![4-Benzyl-2-(naphthalen-1-yl)-[1,2,4]thiadiazolidine-3,5-dione structure, CAS 865854-05-3](https://www.2abiotech.com/storage/file/20260617/c00ef16f9300b2d31a2d2bdeee32a3d9f410c351.png)
CAS Number865854-05-3
SynonymsTideglusib [INN]; CS-0613; UNII-Q747Y6TT42; Tideglusib; 4-Benzyl-2-(1-naphthyl)-1,2,4-thiadiazolidine-3,5-dione; cc-675; NP-031112
Molecular FormulaC19H14N2O2S
Molecular Weight334.392
Density1.4±0.1 g/cm3
Boiling Point511.3±43.0 °C at 760 mmHg
Appearancewhite to beige
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 865854-05-3 |
| Catalog No. | 2A-1170336 |
| Chinese Name | 4-苄基-2-(萘-1-基)-[1,2,4]噻二唑烷-3,5-二酮 |
| Synonyms | Tideglusib [INN]; CS-0613; UNII-Q747Y6TT42; Tideglusib; 4-Benzyl-2-(1-naphthyl)-1,2,4-thiadiazolidine-3,5-dione; cc-675; NP-031112 |
| Molecular Formula | C19H14N2O2S |
| Molecular Weight | 334.392 |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 511.3±43.0 °C at 760 mmHg |
| Appearance | white to beige |
| Water Solubility | DMSO: >15mg/mL |
| Storage Condition | 2-8°C |
| Application | Tideglusib is an irreversible GSK-3 inhibitor with IC50s of 5 nM and 60 nM for GSK-3βWT and GSK-3βC199A respectively. |
| PubChem ID | 16402803 |
| SMILES | O=c1sn(-c2cccc3ccccc23)c(=O)n1Cc1ccccc1 |
| InChI | InChI=1S/C19H14N2O2S/c22-18-20(13-14-7-2-1-3-8-14)19(23)24-21(18)17-12-6-10-15-9-4-5-11-16(15)17/h1-12H,13H2 |
| InChI Key | PMJIHLSCWIDGMD-UHFFFAOYSA-N |
| Hazard Symbols | transportation |
| MSDS | msds/170487_2_865854_05_3.pdf |
| Bioactivity | Tideglusib is an irreversible GSK-3 inhibitor with IC50s of 5 nM and 60 nM for GSK-3βWT (1 h preincubation) and GSK-3βC199A (1 h preincubation), respectively. Related Catalog Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3 Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Neurological Disease Target GSK-3β(WT):5 nM (IC50) GSK-3β(C199A):60 nM (IC50) In Vitro Tideglusib (NP12) is a small heterocyclic thiadiazolidinone (TDZD) derivative, which is an ATP-non competitive inhibitor of GSK-3β with an IC50 value in the micromolar range[2]. Incubation of both astrocyte and microglial cultures with Tideglusib (NP031112) completely abrogates the induction of TNF-α and COX-2 expression after glutamate treatment. These effects of NP031112 are not caused by a loss of cell viability, because the 24 h exposure of astrocyte and microglial cells to this TDZD does not modify cell viability[3]. In Vivo Tideglusib (NP12) treatment correlates with an increase of 46% as an average in the inhibitory phosphorylation of GSK-3β at Ser-9 in the brains of APPsw-tauvlw mice, and the levels of the inactive from of the enzyme in NP12 treated mice are comparable to those found in wild-type littermate controls (p=0.893) (n=6-8 for each treatment). NP12 treatment results in significantly decreased phosphorylation at the putative GSK-3β-directed sites Ser-202 (CP13) and Ser-396/404 (PHF-1) in 15-month-old mice by more than 60% (p=0.023 and p=0.024, respectively)[2]. Injection of Tideglusib (NP031112) (50 mg/kg) into the rat hippocampus dramatically reduces kainic acid-induced inflammation, as measured by edema formation using T2-weighted magnetic resonance imaging and glial activation and has a neuroprotective effect in the damaged areas of the hippocampus[3]. Kinase Assay [35S]Tideglusib (207 Bq/nmol) at 55 μM is incubated with 5 μM GSK-3β for 1 h at 25°C in 315 μL of 50 mM Tris-HCl, pH 7.5, containing 150 mM NaCl and 0.1 mM EGTA. The incubation is extended for another 30 min after having added 35 μL of the same buffer with or without 100 mM DTE. Samples are then processed in three different ways. First, an aliquot of 125 μL of each sample is mixed with 375 μL of 8 M GdnHCl in H2O and heated at 80°C for 5 min. A second aliquot of 125 μL is diluted up to 500 μL with H2O and left at room temperature for 5 min. In both cases, the free drug is removed afterwards by gel filtration through Sephadex G-25, and the amount of bound drug is determined by liquid scintillation counting on a 1450-MicroBeta TriLux counter. Finally, a third 40 μL aliquot of each original sample is mixed with 10 μL of denaturing electrophoresis sample buffer without reducing agents, and 35 μL of this mixture is loaded onto a 10% polyacrylamide gel and subjected to SDS-PAGE (again in the absence of reducing agents except for the DTE already included in the corresponding sample), followed by fluorography of the dried gel[1]. Animal Admin Mice[2] Groups of APPsw-tauvlw mice are administered Tideglusib (n=10-11 for each age) or vehicle (n=10-11 for each age) starting at 9 months and 12 months of age during consecutive 3 months and used for subsequent clinicopathological analyses. Tideglusib is administered at a daily dose of 200 mg/kg. Groups of age and gender-matched wild-type littermate controls (n=10 for each age) receive vehicle alone on a similar timetable schedule. Rats[3] Adult male Wistar rats (8-12 weeks old) are used in this study. Rats (n≥5 per group) are anesthetized by intraperitoneal injection of ketamine (60 mg/kg) and Domtor (5 μg/kg) and placed into a stereotaxic apparatus. KA (1 μg in 2.5 μL PBS) alone or in combination with Tideglusib (2 ng in 2.5 μL PBS) is injected into the hippocampus. Control animals of the same age are injected with vehicle. References [1]. Domínguez JM, et al. Evidence for irreversible inhibition of glycogen synthase kinase-3β by tideglusib. J Biol Chem, 2012, 287(2), 893-90 [2]. Sereno L, et al. A novel GSK-3beta inhibitor reduces Alzheimer's pathology and rescues neuronal loss in vivo. Neurobiol Dis. 2009 Sep;35(3):359-67. [3]. Luna-Medina R, et al. NP031112, a thiadiazolidinone compound, prevents inflammation and neurodegeneration under excitotoxic conditions: potential therapeutic role in brain disorders. J Neurosci, 2007, 27(21), 5766-5776. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 511.3±43.0 °C at 760 mmHg Molecular Formula C19H14N2O2S Molecular Weight 334.392 Flash Point 263.0±28.2 °C Exact Mass 334.077606 PSA 72.24000 LogP 3.28 Appearance of Characters white to beige Vapour Pressure 0.0±1.3 mmHg at 25°C Index of Refraction 1.735 InChIKey PMJIHLSCWIDGMD-UHFFFAOYSA-N SMILES O=c1sn(-c2cccc3ccccc23)c(=O)n1Cc1ccccc1 Storage condition 2-8°C Water Solubility DMSO: >15mg/mL |
| Use of | Tideglusib is an irreversible GSK-3 inhibitor with IC50s of 5 nM and 60 nM for GSK-3βWT (1 h preincubation) and GSK-3βC199A (1 h preincubation), respectively. Properties Name 4-benzyl-2-naphthalen-1-yl-1,2,4-thiadiazolidine-3,5-dione Synonym More Synonyms Tideglusib Biological Activity Description Tideglusib is an irreversible GSK-3 inhibitor with IC50s of 5 nM and 60 nM for GSK-3βWT (1 h preincubation) and GSK-3βC199A (1 h preincubation), respectively. Related Catalog Signaling Pathways >> PI3K/Akt/mTOR >> GSK-3 Signaling Pathways >> Stem Cell/Wnt >> GSK-3 Research Areas >> Neurological Disease GSK-3β(WT):5 nM (IC50) GSK-3β(C199A):60 nM (IC50) In Vitro Tideglusib (NP12) is a small heterocyclic thiadiazolidinone (TDZD) derivative, which is an ATP-non competitive inhibitor of GSK-3β with an IC50 value in the micromolar range[2]. Incubation of both astrocyte and microglial cultures with Tideglusib (NP031112) completely abrogates the induction of TNF-α and COX-2 expression after glutamate treatment. These effects of NP031112 are not caused by a loss of cell viability, because the 24 h exposure of astrocyte and microglial cells to this TDZD does not modify cell viability[3]. References [1]. Domínguez JM, et al. Evidence for irreversible inhibition of glycogen synthase kinase-3β by tideglusib. J Biol Chem, 2012, 287(2), 893-90 [2]. Sereno L, et al. A novel GSK-3beta inhibitor reduces Alzheimer's pathology and rescues neuronal loss in vivo. Neurobiol Dis. 2009 Sep;35(3):359-67. [3]. Luna-Medina R, et al. NP031112, a thiadiazolidinone compound, prevents inflammation and neurodegeneration under excitotoxic conditions: potential therapeutic role in brain disorders. J Neurosci, 2007, 27(21), 5766-5776. Chemical & Physical Properties Molecular Formula C19H14N2O2S Exact Mass 334.077606 PSA 72.24000 Appearance of Characters white to beige Index of Refraction 1.735 InChIKey PMJIHLSCWIDGMD-UHFFFAOYSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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