2-[benzyl-(4-methoxyphenyl)sulfonylamino]-5-(diethylaminomethyl)-N-hydroxy-3-methylbenzamide

Description

MMP-9 inhibitor I is an inhibitor of matrix metalloproteinase-9 (MMP-9) that is selective over MMP-1 and MMP-13 (IC₅₀s = 5, 1,050, and 113 nM, respectively).¹ It also decreases the activity of TNF-α converting enzyme (TACE) in a dose-dependent manner (IC₅₀ = 0.54 μM).² MMP-9 inhibitor I decreases TNF-α secretion stimulated by LPS in BV-2 microglial cells when used at concentrations of 50 and 100 μM.

Definition

ChEBI: MMP9 inhibitor I is a hydroxamic acid that is N-hydroxy-3-methylbenzamide in which the the hydrogens at positions 2 and 5 have been replaced by benzyl[(4-methoxyphenyl)sulfonyl]amino and (diethylamino)methyl groups, respectively. It is a cell-permeable, potent, selective, and reversible inhibitor of matrix metallopeptidase-9 (MMP-9, EC 3.4.24.35). It has a role as an EC 3.4.24.35 (gelatinase B) inhibitor. It is a hydroxamic acid, a tertiary amino compound, a sulfonamide and an aromatic ether.

References

1. Levin, J.I., Chen, J., Du, M., et al. The discovery of anthranilic acid-based MMP inhibitors. Part 2: SAR of the 5-position and P11 groups Bioorg. Med. Chem. Lett. 11(16),2189-2192(2001).
2. Lee, E.-J., Moon, P.-G., Baek, M.-C., et al. Comparison of the effects of matrix metalloproteinase inhibitors on TNF-α release from activated microglia and TNF-α converting enzyme activity Biomol. Ther. (Seoul) 22(5),414-419(2014).