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Marimastat

Catalog #: 2631
22 Citations Datasheet
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2631/10
Marimastat | CAS No. 154039-60-8 | Synthetic Metalloprotease Inhibitors
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Description: Broad spectrum MMP inhibitor
Alternative Names: BB 2516,Marimistat

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

Purity: ≥99%

Product Details
Citations (22)
Reviews
Biological Activity Technical Data Background Product Datasheets Calculators

Biological Activity

Marimastat is a broad spectrum inhibitor of MMPs (IC50 values are 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 respectively). Inhibits peritoneal dissemination of human gastric cancer cells in vivo through inhibition of tumor angiogenesis.

Technical Data

M.Wt:
331.41
Formula:
C15H29N3O5
Solubility:
Soluble to 100 mM in DMSO
Purity:
≥99%
Storage:
Store at -20°C
CAS No:
154039-60-8

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.

Background References

  1. The enhanced susceptibility of ADAM-17 hypomorphic mice to DSS-induced colitis is not ameliorated by loss of RIPK3, revealing an unexpected function of ADAM-17 in necroptosis
    J Fuchsloche, M Falk-Pauls, A Luzius, C Saggau, B Ruder, J Bolik, D Schmidt-Ar, A Linkermann, C Becker, P Rosenstiel, S Rose-John, D Adam
    Oncotarget, 2018;9(16):12941-12958.
  2. Regulation of endodermal differentiation of human embryonic stem cells through integrin-ECM interactions.
    Brafman D, Phung C, Kumar N, Willert K
    Cell Death Differ, 2013;20(3):369-81.
  3. The CD46-Jagged1 interaction is critical for human TH1 immunity.
    Le Friec G, Sheppard D, Whiteman P, Karsten C, Shamoun S, Laing A, Bugeon L, Dallman M, Melchionna T, Chillakuri C, Smith R, Drouet C, Couzi L, Fremeaux-Bacchi V, Kohl J, Waddington S, McDonnell J, Baker A, Handford P, Lea S, Kemper C
    Nat Immunol, 2012;13(12):1213-21.
  4. Function of focal adhesion kinase scaffolding to mediate endophilin A2 phosphorylation promotes epithelial-mesenchymal transition and mammary cancer stem cell activities in vivo.
    Fan, Huaping, Zhao, Xiaofeng, Sun, Shaogang, Luo, Ming, Guan, Jun-Lin
    J Biol Chem, 2013;288(5):3322-33.
  5. Cellular contractility and extracellular matrix stiffness regulate matrix metalloproteinase activity in pancreatic cancer cells.
    Haage A, Schneider I
    FASEB J, 2014;28(8):3589-99.
  6. Mathematical framework for activity-based cancer biomarkers.
    Kwong G, Dudani J, Carrodeguas E, Mazumdar E, Zekavat S, Bhatia S
    Proc Natl Acad Sci U S A, 2015;112(41):12627-32.
  7. Cleavage/alteration of interleukin-8 by matrix metalloproteinase-9 in the female lower genital tract.
    Zariffard, M Reza, Anastos, Kathryn, French, Audrey L, Munyazesa, Elisapha, Cohen, Mardge, Landay, Alan L, Spear, Gregory
    PLoS ONE, 2015;10(1):e0116911.
  8. Basal lamina remodeling at the skeletal muscle stem cell niche mediates stem cell self-renewal
    SS Rayagiri, D Ranaldi, A Raven, NIF Mohamad Az, O Lefebvre, PS Zammit, AG Borycki
    Nat Commun, 2018;9(1):1075.
  9. Composite regulation of ERK activity dynamics underlying tumour-specific traits in the intestine
    Y Muta, Y Fujita, K Sumiyama, A Sakurai, MM Taketo, T Chiba, H Seno, K Aoki, M Matsuda, M Imajo
    Nat Commun, 2018;9(1):2174.
  10. Matrix degradability controls multicellularity of 3D cell migration
    B Trappmann, BM Baker, WJ Polacheck, CK Choi, JA Burdick, CS Chen
    Nat Commun, 2017;8(1):371.
  11. Astrocytes directly influence tumor cell invasion and metastasis in vivo.
    Wang, Ling, Cossette, Stephani, Rarick, Kevin R, Gershan, Jill, Dwinell, Michael, Harder, David R, Ramchandran, Ramani
    PLoS ONE, 2013;8(12):e80933.
  12. Functional impact of NOTCH1 mutations in chronic lymphocytic leukemia.
    Arruga F, Gizdic B, Serra S, Vaisitti T, Ciardullo C, Coscia M, Laurenti L, D'Arena G, Jaksic O, Inghirami G, Rossi D, Gaidano G, Deaglio S
    Leukemia, 2014;28(5):1060-70.
  13. Signaling pathways induced by serine proteases to increase intestinal epithelial barrier function
    KA Lahey, NJ Ronaghan, J Shang, SP Dion, A Désilets, R Leduc, WK MacNaughto
    PLoS ONE, 2017;12(7):e0180259.
  14. Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat.
    Rasmussen and McCann
    Pharmacol.Ther., 1997;75:69
  15. Reduced angiogenesis in peritoneal dissemination of gastric cancer through gelatinase inhibition.
    Wada et al.
    Clin.Exp.Metastasis, 2003;20:431
  16. Matrix metalloproteinases participate in osteosarcoma invasion.
    Bjornland et al.
    J.Surg.Res., 2005;127:151

Product Datasheets

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Citations for Marimastat

The citations listed below are publications that use Tocris products. Selected citations for Marimastat include:

22 Citations: Showing 1 - 10

  1. Matrix mechanical plasticity regulates cancer cell migration through confining microenvironments.
    Authors: Wisdom Et al.
    Nat Commun  2018;9:4144
  2. Evaluating the potential of endothelial cells derived from human induced pluripotent stem cells to form microvascular networks in 3D cultures.
    Authors: Bezenah
    Sci Rep  2018;8(1):2671
  3. Bimodal fluorogenic sensing of matrix proteolytic signatures in lung cancer.
    Authors: Megía-Fernández Et al.
    Org Biomol Chem  2018;16:8056
  4. Human stem cells alter the invasive properties of somatic cells via paracrine activation of mTORC1.
    Authors: Rosner Et al.
    Nat Commun  2017;8:595
  5. Matrix degradability controls multicellularity of 3D cell migration.
    Authors: Trappmann
    Nat Commun  2017;8(1):371
  6. Adam17 Deficiency Promotes Atherosclerosis by Enhanced TNFR2 Signaling in Mice.
    Authors: Nicolaou Et al.
    Arterioscler Thromb Vasc Biol  2017;37:247
  7. Neuroprotective astrocyte-derived Ins/IGF-1 stimulates endocytic processing and extracellular release of neuron-bound Aβ oligomers.
    Authors: Pitt Et al.
    Mol Biol Cell  2017;28:2623
  8. Signaling pathways induced by serine proteases to increase intestinal epithelial barrier function.
    Authors: Lahey Et al.
    PLoS One  2017;12:e0180259
  9. Discovery of an enzyme and substrate selective inhibitor of ADAM10 using an exosite-binding glycosylated substrate.
    Authors: Madoux Et al.
    Sci Rep  2016;6:11
  10. SAR Studies of Exosite-Binding Substrate-Selective Inhibitors of A Disintegrin And Metalloprotease 17 (ADAM17) and Application as Selective in Vitro Probes.
    Authors: Knapinska Et al.
    J Med Chem  2015;58:5808
  11. WISP-2 in human gastric cancer and its potential metastatic suppressor role in gastric cancer cells mediated by JNK and PLC-γ pathways.
    Authors: Ji Et al.
    Br J Cancer  2015;113:921
  12. Cleavage/Alteration of interleukin-8 by matrix metalloproteinase-9 in the female lower genital tract.
    Authors: Zariffard Et al.
    Hum Reprod  2015;10:e0116911
  13. Nestin depletion induces melanoma matrix metalloproteinases and invasion.
    Authors: Lee Et al.
    Lab Invest  2014;94:1382
  14. Inhibition of ADAM-17 more effectively down-regulates the Notch pathway than that of γ-secretase in renal carcinoma.
    Authors: Guo Et al.
    J Exp Clin Cancer Res  2013;32:26
  15. NME1 suppression promotes growth, adhesion and implantation of endometrial stromal cells via Akt and MAPK/Erk1/2 signal pathways in the endometriotic milieu.
    Authors: Li Et al.
    J Biol Chem  2013;28:2822
  16. Regulation of endodermal differentiation of human embryonic stem cells through integrin-ECM interactions.
    Authors: Brafman Et al.
    PLoS One  2013;20:369
  17. Tumor selective cytotoxic action of a thiomorpholin hydroxamate inhibitor (TMI-1) in breast cancer.
    Authors: Mezil Et al.
    PLoS One  2012;7:e43409
  18. Self-cleavage of human CLCA1 protein by a novel internal metalloprotease domain controls calcium-activated chloride channel activation.
    Authors: Yurtsever Et al.
    Development  2012;287:42138
  19. Bone marrow stromal cells stimulate an angiogenic program that requires endothelial MT1-MMP.
    Authors: Kachgal Et al.
    J Cell Physiol  2012;227:3546
  20. The metalloproteinase inhibitor Reck is essential for zebrafish DRG development.
    Authors: Prendergast Et al.
    Arthritis Res Ther  2012;139:1141
  21. Mesenchymal stem cells from adipose and bone marrow promote angiogenesis via distinct cytokine and protease expression mechanisms.
    Authors: Kachgal and Putnam
    Angiogenesis  2011;14:47
  22. Mesenchymal cells stimulate capillary morphogenesis via distinct proteolytic mechanisms.
    Authors: Ghajar Et al.
    Exp Cell Res  2010;316:813

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