Epoxomicin

Epoxomicin ^[1]

Names
IUPAC name (2S,3S)-N-((2S,3R)-3-hydroxy-1-(((S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl)amino)-1-oxobutan-2-yl)-3-methyl-2-((2S,3S)-3-methyl-2-(N-methylacetamido)pentanamido)pentanamide
Other names BU 4061T
Identifiers
CAS Number	134381-21-8  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL207990  N
ChemSpider	9401737
PubChem CID	16760412
UNII	Y0900I3U8U  Y
CompTox Dashboard (EPA)	DTXSID5044073
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 Key: DOGIDQKFVLKMLQ-BPHQUOOUSA-N
SMILES O=C([C@@]1(C)CO1)[C@H](CC(C)C)NC([C@@H](NC([C@H]([C@@H](C)CC)NC([C@H]([C@@H](C)CC)N(C)C(C)=O)=O)=O)[C@H](O)C)=O
Properties
Chemical formula	C28H50N4O7
Molar mass	554.729 g·mol−1
Appearance	White solid
Solubility in DMSO	10 mg/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Epoxomicin is a naturally occurring selective proteasome inhibitor with anti-inflammatory activity. ^[2] It was originally discovered in 1992. ^[3] Injected, it can induce Parkinson's-like symptoms in rats.

Derivatives of epoxomicin include carfilzomib.

References

1. Epoxomicin, Santa Cruz Biotechnology
2. Meng, L; Mohan, R; Kwok, BH; Elofsson, M; Sin, N; Crews, CM (1999). "Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity". PNAS. 96 (18): 10403–10408. Bibcode:1999PNAS...9610403M. doi: 10.1073/pnas.96.18.10403 . PMC   17900 . PMID   10468620.
3. Epoxomicin, Peptide Institute, Inc.

Further reading

• Hanada, M; Sugawara, K; Kaneta, K; Toda, S; Nishiyama, Y; Tomita, K; Yamamoto, H; Konishi, M; Oki, T (November 1992). "Epoxomicin, a new antitumor agent of microbial origin". J. Antibiot. 45 (11): 1746–52. doi: 10.7164/antibiotics.45.1746 . PMID   1468981.
• Meng, L.; et al. (1999). "Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity". Proc. Natl. Acad. Sci. U.S.A. 96 (18): 10403–10408. Bibcode:1999PNAS...9610403M. doi: 10.1073/pnas.96.18.10403 . PMC   17900 . PMID   10468620.
• Schwarz, K.; et al. (2000). "The selective proteasome inhibitors lactacystin and epoxomicin can be used to either up- or down-regulate antigen presentation at nontoxic doses". J. Immunol. 164 (12): 6147–6157. doi:10.4049/jimmunol.164.12.6147. PMC   2507740 . PMID   10843664.
• Princiotta, M.F.; et al. (2001). "Cells adapted to the proteasome inhibitor 4-hydroxy- 5-iodo-3-nitrophenylacetyl-Leu-Leu-leucinal-vinyl sulfone require enzymatically active proteasomes for continued survival". Proc. Natl. Acad. Sci. U.S.A. 98 (2): 513–518. doi: 10.1073/pnas.021132398 . PMC   14618 . PMID   11149939.
• Garrett, I.R.; et al. (2003). "Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro". J. Clin. Invest. 111 (11): 1771–1782. doi:10.1172/JCI16198. PMC   156102 . PMID   12782679.
• McNaught, K.S.; et al. (2004). "Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson's disease". Annals of Neurology. 56 (1): 149–162. doi:10.1002/ana.20186. PMID   15236415. S2CID   25314945.