. 22. Lu Z, Zhang G, Zhang Y, et al. Isoalantolactone induces apoptosis through reactive oxygen species-dependent upregulation of death receptor 5 in human esophageal cancer cells. Toxicology and applied pharmacology. 2018, 352: 46-58. 23. Zhang P, Zhang J, Quan H, et al. Effects of butein on human osteosarcoma cell proliferation, apoptosis, and autophagy through oxidative stress. Human & Experimental Toxicology. 2022, 41: 09603271221074346. 24. Shan G, Bi G, Zhao G, et al.Inhibition of PKA/CREB1 pathway confers sensitivity to ferroptosis in non-small cell lung cancer.Respiratory Research.2023, 24(1): 1-15. 25. Wang Y, Zhang B, Liu S, et al.The traditional herb Sargentodoxa cuneata alleviates DSS-induced colitis by attenuating epithelial barrier damage via blocking necroptotic signaling.Journal of Ethnopharmacology.2023: 117373. 26. Heber N, Kuhn B J, Strobel T D, et al.The impact of cycling hypoxia on the phenotype of HPV‐positive cervical cancer cells.Journal of Medical Virology.2023, 95(12): e29280. 27. Xin Y F, Dai P, Shao H, et al.Discovery of novel biaryl benzoxazepinones as dual-mode receptor-interacting protein kinase-1 (RIPK1) inhibitors.Bioorganic & Medicinal Chemistry.2024: 117611.
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Related compound libraries

This product is contained In the following compound libraries:
Preclinical Compound Library Covalent Inhibitor Library Bioactive Compound Library Protease Inhibitor Library Anti-Neurodegenerative Disease Compound Library Anti-Cancer Compound Library Peptide Compound Library NO PAINS Compound Library Fluorochemical Library Pyroptosis Compound Library

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Keywords

Z-VAD(OMe)-FMK 187389-52-2 Apoptosis Proteases/Proteasome Caspase Inhibitor Z-VAD-FMK ZVAD(OMe)FMK inhibit Z-Val-Ala-Asp(OMe)-FMK Z VAD(OMe) FMK inhibitor

 

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