SB-3CT

Names

[ Name ]:
SB-3CT

[Synonym ]:
2-[[(4-phenoxyphenyl)sulfonyl]methyl]-Thiirane
2-((4-phenoxyphenylsulfonyl)methyl)thiirane
IN1250
2-{[(4-Phenoxyphenyl)sulfonyl]methyl}thiirane
Thiirane, 2-[[(4-phenoxyphenyl)sulfonyl]methyl]-
MMP-2/MMP-9 Inhibitor IV
SB-3CT

Biological Activity

[Description]:

SB-3CT is a potent and competitive inhibitor of matrix metalloproteinase (MMP-2) and MMP-9.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

Research Areas >> Cancer

[Target]

MMP-2, MMP-9[1]

[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[1]. 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[2].

[In Vivo]

Post-ischemic treatment with SB-3CT significantly diminishes brain damage and reduced infarct volume to about 20% of the total hemisphere. SB-3CT treatment ameliorates neurobehavioral outcomes, particularly in the motor and sensory functions[3].

[Cell Assay]

PC3 cells are seeded in 35-mm dishes (5×104 cells/dish) in complete culture medium. The next day, the medium is replaced with complete medium supplemented with 1% DMSO alone (vehicle) or SB-3CT (final concentrations 0.1-50 μM) in 1%DMSO. At various times, the cells are harvested with trypsin and counted[2].

[Animal admin]

Adult male C57Bl/6 J mice, 6-9 weeks of age and weighing 20-28 g are divided into four groups: vehicle-treated group and SB-3CT-treated one with treatment for either one day or seven days after embolic MCA occlusion. SB-3CT (12.5 mg/mL) is freshly dissolved in 25% DMSO/65% PEG-200/10% water and filtered through an Acrodisc syringe filter with a 0.2 μm, 13-mm diameter sterile hydrophobic PTFE membrane. Mice are ip injected with 2 μL/gram body weight of this solution (equivalent to 25 mg/kg) 2 hours after embolic ischemia, followed by an additional dose at 4 hours. In repeated-dose treatment conditions, the same dose of SB-3CT is ip administered 2 and 4 hours after embolic ischemia, followed by once daily from post-ischemia day 1 to 6. Earlier work indicated that ip administration of SB-3CT does not alter mean arterial blood pressure, pH, PCO2, and PO2.

[References]

[1]. Lee M, et al. Water-Soluble MMP-9 Inhibitor Reduces Lesion Volume after Severe Traumatic Brain Injury. ACS Chem Neurosci. 2015 Oct 21;6(10):1658-64.

[2]. Bonfil RD, et al. Inhibition of human prostate cancer growth, osteolysis and angiogenesis in a bone metastasis model by a novel mechanism-based selective gelatinase inhibitor. Int J Cancer. 2006, 118(11), 2721-2726.

[3]. Cui J, et al. Inhibition of MMP-9 by a selective gelatinase inhibitor protects neurovasculature from embolic focal cerebral ischemia. Mol Neurodegener. 2012, 15, 7-21.

[4]. Zhang S, et al. Autophagy- and MMP-2/9-mediated Reduction and Redistribution of ZO-1 Contribute to Hyperglycemia-increased Blood-Brain Barrier Permeability During Early Reperfusion in Stroke. Neuroscience. 2018 May 1;377:126-137.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
501.4±46.0 °C at 760 mmHg

[ Melting Point ]:
101 °C

[ Molecular Formula ]:
C₁₅H₁₄O₃S₂

[ Molecular Weight ]:
306.400

[ Flash Point ]:
257.1±29.0 °C

[ Exact Mass ]:
306.038422

[ PSA ]:
77.05000

[ LogP ]:
3.36

[ Appearance of Characters ]:
white to off-white

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.628

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: >20mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36

[ Safety Phrases ]:
26

[ RIDADR ]:
NONH for all modes of transport

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