Epoxomicin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01701 |
| CAS | 134381-21-8 |
| Molecular Weight | 554.72 |
| Molecular Formula | C28H50N4O7 |
| Purity | >98% |
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Description
Epoxomicin is a naturally occurring selective proteasome inhibitor with anti-inflammatory activity.
Specification
| Synonyms | BU-4061T |
| Storage | -20°C |
| IUPAC Name | (2S,3S)-2-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-N-[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]-3-methylpentanamide |
| Canonical SMILES | CCC(C)C(C(=O)NC(C(C)O)C(=O)NC(CC(C)C)C(=O)C1(CO1)C)NC(=O)C(C(C)CC)N(C)C(=O)C |
| InChI | InChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1 |
| InChI Key | DOGIDQKFVLKMLQ-JTHVHQAWSA-N |
Properties
| Appearance | White to Off-White Solid |
| Application | Proteasome Inhibitors |
| Boiling Point | 739.2°C at 760 mmHg |
| Melting Point | 107-109°C |
| Density | 1.117 g/cm3 |
| Solubility | Soluble in Methanol, Ethyl acetate, DMSO |
Reference Reading
1.Morphological Changes within the Rat Lateral Ventricle after the Administration of Proteasome Inhibitors.
Wójcik S1, Spodnik JH1, Dziewiątkowski J1, Spodnik E1, Moryś J1. PLoS One. 2015 Oct 19;10(10):e0140536. doi: 10.1371/journal.pone.0140536. eCollection 2015.
The broad variety of substances that inhibit the action of the ubiquitin-proteasome system (UPS)-known as proteasome inhibitors-have been used extensively in previous studies, and they are currently frequently proposed as a novel form of cancer treatment and as a protective factor in intracerebral hemorrhage treatment. The experimental data on the safest route of proteasome inhibitor administration, their associated side effects, and the possible ways of minimizing these effects have recently become a very important topic. The aim of our present study was to determine the effects of administering of MG-132, lactacystin and epoxomicin, compounds belonging to three different classes of proteasome inhibitors, on the ependymal walls of the lateral ventricle. Observations were made 2 and 8 weeks after the intraventricular administration of the studied substances dissolved in dimethyl sulfoxide (DMSO) into the lateral ventricle of adult Wistar rats.
2.Reduced Levels of Proteasome Products in a Mouse Striatal Cell Model of Huntington's Disease.
Dasgupta S1, Fishman MA1, Mahallati H1, Castro LM2, Tashima AK3, Ferro ES4, Fricker LD1,5. PLoS One. 2015 Dec 21;10(12):e0145333. doi: 10.1371/journal.pone.0145333. eCollection 2015.
Huntington's disease is the result of a long polyglutamine tract in the gene encoding huntingtin protein, which in turn causes a large number of cellular changes and ultimately results in neurodegeneration of striatal neurons. Although many theories have been proposed, the precise mechanism by which the polyglutamine expansion causes cellular changes is not certain. Some evidence supports the hypothesis that the long polyglutamine tract inhibits the proteasome, a multiprotein complex involved in protein degradation. However, other studies report normal proteasome function in cells expressing long polyglutamine tracts. The controversy may be due to the methods used to examine proteasome activity in each of the previous studies. In the present study, we measured proteasome function by examining levels of endogenous peptides that are products of proteasome cleavage. Peptide levels were compared among mouse striatal cell lines expressing either 7 glutamines (STHdhQ7/Q7) or 111 glutamines in the huntingtin protein, either heterozygous (STHdhQ7/Q111) or homozygous (STHdhQ111/Q111).
3.Regulation of Sperm Capacitation by the 26S Proteasome: An Emerging New Paradigm in Spermatology.
Kerns K, Morales P, Sutovsky P. Biol Reprod. 2016 Apr 6. pii: biolreprod.115.136622. [Epub ahead of print]
The ubiquitin proteasome system (UPS) participates in many biological processes ranging from cell cycle and antigen processing to cellular defense and signaling. Work of the last decade has made it evident that the UPS is involved in many sperm-related processes leading up to and as part of fertilization. The current knowledge of UPS involvement and changes during sperm capacitation is reviewed together with a list of known proteasome-associated sperm proteins is included and a discussion of the relationships between these proteins and the proteasome. Proteasomal inhibitors such as MG-132 and epoxomicin significantly alter capacitation and prevent acrosome reaction. The 26S proteasome degrades AKAP3, an A-kinase anchoring protein, partially regulating the release of protein-kinase A (PKA), a vital component necessary for the steps leading up to capacitation. Further, changes occur in 20S core subunit localization and abundance throughout capacitation.
4.The regulation of glucose on milk fat synthesis is mediated by the ubiquitin-proteasome system in bovine mammary epithelial cells.
Liu L1, Jiang L1, Ding XD1, Liu JF1, Zhang Q2. Biochem Biophys Res Commun. 2015 Sep 11;465(1):59-63. doi: 10.1016/j.bbrc.2015.07.129. Epub 2015 Jul 29.
Glucose as one of the nutrition factors plays a vital role in the regulation of milk fat synthesis. Ubiquitin-proteasome system (UPS) is a vital proteolytic pathway in all eukaryotic cells through timely marking, recognizing and degrading the poly-ubiquitinated protein substrates. Previous studies indicated that UPS plays a considerable role in controlling the triglyceride (TG) synthesis. Therefore, the aim of this study is to confirm the link between high-glucose and UPS and its regulation mechanism on milk fat synthesis in BMEC (bovine mammary epithelial cells). We incubated BMEC with normal (17.5 mm/L) and high-glucose (25 mm/L) with and without proteasome inhibitor epoxomicin and found that, compared with the control (normal glucose and without proteasome inhibitor), both high-glucose concentration and proteasome inhibitor epoxomicin could increase the accumulation of TG and poly-ubiquitinated proteins, and reduce significantly three proteasome activities (chymotrypsin-like, caspase-like, and trypsin-like).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
