Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C34H63N5O9 |
| Molecular Weight | 685.8921 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CC(C)C)C(C)C)C(C)C)[C@@H](O)CC(O)=O
InChI
InChIKey=FAXGPCHRFPCXOO-LXTPJMTPSA-N
InChI=1S/C34H63N5O9/c1-17(2)12-23(37-33(47)31(21(9)10)39-34(48)30(20(7)8)38-27(42)14-19(5)6)25(40)15-28(43)35-22(11)32(46)36-24(13-18(3)4)26(41)16-29(44)45/h17-26,30-31,40-41H,12-16H2,1-11H3,(H,35,43)(H,36,46)(H,37,47)(H,38,42)(H,39,48)(H,44,45)/t22-,23-,24-,25-,26-,30-,31-/m0/s1
| Molecular Formula | C34H63N5O9 |
| Molecular Weight | 685.8921 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Pepstatin is a pentapeptide of microbial origin. The peptide inhibits the acid proteases pepsin and cathepsin D and the pressor enzyme renin. Pepstatin was shown to provide long-lasting inhibition (3 to 6 days) of cathepsin D in vivo in non-tumor bearers particularly in spleen, liver, kidney, lung, and heart. Pepstatin may prove useful as "anticachexia" agent by decreasing proteolysis in muscle and other tissues. The in vivo pepstatin and IL-2 treatment decreased the T-cells and increased the natural killer-like LAK precursor cells, possibly also with an increase in its activity, which were further induced by in vitro IL-2 culture to generate an augmented LAK cell activity. This suggests the clinical potential of pepstatin in IL-2-related immunotherapy. In rats injected centrally with the specific cathepsin D inhibitor, pepstatin, the protease activity was inhibited up to 90% in most brain regions.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2714 |
1.0 nM [Ki] | ||
Target ID: CHEMBL2581 |
0.5 nM [Kd] | ||
Target ID: CHEMBL286 |
0.13 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Reconstitution of licensed replication origins on Xenopus sperm nuclei using purified proteins. | 2001 |
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| Generation of choline for acetylcholine synthesis by phospholipase D isoforms. | 2001 |
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| The fission yeast COP9/signalosome is involved in cullin modification by ubiquitin-related Ned8p. | 2001 |
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| Evidence for the involvement of Gi2 in activation of extracellular signal-regulated kinases in hepatocytes. | 2001 |
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| The C-terminal domain of the Bloom syndrome DNA helicase is essential for genomic stability. | 2001 |
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| Pathological apoptosis by xanthurenic acid, a tryptophan metabolite: activation of cell caspases but not cytoskeleton breakdown. | 2001 |
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| Purification and characterization of a novel salt-tolerant protease from Aspergillus sp. FC-10, a soy sauce koji mold. | 2001 Apr |
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| Immune complexes (IC) down-regulate the basal and interferon-gamma-induced expression of MHC class II on human monocytes. | 2001 Aug |
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| Proteolytic loss of bcl-x(L) in FL5.12 Cells undergoing apoptosis induced by MK886. | 2001 Aug 1 |
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| Human muscle protein degradation in vitro by eosinophil cationic protein (ECP). | 2001 Dec |
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| Transient prevention of ethanol-induced gastric lesion by capsaicin due to release of endogenous calcitonin gene-related peptide in rats. | 2001 Jul |
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| Inhibition of proteasome activity strongly affects kiwifruit pollen germination. Involvement of the ubiquitin/proteasome pathway as a major regulator. | 2001 Jul |
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| Aspartyl protease inhibitor pepstatin binds to the presenilins of Alzheimer's disease. | 2001 Jul 27 |
|
| Invasion of ras-transformed breast epithelial cells depends on the proteolytic activity of cysteine and aspartic proteinases. | 2001 May |
|
| Myocardial enzymatic activity of renin and cathepsin D before and after bilateral nephrectomy. | 2001 Nov |
|
| Corpuscles of Stannius secrete renin or an isorenin that regulates cardiovascular function in freshwater North American eels, Anguilla rostrata LeSueur. | 2001 Nov |
|
| Structure of human uropepsin at 2.45 A resolution. | 2001 Nov |
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| Biochemical mechanisms that interact with membrane-associated IL-1 RII (60-kDa decoy) receptors in populations of adherent macrophages and vascular endothelium. | 2001 Oct |
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| Sphingosylphosphorylcholine is an activator of transglutaminase activity in human keratinocytes. | 2001 Oct |
|
| Hemoglobin-degrading, aspartic proteases of blood-feeding parasites: substrate specificity revealed by homology models. | 2001 Oct 19 |
|
| Free-energy analysis of enzyme-inhibitor binding: aspartic proteinase-pepstatin complexes. | 2001 Oct-Dec |
|
| Biochemical alteration of membrane-associated IL-6 RI (80-kDa) in adherent macrophages and vascular endothelium. | 2001 Sep |
|
| Investigation of sequential behavior of carboxyl protease and cysteine protease activities in virus-infected Sf-9 insect cell culture by inhibition assay. | 2001 Sep |
|
| Ab initio molecular dynamics-based assignment of the protonation state of pepstatin A/HIV-1 protease cleavage site. | 2001 Sep 12 |
|
| Molecular model for the binary complex of uropepsin and pepstatin. | 2001 Sep 14 |
|
| Structural and mechanistic insight into the inhibition of aspartic proteases by a slow-tight binding inhibitor from an extremophilic Bacillus sp.: correlation of the kinetic parameters with the inhibitor induced conformational changes. | 2001 Sep 25 |
|
| The farnesyl transferase inhibitor RPR-130401 does not alter radiation susceptibility in human tumor cells with a K-Ras mutation in spite of large changes in ploidy and lamin B distribution. | 2002 |
|
| Ca2+-mediated activation of ERK in hepatocytes by norepinephrine and prostaglandin F2 alpha: role of calmodulin and Src kinases. | 2002 |
|
| Cytokine-stimulated T cells induce macrophage IL-10 production dependent on phosphatidylinositol 3-kinase and p70S6K: implications for rheumatoid arthritis. | 2002 |
|
| A selective plasmin inhibitor, trans-aminomethylcyclohexanecarbonyl-L-(O-picolyl)tyrosine-octylamide (YO-2), induces thymocyte apoptosis. | 2002 Apr 1 |
|
| Lens epithelial cell apoptosis and intracellular Ca2+ increase in the presence of xanthurenic acid. | 2002 Apr 5 |
|
| Phosphorothioate oligonucleotides, suramin and heparin inhibit DNA-dependent protein kinase activity. | 2002 Apr 8 |
|
| Linear non-competitive inhibition of solubilized human gamma-secretase by pepstatin A methylester, L685458, sulfonamides, and benzodiazepines. | 2002 Aug 30 |
|
| Combinatorial diversity of fission yeast SCF ubiquitin ligases by homo- and heterooligomeric assemblies of the F-box proteins Pop1p and Pop2p. | 2002 Aug 7 |
|
| Absorption, transportation and digestion of egg white in quail embryos. | 2002 Feb |
|
| Molecular cloning of an extracellular aspartic proteinase from Rhizopus microsporus and evidence for its expression during infection. | 2002 Feb |
|
| Mxi1 inhibits the proliferation of U87 glioma cells through down-regulation of cyclin B1 gene expression. | 2002 Feb 1 |
|
| Src tyrosine kinase augments taxotere-induced apoptosis through enhanced expression and phosphorylation of Bcl-2. | 2002 Feb 1 |
|
| Lysosomal proteases as potential targets for the induction of apoptotic cell death in human neuroblastomas. | 2002 Feb 20 |
|
| Correlation between beta-amyloid peptide production and human APP-induced neuronal death. | 2002 Jul |
|
| Microinjection of cathepsin d induces caspase-dependent apoptosis in fibroblasts. | 2002 Jul |
|
| Enzymes with gelatinolytic activity can be found in Tityus bahiensis and Tityus serrulatus venoms. | 2002 Jul |
|
| Complexity of agonist- and cyclic AMP-mediated downregulation of the human beta 1-adrenergic receptor: role of internalization, degradation, and mRNA destabilization. | 2002 Jun 25 |
|
| Probing the importance and potential roles of the binding of the PH-domain protein Boi1 to acidic phospholipids. | 2002 Jun 27 |
|
| Decreased apoptotic response of inclusion-cell disease fibroblasts: a consequence of lysosomal enzyme missorting? | 2002 Mar 10 |
|
| Auto-protective redox buffering systems in stimulated macrophages. | 2002 Mar 12 |
|
| Endosomal proteolysis of internalized insulin at the C-terminal region of the B chain by cathepsin D. | 2002 Mar 15 |
|
| The regulation of protein synthesis and translation factors by CD3 and CD28 in human primary T lymphocytes. | 2002 May 17 |
|
| Aspartic proteinase in Dugesia tigrina (Girard) planaria. | 2002 May-Jun |
|
| Endothelial tubulogenesis within fibrin gels specifically requires the activity of membrane-type-matrix metalloproteinases (MT-MMPs). | 2002 Sep 1 |
Patents
Sample Use Guides
Pepstatin A was added to the culture medium at a final concentration of 10-4 M in 0.2% DMSO. Pepstatin A had no effects on growing HeLa cells that were not treated with IFN-gamma. Addition of pepstatin A to the IFN-gamma-treated DHFR-transfected cells inhibited, to some extent, the killing process, as reflected by the elevated values of neutral red dye uptake.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:53:44 GMT 2023
by
admin
on
Fri Dec 15 18:53:44 GMT 2023
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| Record UNII |
V6Y2T27Q1U
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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NCI_THESAURUS |
C783
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V6Y2T27Q1U
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m8530
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7989
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100000082520
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PEPSTATIN
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247-600-0
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CHEMBL296588
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C031375
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DTXSID7046095
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SUB09709MIG
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3316
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26305-03-3
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5478883
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C96295
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272671
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ACTIVE MOIETY |
