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Phepropeptin D Proteasome Inhibitor

Product#: FNK-16967

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Phepropeptin D Proteasome Inhibitor

Cat No.: FNK-16967
Size: 1mg

Specifications

Code No : 16967
CAS# : 396729-26-3
Size: 1mg
Molecular Formula : C41H58N6O6
Molecular Weight : 730.951
Source : Streptomyces sp. MK600-cF7
Appearance : Powder
Purity : > 98% (HPLC)
Long Term Storage : at - 20 °C
Solubility : Soluble in MeOH, DMSO, DMF
Insoluble in H2O

Application Notes
Phepropeptin D was isolated from cultured broth of Streptomyces sp. MK600-cF7 as an inhibitor of
proteasome (IC50 value 7.8 μg/ml). It showed no inhibition toward proteasomal trypsin-like activity
and α-chymotrypsin from bovine pancreas at 100 μg/ml.

Description
Phepropeptin D is a cyclic hexapeptide that functions as a proteasome inhibitor. It is one of four related compounds (Phepropeptins A, B, C, and D) isolated from Streptomyces sp. MK600-cF7.

Phepropeptin D specifically inhibits the β5 subunit of the proteasome with an IC50 of 10.7 μM, making it the most potent among the phepropeptins. The structure of these cyclic peptides allows them to interact with the proteasome primarily through van der Waals and hydrophobic interactions, rather than forming covalent bonds.

The general structure of phepropeptins, including Phepropeptin D, is cyclo(-L-Leu-D-Phe-L-Pro-L-Phe-D-Leu-L-Val-), with slight variations in two of the amino acid residues among the different phepropeptins. This structural information was determined through NMR analysis and confirmed by comparing the natural compounds with synthesized versions.

As a proteasome inhibitor, Phepropeptin D may have potential applications in research related to cellular functions regulated by the proteasome, which is involved in various important cellular processes. However, it's important to note that while Phepropeptin D shows inhibitory activity against the proteasomal chymotrypsin-like activity, it does not inhibit α-chymotrypsin, indicating some level of specificity in its action.

References
1) Isolation and structural determination of pheptopeptins A, B, C and D, new proteasome inhibitors produced by
Streptomyces sp. Sekizawa R, et al. J Antibiot. 2001 54(11) 874-881.

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Enzyme Inhibitors	Compound Name	Product Code	Link
Serine carboxypeptidase inhibitor	Belactin A	FNK-17736
Tyrosine hydroxylase inhibitor	Oudenone (Potassium Salt)	FNK-16640
Proteasome inhibitor	Phepropeptin A	FNK-16964
	Phepropeptin B	FNK-16965
	Phepropeptin C	FNK-16966
	Phepropeptin D	FNK-16967	Current Link
Angiotensin-converting enzyme (ACE) inhibitor	Foroxymithine	FNK-16968
Biological Activity on Cells and Organisms	Compound Name	Product Code	Link
Inhibition of NO production in macrophage	SF2425 (Sulfate)	FNK-17577
Antitumor effect/Cytotoxicity/Anti-angiogenesis	Bactobolin A (Hydrochloride)	FNK-08465
	Clazamycin A (Hydrochloride)	FNK-16715
	Lavendamycin	FNK-16734
	MC-1	FNK-16479
Immunomodulation/Immunosuppressant effect	Bactobolamine	FNK-15160
Immunomodulation/Immunosuppressant effect	Conagenin	FNK-16969
Siderophore	Foroxymithine	FNK-16968
Antihypertensive effect	Oudenone (Potassium Salt)	FNK-16640
Infectious Disease Prevention	Compound Name	Product Code	Link
Antibacterial activity/Antifungal activity	SF2425 (Sulfate)	FNK-17577
Antibacterial activity/Antifungal activity	Lavendamycin	FNK-16734
Antimalarial	Aplasmomycin (Sodium Salt)	FNK-17683
Bacterial proteins/Inhibition of DNA synthesis	Actinobolin (Sulfate)	FNK-15172
Bacterial proteins/Inhibition of DNA synthesis	Clazamycin A (Hydrochloride)	FNK-16715

Natural macrocyclic compounds from microorganisms:

Structural classification	Compound Name	Property / Biological activity	Link
Bacterial proteins/Inhibition of DNA synthesis	Aplasmomycin (Sodium Salt)	Aplasmomycin A Inhibited the growth of gram-positive bacteria including mycobacteria and showed an antimalarial activity in mice infected with Plasmodium berghei.
Bacterial proteins/Inhibition of DNA synthesis	Migrastatin	Migrastatin inhibited metastasis of human esophageal cancer cells and anchorage-independent growth of human small cell lung carcinoma cells.
Macrolactams	Bisucaberin	Bisucaberin is a siderophore with iron-affinity and induced concentration dependent macrophage-mediated tumor cell lysis.
Cyclic peptides	Bottromycin A2	Bottromycin A2 showed growth inhibitory activity against gram-positive bacteria, MRSA (Methicillin-resistant Staphylococcus aureus), and VRE (Vancomycin-resistant Enterococci).
	Iturin A-2	Iturin A-2 showed the control of damping-off of tomato (a seedling disease) and cytotoxicity to human breast cancer cell line BT-474.
	Plipastatin A1	Plipastatin A1 inhibited phospholipase A2 and induced ISR (induced-systemic-resistance).
	Phepropeptin A	Phepropeptin A inhibited proteasomal chymotrypsin-like activity.
	Phepropeptin B	Phepropeptin B inhibited proteasomal chymotrypsin-like activity.
	Phepropeptin C	Phepropeptin C inhibited proteasomal chymotrypsin-like activity.
	Phepropeptin D	Phepropeptin D inhibited proteasomal chymotrypsin-like activity.	Current Link
Cycloalkenes	Rubratoxin A	Rubratoxin A inhibited protein phosphatase 2A (PP2A) in a competitive manner.