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

SKA-121
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 532702

CAS#: 1820708-73-3

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

Chemical Structure

SKA-121

CAS# 1820708-73-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 532702
Name: SKA-121
CAS#: 1820708-73-3
Chemical Formula: C12H10N2O
Exact Mass: 198.08
Molecular Weight: 198.230
Elemental Analysis: C, 72.71; H, 5.09; N, 14.13; O, 8.07

Price and Availability

Size	Price	Availability
5mg	USD 430	2 weeks
10mg	USD 880	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

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

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:	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.
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.

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1: 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. eCollection 2017. PubMed PMID: 28197106; PubMed Central PMCID: PMC5281581.

2: 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. PubMed PMID: 26821335.

3: 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. Review. PubMed PMID: 26217968; PubMed Central PMCID: PMC4850045.

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. PubMed PMID: 24958817; PubMed Central PMCID: PMC4152908.

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