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N2538

Sigma-Aldrich

NS8593 hydrochloride

≥98% (HPLC), powder

Synonym(s):

N-[(1R)-1,2,3,4-Tetrahydro-1-naphthalenyl]-1H-Benzimidazol-2-amine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H17N3 · HCl
CAS Number:
875755-24-1
Molecular Weight:
299.80
UNSPSC Code:
12352200
PubChem Substance ID:
329818415
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +54 to +62°, c = 0.5 in methanol

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

Cl[H].C1C[C@@H](Nc2nc3ccccc3[nH]2)c4ccccc4C1

InChI

1S/C17H17N3.ClH/c1-2-8-13-12(6-1)7-5-11-14(13)18-17-19-15-9-3-4-10-16(15)20-17;/h1-4,6,8-10,14H,5,7,11H2,(H2,18,19,20);1H/t14-;/m1./s1

InChI key

VWEKCDTXUUPBNA-PFEQFJNWSA-N

Application

NS8593 hydrochloride has been used to study its effect on the growth of MDA-MB-231 cells (M.D. Anderson and metastasis breast cancer cells).

Biochem/physiol Actions

The compound (R)-N-(benzimidazol-2-yl)-1,2,3,4-tetrahydro-1-naphtylamine (NS8593) reversibly inhibited recombinant SK3-mediated currents (human and rat SK3) with potencies around 100 nM. NS8593 did not inhibit 125I-apamin binding. NS8593 decreased the calcium sensitivity by shifting the activation curve for Ca2+ to the right, only slightly affecting the maximal Ca2+-activated SK current. NS8593 inhibited all the SK1-3 subtypes Ca2+-dependently (Kd = 0.42, 0.60, and 0.73 μM, respectively, at 0.5 μM Ca2+. NS8593 did not affect the calcium-activated potassium channels of intermediate and large conductance (hIK and hBK channels, respectively). NS8593-mediated inhibition was prevented in the presence of a high concentration of the positive modulator NS309.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Knockdown of the small conductance Ca2+-activated K+ channels is potently cytotoxic in breast cancer cell lines
Abdulkareem ZA, et al.
British Journal of Pharmacology, 173(1), 177-190 (2016)
Michiko Tashiro et al.
The journal of physiological sciences : JPS, 69(1), 97-102 (2018-06-18)
To examine whether TRPM7, a member of the melastatin family of transient receptor potential channels, is a physiological pathway for Mg2+ entry in mammalian cells, we studied the effect of TRPM7 regulators on cytoplasmic free Mg2+ concentration ([Mg2+]i) of rat
Alayna Mellott et al.
Pflugers Archiv : European journal of physiology, 472(11), 1589-1606 (2020-09-24)
TRPM7 is a cation channel-protein kinase highly expressed in T lymphocytes and other immune cells. It has been proposed to constitute a cellular entry pathway for Mg2+ and divalent metal cations such as Ca2+, Zn2+, Cd2+, Mn2+, and Ni2+. TRPM7
Francesca Luongo et al.
Nutrients, 10(6) (2018-06-19)
Intestinal magnesium (Mg) uptake is essential for systemic Mg homeostasis. Colon cells express the two highly homologous transient receptor potential melastatin type (TRPM) 6 and 7 Mg2+ channels, but their precise function and the consequences of their mutual interaction are
Goli Ardestani et al.
Cell calcium, 87, 102181-102181 (2020-02-26)
Prior to maturation, mouse oocytes are arrested at the germinal vesicle (GV) stage during which they experience constitutive calcium (Ca2+) influx and spontaneous Ca2+ oscillations. The oscillations cease during maturation but Ca2+ influx continues, as the oocytes' internal stores attain
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