CAS Number40172-65-4
SynonymsF1386-0401; naphtho[1,2-d]thiazol-2-amine; MFCD00051329; 2-Aminonaphthiazole; EINECS 254-822-1; 2-amminonafto<1,2-a>tiazolo; 2-Aminonaphtol<1,2-d>thiazole; Naphtho[1,2-d]thiazol-2-ylamine; 2-Aminonaphtho<thiazol
Molecular FormulaC11H8N2S
Molecular Weight200.26
Purity≥98 (HPLC)%
Density1.403g/cm3
Boiling Point417.1ºC at 760 mmHg
Melting Point184-188ºC
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 40172-65-4 |
| Catalog No. | 2A-9080468 |
| Chinese Name | 萘并(1,2-d)噻唑-2-胺 |
| Synonyms | F1386-0401; naphtho[1,2-d]thiazol-2-amine; MFCD00051329; 2-Aminonaphthiazole; EINECS 254-822-1; 2-amminonafto<1,2-a>tiazolo; 2-Aminonaphtol<1,2-d>thiazole; Naphtho[1,2-d]thiazol-2-ylamine; 2-Aminonaphtho<thiazol |
| Molecular Formula | C11H8N2S |
| Molecular Weight | 200.26 |
| Purity | ≥98 (HPLC) |
| Density | 1.403g/cm3 |
| Boiling Point | 417.1ºC at 760 mmHg |
| Melting Point | 184-188ºC |
| Appearance | solid |
| Storage Condition | Store at +4°C |
| Application | SKA-31 is an activator of potassium ion channels KCa3.1, KCa2.2, KCa2.1 and KCa2.3, with EC50 values of 260 nM, 1.9 μM, 2.9 μM, and 2.9 μM respectively. It can enhance the endothelium-derived hyperp |
| HTC | 2934999090 |
| PubChem ID | 329824457 |
| MDL Number | MFCD00051329 |
| SMILES | Nc1nc2c(ccc3ccccc23)s1 |
| InChI | 1S/C11H8N2S/c12-11-13-10-8-4-2-1-3-7(8)5-6-9(10)14-11/h1-6H,(H2,12,13) |
| InChI Key | FECQXVPRUCCUIL-UHFFFAOYSA-N |
| NACRES Code | NA.25 |
| UNSPSC | 12352202 |
| Hazard Symbols | transportation |
| MSDS | msds/80468_1_40172_65_4.pdf |
| Bioactivity | SKA-31 is a potent potassium channel activator with EC50s of 260 nM, 1.9 μM, 2.9 μM, and 2.9 μM for KCa3.1, KCa2.2, KCa2.1 and KCa2.3, respectively. SKA-31 potentiates endothelium-derived hyperpolarizing factor response and lowers blood pressure[1]. Related Catalog Research Areas >> Cardiovascular Disease Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel Target EC50: 2.9 μM (KCa2.1), 1.9 μM (KCa2.2), 2.9 μM (KCa2.3), 260 nM (KCa3.1)[1] In Vitro SKA-31 activates KCa2/3 Channels more potently than Riluzole, and is more selective over other Ion channels[1]. SKA-31 reduces cell viability with IC50s of 5.3 μM , 46.9 μm in HCT-116 cells and HCT-8 cells, respectively[2]. SKA-31 (5.3 μM; 0-96 hours) reduces HCT-116 cells proliferation when added at time zero at IC50 value[2]. SKA-31 triggers apoptosis in HCT-116 cells at 5 μM, and the effect is smaller in HCT-8 cells at 45 μM[2]. SKA-31 increases the percentage of cells in G0/G1 phase in HCT-116 and HCT-8 cell lines at 5 μM and 45 μM, respectively[2]. SKA-31 further activates Caspase 3 and reduces Akt phosphorylation induced by Cisplatin[2]. SKA-31 has a synergic effect with Cisplatin also on the inhibition of HCT-116 cell proliferation[2]. Cell Viability Assay[2] Cell Line: HCT-116 cells, HCT-8 cells Concentration: Incubation Time: 24 hours Result: Reduced cell viability with IC50s of 5.3 μM , 46.9 μm in HCT-116 and HCT-8, respectively. Cell Proliferation Assay[2] Cell Line: HCT-116 cells Concentration: 5.3 μM Incubation Time: 0-96 hours Result: Reduced HCT-116 cells proliferation when added at time zero at IC50S value. Apoptosis Analysis[2] Cell Line: HCT-116 cells, HCT-8 cells Concentration: 5 μM (HCT-116 cells), 45 μM (HCT-8 cells) Incubation Time: 24 hours Result: Triggered apoptosis in HCT-116 cells, and the effect was smaller in HCT-8 cells. Cell Cycle Analysis[2] Cell Line: HCT-116cells, HCT-8 cells Concentration: 5 μM (HCT-116), 45 μM (HCT-8) Incubation Time: 24 hours Result: Increased the percentage of cells in G0/G1 phase in HCT-116 and HCT-8 cell lines. Western Blot Analysis[2] Cell Line: HCT-116 cells Concentration: Incubation Time: 24 hours Result: Further activated Caspase 3 and reduced Akt phosphorylation when co-treatment with Cisplatin in HCT-116 cells. In Vivo SKA-31 Is not acutely toxic and has good pharmacokinetic properties[1]. SKA-31 potentiates native KCa3.1 and KCa2.3 in murine carotid endothelium with EC50 values of 225 nM and 1.6 μM for KCa3.1 and KCa2.3, respectively[1]. SKA-31 stimulates KCa3.1 and KCa2.3 in vascular endothelial cells and increases acetylcholine-induced endothelium-derived hyperpolarizing factor (EDHF) -mediated vasodilation[1]. SKA-31 potentiates EDHF-type vasodilations and lowers blood pressure in mice. Injections of SKA-31 (1-30 mg/kg; i.p.) lower MAP over 24 hours in normotensive wild-type mice but not in KCa3.1(-/-) mice (-/-)[1]. Animal Model: 16-25 weeks mice[1] Dosage: 1 mg/kg, 10 mg/kg, and 30 mg/kg Administration: Intraperitoneal injection Result: Lower MAP over 24 hours in normotensive wild-type mice but not in KCa3.1(-/-) mice (-/-). References [1]. Sankaranarayanan A, et al. Naphtho[1,2-d]thiazol-2-ylamine (SKA-31), a new activator of KCa2 and KCa3.1 potassium channels, potentiates the endothelium-derived hyperpolarizing factor response and lowers blood pressure. Mol Pharmacol. 2009 Feb;75(2):281-95. [2]. Serena Pillozzi, et al. The combined activation of KCa3.1 and inhibition of Kv11.1/hERG1 currents contribute to overcome Cisplatin resistance in colorectal cancer cells. Br J Cancer. 2018 Jan; 118(2): 200-212. Chemical & Physical Properties Density 1.403g/cm3 Boiling Point 417.1ºC at 760 mmHg Melting Point 184-188ºC Molecular Formula C11H8N2S Molecular Weight 200.26 Flash Point 206.1ºC Exact Mass 200.04100 PSA 67.15000 LogP 3.61290 Index of Refraction 1.83 InChIKey FECQXVPRUCCUIL-UHFFFAOYSA-N SMILES Nc1nc2c(ccc3ccccc32)s1 Storage condition Store at +4°C |
| Use of | SKA-31 is a potent potassium channel activator with EC50s of 260 nM, 1.9 μM, 2.9 μM, and 2.9 μM for KCa3.1, KCa2.2, KCa2.1 and KCa2.3, respectively. SKA-31 potentiates endothelium-derived hyperpolarizing factor response and lowers blood pressure[1]. Properties Name benzo[e][1,3]benzothiazol-2-amine Synonym More Synonyms SKA-31 Biological Activity Description SKA-31 is a potent potassium channel activator with EC50s of 260 nM, 1.9 μM, 2.9 μM, and 2.9 μM for KCa3.1, KCa2.2, KCa2.1 and KCa2.3, respectively. SKA-31 potentiates endothelium-derived hyperpolarizing factor response and lowers blood pressure[1]. Related Catalog Research Areas >> Cardiovascular Disease Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel EC50: 2.9 μM (KCa2.1), 1.9 μM (KCa2.2), 2.9 μM (KCa2.3), 260 nM (KCa3.1)[1] References [1]. Sankaranarayanan A, et al. Naphtho[1,2-d]thiazol-2-ylamine (SKA-31), a new activator of KCa2 and KCa3.1 potassium channels, potentiates the endothelium-derived hyperpolarizing factor response and lowers blood pressure. Mol Pharmacol. 2009 Feb;75(2):281-95. Chemical & Physical Properties Molecular Formula C11H8N2S Exact Mass 200.04100 PSA 67.15000 LogP 3.61290 Index of Refraction 1.83 InChIKey FECQXVPRUCCUIL-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 97.0% |
| 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 Names specified by the United Nations (UN) 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 Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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