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S1326

Sigma-Aldrich

SB−3CT

≥98% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H14O3S2
CAS Number:
292605-14-2
Molecular Weight:
306.40
MDL number:
MFCD09836266
UNSPSC Code:
12352200
PubChem Substance ID:
329824474
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

SMILES string

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

InChI key

LSONWRHLFZYHIN-UHFFFAOYSA-N

Application

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

Biochem/physiol Actions

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).

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Patricia C Villalta et al.
American journal of physiology. Lung cellular and molecular physiology, 307(8), L652-L659 (2014-08-26)
Ca(2+) entry through transient receptor potential vanilloid 4 (TRPV4) results in swelling, blebbing, and detachment of the epithelium and capillary endothelium in the intact lung. Subsequently, increased permeability of the septal barrier and alveolar flooding ensue. In this study, we
Craig C Ulrich et al.
Biology of reproduction, 100(6), 1597-1604 (2019-04-06)
Matrix metalloproteinases 2 and 9 (MMP2/9) have previously been shown to be elevated in serum and amniotic fluid from women undergoing preterm birth. We performed experiments to determine the effects of MMP2/9 on uterine contraction and birth timing. Pregnant mice
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)
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