| Identification | Back Directory | [Name]
MarizoMib | [CAS]
437742-34-2 | [Synonyms]
ML 858
NPI 0052
MarizoMib
SalinosporaMide A
Marizomib
(NPI 0052
(-)-SalinosporaMide A
Marizomib (Salinosporamide A)
Salinosporamide A (NPI-0052, Marizomib)
MarizoMib (NPI-0052, (-)-SalinosporaMide A)
(1R,4R,5S)-4-(2-Chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
6-Oxa-2-azabicyclo[3.2.0]heptane-3,7-dione, 4-(2-chloroethyl)-1-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-5-methyl-, (1R,4R,5S)-
(1S,2R,5R)-2-(2-chloroethyl)-5-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-1-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione | [Molecular Formula]
C15H20ClNO4 | [MDL Number]
MFCD16037703 | [MOL File]
437742-34-2.mol | [Molecular Weight]
313.78 |
| Chemical Properties | Back Directory | [Melting point ]
168-170 °C | [Boiling point ]
547.0±50.0 °C(Predicted) | [density ]
1.348±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Soluble in DMSO | [form ]
powder | [pka]
13.10±0.20(Predicted) | [color ]
white to beige |
| Hazard Information | Back Directory | [Uses]
Marizomib has been used as a proteasome inhibitor:
- to study its effects on glioblastoma cell lines
- to analyze its effects on the aging of killifish brain
- to test its effect on protein kinase B (PKB/AKT) levels in multiple myeloma cells
| [Definition]
ChEBI: A salinosporamide in which the core (1R)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione skeleton is substituted at positions 1, 4, and 5 by (1S)-cyclohex-2-en-1-yl(hydroxy)methyl, 2-chloroethyl, and methyl groups, respectively
(the 1R,4R,5S diastereoisomer). A potent proteasome inhibitor, it has attracted interest for potential use in the treatment of various cancers. | [Biological Activity]
salinosporamide a is a potent inhibitor of 20s proteasome with ic50 value of 1.3 nm [1].salinosporamide a was isolated from the crude extract of a salinospora strain cnb-392. it showed potent anti-tumor activity with an ic50 value of 11 ng/ml in hct-116 cells. it also exerted a mean gi50 value of less than 10 nm in the nci’s 60 cell line-panel. among these cell lines, salinosporamide a showed the greatest potent efficacies in nci-h226, sf-539, sk-mel-28 and mda-mb-435 cells. salinosporamide a inhibited the purified 20s proteasome with ic50 value of 1.3 nm. it was about 35-fold more potent than the first discovered specific proteasome inhibitor, omuralide [1]. | [Biochem/physiol Actions]
Marizomib is a second generation proteasome inhibitor with anti-cancer activity. Marizomib binds irreversibly and potently inhibits all three 20S proteasome subunits. | [target]
CT-L (EC50） | [References]
[1] feling r h, buchanan g o, mincer t j, et al. salinosporamide a: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora. angewandte chemie international edition, 2003, 42(3): 355-357. |
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