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  • Product Name: SKA-31
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40172-65-4

40172-65-4 structure
40172-65-4 structure
  • Name: SKA-31
  • Chemical Name: benzo[e][1,3]benzothiazol-2-amine
  • CAS Number: 40172-65-4
  • Molecular Formula: C11H8N2S
  • Molecular Weight: 200.26
  • Catalog: Signaling Pathways Membrane Transporter/Ion Channel Potassium Channel
  • Create Date: 2018-06-12 11:35:13
  • Modify Date: 2024-01-10 19:00:52
  • 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].

Name benzo[e][1,3]benzothiazol-2-amine
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
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
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.

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
Storage condition Store at +4°C
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H319
Precautionary Statements P305 + P351 + P338
Hazard Codes Xn
Risk Phrases 20/21/22-36/37/38
Safety Phrases 22-36/37/39
RIDADR NONH for all modes of transport
HS Code 2934999090

~89%

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Literature: Zhao, Jinwu; Huang, Huawen; Wu, Wanqing; Chen, Huoji; Jiang, Huanfeng Organic Letters, 2013 , vol. 15, # 11 p. 2604 - 2607

~80%

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Literature: Liu; Lee; Shih; Chen; Tao Archiv der Pharmazie, 1982 , vol. 315, # 10 p. 872 - 877

~61%

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Literature: Moradi Rufchahi; Yousefi, Hessamoddin; Mohammadinia, Mojgan Journal of Molecular Liquids, 2013 , vol. 188, p. 173 - 177

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Literature: Ubaldini; Fiorenza Gazzetta Chimica Italiana, 1946 , vol. 76, p. 215,221

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Literature: Freund Chemische Berichte, 1891 , vol. 24, p. 4187

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Literature: Kajino; Mizuno; Tawada; Shibouta; Nishikawa; Meguro Chemical and Pharmaceutical Bulletin, 1991 , vol. 39, # 11 p. 2888 - 2895

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Literature: Gorelik,M.V.; Lomzakova,V.I. Zhurnal Organicheskoi Khimii, 1978 , vol. 14, # 5 p. 1051 - 1055,981 - 985
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%