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HomeProduct name listPepstatin

Pepstatin

Synonym(s):Pepstatin A;Cathepsin D;Cathepsin D heavy chain;Cathepsin D light chain;CPSD

  • CAS NO.:26305-03-3
  • Empirical Formula: C34H63N5O9
  • Molecular Weight: 685.89
  • MDL number: MFCD00060740
  • EINECS: 247-600-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-01 18:09:03
Pepstatin Structural

What is Pepstatin?

Description

Pepstatin A is a bacterial-derived chemotactic pentapeptide that irreversibly inhibits aspartic proteases, including pepsin, gastricsin, renin, cathepsin E, and cathepsin D. Pepstatin A has been reported to stimulate human neutrophil degranulation (EC50 = 0.75 μM) and super oxide production (EC50 = 1.5 μM). Pepstatin A has been widely used as a research tool in studies of protease mechanisms and biological functions and has been examined as a therapeutic agent for inflammatory conditions including gastric ulcer, edema, and hypertension.

Chemical properties

solid

The Uses of Pepstatin

Pepstatin A are natural, statine-containing peptides that acts as inhibitor of aspartic protease enzymes.

The Uses of Pepstatin

Antiviral;Aspartic proteases irreversible inhibitor

The Uses of Pepstatin

As an aspartic proteases irreversible inhibitor, Pepstain A can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes.

What are the applications of Application

Pepstatin A is an inhibitor of HIV-1 and aspartic proteases and can be used in the study of protease mechanisms

Definition

ChEBI: Pepstatin A is a pentapeptide isolated from Streptomyces testaceus. It is a potent inhibitor of aspartyl proteases. It has a role as a bacterial metabolite and an EC 3.4.23.* (aspartic endopeptidase) inhibitor. It is a pentapeptide and a secondary carboxamide. It is a conjugate acid of a pepstatin A(1-).

General Description

Pepstatin A is a naturally occurring chemotactic peptide and inhibitor of aspartic proteases that was initially isolated from culture filtrates of various Actinomycetes species, with the initial name simply of “pepstatin”. This name was later modified to “pepstatin A” to distinguish the original pepstatin from later derivatives. Pepstatin A notably contains the unusual amino acid 4-amino-hydroxy-6-methylheptanoic acid (AHMHA), which is known also as statine. The amino acid sequence of pepstatin A is N-Isovaleryl-L-Valyl-L-Valyl-AHMHA-L-Alanyl-AHMHA.

Biochem/physiol Actions

Primary Targetaspartic proteases

Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.

Enzyme inhibitor

This naturally occurring statine-containing peptidomimetic (FWfree-acid = 685.90 g/mol; CAS 26305-03-3), also called pepstatin A and isovalerylpepstatin and named systematically as N-(isovaleryl)-L-valyl-L-valyl-statylL-alanyl-statine (where the statyl residue is a (3S,4S)-4-amino-3-hydroxy-6- methylheptanoyl residue and the C-terminal statine is the corresponding acid), is a presumptive transition-state analogue for prototypical aspartate proteinase pepsin (Ki = 46 pM). Pepstatin will also inhibit other carboxy proteinases. The inhibitory effectiveness of statine-containing peptides has been widely exploited by incorporating the statine residue into peptides that otherwise match sequence preferences of the target enzyme’s sub-sites. Because pepstatin has a low solubility in water, it is often dissolved indimethyl sulfoxide, methanol, or ethanol. Note that many derivatives of pepstatin are available, each displaying a different spectrum of inhibitory effects. Pepstatin B and C are the N-(n-caproyl)- and N-(iso-caproyl)- derivatives, respectively. Note: Above a critical concentration of 0.1 mM in low ionic-strength and neutral buffers, pepstatin often polymerizes into filaments that be several micrometers in length and have characteristic diameters ranging between 6 and 12 nm

storage

+4°C

References

1) Merck Index 14:7147 2) Marciniszyn?et al.?(1976)?Mode of inhibition of acid proteases by pepstatin; J. Biol. Chem.,?251?7088 3) Oda (2012)?New families of carboxy peptidases: serine-carboxyl peptidases and glutamic peptidases; J. Biochem.,?151?13 4) Yoshida?et al. (2006)?Pepstatin A, an aspartic proteinase inhibitor, suppresses RANKL-induced osteoclast differentiation; J. Biochem.,?139?583

Properties of Pepstatin

Melting point: 233 °C (dec.)(lit.)
Boiling point: 695.91°C (rough estimate)
alpha  D27 -90.3° (c = 0.288 in methanol)
Density  1.1340 (rough estimate)
refractive index  1.7500 (estimate)
storage temp.  2-8°C
solubility  10% acetic acid in methanol: 1 mg/mL
form  White solid
pka 4.17±0.10(Predicted)
color  Colorless needles
optical activity Optical rotation: -90.0 ± 5° (c = 0.5, MeOH, 20°C).
Water Solubility  It is soluble in 10% (v/v) acetic acid in methanol (9:1 methanol:acetic acid) (1 mg/ml), ethanol (1-2 mg/ml with heat up to 60°C), DMSO (5 mg/ml), methanol (1 mg/ml), and acetic acid. Insoluble in benzene, chloroform, water, 1 M NaOH, and ether.
BRN  2201362
Stability: Stable. Incompatible with strong bases, strong acids.
CAS DataBase Reference 26305-03-3(CAS DataBase Reference)

Safety information for Pepstatin

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Pepstatin

InChIKey JKGWASGTXVCDML-LXTPJMTPSA-N

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