SKA-31 | CAS#40172-65-4 | potassium channel activator

MedKoo Cat#: 562613 | Name: SKA-31

Featured

Description:

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

SKA-31 is an activator of KCa2 and KCa3.1 calcium-activated potassium channels. SKA-31 attenuated hyperpolarization of DSM cells.

Chemical Structure

SKA-31

CAS#40172-65-4

Theoretical Analysis

MedKoo Cat#: 562613

Name: SKA-31

CAS#: 40172-65-4

Chemical Formula: C11H8N2S

Exact Mass: 200.0400

Molecular Weight: 200.26

Elemental Analysis: C, 65.98; H, 4.03; N, 13.99; S, 16.01

Price and Availability

Size	Price	Availability
5mg	USD 300.00	2 weeks
10mg	USD 450.00	2 weeks
50mg	USD 850.00	2 weeks
100mg	USD 1,350.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

SKA-31; SKA 31; SKA31;

IUPAC/Chemical Name

Naphtho[1,2-d]thiazol-2-ylamine

InChi Key

FECQXVPRUCCUIL-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

NC1=NC2=C3C=CC=CC3=CC=C2S1

Appearance

Solid powder

Purity

>98% (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 and ethanol

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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SKA-31 is an activator of KCa3.1 and KCa2 channels (EC50 values are 260, 2900, 2900 nM for KCa3.1, KCa2.1 and KCa2.2 respectively).

In vitro activity:

To be determined

In vivo activity:

SKA-31 has potential as a therapeutic agent for hypertension. SKA-31 was 10 to 20 times more potent than riluzole. SKA-31 effectively activated KCa2.1 (EC50 = 2.9mM), KCa2.2 (EC50 = 1.9mM), KCa2.3 (EC50 = 2.9mM), and KCa3.1 (EC50 = 260nM) channels and potentiated dilations of carotid arteries in KCa3.1(+/+) mice. Furthermore, SKA-31 exhibited a blood pressure-lowering effect in normotensive mice and angiotensin-II-induced hypertension. Reference: Mol Pharmacol. 2009 Feb;75(2):281-95. https://pubmed.ncbi.nlm.nih.gov/18955585/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	100.00
	Ethanol	20.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 200.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Brähler S, Kaistha A, Schmidt VJ, Wölfle SE, Busch C, Kaistha BP, Kacik M, Hasenau AL, Grgic I, Si H, Bond CT, Adelman JP, Wulff H, de Wit C, Hoyer J, Köhler R. Genetic deficit of SK3 and IK1 channels disrupts the endothelium-derived hyperpolarizing factor vasodilator pathway and causes hypertension. Circulation. 2009 May 5;119(17):2323-32. doi: 10.1161/CIRCULATIONAHA.108.846634. Epub 2009 Apr 20. PMID: 19380617. 2. Sankaranarayanan A, Raman G, Busch C, Schultz T, Zimin PI, Hoyer J, Köhler R, Wulff H. 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. doi: 10.1124/mol.108.051425. Epub 2008 Oct 27. PMID: 18955585; PMCID: PMC2635097.

In vitro protocol:

To be determined

In vivo protocol:

1: Mishra RC, Belke DD, Singh L, Wulff H, Braun AP. Targeting endothelial KCa channels in vivo restores arterial and endothelial function in type 2 diabetic rats. Metabolism. 2024 Nov;160:156001. doi: 10.1016/j.metabol.2024.156001. Epub 2024 Aug 18. PMID: 39163925. 2: Cozzolino M, Panyi G. Intracellular acidity impedes KCa3.1 activation by Riluzole and SKA-31. Front Pharmacol. 2024 Apr 4;15:1380655. doi: 10.3389/fphar.2024.1380655. PMID: 38638868; PMCID: PMC11024243. 3: Bhebhe CN, Higham JP, Gupta RA, Raine T, Bulmer DC. KV7 but not dual small and intermediate KCa channel openers inhibit the activation of colonic afferents by noxious stimuli. Am J Physiol Gastrointest Liver Physiol. 2023 Nov 1;325(5):G436-G445. doi: 10.1152/ajpgi.00141.2023. Epub 2023 Sep 5. PMID: 37667839; PMCID: PMC10894664. 4: Lu C, Zhang L, Chen X, Wan H, Dong H. Cl- induces endothelium- dependent mesenteric arteriolar vasorelaxation through the NKCC1/TRPV4/NCX axis. Life Sci. 2023 Oct 1;330:121942. doi: 10.1016/j.lfs.2023.121942. Epub 2023 Jul 13. PMID: 37451399. 5: Vera OD, Wulff H, Braun AP. Endothelial KCa channels: Novel targets to reduce atherosclerosis-driven vascular dysfunction. Front Pharmacol. 2023 Mar 31;14:1151244. doi: 10.3389/fphar.2023.1151244. PMID: 37063294; PMCID: PMC10102451. 6: Back V, Asgari A, Franczak A, Saito M, Castaneda Zaragoza D, Sandow SL, Plane F, Jurasz P. Inhibition of platelet aggregation by activation of platelet intermediate conductance Ca2+ -activated potassium channels. J Thromb Haemost. 2022 Nov;20(11):2587-2600. doi: 10.1111/jth.15827. Epub 2022 Aug 7. PMID: 35867883. 7: Li J, Liu T, Li N, Dong F, Wang P. SKA-31-induced activation of small- conductance calcium-activated potassium channels decreased modulation of detrusor smooth muscle function in a rat model of obesity. J Bioenerg Biomembr. 2022 Jun;54(3):135-144. doi: 10.1007/s10863-022-09939-2. Epub 2022 Apr 27. PMID: 35478071. 8: Kendrick DJ, Mishra RC, John CM, Zhu HL, Braun AP. Effects of Pharmacological Inhibitors of NADPH Oxidase on Myogenic Contractility and Evoked Vasoactive Responses in Rat Resistance Arteries. Front Physiol. 2022 Jan 24;12:752366. doi: 10.3389/fphys.2021.752366. PMID: 35140625; PMCID: PMC8818784. 9: Hamad A, Ozkan MH, Uma S. Trimethylamine-N-oxide (TMAO) Selectively Disrupts Endothelium-Dependent Hyperpolarization-Type Relaxations in a Time-Dependent Manner in Rat Superior Mesenteric Artery. Biol Pharm Bull. 2021;44(9):1220-1229. doi: 10.1248/bpb.b20-00767. PMID: 34471050. 10: Hansen FB, Secher N, Mattson T, Løfgren B, Simonsen U, Granfeldt A. Effect of the KCa3.1 blocker, senicapoc, on cerebral edema and cardiovascular function after cardiac arrest - A randomized experimental rat study. Resusc Plus. 2021 Apr 2;6:100111. doi: 10.1016/j.resplu.2021.100111. PMID: 34223371; PMCID: PMC8244250. 11: Zhang LY, Chen XY, Dong H, Xu F. Cyclopiazonic Acid-Induced Ca2+ Store Depletion Initiates Endothelium-Dependent Hyperpolarization-Mediated Vasorelaxation of Mesenteric Arteries in Healthy and Colitis Mice. Front Physiol. 2021 Mar 9;12:639857. doi: 10.3389/fphys.2021.639857. PMID: 33767636; PMCID: PMC7985063. 12: Bukhari M, Deng H, Sipes D, Ruane-Foster M, Purdy K, Woodworth CD, Sur S, Samways DSK. KCa3.1-dependent uptake of the cytotoxic DNA-binding dye Hoechst 33258 into cancerous but not healthy cervical cells. J Biol Chem. 2021 Jan-Jun;296:100084. doi: 10.1074/jbc.RA120.013997. Epub 2020 Nov 23. PMID: 33199365; PMCID: PMC7948979. 13: Mishra RC, Kyle BD, Kendrick DJ, Svystonyuk D, Kieser TM, Fedak PWM, Wulff H, Braun AP. KCa channel activation normalizes endothelial function in Type 2 Diabetic resistance arteries by improving intracellular Ca2+ mobilization. Metabolism. 2021 Jan;114:154390. doi: 10.1016/j.metabol.2020.154390. Epub 2020 Oct 8. PMID: 33039407; PMCID: PMC7736096. 14: Liu Y, Kabakov AY, Xie A, Shi G, Singh AK, Sodha NR, Ehsan A, Usheva A, Agbortoko V, Koren G, Dudley SC Jr, Sellke FW, Feng J. Metabolic regulation of endothelial SK channels and human coronary microvascular function. Int J Cardiol. 2020 Aug 1;312:1-9. doi: 10.1016/j.ijcard.2020.03.028. Epub 2020 Mar 12. PMID: 32199682; PMCID: PMC7388214. 15: John CM, Khaddaj Mallat R, Mishra RC, George G, Singh V, Turnbull JD, Umeshappa CS, Kendrick DJ, Kim T, Fauzi FM, Visser F, Fedak PWM, Wulff H, Braun AP. SKA-31, an activator of Ca2+-activated K+ channels, improves cardiovascular function in aging. Pharmacol Res. 2020 Jan;151:104539. doi: 10.1016/j.phrs.2019.104539. Epub 2019 Nov 7. PMID: 31707036; PMCID: PMC6956598. 16: Kloza M, Baranowska-Kuczko M, Toczek M, Kusaczuk M, Sadowska O, Kasacka I, Kozłowska H. Modulation of Cardiovascular Function in Primary Hypertension in Rat by SKA-31, an Activator of KCa2.x and KCa3.1 Channels. Int J Mol Sci. 2019 Aug 23;20(17):4118. doi: 10.3390/ijms20174118. PMID: 31450834; PMCID: PMC6747311. 17: Khaddaj Mallat R, Mathew John C, Mishra RC, Kendrick DJ, Braun AP. Pharmacological Targeting of KCa Channels to Improve Endothelial Function in the Spontaneously Hypertensive Rat. Int J Mol Sci. 2019 Jul 16;20(14):3481. doi: 10.3390/ijms20143481. PMID: 31315169; PMCID: PMC6678254. 18: Chen H, Vanhoutte PM, Leung SWS. Acute activation of endothelial AMPK surprisingly inhibits endothelium-dependent hyperpolarization-like relaxations in rat mesenteric arteries. Br J Pharmacol. 2019 Aug;176(16):2905-2921. doi: 10.1111/bph.14716. Epub 2019 Jul 4. PMID: 31116877; PMCID: PMC6637042. 19: Mishra RC, Rahman MM, Davis MJ, Wulff H, Hill MA, Braun AP. Alpha1 -adrenergic stimulation selectively enhances endothelium- mediated vasodilation in rat cremaster arteries. Physiol Rep. 2018 May;6(9):e13703. doi: 10.14814/phy2.13703. PMID: 29756401; PMCID: PMC5949301. 20: Khaddaj-Mallat R, Mathew John C, Braun AP. SKA-31, an activator of endothelial Ca2+-activated K+ channels evokes robust vasodilation in rat mesenteric arteries. Eur J Pharmacol. 2018 Jul 15;831:60-67. doi: 10.1016/j.ejphar.2018.05.006. Epub 2018 May 9. PMID: 29753043.