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ChemicalBook--->CAS DataBase List--->292605-14-2

292605-14-2

292605-14-2 Structure

292605-14-2 Structure
IdentificationBack 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 PropertiesBack Directory
[Melting point ]

92-96°C
[storage temp. ]

?20°C
[solubility ]

DMSO: >20mg/mL
[form ]

powder
[color ]

white to off-white
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36
[Safety Statements ]

26
[WGK Germany ]

3
[HS Code ]

29349990
Hazard InformationBack 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.
[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

MMP-2/MMP-9 INHIBITOR IV(292605-14-2)1HNMR
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