TMI 1

Cat. No. 5960

TMI 1 C17H22N2O5S2 [287403-39-8]

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Chemical Name: (3S)-4-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-3-thiomorpholinecarboxamide

Biological Activity

Adam 17 (TACE) and MMP inhibitor (IC50 values are 3, 4.7, 6.6, 8.4, 12, 26 and 26 nM for MMP-13, MMP-2, MMP-1, ADAM 17, MMP-9, MMP-7 and MMP-14, respectively). Suppresses TNF-α production in an acute LPS-mouse model. Reduces severity score in an in vivo model of rheumatoid arthritis. Displays selective cytotoxicity to tumor cells and cancer stem cells in vitro. Induces tumor apoptosis in a breast cancer in vivo model. Orally bioavailable.

Licensing Information

Sold for research purposes under agreement from Pfizer Inc

Technical Data

M.Wt:
398.49
Formula:
C17H22N2O5S2
Solubility:
Soluble to 100 mM in DMSO and to 20 mM in ethanol
Purity:
>98 %
Storage:
Store at -20°C
CAS No:
287403-39-8

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

Certificate of Analysis / Product Datasheet / Safety Datasheet

Mezil et al (2012) Tumor selective cytotoxic action of a thiomorpholin hydroxamate inhibitor (TMI-1) in breast cancer PLoS One 7 e43409. PMID: 23028451.

Levin (2006) Heterocyclic inhibitors of tumor necrosis factor-α converting enzyme (TACE) Heterocycles 70 691.

Zhang et al (2004) Identification and characterization of 4-[[4-(2-butynyloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-(3S)thiomorpholinecarboxamide (TMI-1), a novel dual tumor necrosis factor-α-converting enzyme/matrix metalloprotease inhibitor for the treatment of rheumatoid arthritis. J.Pharmacol.Exp.Ther. 309 348. PMID: 14718605.

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