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Laduviglusib

CAT: 0804-HY-10182-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-10182-01Size:5 mg
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Description
Laduviglusib (CHIR-99021) is a potent, selective and orally active GSK-3α/β inhibitor with IC50s of 10 nM and 6.7 nM. Laduviglusib shows >500-fold selectivity for GSK-3 over CDC2, ERK2 and other protein kinases. Laduviglusib is also a potent Wnt/β-catenin signaling pathway activator. Laduviglusib enhances mouse and human embryonic stem cells self-renewal. Laduviglusib induces autophagy[1][2][3].
CAS Number
252917-06-9
Product Name Alternative
CHIR-99021; CT99021
UNSPSC
12352005
Hazard Statement
H300, H312+H332, H315, H319, H335
Target
Autophagy; GSK-3; Organoid; Wnt; β-catenin
Type
Reference compound
Related Pathways
Autophagy; PI3K/Akt/mTOR; Stem Cell/Wnt
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/laduviglusib.html
Purity
99.76
Solubility
DMSO : 16.67 mg/mL (ultrasonic)
Smiles
N#CC1=CC=C(N=C1)NCCNC2=NC=C(C(C3=CC=C(Cl)C=C3Cl)=N2)C4=NC=C(N4)C
Molecular Formula
C22H18Cl2N8
Molecular Weight
465.34
Precautions
H300, H312+H332, H315, H319, H335
References & Citations
[1]Ring DB, et al. Selective glycogen synthase kinase 3 inhibitors potentiate activation of glucose transport and utilization in vitro and in vivo. Diabetes. 2003 Mar;52 (3) :588-95.|[2]Bennett CN, et al. Regulation of Wnt signaling during adipogenesis. J Biol Chem. 2002 Aug 23;277 (34) :30998-1004.|[3]Naujok O, et al. 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.|[4]Wang X, et al. Pharmacologically blocking p53-dependent apoptosis protects intestinal stem cells and mice from radiation. Sci Rep. 2015 Apr 10;5:8566.|[5]Ye S, et al. 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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
GSK-3α; GSK-3β
Citation 01
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Chemical Information

Laduviglusib

CHIR 99021 is a member of the class of aminopyrimidines that is 2-aminopyrimidine substituted at positions N2, 5 and 6 by (5-cyanopyridin-2-yl)ethyl, 4-methylimidazol-2-yl and 2,4-dichlorophenyl groups respectively. It has a role as an EC 2.7.11.26 (tau-protein kinase) inhibitor. It is a cyanopyridine, a diamine, a dichlorobenzene, a member of imidazoles, an aminopyridine, an aminopyrimidine and a secondary amino compound.

CAS Number252917-06-9
PubChem CID9956119
IUPAC Name6-[2-[[4-(2,4-dichlorophenyl)-5-(5-methyl-1H-imidazol-2-yl)pyrimidin-2-yl]amino]ethylamino]pyridine-3-carbonitrile
Molecular FormulaC22H18Cl2N8
Molecular Weight465.3
XLogP4.3
Topological Polar Surface Area115
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Heavy Atom Count32
Formal Charge0
Complexity645
SMILES
CC1=CN=C(N1)C2=CN=C(N=C2C3=C(C=C(C=C3)Cl)Cl)NCCNC4=NC=C(C=C4)C#N
InChI
InChI=1S/C22H18Cl2N8/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)
InChIKey
AQGNHMOJWBZFQQ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Laduviglusib
CAS: 252917-06-9
CID: 9956119
Formula: C22H18Cl2N8
MW: 465.3
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight465.3
XLogP34.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass464.1031480
Monoisotopic Mass464.1031480
Topological Polar Surface Area115 Ų
Heavy Atom Count32
Formal Charge0
Complexity645
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes