SB-3CT
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MedKoo CAT#: 406563

CAS#: 292605-14-2

Description: 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 Structure

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SB-3CT
CAS# 292605-14-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406563
Name: SB-3CT
CAS#: 292605-14-2
Chemical Formula: C15H14O3S2
Exact Mass: 306.04
Molecular Weight: 306.400
Elemental Analysis: C, 58.80; H, 4.61; O, 15.67; S, 20.93

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2450 Ready to ship
1g USD 3450 Ready to ship
2g USD 5950 Ready to ship
5mg USD 90 Ready to ship
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Synonym: SB-3CT; SB3CT; SB3-CT

IUPAC/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

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

Biological target: SB-3CT is a matrix metalloproteinase MMP-2 and MMP-9 inhibitor with Ki values of 13.9 and 600 nM, respectively.
In vitro activity: MMP9 inhibition with SB-3CT dose-dependently enhanced the (basolateral-to-apical) transit of monomeric Aβ(1-42) across an in vitro model of the BBB (Figure 4). Aβ BBB clearance was increased by >50% at 100nM SB-3CT compared to control, and statistically significant increases were observed at SB-3CT concentrations 5μM and higher (2.5-fold). Moreover, to assess the potential impact of SB-3CT on BBB monolayer integrity, this study evaluated the movement of a paracellular marker (10kDa lucifer yellow dextran) across the in vitro BBB model and observed no difference between each SB-3CT group and control conditions, indicating the barrier properties of the BBB model are maintained in the presence of SB-3CT exposure (data not shown). Reference: Mol Neurobiol. 2019 Dec; 56(12): 8296–8305. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6842100/
In vivo activity: The altered anxiety in the E4FAD mice indicates that treatment with SB-3CT may be efficacious, however, due to limitations in detection, the proteolytic activity of MMP9 in the brain could not be measured and this study could not confirm target engagement. This finding is consistent with other reports owing to the rapid degradation of the activated MMP9 enzyme in vivo. The mechanism of action of SB-3CT is to modulate MMP9 activity, not MMP9 expression. As expected, total MMP9 levels in the E4FAD brains remained unaltered, emphasizing that MMP9 expression is not a good indicator of target engagement when assessing SB-3CT. Owing to this limitation, it is not certain whether the observed effect on anxiety in the current studies was caused by the inhibition of MMP9 activity or another effect of the drug. In prior reporting, the same dose of SB-3CT used in these studies showed significant reductions in MMP9 activity in the brain using a treatment paradigm more acute than that used in the present studie. Thus, it seems likely MMP9 activity was inhibited in the current studies, but a more chronic treatment paradigm may be necessary to overcome the AD phenotype. Reference: BMC Neurosci. 2021; 22: 39. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152085/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 39.2 127.81
DMF 25.0 81.59
DMF:PBS (pH 7.2) (1:5) 0.1 0.33
Ethanol 6.0 19.71

Preparing Stock Solutions

The following data is based on the product molecular weight 306.400000000000000000000000000000 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Shackleton B, Ringland C, Abdullah L, Mullan M, Crawford F, Bachmeier C. Influence of Matrix Metallopeptidase 9 on Beta-Amyloid Elimination Across the Blood-Brain Barrier. Mol Neurobiol. 2019 Dec;56(12):8296-8305. doi: 10.1007/s12035-019-01672-z. Epub 2019 Jun 18. PMID: 31209784; PMCID: PMC6842100. 2. Liu X, Su P, Meng S, Aschner M, Cao Y, Luo W, Zheng G, Liu M. Role of matrix metalloproteinase-2/9 (MMP2/9) in lead-induced changes in an in vitro blood-brain barrier model. Int J Biol Sci. 2017 Oct 31;13(11):1351-1360. doi: 10.7150/ijbs.20670. PMID: 29209140; PMCID: PMC5715519. 3. Ringland C, Schweig JE, Eisenbaum M, Paris D, Ait-Ghezala G, Mullan M, Crawford F, Abdullah L, Bachmeier C. MMP9 modulation improves specific neurobehavioral deficits in a mouse model of Alzheimer's disease. BMC Neurosci. 2021 May 25;22(1):39. doi: 10.1186/s12868-021-00643-2. PMID: 34034683; PMCID: PMC8152085. 4. Pirbhoy PS, Rais M, Lovelace JW, Woodard W, Razak KA, Binder DK, Ethell IM. Acute pharmacological inhibition of matrix metalloproteinase-9 activity during development restores perineuronal net formation and normalizes auditory processing in Fmr1 KO mice. J Neurochem. 2020 Dec;155(5):538-558. doi: 10.1111/jnc.15037. Epub 2020 Jun 8. PMID: 32374912; PMCID: PMC7644613.
In vitro protocol: 1. Shackleton B, Ringland C, Abdullah L, Mullan M, Crawford F, Bachmeier C. Influence of Matrix Metallopeptidase 9 on Beta-Amyloid Elimination Across the Blood-Brain Barrier. Mol Neurobiol. 2019 Dec;56(12):8296-8305. doi: 10.1007/s12035-019-01672-z. Epub 2019 Jun 18. PMID: 31209784; PMCID: PMC6842100. 2. Liu X, Su P, Meng S, Aschner M, Cao Y, Luo W, Zheng G, Liu M. Role of matrix metalloproteinase-2/9 (MMP2/9) in lead-induced changes in an in vitro blood-brain barrier model. Int J Biol Sci. 2017 Oct 31;13(11):1351-1360. doi: 10.7150/ijbs.20670. PMID: 29209140; PMCID: PMC5715519.
In vivo protocol: 1. Ringland C, Schweig JE, Eisenbaum M, Paris D, Ait-Ghezala G, Mullan M, Crawford F, Abdullah L, Bachmeier C. MMP9 modulation improves specific neurobehavioral deficits in a mouse model of Alzheimer's disease. BMC Neurosci. 2021 May 25;22(1):39. doi: 10.1186/s12868-021-00643-2. PMID: 34034683; PMCID: PMC8152085. 2. Pirbhoy PS, Rais M, Lovelace JW, Woodard W, Razak KA, Binder DK, Ethell IM. Acute pharmacological inhibition of matrix metalloproteinase-9 activity during development restores perineuronal net formation and normalizes auditory processing in Fmr1 KO mice. J Neurochem. 2020 Dec;155(5):538-558. doi: 10.1111/jnc.15037. Epub 2020 Jun 8. PMID: 32374912; PMCID: PMC7644613.

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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. 4: 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.