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Description: Adam 17 (TACE) and MMP inhibitor; orally bioavailable
Chemical Name: (3S)-4-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-3-thiomorpholinecarboxamide
Purity: ≥98% (HPLC)
Citations (2)
Reviews (1)
Literature (1)

Biological Activity for TMI 1

TMI 1 is an ADAM17 (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

Compound Libraries for TMI 1

TMI 1 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.

Technical Data for TMI 1

M. Wt 398.49
Formula C17H22N2O5S2
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 287403-39-8
PubChem ID 5288615
Smiles CC1(C)SCCN(S(C2=CC=C(OCC#CC)C=C2)(=O)=O)[C@H]1C(NO)=O

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 TMI 1

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 39.85 100
ethanol 7.97 20

Preparing Stock Solutions for TMI 1

The following data is based on the product molecular weight 398.49. 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.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.51 mL 12.55 mL 25.09 mL
5 mM 0.5 mL 2.51 mL 5.02 mL
10 mM 0.25 mL 1.25 mL 2.51 mL
50 mM 0.05 mL 0.25 mL 0.5 mL

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References for TMI 1

References are publications that support the biological activity of the product.

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 meta J.Pharmacol.Exp.Ther. 309 348 PMID: 14718605

If you know of a relevant reference for TMI 1, please let us know.

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Keywords: TMI 1, TMI 1 supplier, TMI1, Adam, 17, TACE, MMP, inhibitors, inhibits, tumor, necrosis, factor-α, TNF-α, converting, enzyme, rheumatoid, arthritis, cancer, stem, cells, anticancer, cytotoxic, orally, bioavailable, matrixins, matrix, metalloproteinases, proteinases, proteases, disintegrin, meta, Matrix, Metalloprotease, Cancer, Stem, Cells, ADAMs, 5960, Tocris Bioscience

2 Citations for TMI 1

Citations are publications that use Tocris products. Selected citations for TMI 1 include:

J Philip et al (2020) Dendritic Cell-Restricted Progenitors Contribute to Obesity-Associated Airway Inflammation via Adam17-p38 MAPK-Dependent Pathway. Front Immunol 11 363 PMID: 32184787

Bent et al (2017) The LIM-Only Protein Four and a Half LIM Domain Protein 2 Attenuates Development of Psoriatic Arthritis by Blocking Adam17-Mediated Tumor Necrosis Factor Release. Am J Pathol 187 2388-2398 PMID: 28823868

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Reviews for TMI 1

Average Rating: 5 (Based on 1 Review.)

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Selective effect of TMI-1 was observed for caspase-dependent apoptosis.
By Anonymous on 10/12/2019
Species: Human

Selective effect of TMI-1 was observed for caspase-dependent apoptosis. TMI-1 was observed for efficient in 34/40 tumor cell lines of various origins.

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Literature in this Area

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