OXSI-2 | CAS#622387-85-3 | Syk Inhibitor

MedKoo Cat#: 530952 | Name: OXSI-2

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Description:

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

OXSI-2 is an Syk Inhibitor. OXSI-2 blocks nigericin-induced inflammasome signaling and pyroptosis independent of potassium efflux. OXSI-2 inhibits inflammasome assembly, caspase-1 activation, IL-1β processing and release, mitochondrial ROS generation, and pyroptotic cell death. Using a novel live cell potassium sensor it is shown that Syk inhibition with OXSI-2 has no effect on potassium efflux kinetics and that blockade of potassium efflux with extracellular potassium alters Syk phosphorylation.

Chemical Structure

OXSI-2

CAS#622387-85-3

Theoretical Analysis

MedKoo Cat#: 530952

Name: OXSI-2

CAS#: 622387-85-3

Chemical Formula: C18H15N3O3S

Exact Mass: 353.0834

Molecular Weight: 353.40

Elemental Analysis: C, 61.18; H, 4.28; N, 11.89; O, 13.58; S, 9.07

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 500.00
10mg	USD 750.00

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Synonym

Syk Inhibitor, OXSI-2; OXSI2; OXSI 2.

IUPAC/Chemical Name

2,3-Dihydro-3-[(1-methyl-1H-indol-3-yl)methylene]-2-oxo-1H-indole-5-sulfonamide

InChi Key

MLKHXLFEYOOYEY-OVCLIPMQSA-N

InChi Code

InChI=1S/C18H15N3O3S/c1-21-10-11(13-4-2-3-5-17(13)21)8-15-14-9-12(25(19,23)24)6-7-16(14)20-18(15)22/h2-10H,1H3,(H,20,22)(H2,19,23,24)/b15-8+

SMILES Code

O=S(C1=CC2=C(NC(/C2=C/C3=CN(C)C4=C3C=CC=C4)=O)C=C1)(N)=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

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

Instruction

View handling instruction

Biological target:

OXSI-2 is a bioavailable, cell-permeable S yk inhibitor with an EC50 of 313 nM and an IC50 of 14 nM.

In vitro activity:

The aim of the present study is to explore in detail the effects of the oxindole Syk inhibitor OXSI-2 on various aspects of nigericin-induced inflammasome signaling. These results indicate that OXSI-2 inhibits inflammasome assembly, caspase-1 activation, IL-1β processing and release, mitochondrial ROS generation, and pyroptotic cell death. Using a novel live cell potassium sensor we show that Syk inhibition with OXSI-2 has no effect on potassium efflux kinetics and that blockade of potassium efflux with extracellular potassium alters Syk phosphorylation. Reference: Biochem Biophys Res Commun. 2016 Apr 8;472(3):545-50. https://pubmed.ncbi.nlm.nih.gov/26970308/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	28.30

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 353.40 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. Yaron JR, Rao MY, Gangaraju S, Zhang L, Kong X, Su F, Tian Y, Glenn HL, Meldrum DR. The oxindole Syk inhibitor OXSI-2 blocks nigericin-induced inflammasome signaling and pyroptosis independent of potassium efflux. Biochem Biophys Res Commun. 2016 Apr 8;472(3):545-50. doi: 10.1016/j.bbrc.2016.03.021. Epub 2016 Mar 9. PMID: 26970308. 2. Buitrago L, Langdon WY, Sanjay A, Kunapuli SP. Tyrosine phosphorylated c-Cbl regulates platelet functional responses mediated by outside-in signaling. Blood. 2011 Nov 17;118(20):5631-40. doi: 10.1182/blood-2011-01-328807. Epub 2011 Oct 3. PMID: 21967979; PMCID: PMC3217362.

In vitro protocol:

In vivo protocol:

TBD

1: Teske KA, Corona C, Wilkinson J, Mamott D, Good DA, Zambrano D, Lazar DF, Cali JJ, Robers MB, O'Brien MA. Interrogating direct NLRP3 engagement and functional inflammasome inhibition using cellular assays. Cell Chem Biol. 2024 Feb 15;31(2):349-360.e6. doi: 10.1016/j.chembiol.2023.09.016. Epub 2023 Oct 18. PMID: 37858335. 2: Badolia R, Kostyak JC, Dangelmaier C, Kunapuli SP. Syk Activity Is Dispensable for Platelet GP1b-IX-V Signaling. Int J Mol Sci. 2017 Jun 9;18(6):1238. doi: 10.3390/ijms18061238. PMID: 28598382; PMCID: PMC5486061. 3: Yaron JR, Rao MY, Gangaraju S, Zhang L, Kong X, Su F, Tian Y, Glenn HL, Meldrum DR. The oxindole Syk inhibitor OXSI-2 blocks nigericin-induced inflammasome signaling and pyroptosis independent of potassium efflux. Biochem Biophys Res Commun. 2016 Apr 8;472(3):545-50. doi: 10.1016/j.bbrc.2016.03.021. Epub 2016 Mar 9. PMID: 26970308. 4: Buitrago L, Manne BK, Andre P, McKenzie S, Kunapuli S. Identification of novel Syk-independent functional roles of FcγRIIa in platelet outside-in signaling using transgenic mice expressing human FcγRIIa. Platelets. 2016 Jul;27(5):488-90. doi: 10.3109/09537104.2015.1119813. Epub 2016 Jan 25. PMID: 26809427; PMCID: PMC4975857. 5: Getz TM, Manne BK, Buitrago L, Mao Y, Kunapuli SP. Dextran sulphate induces fibrinogen receptor activation through a novel Syk-independent PI-3 kinase- mediated tyrosine kinase pathway in platelets. Thromb Haemost. 2013 Jun;109(6):1131-40. doi: 10.1160/TH12-09-0645. Epub 2013 Mar 28. PMID: 23571309. 6: Qu L, Li Y, Pan X, Zhang P, LaMotte RH, Ma C. Transient receptor potential canonical 3 (TRPC3) is required for IgG immune complex-induced excitation of the rat dorsal root ganglion neurons. J Neurosci. 2012 Jul 11;32(28):9554-62. doi: 10.1523/JNEUROSCI.6355-11.2012. PMID: 22787041; PMCID: PMC3437229. 7: Buitrago L, Langdon WY, Sanjay A, Kunapuli SP. Tyrosine phosphorylated c-Cbl regulates platelet functional responses mediated by outside-in signaling. Blood. 2011 Nov 17;118(20):5631-40. doi: 10.1182/blood-2011-01-328807. Epub 2011 Oct 3. PMID: 21967979; PMCID: PMC3217362. 8: Singh D, Rani R, Rajendran R, Kaur NJ, Pandey A, Chopra P, Jain T, Jain MK, Grover S, Arya R, Saini KS. Human spleen tyrosine kinase (Syk) recombinant expression systems for high-throughput assays. Biotechnol J. 2010 Feb;5(2):201-12. doi: 10.1002/biot.200900139. PMID: 20013945. 9: Speich HE, Grgurevich S, Kueter TJ, Earhart AD, Slack SM, Jennings LK. Platelets undergo phosphorylation of Syk at Y525/526 and Y352 in response to pathophysiological shear stress. Am J Physiol Cell Physiol. 2008 Oct;295(4):C1045-54. doi: 10.1152/ajpcell.90644.2007. Epub 2008 Aug 20. PMID: 18715989. 10: Bhavaraju K, Kim S, Daniel JL, Kunapuli SP. Evaluation of [3-(1-methyl-1H-indol-3-yl-methylene)-2-oxo-2, 3-dihydro-1H-indole-5-sulfonamide] (OXSI-2), as a Syk-selective inhibitor in platelets. Eur J Pharmacol. 2008 Feb 12;580(3):285-90. doi: 10.1016/j.ejphar.2007.11.009. Epub 2007 Nov 17. PMID: 18068154; PMCID: PMC2279182.