Marimastat

• CAT Number: I001938
• CAS Number: 154039-60-8
• Molecular Formula: C₁₅H₂₉N₃O₅
• Molecular Weight: 331.41
• Purity: ≥95%
• Target: MMP
• Solubility: 10 mM in DMSO
• Storage: -20°C
• IC50: 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7
• IUPAC Name: (2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N',3-dihydroxy-2-(2-methylpropyl)butanediamide
• InChI: 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
• InChIKey: OCSMOTCMPXTDND-OUAUKWLOSA-N
• SMILES: CC(C)CC(C(C(=O)NO)O)C(=O)NC(C(=O)NC)C(C)(C)C

Marimastat（Cat No.:I001938）, also known as BB 2516 or TA2516, is a potent inhibitor of matrix metalloproteinases (MMPs). It exhibits a broad spectrum of activity against various MMPs with impressive potency. The IC50 values for Marimastat are 3 nM, 5 nM, 6 nM, 9 nM, and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14, and MMP-7, respectively. By inhibiting these MMPs, Marimastat interferes with the degradation of the extracellular matrix, which is important in processes such as tissue remodeling and tumor invasion.

Reference

1:Intraosseous infusion of the distal phalanx compared to systemic intravenous infusion for marimastat delivery to equine lamellar tissue. Underwood C, Collins SN, van Eps AW, Mills PC, Allavena RE, Bailey SR, Medina Torres CE, Meizler A, Pollitt CC.Vet J. 2015 Sep;205(3):357-63. doi: 10.1016/j.tvjl.2015.05.010. Epub 2015 May 19. PMID: 26073286 2:Regional intravenous limb perfusion compared to systemic intravenous administration for marimastat delivery to equine lamellar tissue. Underwood C, Collins SN, Mills PC, Van Eps AW, Allavena RE, Medina Torres CE, Pollitt CC.J Vet Pharmacol Ther. 2015 Aug;38(4):392-9. doi: 10.1111/jvp.12198. Epub 2015 Jan 30. PMID: 25641095 3:Incorporation of Bulky and Cationic Cyclam-Triazole Moieties into Marimastat Can Generate Potent MMP Inhibitory Activity without Inducing Cytotoxicity. Yu M, Lim NH, Ellis S, Nagase H, Triccas JA, Rutledge PJ, Todd MH.ChemistryOpen. 2013 Jun;2(3):99-105. doi: 10.1002/open.201300014. Epub 2013 Jun 12. PMID: 24551546 Free PMC Article4:The matrix metalloproteinase inhibitor marimastat promotes neural progenitor cell differentiation into neurons by gelatinase-independent TIMP-2-dependent mechanisms. Sinno M, Biagioni S, Ajmone-Cat MA, Pafumi I, Caramanica P, Medda V, Tonti G, Minghetti L, Mannello F, Cacci E.Stem Cells Dev. 2013 Feb 1;22(3):345-58. doi: 10.1089/scd.2012.0299. Epub 2012 Dec 7. PMID: 23098139 5:Labeling and enrichment of Arabidopsis thaliana matrix metalloproteases using an active-site directed, marimastat-based photoreactive probe. Lenger J, Kaschani F, Lenz T, Dalhoff C, Villamor JG, Köster H, Sewald N, van der Hoorn RA.Bioorg Med Chem. 2012 Jan 15;20(2):592-6. doi: 10.1016/j.bmc.2011.06.068. Epub 2011 Jun 29. PMID: 21775155 6:Novel matrix metalloproteinase inhibitor [18F]marimastat-aryltrifluoroborate as a probe for in vivo positron emission tomography imaging in cancer. auf dem Keller U, Bellac CL, Li Y, Lou Y, Lange PF, Ting R, Harwig C, Kappelhoff R, Dedhar S, Adam MJ, Ruth TJ, Bénard F, Perrin DM, Overall CM.Cancer Res. 2010 Oct 1;70(19):7562-9. doi: 10.1158/0008-5472.CAN-10-1584. Epub 2010 Aug 20. PMID: 20729277 Free Article7: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. van Wijngaarden J, Snoeks TJ, van Beek E, Bloys H, Kaijzel EL, van Hinsbergh VW, Löwik CW.Biochem Biophys Res Commun. 2010 Jan 8;391(2):1161-5. doi: 10.1016/j.bbrc.2009.11.097. Epub 2009 Dec 14. PMID: 20004648 8:In vivo efficacy of marimastat and chemoradiation in head and neck cancer xenografts. Skipper JB, McNally LR, Rosenthal EL, Wang W, Buchsbaum DJ.ORL J Otorhinolaryngol Relat Spec. 2009;71(1):1-5. doi: 10.1159/000163217. Epub 2008 Oct 16. PMID: 18931526 Free PMC Article9:Metalloelastase (MMP-12) induced inflammatory response in mice airways: effects of dexamethasone, rolipram and marimastat. Nénan S, Lagente V, Planquois JM, Hitier S, Berna P, Bertrand CP, Boichot E.Eur J Pharmacol. 2007 Mar 15;559(1):75-81. Epub 2006 Dec 12. PMID: 17234180 10:Towards bioreductively activated prodrugs: Fe(III) complexes of hydroxamic acids and the MMP inhibitor marimastat. Failes TW, Hambley TW.J Inorg Biochem. 2007 Mar;101(3):396-403. Epub 2006 Nov 15. PMID: 17197030