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S1326

Sigma-Aldrich

SB−3CT

≥98% (HPLC), powder

Synonyme(s) :

2-[[(4-phenoxyphenyl)sulfonyl]methyl]-Thiirane

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About This Item

Formule empirique (notation de Hill):
C15H14O3S2
Numéro CAS:
292605-14-2
Poids moléculaire :
306.40
Numéro MDL:
MFCD09836266
Code UNSPSC :
12352200
ID de substance PubChem :
329824474
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to off-white

Solubilité

DMSO: >20 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

O=S(=O)(CC1CS1)c2ccc(Oc3ccccc3)cc2

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

Clé InChI

LSONWRHLFZYHIN-UHFFFAOYSA-N

Application

SB−3CT has been used as irreversible inhibitor of matrix metallopeptidase 9 (MMP9) in cell cultures to exclude reciprocal regulation.

Actions biochimiques/physiologiques

SB-3CT is a potent matrix metalloproteinase MMP-2 and MMP-9 inhibitor. Matrix metalloproteinases (MMPs) are involved in a number of activities including angiogenesis and embryogenesis. In particular, gelatinases A (MMP-2) and B (MMP-9), are thought to facilitate tumor metastasis. SB-3CT exhibits a covalent mechanism based behavior in inhibition of MMP-2 and MMP-9. This inhibitor appears to have similarity to TIMP-1 and TIMP-2 in the slow-binding component of inhibition. SB-3CT has been shown to directly bind to the zinc in the catalytic site of MMP-2. SB-3CT does not affect the activities of MMP-1 (Ki = 206 μM) MMP-3 (Ki = 15 μM), or MMP-7 (Ki = 96 μM).

Informations légales

Sold under license of U.S. Patent 6,703,415.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Chiara Sassoli et al.
Stem cells international, 2018, 5034679-5034679 (2018-05-02)
Bone marrow-derived mesenchymal stromal cell- (BM-MSC-) based therapy is a promising option for regenerative medicine. An important role in the control of the processes influencing the BM-MSC therapeutic efficacy, namely, extracellular matrix remodelling and proliferation and secretion ability, is played
Youqiong Ye et al.
Genome medicine, 12(1), 83-83 (2020-09-30)
Immune checkpoint blockade (ICB) therapy has demonstrated considerable clinical benefit in several malignancies, but has shown favorable response in only a small proportion of cancer patients. Recent studies have shown that matrix metalloproteinases (MMPs) are highly associated with the microenvironment
Adipose progenitor cell secretion of GM-CSF and MMP9 promotes a stromal and immunological microenvironment that supports breast cancer progression
Reggiani F, et al.
Cancer Research, 77(18), 5169-5182 (2017)
Hongxia Cai et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 25(6), 1448-1459 (2017-04-12)
Matrix metalloproteinase 9 (MMP-9) plays a beneficial role in the delayed phase of middle cerebral artery occlusion (MCAO). However, the mechanism is obscure. Here, we constructed hypoxia response element (HRE)-regulated MMP-9 to explore its effect on glial scars and neurogenesis in
Hong-Ru Chen et al.
PLoS pathogens, 14(4), e1007033-e1007033 (2018-04-28)
Vascular leakage is one of the salient characteristics of severe dengue. Nonstructural protein 1 (NS1) of dengue virus (DENV) can stimulate endothelial cells to secrete endothelial hyperpermeability factor, macrophage migration inhibitory factor (MIF), and the glycocalyx degradation factor heparanase 1
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