SB-3CT - CAS# 292605-14-2

SB-3CT is a potent matrix metalloproteinase MMP-2 and MMP-9 inhibitor. SB-3CT, CAS No. 292605-14-2, 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.

Product information

CAS Number: 292605-14-2

Molecular Weight: 306.40

Formula: C15H14O3S2

Synonym:

SB-3CT

SB3CT

SB3-CT

Chemical Name: 2-(((4-phenoxyphenyl)sulfonyl)methyl)thiirane

Smiles: O=S(=O)(CC1CS1)C1C=CC(=CC=1)OC1C=CC=CC=1

InChiKey: LSONWRHLFZYHIN-UHFFFAOYSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

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:

1. 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.
2. 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.
3. 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.

Products are for research use only. Not for human use.