Molecular structure of Epoxomicin, CAS Number: 134381-21-8
Epoxomicin (CAS 134381-21-8)
See product citations (19)
Application:
Epoxomicin is a potent chymotrypsin-like proteasome inhibitor (CTRL) which has also been used as an inhibitor in pheochromocytoma PC12 cells
CAS Number:
134381-21-8
Purity:
≥95%
Molecular Weight:
554.70
Molecular Formula:
C28H50N4O7
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
QUICK LINKS
Ordering Information
Product Citations
Description
Technical Information
Safety Information
SDS & Certificate of Analysis
Epoxomicin is a potent proteasome inhibitor. Epoxomicin primarily inhibits the activity of CTRL(chymotrypsin-like proteasome). The novel alpha-epoxy ketone moiety of Epoxomicin forms covalent bonds with residues in particular catalytic subunits of the enzyme, disabling activity. The trypsin-like and peptidyl-glutamyl peptide hydrolyzing behavior of the proteasome were both inhibited by Epoxomicin as well (at 100 and 1,000-fold slower rates, respectively). Bone formation is heavily regulated by the ubiquitin-proteasome pathway, and Epoxomicin was shown to increase both bone volume and bone formation rates in rodents. Another study demonstrates that exposure to Epoxomicin and other proteasome inhibitors leads to dopaminergic cell death, producing a model of Parkinson′s disease in vivo. Epoxomicin is an inhibitor of 20S Proteasome.
Epoxomicin (CAS 134381-21-8) References
- Total synthesis of the potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology. | Sin, N., et al. 1999. Bioorg Med Chem Lett. 9: 2283-8. PMID: 10465562
- Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity. | Meng, L., et al. 1999. Proc Natl Acad Sci U S A. 96: 10403-8. PMID: 10468620
- The selective proteasome inhibitors lactacystin and epoxomicin can be used to either up- or down-regulate antigen presentation at nontoxic doses. | Schwarz, K., et al. 2000. J Immunol. 164: 6147-57. PMID: 10843664
- Cells adapted to the proteasome inhibitor 4-hydroxy- 5-iodo-3-nitrophenylacetyl-Leu-Leu-leucinal-vinyl sulfone require enzymatically active proteasomes for continued survival. | Princiotta, MF., et al. 2001. Proc Natl Acad Sci U S A. 98: 513-8. PMID: 11149939
- Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro. | Garrett, IR., et al. 2003. J Clin Invest. 111: 1771-82. PMID: 12782679
- Epoxomicin, a new antitumor agent of microbial origin. | Hanada, M., et al. 1992. J Antibiot (Tokyo). 45: 1746-52. PMID: 1468981
- Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson's disease. | McNaught, KS., et al. 2004. Ann Neurol. 56: 149-62. PMID: 15236415
- The proteasome inhibitor epoxomicin has potent Plasmodium falciparum gametocytocidal activity. | Czesny, B., et al. 2009. Antimicrob Agents Chemother. 53: 4080-5. PMID: 19651911
- Evaluation of the in vitro growth-inhibitory effect of epoxomicin on Babesia parasites. | Aboulaila, M., et al. 2010. Vet Parasitol. 167: 19-27. PMID: 19896277
- From epoxomicin to carfilzomib: chemistry, biology, and medical outcomes. | Kim, KB. and Crews, CM. 2013. Nat Prod Rep. 30: 600-4. PMID: 23575525
- SH-SY5Y and LUHMES cells display differential sensitivity to MPP+, tunicamycin, and epoxomicin in 2D and 3D cell culture. | Ko, KR., et al. 2020. Biotechnol Prog. 36: e2942. PMID: 31756288
- Suppression of the TRIF-dependent signaling pathway of TLRs by epoxomicin. | Kim, SY., et al. 2021. Arch Pharm (Weinheim). 354: e2100130. PMID: 34060134
- Epoxomicin, a Selective Proteasome Inhibitor, Activates AIM2 Inflammasome in Human Retinal Pigment Epithelium Cells. | Sridevi Gurubaran, I., et al. 2022. Antioxidants (Basel). 11: PMID: 35883779
Inhibitor of:
20S Proteasome, 20S Proteasome α2, 20S Proteasome α8, 20S Proteasome β1, 20S Proteasome β5, 20S Proteasome β7, 26S Proteasome p58, 2900016B01Rik, 2B28, 3830417A13Rik, 4930524E20Rik, 4931431F19Rik, 4933422H20Rik, 9930039A11Rik, AFG3L1, APC11, APC2, ARIH1, ASB-1, ASB-11, ASB-12, ASB-2, ASB-3, ASB-7, ASB-9, ASXL2, Bet1, BET3, Bles03, BTBD2, BTBD6, C12orf39, C1orf112, C4orf30, C6orf113, C7orf50, CacyBP, Cdc23, Cdc26, CLPX, CSN3, CSN7a, CSN7b, CTRL, cystatin 10, cystatin 12, cystatin 13, Cystatin D, Dcun1D5, Dda1, DDI2, DEME-6, Derlin-1, DET1, Dorfin, E2ig5, EG229571, EG382106, EG382156, EG667977, EULIR, Fbxo12, Fbxo12J, FBXO21, FBXO24, FBXO38, FBXO41, FBXO48, FBXW10, Fbxw12, Fbxw13, Fbxw16, FBXW17, Fbxw19, FBXW2, FBXW5, FNDC1, Fussel-18, G2E3, Gigaxonin, Glomulin, Gm410, Gm514, Gm757, GMCL1L, GOLGA7, H2-M10.2, H2-Q1, H2-Q10, H2-T10, H2-T22, H2-T9, HECTD1, HECTD2, HECTD3, HECTD4, Herc1, Herc2, Herc4, Herc6, Histone cluster 2 H2AA1, HLA-B, IBRDC2, IDE, Igkv1-117, IQUB, Jade-1, Josephin-2, Josephin-3, KBTBD11, KBTBD13, KBTBD4, KBTBD5, KCMF1, KLHDC10, KLHDC2, KLHDC4, KLHDC7A, KLHL10, KLHL11, KLHL33, KLHL35, LNX1, LOC642612, LOC728369, LONRF1, LONRF2, LONRF3, LPPR3, LRRC31, LRRC41, LRSAM1, MAGE-L2, MHC class IIβ, MHC Ts H-2s,f, Mps1, MuRF2, NEDL1, NEURL4, NOB1P, NP220, Nulp1, PARC, PCIA1, PDILT, Pellino 3, PGPEP1L, PI-9, Pi15, PIH1D2, PJA1, PJA2, PLIC-1, PNAd, PNGase, PPWD1, Proteassemblin, PSMB11, PSMC2, PSMC4, PSMC6, PSMD11, PSMD12, PSMD13, PSMD3, PSMD5, PSMD7, PSMD8, PSME proteasome activator subunits (PA28), Psmg2, PTGES3L-AARSD1, Rad23, Rbx2, Rfp2, RHBDD1, RING1B, RMND5B, RNF103, RNF113A, RNF113A1, RNF121, RNF130, RNF133, RNF145, RNF148, RNF150, RNF151, RNF152, RNF166, RNF180, RNF182, RNF184, RNF187, RNF207, RNF214, RNF219, RNF24, RNF26, RNF32, RNF38, RNF44, RNF5, Rpn11, SAMD9, SEL-10, SHFM3, Skeletrophin, Slimb, SPCS3, SPINK10, Staf-50, SUG1, SUMO-4, TAP1, TAPBPL, TIP120B, TMEM129, TPPII, TRAPPC10, TRIM11, TRIM23, TRIM26, Trim29, TRIM30B, TRIM31, TRIM37, TRIM40, TRIM41, TRIM43, TRIM44, TRIM45, TRIM47, TRIM49B, TRIM6, TRIM6-TRIM34, TRIM64B, TRIM64C, TRIM79, TRIP12, TRIP15, UBC2, UBE1L2, UBE2CBP, UBE2Q1, UBE2Z, UBE3B, UBE3C, UBE4A, UBQLN3, UBQLNL, Ubr2, Ubr3, UBTD2, UBXD7, UFM1, UFSP2, UIP5, Ula1, UNKL, USP17L, USP21, USP28, USP29, USP41, USP44, V1RH5, Vta1, WDR20a, WDR61, WDYHV1, ZBTB26, ZBTB5, ZFAND2B, ZNF114, ZNF121, ZNF213, ZNF216, ZUFSP, and ZYG11B.Activator of:
20S Proteasome α1, 20S Proteasome α3, 20S Proteasome α4, 20S Proteasome α5, 20S Proteasome α6, 20S Proteasome α7, 20S Proteasome β3, 26S Proteasome α, 4933402E13Rik, A1Up, ADRM1, ASB-13, ASB-17, ASB-2, Atg16L2, BTBD14B, BTBD18, CCDC46, CCP2, CD109, COP1, CRLF3, CSN8, CUL-7, Derlin-3, Desc4, ECM29, ELYS, ENOPH1, EOGT_A130022J15Rik, ERAP2, FBL14, FBL2, FBL3A, FBX23, Fbxo12J, FBXO21, FBXO29, FBXO3, FBXO35, FBXO41, Fbxw13, Fbxw19, FBXW9, FER1L5, FIGNL2, Fliz1, Gm410, Gm514, group VI iPLA2, H2-Db, HECTD4, HEPN1, HIV-1 Vif, HSPA12B, HSPB2, Josephin-1, KBTBD7, KIAA1468, KLF16, KLHDC7B, KLHL10, KLHL11, KLHL14, KLHL15, KLHL36, KLHL9, LNX3, LOC728677, LONRF1, MARCH8, MASP-2, MECL-1, Mex3c, Nek6, Neuralized-2, NIRF, OTUD1, OTUD6A, PI31, PL6, PLIC-2, POH1, PROS-30, PSMB6, PSMC1, PSMD1, PSMD2, PSMD8, Rad23A, RAD51AP2, Rbx2, RFPL1, RMND5A, RNF10, RNF113B, RNF115, RNF122, RNF126, RNF149, RNF151, RNF175, RNF180, RNF213, RNF222, RNF23, Rpn11, RWDD3, SEC22B, SEL-10, SENP5, STAMBPL1, TAP1, TAP2, TELO2, TEX264, TIP120A, TRC8, TRIM30A, TRIM36, TRIM48, TRIM49, TRIM69, TRIM7, tsg 101, Ub-RPS27A, UBA2, UBAP1, UBC2, UBE1L, UBE2D1, UBE2Q2, UBE2QL1, UBE4A, UBL5, Ubr1, UBTD1, UBXD4, UBXN2B, UCH-L3, USP10, USP17L29, USP27X, USP31, USP37, USP45, USP47, USP48, USP9Y, VPS36, VPS37, ZFAND1, and ZNF216.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Epoxomicin, 50 µg | sc-201298C | 50 µg | $134.00 | |||
Epoxomicin, 100 µg | sc-201298 | 100 µg | $215.00 | |||
Epoxomicin, 250 µg | sc-201298A | 250 µg | $440.00 | |||
Epoxomicin, 500 µg | sc-201298B | 500 µg | $496.00 |