CHIR99021 trihydrochloride
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530958

CAS#: 1782235-14-6 (3HCl)

Description: CHIR99021, CHIR-73911, also known as CT-99021, or CHIR-911, is an orally active and potent GSK3 inhibitor. CHIR-73911 exhibited GSK3 IC50 in the low nanomolar range and excellent selectivity. CHIR-73911 activates glycogen synthase in insulin receptorexpressing CHO-IR cells and primary rat hepatocytes.


Price and Availability

Size
Price

10mg
USD 385
Size
Price

50mg
USD 1450
Size
Price

CHIR99021 trihydrochloride, purity > 95%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530958
Name: CHIR99021 trihydrochloride
CAS#: 1782235-14-6 (3HCl)
Chemical Formula: C22H21Cl5N8
Exact Mass: 464.1031
Molecular Weight: 574.72
Elemental Analysis: C, 45.98; H, 3.68; Cl, 30.84; N, 19.50


Related CAS #: 252917-06-9 (free base)   1782235-14-6 (3HCl)   2109414-84-6 (2HCl)   1797989-42-4 (HCl)    

Synonym: CHIR-911; CHIR911; CHIR 911; CT- 99021; CT-99021; CT- 99021; CHIR-73911; CHIR73911; CHIR 73911; GSK 3 inhibitor XVI; GSK 3IXV; CHIR99021; CHIR 99021;

IUPAC/Chemical Name: 6-((2-((4-(2,4-dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)pyrimidin-2-yl)amino)ethyl)amino)nicotinonitrile trichloride

InChi Key: DSFVSCNMMZRCIA-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H18Cl2N8.3ClH/c1-13-10-29-21(31-13)17-12-30-22(32-20(17)16-4-3-15(23)8-18(16)24)27-7-6-26-19-5-2-14(9-25)11-28-19;;;/h2-5,8,10-12H,6-7H2,1H3,(H,26,28)(H,29,31)(H,27,30,32);3*1H

SMILES Code: N#CC1=CN=C(NCCNC2=NC=C(C3=NC(C)=CN3)C(C4=CC=C(Cl)C=C4Cl)=N2)C=C1.[H]Cl.[H]Cl.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>95% (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).

Harmonized System Code:
293490


Additional Information

Glycogen synthase kinase-3 beta (GSK3b) is a multifunctional serine/threonine kinase which was originally identified as a
regulator of glycogen metabolism. It plays a key role in the regulation of numerous signalling pathways including cellular
process such as cell cycle, inflammation and cell proliferation.


References

1: Bock AS, Leigh ND, Bryda EC. Effect of Gsk3 inhibitor CHIR99021 on aneuploidy levels in rat embryonic stem cells. In Vitro Cell Dev Biol Anim. 2014 Jun;50(6):572-9. doi: 10.1007/s11626-014-9734-5. Epub 2014 Feb 12. PubMed PMID: 24519175; PubMed Central PMCID: PMC4062835.

2: Wu Y, Liu F, Liu Y, Liu X, Ai Z, Guo Z, Zhang Y. GSK3 inhibitors CHIR99021 and 6-bromoindirubin-3'-oxime inhibit microRNA maturation in mouse embryonic stem cells. Sci Rep. 2015 Mar 2;5:8666. doi: 10.1038/srep08666. PubMed PMID: 25727520; PubMed Central PMCID: PMC4345320.

3: Li C, Zhang S, Lu Y, Zhang Y, Wang E, Cui Z. The roles of Notch3 on the cell proliferation and apoptosis induced by CHIR99021 in NSCLC cell lines: a functional link between Wnt and Notch signaling pathways. PLoS One. 2013 Dec 18;8(12):e84659. doi: 10.1371/journal.pone.0084659. eCollection 2013. PubMed PMID: 24367688; PubMed Central PMCID: PMC3867546.

4: Wu Y, Ai Z, Yao K, Cao L, Du J, Shi X, Guo Z, Zhang Y. CHIR99021 promotes self-renewal of mouse embryonic stem cells by modulation of protein-encoding gene and long intergenic non-coding RNA expression. Exp Cell Res. 2013 Oct 15;319(17):2684-99. doi: 10.1016/j.yexcr.2013.08.027. Epub 2013 Sep 7. PubMed PMID: 24021571.

5: Petkov S, Hyttel P, Niemann H. The small molecule inhibitors PD0325091 and CHIR99021 reduce expression of pluripotency-related genes in putative porcine induced pluripotent stem cells. Cell Reprogram. 2014 Aug;16(4):235-40. doi: 10.1089/cell.2014.0010. Epub 2014 Jun 24. PubMed PMID: 24960205.

6: Ye S, Tan L, Yang R, Fang B, Qu S, Schulze EN, Song H, Ying Q, Li P. Pleiotropy of glycogen synthase kinase-3 inhibition by CHIR99021 promotes self-renewal of embryonic stem cells from refractory mouse strains. PLoS One. 2012;7(4):e35892. doi: 10.1371/journal.pone.0035892. Epub 2012 Apr 23. PubMed PMID: 22540008; PubMed Central PMCID: PMC3335080.

7: Yin X, Farin HF, van Es JH, Clevers H, Langer R, Karp JM. Niche-independent high-purity cultures of Lgr5+ intestinal stem cells and their progeny. Nat Methods. 2014 Jan;11(1):106-12. doi: 10.1038/nmeth.2737. Epub 2013 Dec 1. PubMed PMID: 24292484; PubMed Central PMCID: PMC3951815.

8: Ai Z, Shao J, Wu Y, Yu M, Du J, Shi X, Shi X, Zhang Y, Guo Z. CHIR99021 enhances Klf4 Expression through β-Catenin Signaling and miR-7a Regulation in J1 Mouse Embryonic Stem Cells. PLoS One. 2016 Mar 3;11(3):e0150936. doi: 10.1371/journal.pone.0150936. eCollection 2016. PubMed PMID: 26938105; PubMed Central PMCID: PMC4777400.

9: Singh VK, Kumar N, Kalsan M, Saini A, Chandra R. Mechanism of Induction: Induced Pluripotent Stem Cells (iPSCs). J Stem Cells. 2015;10(1):43-62. Review. PubMed PMID: 26665937.

10: Lam AQ, Freedman BS, Morizane R, Lerou PH, Valerius MT, Bonventre JV. Rapid and efficient differentiation of human pluripotent stem cells into intermediate mesoderm that forms tubules expressing kidney proximal tubular markers. J Am Soc Nephrol. 2014 Jun;25(6):1211-25. doi: 10.1681/ASN.2013080831. Epub 2013 Dec 19. PubMed PMID: 24357672; PubMed Central PMCID: PMC4033376.

11: Wang X, Wei L, Cramer JM, Leibowitz BJ, Judge C, Epperly M, Greenberger J, Wang F, Li L, Stelzner MG, Dunn JC, Martin MG, Lagasse E, Zhang L, Yu J. Pharmacologically blocking p53-dependent apoptosis protects intestinal stem cells and mice from radiation. Sci Rep. 2015 Apr 10;5:8566. doi: 10.1038/srep08566. PubMed PMID: 25858503; PubMed Central PMCID: PMC4392360.

12: Fu Y, Huang C, Xu X, Gu H, Ye Y, Jiang C, Qiu Z, Xie X. Direct reprogramming of mouse fibroblasts into cardiomyocytes with chemical cocktails. Cell Res. 2015 Sep;25(9):1013-24. doi: 10.1038/cr.2015.99. Epub 2015 Aug 21. PubMed PMID: 26292833; PubMed Central PMCID: PMC4559819.

13: Qin H, Hejna M, Liu Y, Percharde M, Wossidlo M, Blouin L, Durruthy-Durruthy J, Wong P, Qi Z, Yu J, Qi LS, Sebastiano V, Song JS, Ramalho-Santos M. YAP Induces Human Naive Pluripotency. Cell Rep. 2016 Mar 15;14(10):2301-12. doi: 10.1016/j.celrep.2016.02.036. Epub 2016 Mar 3. PubMed PMID: 26947063; PubMed Central PMCID: PMC4807727.

14: Ninomiya H, Mizuno K, Terada R, Miura T, Ohnuma K, Takahashi S, Asashima M, Michiue T. Improved efficiency of definitive endoderm induction from human induced pluripotent stem cells in feeder and serum-free culture system. In Vitro Cell Dev Biol Anim. 2015 Jan;51(1):1-8. doi: 10.1007/s11626-014-9801-y. Epub 2014 Aug 15. PubMed PMID: 25124871.

15: Uhl FE, Vierkotten S, Wagner DE, Burgstaller G, Costa R, Koch I, Lindner M, Meiners S, Eickelberg O, Königshoff M. Preclinical validation and imaging of Wnt-induced repair in human 3D lung tissue cultures. Eur Respir J. 2015 Oct;46(4):1150-66. doi: 10.1183/09031936.00183214. Epub 2015 Apr 30. PubMed PMID: 25929950.

16: Besing RC, Paul JR, Hablitz LM, Rogers CO, Johnson RL, Young ME, Gamble KL. Circadian rhythmicity of active GSK3 isoforms modulates molecular clock gene rhythms in the suprachiasmatic nucleus. J Biol Rhythms. 2015 Apr;30(2):155-60. doi: 10.1177/0748730415573167. Epub 2015 Feb 27. PubMed PMID: 25724980; PubMed Central PMCID: PMC4586074.

17: Cheng L, Gao L, Guan W, Mao J, Hu W, Qiu B, Zhao J, Yu Y, Pei G. Direct conversion of astrocytes into neuronal cells by drug cocktail. Cell Res. 2015 Nov;25(11):1269-72. doi: 10.1038/cr.2015.120. Epub 2015 Oct 2. PubMed PMID: 26427716; PubMed Central PMCID: PMC4650423.

18: Naujok O, Lentes J, Diekmann U, Davenport C, Lenzen S. Cytotoxicity and activation of the Wnt/beta-catenin pathway in mouse embryonic stem cells treated with four GSK3 inhibitors. BMC Res Notes. 2014 Apr 29;7:273. doi: 10.1186/1756-0500-7-273. PubMed PMID: 24779365; PubMed Central PMCID: PMC4008422.

19: Naujok O, Diekmann U, Lenzen S. The generation of definitive endoderm from human embryonic stem cells is initially independent from activin A but requires canonical Wnt-signaling. Stem Cell Rev. 2014 Aug;10(4):480-93. doi: 10.1007/s12015-014-9509-0. PubMed PMID: 24913278.

20: Kim S, Bong N, Kim OS, Jin J, Kim DE, Lee DK. Lithium chloride suppresses LPS-mediated matrix metalloproteinase-9 expression in macrophages through phosphorylation of GSK-3β. Cell Biol Int. 2015 Feb;39(2):177-84. doi: 10.1002/cbin.10352. Epub 2014 Aug 14. PubMed PMID: 25053111.