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SML2453

Sigma-Aldrich

GSK-A1

≥98% (HPLC)

Sinônimo(s):

5-(2-Amino-1-(4-morpholinophenyl)-1H-benzimidazol-6-yl)-N-(2-fluorophenyl)-2-methoxypyridine-3-sulfonamide, 5-(2-Amino-1-(4-morpholinophenyl)-1H-benzo[d]imidazol-6-yl)-N-(2-fluorophenyl)-2-methoxypyridine-3-sulfonamide, 5-[2-Amino-1-[4-(4-morpholinyl)phenyl]-1H-benzimidazol-6-yl]-N-(2-fluorophenyl)-2-methoxy-3-pyridinesulfonamide, Compound A1, PI4KA Inhibitor A1

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About This Item

Fórmula empírica (Notação de Hill):
C29H27FN6O4S
Número CAS:
1416334-69-4
Peso molecular:
574.63
Número MDL:
MFCD29770784
Código UNSPSC:
12352200
NACRES:
NA.77

Ensaio

≥98% (HPLC)

Formulário

powder

cor

white to beige

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

O=S(C1=CC(C2=CC=C3C(N(C4=CC=C(N5CCOCC5)C=C4)C(N)=N3)=C2)=CN=C1OC)(NC6=CC=CC=C6F)=O

InChI

1S/C29H27FN6O4S/c1-39-28-27(41(37,38)34-24-5-3-2-4-23(24)30)17-20(18-32-28)19-6-11-25-26(16-19)36(29(31)33-25)22-9-7-21(8-10-22)35-12-14-40-15-13-35/h2-11,16-18,34H,12-15H2,1H3,(H2,31,33)

chave InChI

AJOGHKUZDLYXKS-UHFFFAOYSA-N

Ações bioquímicas/fisiológicas

ATP site-targeting, highly potent and selective phosphatidylinositol 4-kinase type IIIα (PI4KA, PI4KIIIα) inhibitor.
GSK-A1 is an ATP site-targeting, highly potent and selective type III phosphatidylinositol 4-kinase PI4KA (PI4KIIIα) inhibitor (pIC50 = 8.5-9.8) that selectively downregulates cellular PtdIns(4)P, but not PtdIns(4,5)P2, level (HEK293 IC50 = 3 nM, complete depletion of HEK293 & COS-7 plasma membrane PtdIns(4)P by 100 nM post 10 min treatment) with much reduced potency toward PI4KB (pIC50 = 7.2-7.7), PI3KA/B/D/G (pIC50 = 7.3/7/7.1/7.8) or PI4K/2A/2B (pIC50 <5). GSK-A1 is a useful tool for probing PI4KA-dependent cellular processes and viral replication (typical culture treatment conc. range: 10-100 nM).

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
0000185146
0000185147
0000171473
0000185147
0000185146

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Colleen P Doyle et al.
Contact (Thousand Oaks (Ventura County, Calif.)), 7, 25152564241232196-25152564241232196 (2024-02-26)
The lipid phosphatidylinositol 4-phosphate (PI4P) plays a master regulatory role at Golgi membranes, orchestrating membrane budding, non-vesicular lipid transport and membrane organization. It follows that harmonious Golgi function requires strictly maintained PI4P homeostasis. One of the most abundant PI4P effector
Alejandro Alvarez-Prats et al.
Cell reports, 23(10), 2881-2890 (2018-06-07)
Active membrane remodeling during myelination relies on phospholipid synthesis and membrane polarization, both of which are known to depend on inositol phospholipids. Here, we show that sciatic nerves of mice lacking phosphatidylinositol 4-kinase alpha (PI4KA) in Schwann cells (SCs) show
Cristina M Dorobantu et al.
mSphere, 1(3) (2016-06-16)
Positive-strand RNA [(+)RNA] viruses are true masters of reprogramming host lipid trafficking and synthesis to support virus genome replication. Via their membrane-associated 3A protein, picornaviruses of the genus Enterovirus (e.g., poliovirus, coxsackievirus, and rhinovirus) subvert Golgi complex-localized phosphatidylinositol 4-kinase IIIβ
Rafael Gil de Rubio et al.
Science signaling, 11(547) (2018-09-13)
Phospholipase C (PLC) enzymes hydrolyze the plasma membrane (PM) lipid phosphatidylinositol 4,5-bisphosphate (PI4,5P2) to generate the second messengers inositol trisphosphate (IP3) and diacylglycerol (DAG) in response to receptor activation in almost all mammalian cells. We previously found that stimulation of
Gergő Gulyás et al.
The Journal of biological chemistry, 292(46), 18862-18877 (2017-09-25)
Plasma membrane (PM) localization of Ras proteins is crucial for transmitting signals upon mitogen stimulation. Post-translational lipid modification of Ras proteins plays an important role in their recruitment to the PM. Electrostatic interactions between negatively charged PM phospholipids and basic
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