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SML2453

Sigma-Aldrich

GSK-A1

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C29H27FN6O4S
CAS Number:
1416334-69-4
Molecular Weight:
574.63
MDL number:
MFCD29770784
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

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

Biochem/physiol Actions

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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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
Cristina M Dorobantu et al.
Antimicrobial agents and chemotherapy, 60(10), 6402-6406 (2016-08-03)
Encephalomyocarditis virus (EMCV), like hepatitis C virus (HCV), requires phosphatidylinositol 4-kinase IIIα (PI4KA) for genome replication. Here, we demonstrate that tyrphostin AG1478, a known epidermal growth factor receptor (EGFR) inhibitor, also inhibits PI4KA activity, both in vitro and in cells.
Colleen P Doyle et al.
Contact (Thousand Oaks (Ventura County, Calif.)), 7, 25152564241229272-25152564241229272 (2024-02-08)
Oxysterol-binding protein (OSBP)-related proteins (ORPs) 5 and 8 have been shown to deplete the lipid phosphatidylinositol 4-phosphate (PI4P) at sites of membrane contact between the endoplasmic reticulum (ER) and plasma membrane (PM). This is believed to be caused by transport
Gillian L Dornan et al.
Journal of molecular biology, 430(18 Pt B), 3129-3142 (2018-07-22)
Phosphatidylinositol 4-kinase IIIα (PI4KIIIα) is the lipid kinase primarily responsible for generating the lipid phosphatidylinositol 4-phosphate (PI4P) at the plasma membrane, which acts as the substrate for generation of the signaling lipids PIP2 and PIP3. PI4KIIIα forms a large heterotrimeric
Joshua A Lees et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(52), 13720-13725 (2017-12-13)
Plasma membrane (PM) phosphoinositides play essential roles in cell physiology, serving as both markers of membrane identity and signaling molecules central to the cell's interaction with its environment. The first step in PM phosphoinositide synthesis is the conversion of phosphatidylinositol
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