A selective inhibitor of MMP-2 and MMP-9
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SB-3CT

Item No. 16337

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(4-phenoxyphenyl)sulfonyl]methyl]-thiirane
CAS Number
292605-14-2
Synonyms
  • Matrix Metalloproteinase-2/9 Inhibitor IV
  • MMP-2/MMP-9 Inhibitor IV
Molecular Formula
C15H14O3S2
Formula Weight
306.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:5): 0.1 mg/mlDMSO: 15 mg/mlEthanol: 2 mg/ml
λmax
244 nm
SMILES
O=S(C(C=C1)=CC=C1OC2=CC=CC=C2)(CC3SC3)=O
InChi Code
InChI=1S/C15H14O3S2/c16-20(17,11-14-10-19-14)15-8-6-13(7-9-15)18-12-4-2-1-3-5-12/h1-9,14H,10-11H2
InChi Key
LSONWRHLFZYHIN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $41

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    1 mg

    $69

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    5 mg

    $293

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    Product Description

    SB-3CT is a selective, mechanism-based inhibitor of the gelatinases, matrix metalloproteinase-2 (MMP-2) and MMP-9 (Kis = 28 and 400 nM, respectively).1,2 First pass metabolism of SB-3CT in vivo produces a monohydroxylated metabolite that has greater inhibitory activity (Kis = 6 and 160 nM for MMP-2 and MMP-9, respectively).2 Both SB-3CT and its active metabolite can cross the blood-brain barrier and have utility in diseases of the central nervous system, such as stroke and traumatic brain injury.2,3 SB-3CT may have applications in other pathologies involving gelatinases, including cancer, cardiovascular diseases, and inflammation.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kleifeld, O., Kotra, L.P., Gervasi, D.C., et al. X-ray absorption studies of human matrix metalloproteinase-2 (MMP-2) bound to a highly selective mechanism-based inhibitor. Comparison with the latent and active forms of the enzyme. The Journal of Biological Chemisty 276(20), 17125-17131 (2001).

    2. Gooyit, M., Suckow, M.A., Schroeder, V.A., et al. Selective gelatinase inhibitor neuroprotective agents cross the blood-brain barrier. ACS Chem. Neurosci. 3(10), 730-736 (2012).

    3. Hadass, O., Tomlinson, B.N., Gooyit, M., et al. Selective inhibition of matrix metalloproteinase-9 attenuates secondary damage resulting from severe traumatic brain injury. PLoS One 8(10), e76904 (2013).

    4. Krüger, A., Arlt, M.J., Gerg, M., et al. Antimetastatic activity of a novel mechanism-based gelatinase inhibitor. Cancer Res. 65(9), 3523-3526 (2005).

    5. Gooyit, M., Lee, M., Schroeder, V.A., et al. Selective water-soluble gelatinase inhibitor prodrugs. J. Med. Chem. 54(19), 6676-6690 (2011).