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M2699

Sigma-Aldrich

Marimastat

≥98% (HPLC), solid, MMP inhibitor

Synonym(s):

BB2516, (2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl] propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide

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About This Item

Empirical Formula (Hill Notation):
C15H29N3O5
CAS Number:
154039-60-8
Molecular Weight:
331.41
MDL number:
MFCD00866242
UNSPSC Code:
12352200
PubChem Substance ID:
329817950
NACRES:
NA.77

product name

Marimastat, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

solid

solubility

DMSO: ≥20 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

CNC(=O)[C@@H](NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO)C(C)(C)C

InChI

1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1

InChI key

OCSMOTCMPXTDND-OUAUKWLOSA-N

Gene Information

Application

Marimastat has been used as an inhibitor of:
  • metalloproteinase 2/9 (MMP2/9), to study its effects on exercise-mediated interleukin-6 (IL-6) release in mice
  • metalloproteinase, to determine protease activity in Pseudomonas aeruginosa cultures
  • metalloproteinase 10 (MMP10), to study its effect on monoclonal antibody H3 binding to MMP10

Biochem/physiol Actions

Marimastat is a broad spectrum matrix metalloprotease (MMP) inhibitor

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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Cystic fibrosis (CF) lung infection is a complex condition where opportunistic pathogens and defective immune system cooperate in developing a constant cycle of infection and inflammation. The major pathogen, Pseudomonas aeruginosa, secretes a multitude of virulence factors involved in host
M Ohshima et al.
Journal of dental research, 89(11), 1315-1321 (2010-08-27)
The underlying mechanism and the therapeutic regimen for the transition of reversible gingivitis to irreversible periodontitis are unclear. Since transforming growth factor (TGF)-β has been implicated in differentially regulated gene expression in gingival fibroblasts, we hypothesized that TGF-β signaling is
Vincent E de Meijer et al.
PloS one, 5(6), e11256-e11256 (2010-07-02)
Liver fibrosis is characterized by excessive synthesis of extracellular matrix proteins, which prevails over their enzymatic degradation, primarily by matrix metalloproteinases (MMPs). The effect of pharmacological MMP inhibition on fibrogenesis, however, is largely unexplored. Inflammation is considered a prerequisite and
Timothy W Failes et al.
Journal of inorganic biochemistry, 101(3), 396-403 (2007-01-02)
Fe(III)-salen (N,N-bis(salicylidene)-ethane-1,2-diimine) complexes of simple hydroxamic acids and the MMP (matrix metalloproteinase) inhibitor marimastat have been evaluated as hypoxia activated drug carriers. The aceto- (aha), propion- (pha), benzohydroxamato (bha), and marimastat complexes were prepared and characterised by single crystal X-ray
Amir S Razai et al.
The Journal of biological chemistry, 295(8), 2464-2472 (2020-01-19)
Since their discovery, the matrix metalloproteinase (MMP) family proteases have been considered as therapeutic targets in numerous diseases and disorders. Unfortunately, clinical trials with MMP inhibitors have failed to yield any clinical benefits of these inhibitors. These failures were largely
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