Description
Cas:292605-14-2
Product Information:
SB-3CT is a potent matrix metalloproteinase MMP-2 and MMP-9 inhibitor. SB-3CT is a 2-[(arylsulfonyl)methyl]thiirane that achieves potent inhibition, by a thiirane-opening mechanism, of the MMP2 and MMP9 zinc metalloproteases. SB-3CT attenuates behavioral impairments and hippocampal loss after traumatic brain injury in rat. 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.
Chemical Formula: C15H14O3S2
Exact Mass: 306.0384
Molecular Weight: 306.4
Elemental Analysis: C, 58.80; H, 4.61; O, 15.67; S, 20.93
Synonym:
SB-3CT
SB3CT
SB3-CT
Chemical Name:
2-(((4-phenoxyphenyl)sulfonyl)methyl)thiirane
InChi Key:
LSONWRHLFZYHIN-UHFFFAOYSA-N
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
Smiles Code:
O=S(CC1SC1)(C2=CC=C(OC3=CC=CC=C3)C=C2)=O
Technical Data:
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
In Vitro:
SB-3CT has shown efficacy in an animal model of severe traumatic brain injury (TBI). SB-3CT inhibits MMP-9 with an inhibition constant Ki of 400±15 nM.
Inhibition of PC3 tumor growth by SB-3CT could also be a direct consequence of reduced extracellular matrix degradation within the bone tissue by the tumor cells themselves and/or by osteoclasts. Indeed, SB-3CT treatment is associated with a reduced osteolytic response, indicating that SB-3CT helps to preserve bone integrity.
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.
References:
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Jia F, Yin YH, Gao GY, Wang Y, Cen L, Jiang JY. MMP-9 inhibitor SB-3CT attenuates behavioral impairments and hippocampal loss after traumatic brain injury in rat. J Neurotrauma. 2014 Jul 1;31(13):1225-34. doi: 10.1089/neu.2013.3230. Epub 2014 Jun 3. PubMed PMID: 24661104; PubMed Central PMCID: PMC4082357.
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Zhou J, Tao P, Fisher JF, Shi Q, Mobashery S, Schlegel HB. QM/MM Studies of the Matrix Metalloproteinase 2 (MMP2) Inhibition Mechanism of (S)-SB-3CT and its Oxirane Analogue. J Chem Theory Comput. 2010 Nov 9;6(11):3580-3587. PubMed PMID: 21076643; PubMed Central PMCID: PMC2976054.
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Tao P, Fisher JF, Shi Q, Mobashery S, Schlegel HB. Matrix metalloproteinase 2 (MMP2) inhibition: DFT and QM/MM studies of the deprotonation-initialized ring-opening reaction of the sulfoxide analogue of SB-3CT. J Phys Chem B. 2010 Jan 21;114(2):1030-7. doi: 10.1021/jp909327y. PubMed PMID: 20039633; PubMed Central PMCID: PMC2821710.
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Tao P, Fisher JF, Mobashery S, Schlegel HB. DFT studies of the ring-opening mechanism of SB-3CT, a potent inhibitor of matrix metalloproteinase 2. Org Lett. 2009 Jun 18;11(12):2559-62. doi: 10.1021/ol9008393. PubMed PMID: 19445474; PubMed Central PMCID: PMC2821186.
Products are for research use only. Not for human use.
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