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Submit ReviewMarimastat
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% (HPLC)
Biological Activity for Marimastat
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 for Marimastat
| M. Wt | 331.41 |
| Formula | C15H29N3O5 |
| Storage | Store at -20°C |
| Purity | ≥99% (HPLC) |
| CAS Number | 154039-60-8 |
| PubChem ID | 119031 |
| InChI Key | OCSMOTCMPXTDND-OUAUKWLOSA-N |
| Smiles | O=C(NO)[C@@H](O)[C@H]([C@](N[C@@H]([C@](C)(C)C)C(NC)=O)=O)CC(C)C |
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.
Solubility Data for Marimastat
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 33.14 | 100 |
Preparing Stock Solutions for Marimastat
The following data is based on the product molecular weight 331.41. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.02 mL | 15.09 mL | 30.17 mL |
| 5 mM | 0.6 mL | 3.02 mL | 6.03 mL |
| 10 mM | 0.3 mL | 1.51 mL | 3.02 mL |
| 50 mM | 0.06 mL | 0.3 mL | 0.6 mL |
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Product Datasheets for Marimastat
References for Marimastat
References are publications that support the biological activity of the product.
Rasmussen and McCann (1997) Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat. Pharmacol.Ther. 75 69 PMID: 9364582
Wada et al (2003) Reduced angiogenesis in peritoneal dissemination of gastric cancer through gelatinase inhibition. Clin.Exp.Metastasis 20 431 PMID: 14524532
Bjornland et al (2005) Matrix metalloproteinases participate in osteosarcoma invasion. J.Surg.Res. 127 151 PMID: 16083752
If you know of a relevant reference for Marimastat, please let us know.
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Keywords: Marimastat, Marimastat supplier, Broad, spectrum, MMP, inhibitors, inhibits, Matrix, Metalloprotease, Matrixins, Metalloproteinase, proteinases, proteases, BB2516, BB, 2516, Marimistat, 2631, Tocris Bioscience
22 Citations for Marimastat
Citations are publications that use Tocris products. Selected citations for Marimastat include:
Wisdom et al (2018) Matrix mechanical plasticity regulates cancer cell migration through confining microenvironments. Nat Commun 9 4144 PMID: 30297715
Megía-Fernández et al (2018) Bimodal fluorogenic sensing of matrix proteolytic signatures in lung cancer. Org Biomol Chem 16 8056 PMID: 30175355
Brafman et al (2013) Regulation of endodermal differentiation of human embryonic stem cells through integrin-ECM interactions. PLoS One 20 369 PMID: 23154389
Li et al (2013) NME1 suppression promotes growth, adhesion and implantation of endometrial stromal cells via Akt and MAPK/Erk1/2 signal pathways in the endometriotic milieu. J Biol Chem 28 2822 PMID: 23856325
Kachgal and Putnam (2011) Mesenchymal stem cells from adipose and bone marrow promote angiogenesis via distinct cytokine and protease expression mechanisms. Angiogenesis 14 47 PMID: 21104120
Trappmann (2017) Matrix degradability controls multicellularity of 3D cell migration. Nat Commun 8 371 PMID: 28851858
Rosner et al (2017) Human stem cells alter the invasive properties of somatic cells via paracrine activation of mTORC1. Nat Commun 8 595 PMID: 28928383
Pitt et al (2017) Neuroprotective astrocyte-derived Ins/IGF-1 stimulates endocytic processing and extracellular release of neuron-bound Aβ oligomers. Mol Biol Cell 28 2623 PMID: 28963439
Lahey et al (2017) Signaling pathways induced by serine proteases to increase intestinal epithelial barrier function. PLoS One 12 e0180259 PMID: 28671992
Nicolaou et al (2017) Adam17 Deficiency Promotes Atherosclerosis by Enhanced TNFR2 Signaling in Mice. Arterioscler Thromb Vasc Biol 37 247 PMID: 28062509
Ji et al (2015) WISP-2 in human gastric cancer and its potential metastatic suppressor role in gastric cancer cells mediated by JNK and PLC-γ pathways. Br J Cancer 113 921 PMID: 26291058
Knapinska et al (2015) SAR Studies of Exosite-Binding Substrate-Selective Inhibitors of A Disintegrin And Metalloprotease 17 (ADAM17) and Application as Selective in Vitro Probes. J Med Chem 58 5808 PMID: 26192023
Guo et al (2013) Inhibition of ADAM-17 more effectively down-regulates the Notch pathway than that of γ-secretase in renal carcinoma. J Exp Clin Cancer Res 32 26 PMID: 23659326
Kachgal et al (2012) Bone marrow stromal cells stimulate an angiogenic program that requires endothelial MT1-MMP. J Cell Physiol 227 3546 PMID: 22262018
Mezil et al (2012) Tumor selective cytotoxic action of a thiomorpholin hydroxamate inhibitor (TMI-1) in breast cancer. PLoS One 7 e43409 PMID: 23028451
Bezenah (2018) Evaluating the potential of endothelial cells derived from human induced pluripotent stem cells to form microvascular networks in 3D cultures. Sci Rep 8 2671 PMID: 29422650
Ghajar et al (2010) Mesenchymal cells stimulate capillary morphogenesis via distinct proteolytic mechanisms. Exp Cell Res 316 813 PMID: 20067788
Zariffard et al (2015) Cleavage/Alteration of interleukin-8 by matrix metalloproteinase-9 in the female lower genital tract. Hum Reprod 10 e0116911 PMID: 25611319
Yurtsever et al (2012) Self-cleavage of human CLCA1 protein by a novel internal metalloprotease domain controls calcium-activated chloride channel activation. Development 287 42138 PMID: 23112050
Prendergast et al (2012) The metalloproteinase inhibitor Reck is essential for zebrafish DRG development. Arthritis Res Ther 139 1141 PMID: 22296847
Madoux et al (2016) Discovery of an enzyme and substrate selective inhibitor of ADAM10 using an exosite-binding glycosylated substrate. Sci Rep 6 11 PMID: 28442704
Lee et al (2014) Nestin depletion induces melanoma matrix metalloproteinases and invasion. Lab Invest 94 1382 PMID: 25365206
Do you know of a great paper that uses Marimastat from Tocris? Please let us know.
Reviews for Marimastat
Average Rating: 5 (Based on 1 Review.)
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great product.
By
Anonymous on 03/26/2020
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Hippocampal neuron
matrix metalloproteinases 1, 2, 3, 7, 9, 14, and 17 (0.1–1 μM batimastat and marimastat)
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Angiogenesis in Cancer Poster
This poster summarizes the pathogenesis of angiogenesis in cancer, as well as some of the main angiogenesis therapeutic targets.