SB-216763 | CAS#280744-09-4 | GSK3 inhibitor

MedKoo Cat#: 401903 | Name: SB-216763

Description:

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

SB-216763 is a glycogen synthase kinase-3 (GSK3) inhibitor, which can maintain mouse embryonic stem cells (mESCs) in a pluripotent state in the absence of exogenous leukemia inhibitory factor (LIF) when cultured on mouse embryonic fibroblasts (MEFs). SB-216763 is the first GSK3 inhibitor that can promote self-renewal of mESC co-cultured with MEFs for more than two months.

Chemical Structure

SB-216763

CAS#280744-09-4

Theoretical Analysis

MedKoo Cat#: 401903

Name: SB-216763

CAS#: 280744-09-4

Chemical Formula: C19H12Cl2N2O2

Exact Mass: 370.0276

Molecular Weight: 371.22

Elemental Analysis: C, 61.47; H, 3.26; Cl, 19.10; N, 7.55; O, 8.62

Price and Availability

Size	Price	Availability
10mg	USD 110.00	Ready to ship
25mg	USD 220.00	Ready to ship
50mg	USD 385.00	Ready to ship
100mg	USD 650.00	Ready to ship
200mg	USD 1,050.00	Ready to ship
500mg	USD 2,250.00	Ready to ship
1g	USD 3,450.00	Ready to ship
2g	USD 6,050.00	Ready to ship

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Related CAS #

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Synonym

SB216763; SB 216763; SB-216763

IUPAC/Chemical Name

3-(2,4-dichlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

InChi Key

JCSGFHVFHSKIJH-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H12Cl2N2O2/c1-23-9-13(11-4-2-3-5-15(11)23)17-16(18(24)22-19(17)25)12-7-6-10(20)8-14(12)21/h2-9H,1H3,(H,22,24,25)

SMILES Code

O=C(C(C1=CC=C(Cl)C=C1Cl)=C2C3=CN(C)C4=C3C=CC=C4)NC2=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#C20R04B07

QC Data

View QC data: current batch, Lot#C20R04B07

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

SB-216763 is an ATP-competitive GSK-3 inhibitor with IC50s of 34.3 nM for both GSK-3α and GSK-3β.

In vitro activity:

In this study, SB-216763 had roles in osteogenesis, anti-adipogenesis, and potential osteoclast inhibition. SB-216763 activated canonical Wnt signaling in ST2 bone marrow stromal cells, promoting osteogenic differentiation and inhibiting adipogenesis. SB-216763 modulated osteoclast cytokines, potentially inhibiting osteoclast differentiation. SB-216763 demonstrated sustained release, supporting cell viability, proliferation, and osteogenic differentiation. Reference: Front Bioeng Biotechnol. 2023 Jul 28;11:1215233. https://pubmed.ncbi.nlm.nih.gov/37576993/

In vivo activity:

In a rat myocardial infarction (MI) model, SB-216763 ameliorated acute cardiac injury and improved myocardial dysfunction. SB-216763 increased the mRNA and protein expression of Kir2.1 during MI. SB-216763 treatment abrogated the decreased expression of Kir2.1 in H9c2 cells under hypoxic conditions. Reference: J Interv Card Electrophysiol. 2021 Feb 20. https://pubmed.ncbi.nlm.nih.gov/33611692/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	53.90

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 371.22 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. Gong W, Li M, Zhao L, Wang P, Wang X, Wang B, Liu X, Tu X. Sustained release of a highly specific GSK3β inhibitor SB216763 in the PCL scaffold creates an osteogenic niche for osteogenesis, anti-adipogenesis, and potential angiogenesis. Front Bioeng Biotechnol. 2023 Jul 28;11:1215233. doi: 10.3389/fbioe.2023.1215233. PMID: 37576993; PMCID: PMC10419179. 2. Gao L, Zhao M, Li P, Kong J, Liu Z, Chen Y, Huang R, Chu J, Quan J, Zeng R. Glycogen synthase kinase 3 (GSK3)-inhibitor SB216763 promotes the conversion of human umbilical cord mesenchymal stem cells into neural precursors in adherent culture. Hum Cell. 2017 Jan;30(1):11-22. doi: 10.1007/s13577-016-0146-6. Epub 2016 Sep 7. Erratum in: Hum Cell. 2017 Jan;30(1):49. PMID: 27604750. 3. Chang C, Wang SH, Xu LN, Su XL, Zeng YF, Wang P, Zhang LR, Han SN. Glycogen synthase kinase 3 beta inhibitor SB216763 improves Kir2.1 expression after myocardia infraction in rats. J Interv Card Electrophysiol. 2021 Feb 20. doi: 10.1007/s10840-021-00963-7. Epub ahead of print. PMID: 33611692. 4. Chen K, Fu Q, Ye C, Zhan X, Lu J, Du M, Feng Y, Liang P, Wang W. The Regulating Role of SB216763 in Pseudomonas aeruginosa Keratitis. Clin Lab. 2019 Oct 1;65(10). doi: 10.7754/Clin.Lab.2019.190128. PMID: 31625371.

In vitro protocol:

In vivo protocol:

1. Chang C, Wang SH, Xu LN, Su XL, Zeng YF, Wang P, Zhang LR, Han SN. Glycogen synthase kinase 3 beta inhibitor SB216763 improves Kir2.1 expression after myocardia infraction in rats. J Interv Card Electrophysiol. 2021 Feb 20. doi: 10.1007/s10840-021-00963-7. Epub ahead of print. PMID: 33611692. 2. Chen K, Fu Q, Ye C, Zhan X, Lu J, Du M, Feng Y, Liang P, Wang W. The Regulating Role of SB216763 in Pseudomonas aeruginosa Keratitis. Clin Lab. 2019 Oct 1;65(10). doi: 10.7754/Clin.Lab.2019.190128. PMID: 31625371.

1: Zhang YD, Ding XJ, Dai HY, Peng WS, Guo NF, Zhang Y, Zhou QL, Chen XL. SB-216763, a GSK-3β inhibitor, protects against aldosterone-induced cardiac, and renal injury by activating autophagy. J Cell Biochem. 2018 Jul;119(7):5934-5943. doi: 10.1002/jcb.26788. Epub 2018 Mar 30. PMID: 29600538; PMCID: PMC6001754. 2: Kirby LA, Schott JT, Noble BL, Mendez DC, Caseley PS, Peterson SC, Routledge TJ, Patel NV. Glycogen synthase kinase 3 (GSK3) inhibitor, SB-216763, promotes pluripotency in mouse embryonic stem cells. PLoS One. 2012;7(6):e39329. doi: 10.1371/journal.pone.0039329. Epub 2012 Jun 26. PMID: 22745733; PMCID: PMC3383737. 3: Guardigni M, Pruccoli L, Santini A, Simone A, Bersani M, Spyrakis F, Frabetti F, Uliassi E, Andrisano V, Pagliarani B, Fernández-Gómez P, Palomo V, Bolognesi ML, Tarozzi A, Milelli A. PROTAC-Induced Glycogen Synthase Kinase 3β Degradation as a Potential Therapeutic Strategy for Alzheimer's Disease. ACS Chem Neurosci. 2023 Jun 7;14(11):1963-1970. doi: 10.1021/acschemneuro.3c00096. Epub 2023 May 23. PMID: 37218653; PMCID: PMC10251479. 4: Wang M, Gao M, Miller KD, Sledge GW, Hutchins GD, Zheng QH. The first synthesis of [(11)C]SB-216763, a new potential PET agent for imaging of glycogen synthase kinase-3 (GSK-3). Bioorg Med Chem Lett. 2011 Jan 1;21(1):245-9. doi: 10.1016/j.bmcl.2010.11.026. Epub 2010 Nov 11. PMID: 21115250. 5: Wickens RH, Quartarone SE, Beninger RJ. Inhibition of glycogen synthase kinase-3 by SB 216763 affects acquisition at lower doses than expression of amphetamine-conditioned place preference in rats. Behav Pharmacol. 2017 Jun;28(4):262-271. doi: 10.1097/FBP.0000000000000283. PMID: 27984209. 6: Sampath C, Srinivasan S, Freeman ML, Gangula PR. Inhibition of GSK-3β restores delayed gastric emptying in obesity-induced diabetic female mice. Am J Physiol Gastrointest Liver Physiol. 2020 Oct 1;319(4):G481-G493. doi: 10.1152/ajpgi.00227.2020. Epub 2020 Aug 19. PMID: 32812777; PMCID: PMC7654647. 7: Schulz L, Pries R, Lanka AS, Drenckhan M, Rades D, Wollenberg B. Inhibition of GSK3α/β impairs the progression of HNSCC. Oncotarget. 2018 Jun 12;9(45):27630-27644. doi: 10.18632/oncotarget.25250. PMID: 29963225; PMCID: PMC6021246. 8: Li L, Shao X, Cole EL, Ohnmacht SA, Ferrari V, Hong YT, Williamson DJ, Fryer TD, Quesada CA, Sherman P, Riss PJ, Scott PJ, Aigbirhio FI. Synthesis and Initial in Vivo Studies with [(11)C]SB-216763: The First Radiolabeled Brain Penetrative Inhibitor of GSK-3. ACS Med Chem Lett. 2015 Mar 10;6(5):548-52. doi: 10.1021/acsmedchemlett.5b00044. PMID: 26005531; PMCID: PMC4434473. 9: Göttert R, Fidzinski P, Kraus L, Schneider UC, Holtkamp M, Endres M, Gertz K, Kronenberg G. Lithium inhibits tryptophan catabolism via the inflammation- induced kynurenine pathway in human microglia. Glia. 2022 Mar;70(3):558-571. doi: 10.1002/glia.24123. Epub 2021 Dec 4. PMID: 34862988. 10: Couvreur N, Tissier R, Pons S, Chenoune M, Waintraub X, Berdeaux A, Ghaleh B. The ceiling effect of pharmacological postconditioning with the phytoestrogen genistein is reversed by the GSK3beta inhibitor SB 216763 [3-(2,4-dichlorophenyl)-4(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione] through mitochondrial ATP-dependent potassium channel opening. J Pharmacol Exp Ther. 2009 Jun;329(3):1134-41. doi: 10.1124/jpet.109.152587. Epub 2009 Mar 24. PMID: 19318592. 11: Alcántara-Hernández R, Carmona-Rosas G, Hernández-Espinosa DA, García-Sáinz JA. Glycogen Synthase Kinase-3 modulates α1A-adrenergic receptor action and regulation. Eur J Cell Biol. 2020 Apr;99(2-3):151072. doi: 10.1016/j.ejcb.2020.151072. Epub 2020 Feb 22. PMID: 32113707. 12: Duspara K, Bojanic K, Pejic JI, Kuna L, Kolaric TO, Nincevic V, Smolic R, Vcev A, Glasnovic M, Curcic IB, Smolic M. Targeting the Wnt Signaling Pathway in Liver Fibrosis for Drug Options: An Update. J Clin Transl Hepatol. 2021 Dec 28;9(6):960-971. doi: 10.14218/JCTH.2021.00065. Epub 2021 Sep 13. PMID: 34966659; PMCID: PMC8666372. 13: Enman NM, Unterwald EM. Inhibition of GSK3 attenuates amphetamine-induced hyperactivity and sensitization in the mouse. Behav Brain Res. 2012 May 16;231(1):217-25. doi: 10.1016/j.bbr.2012.03.027. PMID: 22649795; PMCID: PMC3566781. 14: Lange C, Mix E, Frahm J, Glass A, Müller J, Schmitt O, Schmöle AC, Klemm K, Ortinau S, Hübner R, Frech MJ, Wree A, Rolfs A. Small molecule GSK-3 inhibitors increase neurogenesis of human neural progenitor cells. Neurosci Lett. 2011 Jan 13;488(1):36-40. doi: 10.1016/j.neulet.2010.10.076. Epub 2010 Nov 5. PMID: 21056624. 15: Park HJ, Kim HJ, Bae GS, Seo SW, Kim DY, Jung WS, Kim MS, Song MY, Kim EK, Kwon KB, Hwang SY, Song HJ, Park CS, Park RK, Chong MS, Park SJ. Selective GSK-3beta inhibitors attenuate the cisplatin-induced cytotoxicity of auditory cells. Hear Res. 2009 Nov;257(1-2):53-62. doi: 10.1016/j.heares.2009.08.001. Epub 2009 Aug 8. PMID: 19666099. 16: Gross ER, Hsu AK, Gross GJ. Delayed cardioprotection afforded by the glycogen synthase kinase 3 inhibitor SB-216763 occurs via a KATP- and MPTP- dependent mechanism at reperfusion. Am J Physiol Heart Circ Physiol. 2008 Mar;294(3):H1497-500. doi: 10.1152/ajpheart.01381.2007. Epub 2008 Jan 25. PMID: 18223186. 17: Lei C, Jing G, Jichao W, Xiaohui L, Fang Q, Hua G, Yazhou M, Zhang Y. MiR-137's Tumor Suppression on Prolactinomas by Targeting MITF and Modulating Wnt Signaling Pathway. J Clin Endocrinol Metab. 2019 Dec 1;104(12):6391-6402. doi: 10.1210/jc.2018-02544. PMID: 31162548. 18: Zhong JQ, Xie YK, Ji XK, Fu JH, Wang Y, Zhang QY, Shi HQ, Shan YF. [Effects of glycogen synthase kinase 3β overexpression in rat and glycogen synthase kinase 3β inhibitor SB-216763 on proliferation of hepatic oval cells]. Zhonghua Wai Ke Za Zhi. 2012 Nov;50(11):1003-6. Chinese. PMID: 23302485. 19: Nguyen T, Fan T, George SR, Perreault ML. Disparate Effects of Lithium and a GSK-3 Inhibitor on Neuronal Oscillatory Activity in Prefrontal Cortex and Hippocampus. Front Aging Neurosci. 2018 Jan 12;9:434. doi: 10.3389/fnagi.2017.00434. PMID: 29375364; PMCID: PMC5770585. 20: Miller JS, Tallarida RJ, Unterwald EM. Cocaine-induced hyperactivity and sensitization are dependent on GSK3. Neuropharmacology. 2009 Jun;56(8):1116-23. doi: 10.1016/j.neuropharm.2009.03.006. Epub 2009 Mar 27. PMID: 19328817; PMCID: PMC2721824.