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| MarizoMib Basic information |
| Product Name: | MarizoMib | | Synonyms: | MarizoMib;(-)-SalinosporaMide A;ML 858;NPI 0052;SalinosporaMide A;MarizoMib (NPI-0052, (-)-SalinosporaMide A);Marizomib (Salinosporamide A);(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 | | CAS: | 437742-34-2 | | MF: | C15H20ClNO4 | | MW: | 313.78 | | EINECS: | | Product Categories: | | Mol File: | 437742-34-2.mol |
| MarizoMib Chemical Properties |
| 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 |
| MarizoMib Usage And Synthesis |
| 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. | | 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. |
| MarizoMib Preparation Products And Raw materials |
| Raw materials | 6-Oxa-2-azabicyclo[3.2.0]heptane-3,7-dione, 1-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-4-(2-hydroxyethyl)-5-methyl-, (1R,4R,5S)--->6-Oxa-2-azabicyclo[3.2.0]heptane-3,7-dione, 4-(2-chloroethyl)-1-[(1S)-2-cyclohexen-1-ylcarbonyl]-5-methyl-, (1S,4R,5S)- | | Preparation Products | 6-Oxa-2-azabicyclo[3.2.0]heptane-3,7-dione, 4-(2-chloroethyl)-1-[(R)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-5-methyl-, (1R,4R,5S)- |
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