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Key Documents

SML1916

Sigma-Aldrich

Marizomib

≥95% (HPLC), (Salinospora tropica)

Synonym(s):

(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, NPI-0052, Salinosporamide A

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About This Item

Empirical Formula (Hill Notation):
C15H20ClNO4
CAS Number:
437742-34-2
Molecular Weight:
313.78
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

biological source

(Salinospora tropica)

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

shipped in

wet ice

storage temp.

−20°C

InChI

1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1

InChI key

NGWSFRIPKNWYAO-SHTIJGAHSA-N

Application

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

Biochem/physiol Actions

Marizomib a natural product is a marine-derived β-lactone-γ-lactam. It shows therapeutic effects against hematologic and solid tumor malignancies.. It is involved in the activation of caspase-3,-8, and -9, increases the reactive oxygen species (ROS) and promotes apoptosis. Marizomib can cross the blood-brain barrier and might have the potential to treat primary brain tumors. It possesses anti-tumor properties.
Marizomib is a second generation proteasome inhibitor with anti-cancer activity. Marizomib binds irreversibly and potently inhibits all three 20S proteasome subunits.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nancy Levin et al.
British journal of haematology, 174(5), 711-720 (2016-05-11)
Proteasome inhibitors (PIs) are highly active in multiple myeloma (MM) but resistance is commonly observed. All clinical stage PIs effectively inhibit chymotrypsin-like (CT-L) activity; one possible mechanism of resistance is compensatory hyperactivation of caspase-like (C-L) and trypsin-like (T-L) subunits, in
Kaijun Di et al.
Neuro-oncology, 18(6), 840-848 (2015-12-19)
The proteasome plays a vital role in the physiology of glioblastoma (GBM), and proteasome inhibition can be used as a strategy for treating GBM. Marizomib is a second-generation, irreversible proteasome inhibitor with a more lipophilic structure that suggests the potential
A M Rajan et al.
Blood cancer journal, 6(7), e451-e451 (2016-07-30)
The treatment of multiple myeloma (MM) is rapidly evolving. In the United States, four drugs (panobinostat, ixazomib, daratumumab and elotuzumab) were approved for the treatment of MM in 2015. As a result of improved diagnosis and therapy, there has been
B C Potts et al.
Current cancer drug targets, 11(3), 254-284 (2011-01-21)
The proteasome has emerged as an important clinically relevant target for the treatment of hematologic malignancies. Since the Food and Drug Administration approved the first-in-class proteasome inhibitor bortezomib (Velcade) for the treatment of relapsed/refractory multiple myeloma (MM) and mantle cell
Erika Kelmer Sacramento et al.
Molecular systems biology, 16(6), e9596-e9596 (2020-06-20)
A progressive loss of protein homeostasis is characteristic of aging and a driver of neurodegeneration. To investigate this process quantitatively, we characterized proteome dynamics during brain aging in the short-lived vertebrate Nothobranchius furzeri combining transcriptomics and proteomics. We detected a
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