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Merck

S7809

Sigma-Aldrich

SKF-96365

≥98% (HPLC), solid

Sinónimos:

1-[β-(3-(4-Methoxyphenyl)propoxy)-4-methoxyphenethyl]-1H-imidazole hydrochloride, 1-[2-(4-Methoxyphenyl)-2-[3-(4-methoxyphenyl)propoxy]ethyl]imidazole

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About This Item

Fórmula empírica (notación de Hill):
C22H26N2O3 · HCl
Número de CAS:
Peso molecular:
402.91
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >20 mg/mL
H2O: >20 mg/mL

SMILES string

Cl.COc1ccc(CCCOC(Cn2ccnc2)c3ccc(OC)cc3)cc1

InChI

1S/C22H26N2O3.ClH/c1-25-20-9-5-18(6-10-20)4-3-15-27-22(16-24-14-13-23-17-24)19-7-11-21(26-2)12-8-19;/h5-14,17,22H,3-4,15-16H2,1-2H3;1H

InChI key

FWLPKVQUECFKSW-UHFFFAOYSA-N

Application

SKF-96365 has been used as :
  • a nonselective transient receptor potential 6 (TRPC6) blocker in human podocytes
  • an antagonist of store-operated Ca2+ influx in neurons
  • an inhibitor for transient receptor potential 3 (TRPC3) in mice

Biochem/physiol Actions

SKF-96365 with an alkylated imidazole ring is a selective inhibitor of receptor-mediated Ca2+ entry and voltage-gated Ca2+ entry . SKF-96365 mediated depolarization of smooth cardiac muscle membrane and had no impact on the acetylcholine (ACh)-induced depolarization. It is an inhibitor for SOCE (store-operated calcium entry). It also inhibits Homer1 protein expression. SKF-96365 elicits protective functionality in 1-methyl-4-phenylpyridinium(MPP) mediated cytotoxicity.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análisis (COA)

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Enhanced expression of transient receptor potential channel 3 in uterine smooth muscle tissues of lipopolysaccharide-induced preterm delivery mice
Zheng D, et al.
Iranian Journal of Basic Medical Sciences, 19(5), 567-567 (2016)
Protective effects of SKF-96365, a non-specific inhibitor of SOCE, against MPP+-induced cytotoxicity in PC12 cells: potential role of Homer1
Chen T, et al.
PLoS ONE, 8(1), e55601-e55601 (2013)
J E Merritt et al.
The Biochemical journal, 271(2), 515-522 (1990-10-15)
A novel inhibitor of receptor-mediated calcium entry (RMCE) is described. SK&F 96365 (1-(beta-[3-(4-methoxy-phenyl)propoxy]-4-methoxyphenethyl)-1H- imidazole hydrochloride) is structurally distinct from the known 'calcium antagonists' and shows selectivity in blocking RMCE compared with receptor-mediated internal Ca2+ release. Human platelets, neutrophils and endothelial
The transient receptor potential channel antagonist SKF96365 is a potent blocker of low-voltage-activated T-type calcium channels
Singh A, et al.
British Journal of Pharmacology, 160(6), 1464-1475 (2010)
Calcium-sensing receptor stimulation in cultured glomerular podocytes induces TRPC6-dependent calcium entry and RhoA activation
Zhang L, et al.
Cellular Physiology and Biochemistry, 43(5), 1777-1789 (2017)

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