SB-3CT | CAS#292605-14-2 | MMP-2/9 Inhibitor

MedKoo Cat#: 406563 | Name: SB-3CT

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

SB-3CT

CAS#292605-14-2

Theoretical Analysis

MedKoo Cat#: 406563

Name: SB-3CT

CAS#: 292605-14-2

Chemical Formula: C15H14O3S2

Exact Mass: 306.0384

Molecular Weight: 306.40

Elemental Analysis: C, 58.80; H, 4.61; O, 15.67; S, 20.93

Price and Availability

Size	Price	Availability
5mg	USD 90.00	Ready to ship
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,450.00	Ready to ship
1g	USD 3,450.00	Ready to ship
2g	USD 5,950.00	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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A8T12K18

QC Data

View QC data: current batch, Lot#A8T12K18

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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/

	Solvent	mg/mL	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

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 306.40 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.

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:

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.

1: Ye Y, Kuang X, Xie Z, Liang L, Zhang Z, Zhang Y, Ma F, Gao Q, Chang R, Lee HH, Zhao S, Su J, Li H, Peng J, Chen H, Yin M, Peng C, Yang N, Wang J, Liu J, Liu H, Han L, Chen X. Small-molecule MMP2/MMP9 inhibitor SB-3CT modulates tumor immune surveillance by regulating PD-L1. Genome Med. 2020 Sep 28;12(1):83. doi: 10.1186/s13073-020-00780-z. PMID: 32988398; PMCID: PMC7523356. 2: 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. PMID: 24661104; PMCID: PMC4082357. 3: 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. doi: 10.1021/ct100382k. PMID: 21076643; PMCID: PMC2976054. 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. PMID: 19445474; PMCID: PMC2821186. 5: 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. PMID: 20039633; PMCID: PMC2821710. 6: Zhu W, Han L, Wu Y, Tong L, He L, Wang Q, Yan Y, Pan T, Shen J, Song Y, Shen Y, Zhu Q, Zhou J. Keratin 15 protects against cigarette smoke-induced epithelial mesenchymal transformation by MMP-9. Respir Res. 2023 Nov 25;24(1):297. doi: 10.1186/s12931-023-02598-w. PMID: 38007424; PMCID: PMC10675954. 7: Du HT, Du LL, Tang XL, Ge HY, Liu P. Blockade of MMP-2 and MMP-9 inhibits corneal lymphangiogenesis. Graefes Arch Clin Exp Ophthalmol. 2017 Aug;255(8):1573-1579. doi: 10.1007/s00417-017-3651-8. Epub 2017 Jul 1. PMID: 28669039. 8: Fisher JF, Mobashery S. Mechanism-based profiling of MMPs. Methods Mol Biol. 2010;622:471-87. doi: 10.1007/978-1-60327-299-5_27. PMID: 20135299; PMCID: PMC6986384. 9: Ji Y, Huang W, Chen Y, Zhang X, Wu F, Tang W, Lu Z, Huang C. Inhibition of MMP-2 and MMP-9 attenuates surgery-induced cognitive impairment in aged mice. Brain Res Bull. 2023 Nov;204:110810. doi: 10.1016/j.brainresbull.2023.110810. Epub 2023 Nov 7. PMID: 37939860. 10: Tong J, Zheng Q, Gu X, Weng Q, Yu S, Fang Z, Jafar Hussain HM, Xu J, Ren H, Chen N, Xie J. COL4A3 Mutation Induced Podocyte Apoptosis by Dysregulation of NADPH Oxidase 4 and MMP-2. Kidney Int Rep. 2023 Jun 19;8(9):1864-1874. doi: 10.1016/j.ekir.2023.06.007. PMID: 37705901; PMCID: PMC10496016. 11: Zhang L, Gao YZ, Zhao CJ, Xia JY, Yang JJ, Ji MH. Reduced inhibitory and excitatory input onto parvalbumin interneurons mediated by perineuronal net might contribute to cognitive impairments in a mouse model of sepsis-associated encephalopathy. Neuropharmacology. 2023 Mar 1;225:109382. doi: 10.1016/j.neuropharm.2022.109382. Epub 2022 Dec 18. PMID: 36543316. 12: Raz L, Yang Y, Thompson J, Hobson S, Pesko J, Mobashery S, Chang M, Rosenberg G. MMP-9 inhibitors impair learning in spontaneously hypertensive rats. PLoS One. 2018 Dec 11;13(12):e0208357. doi: 10.1371/journal.pone.0208357. PMID: 30533010; PMCID: PMC6289411. 13: Gooyit M, Lee M, Schroeder VA, Ikejiri M, Suckow MA, Mobashery S, Chang M. Selective water-soluble gelatinase inhibitor prodrugs. J Med Chem. 2011 Oct 13;54(19):6676-90. doi: 10.1021/jm200566e. Epub 2011 Sep 6. PMID: 21866961; PMCID: PMC3190643. 14: Lee M, Chen Z, Tomlinson BN, Gooyit M, Hesek D, Juárez MR, Nizam R, Boggess B, Lastochkin E, Schroeder VA, Wolter WR, Suckow MA, Cui J, Mobashery S, Gu Z, Chang M. Water-Soluble MMP-9 Inhibitor Reduces Lesion Volume after Severe Traumatic Brain Injury. ACS Chem Neurosci. 2015 Oct 21;6(10):1658-64. doi: 10.1021/acschemneuro.5b00140. Epub 2015 Aug 14. PMID: 26241578; PMCID: PMC5800744. 15: Liu H, Lei D, Li J, Xin J, Zhang L, Fu L, Wang J, Zeng W, Yao C, Zhang Z, Wang S. MMP-2 Inhibitor-Mediated Tumor Microenvironment Regulation Using a Sequentially Released Bio-Nanosystem for Enhanced Cancer Photo-Immunotherapy. ACS Appl Mater Interfaces. 2022 Sep 21;14(37):41834-41850. doi: 10.1021/acsami.2c14781. Epub 2022 Sep 8. PMID: 36073504. 16: Hu Y, Hu XD, He ZQ, Liu Y, Gui YK, Zhu SH, Da X, Liu YN, Liu LX, Shen QY, Xu GH. Anesthesia/surgery activate MMP9 leading to blood-brain barrier disruption, triggering neuroinflammation and POD-like behavior in aged mice. Int Immunopharmacol. 2024 Jun 30;135:112290. doi: 10.1016/j.intimp.2024.112290. Epub 2024 May 25. PMID: 38796964. 17: 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. 18: Boguszewska-Czubara A, Budzynska B, Skalicka-Wozniak K, Kurzepa J. Perspectives and New Aspects of Metalloproteinases' Inhibitors in the Therapy of CNS Disorders: From Chemistry to Medicine. Curr Med Chem. 2019;26(18):3208-3224. doi: 10.2174/0929867325666180514111500. PMID: 29756562. 19: Huang HC, Ho HL, Chang CC, Chuang CL, Pun CK, Lee FY, Huang YH, Hou MC, Hsu SJ. Matrix metalloproteinase-9 inhibition or deletion attenuates portal hypertension in rodents. J Cell Mol Med. 2021 Nov;25(21):10073-10087. doi: 10.1111/jcmm.16940. Epub 2021 Oct 14. PMID: 34647412; PMCID: PMC8572799. 20: Wang H, Yuan M, Yang E, Chen D, Su A, Wu Z. Enterovirus 71 infection induced Aquaporin-4 depolarization by increasing matrix metalloproteinase-9 activity. Neurosci Lett. 2021 Aug 10;759:136049. doi: 10.1016/j.neulet.2021.136049. Epub 2021 Jun 12. PMID: 34126180.