| Identification | Back Directory | [Name]
MMP-2/MMP-9 INHIBITOR IV | [CAS]
292605-14-2 | [Synonyms]
SB-3CT
CS-860
MMP-2/MMP-9 INHIBITOR IV
MMP-2/MMP-9 INHIBITITOR IV
[[(4-Phenoxyphenyl)sulfonyl]methyl]thiirane
2-[[(4-phenoxyphenyl)sulfonyl]methyl]-thiirane
Thiirane, [[(4-phenoxyphenyl)sulfonyl]methyl]-
Thiirane, 2-[[(4-phenoxyphenyl)sulfonyl]methyl]-
SB-3CT (This product is only available in Japan.)
MMP-2/MMP-9 Inhibitor IV - CAS 292605-14-2 - Calbiochem | [Molecular Formula]
C15H14O3S2 | [MDL Number]
MFCD03457520 | [MOL File]
292605-14-2.mol | [Molecular Weight]
306.4 |
| Chemical Properties | Back Directory | [Melting point ]
92-96°C | [Boiling point ]
501.4±46.0 °C(Predicted) | [density ]
1.329±0.06 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
DMSO: >20mg/mL | [form ]
powder | [color ]
white to off-white | [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 | [InChIKey]
LSONWRHLFZYHIN-UHFFFAOYSA-N | [SMILES]
O=S(=O)(CC1CS1)c2ccc(Oc3ccccc3)cc2 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36 | [Safety Statements ]
26 | [WGK Germany ]
3 | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Uses]
Competitive, mechanism-based inhibitor of matrix metalloproteinases 2 and 9 (MMP-2 and MMP-9). It possesses Ki values in the nanomolar range against the gelatinases (14nM for MMP-2; 600nM for MMP-9), but in the micromolar range against other metalloproteinases (206μM for MMP-1, 15μM for MMP-3, 96μM for MMP-7, and 4μM for ADAM17/TACE). This inhibitor has also been used in vitro, in vivo, and in tissue culture. In vivo, it is metabolized to an even more potent gelatinase inhibitor. | [Definition]
ChEBI: 2-[(4-phenoxyphenyl)sulfonylmethyl]thiirane is an aromatic ether. | [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). | [Enzyme inhibitor]
This thiirane (FW = 306.41 g/mol), also known as matrix
metalloproteinase-2/matrix metalloproteinase-9 inhibitor IV (MMP-
2/MMP-9 inhibitor IV) and SB-3CT, is a mechanism-based inhibitor of
gelatinase A, or matrux metalloproteinase 2, Ki = 0.014 μM, gelatinase
B, or matrix metalloproteinase 9, Ki = 0.6 μM, membrane-type matrix
metalloproteinase 1, matrix metalloproteinase 14, matrilysin, Ki = 96
μM, stromelysin 1, or matrix metalloproteinase 3, Ki = 15 μM. | [in vivo]
SB-3CT (i.p.; 50 mg/kg; every other day; five weeks) inhibits intraosseous growth of human PC3 cells within the marrow of human fetal femur fragments previously implanted in SCID mice[3]. | Animal Model: | Five-week-old male C.B.-17.SCID mice[3] | | Dosage: | 50 mg/kg | | Administration: | IP; every other day; five weeks | | Result: | Inhibited intraosseous growth of human PC3 cells within the marrow of human fetal femur fragments previously implanted in SCID mice.
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| [IC 50]
MMP-2: 13.9 nM (Ki); MMP-9: 600 nM (Ki) | [storage]
Store at -20°C |
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