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Key Documents

C1230

Sigma-Aldrich

Z-Ile-Glu(O-ME)-Thr-Asp(O-Me) fluoromethyl ketone

≥90% (TLC), powder

Synonym(s):

Z-IETD-FMK

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About This Item

Empirical Formula (Hill Notation):
C30H43FN4O11
CAS Number:
Molecular Weight:
654.68
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

Assay

≥90% (TLC)

form

powder

solubility

methanol: 10 mg/mL
DMSO: 20 mM, clear, colorless to light yellow

shipped in

dry ice

storage temp.

−20°C

SMILES string

CC[C@H](C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)O)C(=O)N[C@@H](CC(O)=O)C(=O)CF

InChI

1S/C28H39FN4O11/c1-4-15(2)23(33-28(43)44-14-17-8-6-5-7-9-17)26(41)30-18(10-11-21(36)37)25(40)32-24(16(3)34)27(42)31-19(12-22(38)39)20(35)13-29/h5-9,15-16,18-19,23-24,34H,4,10-14H2,1-3H3,(H,30,41)(H,31,42)(H,32,40)(H,33,43)(H,36,37)(H,38,39)/t15-,16+,18-,19-,23-,24-/m0/s1

InChI key

CTXDBLYOEUERAT-VUVYEONESA-N

Amino Acid Sequence

Z-Ile-Glu-OMe-Thr-Asp-OMe-FMK

Application

Z-Ile-Glu(O-ME)-Thr-Asp(O-Me) fluoromethyl ketone (Z-IETD-FMK) has been used as a caspase-8 inhibitor:
  • to study the activity of caspase-8 in porcine kidney cells
  • to study its effects on porcine parvovirus (PPV)-induced caspase-3 activity in steroidogenic luteal cells
  • to study its effects on retinal ganglion and astroglia in rat eyes

Biochem/physiol Actions

Z-Ile-Glu(O-ME)-Thr-Asp(O-Me) fluoromethyl ketone (Z-IETD-FMK) is an irreversible and cell-permeable caspase-8 inhibitor.

Features and Benefits

This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yanjie Kong et al.
International journal of cancer, 145(5), 1371-1381 (2019-02-27)
The Cullin 7 (CUL7) gene encodes a member of the cullin family of E3 ubiquitin ligases. Accumulated evidence suggests that CUL7 is oncogenic. However, the mechanism by which CUL7 improves cancer cell survival has not been fully elucidated. Here, we
Lina Hu et al.
Journal of the American Heart Association, 8(24), e005886-e005886 (2019-12-17)
Background Although apoptosis and cell proliferation have been extensively investigated in atherosclerosis and restenosis postinjury, the communication between these 2 cellular events has not been evaluated. Here, we report an inextricable communicative link between apoptosis and smooth muscle cell proliferation
Xiangjun Yang et al.
Neurobiology of disease, 150, 105258-105258 (2021-01-13)
Retinal ganglion cells (RGCs) expanding from the retina to the brain are primary victims of neurodegeneration in glaucoma, a leading cause of blindness; however, the neighboring astroglia survive the glaucoma-related stress and promote neuroinflammation. In light of diverse functions of
Melissa García-Caballero et al.
Frontiers in pharmacology, 8, 802-802 (2017-11-23)
Evasion of apoptosis is a hallmark of cancer especially relevant in the development and the appearance of leukemia drug resistance mechanisms. The development of new drugs that could trigger apoptosis in aggressive hematological malignancies, such as AML and CML, may
Georg Bauer
Mechanisms of ageing and development, 172, 59-77 (2017-11-16)
Tumor cells express NADPH oxidase-1 (NOX1) in their membrane and control NOX1-based intercellular reactive oxygen and nitrogen species (ROS/RNS)-dependent apoptosis-inducing signaling through membrane-associated catalase and superoxide dismutase. of tumor cells with high concentrations of H2O2, peroxnitrite, HOCl, or increasing the

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