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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:
Molecular Weight:
763.88
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
S8758S4939A8171
form

powder

form

powder

form

solid

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

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

solubility

50% acetic acid: 1 mg/mL, clear, colorless

solubility

DMF: 1 mg/mL, clear, colorless to light yellow

solubility

water: 1 mg/mL, clear, colorless

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.

hcodes

pcodes

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)


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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
Turnover of oxidatively damaged nuclear proteins in BV-2 microglial cells is linked to their activation state by poly-ADP-ribose polymerase.
O Ullrich et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 15(8), 1460-1462 (2001-06-02)
T Reinheckel et al.
The Biochemical journal, 335 ( Pt 3), 637-642 (1998-10-31)
Oxidatively modified ferritin is selectively recognized and degraded by the 20S proteasome. Concentrations of hydrogen peroxide (H2O2) higher than 10 micromol/mg of protein are able to prevent proteolytic degradation. Exposure of the protease to high amounts of oxidants (H2O2, peroxynitrite
Izaltina Silva-Jardim et al.
Acta tropica, 91(2), 121-130 (2004-07-06)
Proteasomes are multisubunit proteases that exist universally among eukaryotes. They have multiple proteolytic activities and are believed to have important roles in regulating cell cycle, selective intracellular proteolysis, and antigen presentation. Here we have partially purified Leishmania chagasi proteasome. The
C L Edelstein et al.
Kidney international, 50(4), 1150-1157 (1996-10-01)
The effect of the newly developed, nonpeptide, calpain inhibitor, PD 150606, on hypoxia and ionomycin-induced increases in calpain activity in rat proximal tubules (PT) was determined. PD150606 inhibited both hypoxia and ionomycin-induced calpain activity as determined by the fluorescent substrate

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