Marimastat CAS: 154039-60-8
MF: C15H29N3O5
MW: 331.41
A broad spectrum MMP inhibitor and selective TACE inhibitor.

Marimastat (CAS 154039-60-8)

Marimastat | CAS 154039-60-8 is rated 5.0 out of 5 by 1.
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Alternate Names: BB2516
Application: Marimastat is a broad spectrum MMP inhibitor and selective TACE inhibitor
CAS Number: 154039-60-8
Purity: ≥98%
Molecular Weight: 331.41
Molecular Formula: C15H29N3O5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).

Marimastat (BB-2516) is a broad spectrum matrix metalloprotease (MMP) inhibitor with specificity towards MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 and IC50 values of 3, 5, 6, 9 and 13 nM, respectively. MMPs are a homologous family of enzymes involved in tissue remodeling and morphogenesis. They are collectively capable of degrading all components of the extracellular matrix, and also play an important role in wound healing and other processes involving tissue remodeling. Research shows that marimastat inhibits CD30 shedding in Karpas 299 cells (IC50 = 1 μM) and LPS-induced soluble TNFα production in a dose-dependent manner. The enzyme tumor necrosis factor alpha convertase (TACE), reported to be closely related to matrix metalloproteinases, is responsible for the processing of pro-TNFα to TNFα and is specifically inhibited by marimastat (IC50 = 3.8 nM). Studies show that this peptide hydroxamate compound also inhibits peritoneal dissemination of human gastric cancer cells through tumor angiogenesis inhibition.


References

1. Rasmussen, H S., et al., 1997. Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat. Pharmacology & therapeutics. 75(1): 69-75. PMID: 9364582
2. Barlaam, B., et al., 1999. New alpha-substituted succinate-based hydroxamic acids as TNFalpha convertase inhibitors. Journal of medicinal chemistry. 42(23): 4890-908. PMID: 10579851
3. Whittaker, M., et al., 1999. Design and therapeutic application of matrix metalloproteinase inhibitors. Chemical reviews. 99(9): 2735-76. PMID: 11749499
4. Hansen, Hinrich P., et al., 2002. Inhibition of metalloproteinases enhances the internalization of anti-CD30 antibody Ki-3 and the cytotoxic activity of Ki-3 immunotoxin. International journal of cancer. Journal international du cancer. 98(2): 210-5. PMID: 11857410
5. Tsuji, Fumio., et al., 2002. Differential effects between marimastat, a TNF-alpha converting enzyme inhibitor, and anti-TNF-alpha antibody on murine models for sepsis and arthritis. Cytokine. 17(6): 294-300. PMID: 12061836
6. Wada, Norihito., et al., 2003. Reduced angiogenesis in peritoneal dissemination of gastric cancer through gelatinase inhibition. Clinical & experimental metastasis. 20(5): 431-5. PMID: 14524532
7. Bjørnland, Kristin., et al., 2005. Matrix metalloproteinases participate in osteosarcoma invasion. The Journal of surgical research. 127(2): 151-6. PMID: 16083752
8. van Wijngaarden, Jens., et al., 2010. An in vitro model that can distinguish between effects on angiogenesis and on established vasculature: actions of TNP-470, marimastat and the tubulin-binding agent Ang-510. Biochemical and biophysical research communications. 391(2): 1161-5. PMID: 20004648

Physical State :
Solid
Solubility :
Soluble in DMSO (≥20 mg/ml).
Storage :
Store at -20° C
Melting Point :
148° C
Boiling Point :
617.23° C (Predicted)
Density :
1.14 g/cm3 (Predicted)
Refractive Index :
n20D 1.50 (Predicted)
IC50 :
MMP-1: IC50 = 5 ; MMP-2: IC50 = 6 ; MMP-3: IC50 = 200 ; MMP-7: IC50 = 20 ; MMP-8: IC50 = 2 ; MMP-14: IC50 = 1.8 ; TACE: IC50 = 3.8
Ki Data :
Matrix metalloproteinase-1: Ki= <1 nM (human); Matrix metalloproteinase 9: Ki= <1 nM (human); ADAM17: Ki= 0.4 nM (human); Matrix metalloproteinase-2: Ki= 0.6 nM (human); Matrix metalloproteinase 3: Ki= 2.4 nM (human)
pK Values :
pKa: 9.44 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
119031
Merck Index :
14: 5753
MDL Number :
MFCD00866242
SMILES :
CC(C)C[[email protected]]([[email protected]@H](C(=O)NO)O)C(=O)N[[email protected]](C(=O)NC)C(C)(C)C

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Certificate of Analysis

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Marimastat (CAS 154039-60-8)  Product Citations

See how others have used Marimastat (CAS 154039-60-8). Click on the entry to view the PubMed entry .

Citations 1 to 10 of 15 total

PMID: # 28608951  Harkness, LM.|Weckmann, M.|Kopp, M.|Becker, T.|Ashton, AW.|Burgess, JK.| et al. 2017. J. Cell. Mol. Med. 21: 3288-3297.

PMID: # 25961845  Marshall, DC. et al. 2015. PLoS ONE. 10: e0127063.

PMID: # 25261297  Ekblad, L. et al. 2015. Oral oncology. 51: 46-52.

PMID: # 23645677  Chiluiza, D. et al. 2013. J. Biol. Chem. 288: 18407-20.

PMID: # 23115643  Armstrong, SM. et al. 2012. PLoS ONE. 7: -.

PMID: # 22484054  Lim, AI. et al. 2012. Int. J. Biochem. Cell Biol. 44: 1040-50.

PMID: # 20529858  Mendelson, K. et al. 2010. J. Biol. Chem. 285: 25024-25032.

PMID: # 19586907  Tortorella, MD. et al. 2009. J. Biol. Chem. 284: 24185-24191.

PMID: # 19574220  Franzke, CW. et al. 2009. J. Biol. Chem. 284: 23386-23396.

PMID: # 15381692  Roy, R. et al. 2004. J. Biol. Chem. 279: 51323-51330.

Citations 1 to 10 of 15 total

Is this inhibitor reversible?

Asked by: hawkeye11
This chemical, Marimastat (CAS 154039-60-8), is a reversible inhibitor of MMPs.
Answered by: Chemical Support 1
Date published: 2017-03-08
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Rated 5 out of 5 by from Armstrong et al Armstrong et al. (23115643) used the broad-spectrum matrix metalloprotease inhibitor, Marimastat, to prevent the loss of the claudin-5 tight junction protein that regulates endothelial permeability. -SCBT Publication Review
Date published: 2015-05-11
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