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S6510

Sigma-Aldrich

N-Succinyl-Leu-Leu-Val-Tyr-7-Amido-4-Methylcoumarin

≥90% (HPLC)

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Empirical Formula (Hill Notation):
C40H53N5O10
CAS Number:
94367-21-2
Molecular Weight:
763.88
MDL number:
MFCD00080248
PubChem Substance ID:
24899709
NACRES:
NA.77

Assay

≥90% (HPLC)

form

powder

solubility

0.1% trifluoroacetic acid in acetonitrile: water (3:1): 1 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CC(C)CC(NC(=O)CCC(O)=O)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(Cc1ccc(O)cc1)C(=O)Nc2ccc3C(C)=CC(=O)Oc3c2

InChI

1S/C40H53N5O10/c1-21(2)16-29(42-33(47)14-15-34(48)49)38(52)43-30(17-22(3)4)39(53)45-36(23(5)6)40(54)44-31(19-25-8-11-27(46)12-9-25)37(51)41-26-10-13-28-24(7)18-35(50)55-32(28)20-26/h8-13,18,20-23,29-31,36,46H,14-17,19H2,1-7H3,(H,41,51)(H,42,47)(H,43,52)(H,44,54)(H,45,53)(H,48,49)

InChI key

UVFAEQZFLBGVRM-UHFFFAOYSA-N

Amino Acid Sequence

N-Suc-Leu-Leu-Val-Tyr-7-AMC

Application

N-succinyl-Leu-Leu-Val-Tyr-7-amido-4-methylcoumarin was used in proteasome chymotrypsin-like activity assay in Jurkat cell lysate6 and crude cell lysate of rice.7

Biochem/physiol Actions

In the presence of chymotrypsin-like enzyme activity, the fluorophore, 7-amido-4-methylcoumarin is released from N-succinyl-Leu-Leu-Val-Tyr-7-amido-4-methylcoumarin. The fluorescence obtained is a measure of the enzyme activity.6

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Substrates

Fluorogenic substrate for chymotrypsin-like enzymes, such as cathepsin B and calpain which have been implicated in programmed cell death.

Hazard Statements

H413

Precautionary Statements

P273

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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O Ullrich et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(11), 6223-6228 (1999-05-26)
The 20S proteasome has been shown to be largely responsible for the degradation of oxidatively modified proteins in the cytoplasm. Nuclear proteins are also subject to oxidation, and the nucleus of mammalian cells contains proteasome. In human beings, tumor cells
Madeline R Scott et al.
Molecular psychiatry, 25(4), 776-790 (2019-01-27)
Protein homeostasis is an emerging component of schizophrenia (SZ) pathophysiology. Proteomic alterations in SZ are well-documented and changes in transcript expression are frequently not associated with changes in protein expression in SZ brain. The underlying mechanism driving these changes remains
S Glockzin et al.
The Journal of biological chemistry, 274(28), 19581-19586 (1999-07-03)
The ubiquitin/proteasome pathway mediates the degradation of many short-lived proteins that are critically involved in the regulation of cell proliferation and cell death, including the tumor suppressor protein p53. Accumulation of p53 and induction of apoptosis in RAW 264.7 macrophages
M Kroll et al.
Chemistry & biology, 6(10), 689-698 (1999-10-06)
The fungal epipolythiodioxopiperazine metabolite gliotoxin has a variety of toxic effects such as suppression of antigen processing, induction of macrophagocytic apoptosis and inhibition of transcription factor NF-kappaB activation. How gliotoxin acts remains poorly understood except that the molecule's characteristic disulfide
D E Atsma et al.
Circulation research, 76(6), 1071-1078 (1995-06-01)
Calcium-activated neutral protease (CANP), also known as calpain, has been implicated in the development of cell death in ischemic hearts. CANP is thought to be activated by the calcium overload that develops during ischemia. We studied the involvement of CANP
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