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SML1617

Sigma-Aldrich

GSK2033

≥98% (HPLC)

Synonym(s):

2,4,6-Trimethyl-N-[[3′-(methylsulfonyl)[1,1′-biphenyl]-4-yl]methyl]-N-[[5-(trifluoromethyl)-2-furanyl]methyl]benzenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C29H28F3NO5S2
CAS Number:
1221277-90-2
Molecular Weight:
591.66
MDL number:
MFCD28396416
UNSPSC Code:
12352200
PubChem Substance ID:
329825503
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 3 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CS(C1=CC=CC(C2=CC=C(CN(S(C3=C(C)C=C(C)C=C3C)(=O)=O)CC4=CC=C(C(F)(F)F)O4)C=C2)=C1)(=O)=O

InChI

1S/C29H28F3NO5S2/c1-19-14-20(2)28(21(3)15-19)40(36,37)33(18-25-12-13-27(38-25)29(30,31)32)17-22-8-10-23(11-9-22)24-6-5-7-26(16-24)39(4,34)35/h5-16H,17-18H2,1-4H3

InChI key

PSOXOVKYGWBTPB-UHFFFAOYSA-N

Biochem/physiol Actions

GSK2033 has the ability to repress gluconeogenic gene expression stimulated by GC (glucocorticoids), without altering immune-responsive GR (GC receptor) target genes. It helps to target several nuclear receptors that can alter hepatic gene expression.
GSK2033 is an antagonist of the nuclear receptor liver-X-receptor (LXR) with pIC50 values of 7.0 for LXRα and 7.4 for LXRβ. Treatment of murine CD41 T cells with GSK2033 enhanced cellular proliferation and Th1/Th2/Th17 differentiation. In another study, the conjugated linoleic acid (CLA)-induced expression of efflux protein ATP-binding-cassette transporter A1 (ABCA1) was completely abolished by preincubation with GSK2033, showing that CLA mediated regulation of ABCA-1 expression is LXR dependent.

Storage Class

11 - Combustible Solids

wgk_germany

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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Promiscuous activity of the LXR antagonist GSK2033 in a mouse model of fatty liver disease.
Griffett K and Burris TP
Biochemical and Biophysical Research Communications, 479(3), 424-428 (2016)
Separating the Anti-Inflammatory and Diabetogenic Effects of Glucocorticoids Through LXRβ Antagonism.
Patel R, et al.
Endocrinology, 158(4), 1034-1047 (2017)
Lili Chen et al.
Journal of neurochemistry, 154(2), 205-217 (2019-10-12)
Cerebral ischemia (CI) leads to cognitive dysfunction due to the loss of hippocampal neurons. Liver X receptors (LXRs), including the LXRα and LXRβ isoforms, are critical for neurogenesis, synaptic plasticity, neurodegeneration, and cholesterol metabolism. However, the potential role of LXRs
Louise Ménégaut et al.
Cell reports, 31(7), 107665-107665 (2020-05-21)
Low-grade inflammation is constitutive of atherosclerosis, and anti-inflammatory therapy inhibiting interleukin-1β (IL-1β) reduces the rate of cardiovascular events. While cholesterol accumulation in atheroma plaque and macrophages is a major driver of the inflammatory process, the role of the LXR cholesterol

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