SKA-121 | CAS# 1820708-73-3 |KCa3.1 Gating Modulator

MedKoo Cat#: 532702 | Name: SKA-121

Featured

Description:

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

SKA-121 is a novel KCa3.1-specific positive gating modulator.

Chemical Structure

SKA-121

CAS# 1820708-73-3

Theoretical Analysis

MedKoo Cat#: 532702

Name: SKA-121

CAS#: 1820708-73-3

Chemical Formula: C12H10N2O

Exact Mass: 198.0793

Molecular Weight: 198.23

Elemental Analysis: C, 72.71; H, 5.09; N, 14.13; O, 8.07

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 430.00	2 weeks
10mg	USD 880.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

SKA-121; SKA 121; SKA121.

IUPAC/Chemical Name

5-methylnaphtho[2,1-d]oxazol-2-amine

InChi Key

JEGUERWMMMQFJV-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H10N2O/c1-7-6-10-11(15-12(13)14-10)9-5-3-2-4-8(7)9/h2-6H,1H3,(H2,13,14)

SMILES Code

NC1=NC2=CC(C)=C3C=CC=CC3=C2O1

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-121 is a positive allosteric modulator of KCa3.1 channels (EC50 = 109 nM). SKA-121 displays 40-fold selectivity for KCa3.1 over KCa2.3, and 200 to 400-fold selectivity over KV and NaV channels.

In vitro activity:

SKA-121 may have potential in the treatment of cancer. SKA-121 impeded tumor immune surveillance escape and suppressed tumorigenicity and metastasis mediated by tumor-associated macrophages (TAMs). In THP-1-derived M2 macrophages, SKA-121 significantly decreased the expression of pro-tumorigenic cytokines IL-8 and IL-10 without affecting VEGF and TGF-β1 levels. Additionally, SKA-121 reversed elevated IL-8 and IL-10 levels through the inhibition of ERK-CREB and JNK-c-Jun cascades. Reference: Int J Mol Sci. 2022 Aug 3;23(15):8603. https://pubmed.ncbi.nlm.nih.gov/35955737/

In vivo activity:

SKA-121 has potential in disease treatment involving KCa3.1 channel modulation. SKA-121 selectively activated the KCa3.1 calcium-activated K(+) channel, showing 41-fold selectivity over KCa2.3 and exhibited high selectivity over other channels (KV, NaV, and CaV). SKA-121 shifted the calcium-concentration response curve of KCa3.1. SKA-121 significantly lowered mean arterial blood pressure in normotensive and hypertensive wild-type mice. Reference: Mol Pharmacol. 2014 Sep;86(3):342-57. https://pubmed.ncbi.nlm.nih.gov/24958817/

	Solvent	mg/mL	mM
Solubility
	DMSO	19.8	100.00
	Ethanol	9.9	50.00

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 198.23 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. Ohya S, Matsui M, Kajikuri J, Kito H, Endo K. Downregulation of IL-8 and IL-10 by the Activation of Ca2+-Activated K+ Channel KCa3.1 in THP-1-Derived M2 Macrophages. Int J Mol Sci. 2022 Aug 3;23(15):8603. doi: 10.3390/ijms23158603. PMID: 35955737; PMCID: PMC9368915. 2. Brown BM, Shim H, Zhang M, Yarov-Yarovoy V, Wulff H. Structural Determinants for the Selectivity of the Positive KCa3.1 Gating Modulator 5-Methylnaphtho[2,1-d]oxazol-2-amine (SKA-121). Mol Pharmacol. 2017 Oct;92(4):469-480. doi: 10.1124/mol.117.109421. Epub 2017 Jul 31. PMID: 28760780; PMCID: PMC5588545. 3. Oliván-Viguera A, Valero MS, Pinilla E, Amor S, García-Villalón ÁL, Coleman N, Laría C, Calvín-Tienza V, García-Otín ÁL, Fernández-Fernández JM, Murillo MD, Gálvez JA, Díaz-de-Villegas MD, Badorrey R, Simonsen U, Rivera L, Wulff H, Köhler R. Vascular Reactivity Profile of Novel KCa 3.1-Selective Positive-Gating Modulators in the Coronary Vascular Bed. Basic Clin Pharmacol Toxicol. 2016 Aug;119(2):184-92. doi: 10.1111/bcpt.12560. Epub 2016 Feb 29. PMID: 26821335; PMCID: PMC5720859. 4. Coleman N, Brown BM, Oliván-Viguera A, Singh V, Olmstead MM, Valero MS, Köhler R, Wulff H. New positive Ca2+-activated K+ channel gating modulators with selectivity for KCa3.1. Mol Pharmacol. 2014 Sep;86(3):342-57. doi: 10.1124/mol.114.093286. Epub 2014 Jun 23. PMID: 24958817; PMCID: PMC4152908.

In vitro protocol:

In vivo protocol:

1. Oliván-Viguera A, Valero MS, Pinilla E, Amor S, García-Villalón ÁL, Coleman N, Laría C, Calvín-Tienza V, García-Otín ÁL, Fernández-Fernández JM, Murillo MD, Gálvez JA, Díaz-de-Villegas MD, Badorrey R, Simonsen U, Rivera L, Wulff H, Köhler R. Vascular Reactivity Profile of Novel KCa 3.1-Selective Positive-Gating Modulators in the Coronary Vascular Bed. Basic Clin Pharmacol Toxicol. 2016 Aug;119(2):184-92. doi: 10.1111/bcpt.12560. Epub 2016 Feb 29. PMID: 26821335; PMCID: PMC5720859. 2. Coleman N, Brown BM, Oliván-Viguera A, Singh V, Olmstead MM, Valero MS, Köhler R, Wulff H. New positive Ca2+-activated K+ channel gating modulators with selectivity for KCa3.1. Mol Pharmacol. 2014 Sep;86(3):342-57. doi: 10.1124/mol.114.093286. Epub 2014 Jun 23. PMID: 24958817; PMCID: PMC4152908.

1: Ohya S, Matsui M, Kajikuri J, Kito H, Endo K. Downregulation of IL-8 and IL-10 by the Activation of Ca2+-Activated K+ Channel KCa3.1 in THP-1-Derived M2 Macrophages. Int J Mol Sci. 2022 Aug 3;23(15):8603. doi: 10.3390/ijms23158603. PMID: 35955737; PMCID: PMC9368915. 2: Brown BM, Shim H, Wulff H. Are there superagonists for calcium-activated potassium channels? Channels (Austin). 2017 Nov 2;11(6):504-506. doi: 10.1080/19336950.2017.1376971. Epub 2017 Oct 5. PMID: 28876978; PMCID: PMC5786189. 3: Brown BM, Shim H, Zhang M, Yarov-Yarovoy V, Wulff H. Structural Determinants for the Selectivity of the Positive KCa3.1 Gating Modulator 5-Methylnaphtho[2,1-d]oxazol-2-amine (SKA-121). Mol Pharmacol. 2017 Oct;92(4):469-480. doi: 10.1124/mol.117.109421. Epub 2017 Jul 31. PMID: 28760780; PMCID: PMC5588545. 4: Oliván-Viguera A, Lozano-Gerona J, López de Frutos L, Cebolla JJ, Irún P, Abarca-Lachen E, García-Malinis AJ, García-Otín ÁL, Gilaberte Y, Giraldo P, Köhler R. Inhibition of Intermediate-Conductance Calcium-Activated K Channel (KCa3.1) and Fibroblast Mitogenesis by α-Linolenic Acid and Alterations of Channel Expression in the Lysosomal Storage Disorders, Fabry Disease, and Niemann Pick C. Front Physiol. 2017 Jan 31;8:39. doi: 10.3389/fphys.2017.00039. PMID: 28197106; PMCID: PMC5281581. 5: Oliván-Viguera A, Valero MS, Pinilla E, Amor S, García-Villalón ÁL, Coleman N, Laría C, Calvín-Tienza V, García-Otín ÁL, Fernández-Fernández JM, Murillo MD, Gálvez JA, Díaz-de-Villegas MD, Badorrey R, Simonsen U, Rivera L, Wulff H, Köhler R. Vascular Reactivity Profile of Novel KCa 3.1-Selective Positive-Gating Modulators in the Coronary Vascular Bed. Basic Clin Pharmacol Toxicol. 2016 Aug;119(2):184-92. doi: 10.1111/bcpt.12560. Epub 2016 Feb 29. PMID: 26821335; PMCID: PMC5720859. 6: Christophersen P, Wulff H. Pharmacological gating modulation of small- and intermediate-conductance Ca(2+)-activated K(+) channels (KCa2.x and KCa3.1). Channels (Austin). 2015;9(6):336-43. doi: 10.1080/19336950.2015.1071748. Epub 2015 Jul 28. PMID: 26217968; PMCID: PMC4850045. 7: Coleman N, Brown BM, Oliván-Viguera A, Singh V, Olmstead MM, Valero MS, Köhler R, Wulff H. New positive Ca2+-activated K+ channel gating modulators with selectivity for KCa3.1. Mol Pharmacol. 2014 Sep;86(3):342-57. doi: 10.1124/mol.114.093286. Epub 2014 Jun 23. PMID: 24958817; PMCID: PMC4152908.