Epoxomicin__Proteasome inhibitor Olmutinib
Product Name
Epoxomicin
Description
Proteasome inhibitor
Purity
>95%
CAS No.
134381-21-8
Molecular Formula
C28H50N4O7
Molecular Weight
554.7
Storage Temperature
-20ºC
Shipping Temperature
Shipped Ambient
Product Type
Inhibitor
Solubility
Soluble in DMSO (15 mg/ml) or dichloromethane:methanol (9:1); insoluble in water.
Source
Synthetic
Appearance
White solid
SMILES
C@@H(CC)(C)C@@H(C(Nemail protected(C(NC@@H(C@@H(C)O)C(=O)Nemail protected(C(=O)NCC(=O)C@1(C)OC1)CC(C)C)=O)email protected(CC)C)=O)N(C)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
InChIKey
DOGIDQKFVLKMLQ-JTHVHQAWSA-N
Safety Phrases
Classification: Caution. Substance not yet fully tested.
Safety Phrases:
S22 – Do not breathe dust
S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection
S24/25 – Avoid contact with skin and eyes
Cite This Product
Epoxomicin (StressMarq Biosciences Inc., Victoria BC CANADA, Catalog # SIH-388)
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/19123158
Alternative Names
N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-(1S)-3-methyl-1-(2R)-2-methyloxiranylcarbonylbutyl-L-threoninamide
Research Areas
Cell Signaling
PubChem ID
11226684
Scientific Background
Epoxomicin is a cell permeable, potent and selective proteasome inhibitor originally isolated from Actinomycetes strain based on its potent in vivo antitumor activity. It is a more potent inhibitor of the chymotrypsin-like activity of the proteasome than lactacystin. Epoxomicin also blocks trypsin-like and PGPH activities of the proteasome and regulates antigen presentation at non-toxic doses. It effectively inhibits NF-κB activation in vitro and potently blocks inflammation in vivo in the mouse ear edema assay. The ubiquitin-proteasome system (UPS) and autophagy serve as two complementary, reciprocally regulated protein degradation systems, thus inhibition of UPS by Epoxomicin activates autophagy.
References
1. F. Yang, et al. (2009) Neurosci. Lett. 454: 203.
2. K. Ohkawa, et al. (2004) Int. J. Oncol. 24: 425.
3. K. Schwarz, et al. (2000) J. Immunol. 164: 6147.
4. L. Meng, et al. (1999) PNAS. 96: 10403.
5. K.B. Kim, et al. (1999) Bioorg. Med. Chem. Lett. 9: 3335.
6. N. Sin, et al. (1999) Bioorg. Med. Chem. Lett. 9: 2283.
7. M. Hanada, et al. (1992) J. Antibiot. (Tokyo) 45: 1746.
Proteasome inhibitor
Safety Phrases:
S22 – Do not breathe dust
S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection
S24/25 – Avoid contact with skin and eyes
2. K. Ohkawa, et al. (2004) Int. J. Oncol. 24: 425.
3. K. Schwarz, et al. (2000) J. Immunol. 164: 6147.
4. L. Meng, et al. (1999) PNAS. 96: 10403.
5. K.B. Kim, et al. (1999) Bioorg. Med. Chem. Lett. 9: 3335.
6. N. Sin, et al. (1999) Bioorg. Med. Chem. Lett. 9: 2283.
7. M. Hanada, et al. (1992) J. Antibiot. (Tokyo) 45: 1746.