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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| Serine carboxypeptidase inhibitor | Belactin A | FNK-17736 |  |
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| Tyrosine hydroxylase inhibitor | Oudenone (Potassium Salt) | FNK-16640 | |
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| Proteasome inhibitor | Phepropeptin A | FNK-16964 | |
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| Phepropeptin B | FNK-16965 | |
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| Phepropeptin C | FNK-16966 | |
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| Phepropeptin D | FNK-16967 | Current Link | |||||
| Angiotensin-converting enzyme (ACE) inhibitor | Foroxymithine | FNK-16968 | |
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| Biological Activity on Cells and Organisms | Compound Name | Product Code | Link | ||||
| Inhibition of NO production in macrophage | SF2425 (Sulfate) | FNK-17577 | |
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| Antitumor effect/Cytotoxicity/Anti-angiogenesis | Bactobolin A (Hydrochloride) | FNK-08465 | |
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| Clazamycin A (Hydrochloride) | FNK-16715 | |
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| Lavendamycin | FNK-16734 | |
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| MC-1 | FNK-16479 | |
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| Immunomodulation/Immunosuppressant effect | Bactobolamine | FNK-15160 | |
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| Conagenin | FNK-16969 | |
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| Siderophore | Foroxymithine | FNK-16968 | |
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| Antihypertensive effect | Oudenone (Potassium Salt) | FNK-16640 | |
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| Infectious Disease Prevention | Compound Name | Product Code | Link | ||||
| Antibacterial activity/Antifungal activity | SF2425 (Sulfate) | FNK-17577 | |
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| Lavendamycin | FNK-16734 | |
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| Antimalarial | Aplasmomycin (Sodium Salt) | FNK-17683 | |
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| Bacterial proteins/Inhibition of DNA synthesis | Actinobolin (Sulfate) | FNK-15172 | |
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| Clazamycin A (Hydrochloride) | FNK-16715 | |
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Natural macrocyclic compounds from microorganisms:
| Structural classification | Compound Name | Chemical Structure | 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. | |
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| Migrastatin |  |
Migrastatin inhibited metastasis of human esophageal cancer cells and anchorage-independent growth of human small cell lung carcinoma cells. | |
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| 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. | |
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| Plipastatin A1 |  |
Plipastatin A1 inhibited phospholipase A2 and induced ISR (induced-systemic-resistance). | |
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| Phepropeptin A |  |
Phepropeptin A inhibited proteasomal chymotrypsin-like activity. | |
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| Phepropeptin B |  |
Phepropeptin B inhibited proteasomal chymotrypsin-like activity. | |
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| Phepropeptin C |  |
Phepropeptin C inhibited proteasomal chymotrypsin-like activity. | |
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| 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. | |
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