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S8951

Sigma-Aldrich

SR11237

≥98% (HPLC)

Synonym(s):

4-[2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1,3-dioxolan-2-yl]-benzoic acid, BMS 188649, BMS649

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About This Item

Empirical Formula (Hill Notation):
C24H28O4
CAS Number:
146670-40-8
Molecular Weight:
380.48
MDL number:
MFCD00864137
UNSPSC Code:
12352200
PubChem Substance ID:
329824615
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >28 mg/mL (warmed)

storage temp.

2-8°C

SMILES string

CC1(C)CCC(C)(C)c2cc(ccc12)C3(OCCO3)c4ccc(cc4)C(O)=O

InChI

1S/C24H28O4/c1-22(2)11-12-23(3,4)20-15-18(9-10-19(20)22)24(27-13-14-28-24)17-7-5-16(6-8-17)21(25)26/h5-10,15H,11-14H2,1-4H3,(H,25,26)

InChI key

ZZUKALQMHNSWTK-UHFFFAOYSA-N

Application

SR11237 may be used in RXR-mediated cell signaling studies.

Biochem/physiol Actions

SR11237 and other ligands of retinoid X receptor (RXR) activate various nuclear receptors during development process. This produces malformations in Xenopus embryos, involving the anterior-posterior axis.1
SR11237 is a selective pan retinoid X receptor (RXR) agonist with no retinoid A receptor (RAR) activity.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Detection of a receptor-ligand non-covalent complex using a triple quadrupole mass spectrometer.
Johan Lengqvist et al.
Rapid communications in mass spectrometry : RCM, 16(20), 2003-2006 (2002-10-04)
G Benoit et al.
The EMBO journal, 18(24), 7011-7018 (1999-12-22)
Although retinoic acid receptor alpha (RARalpha) agonists induce the maturation of t(15;17) acute promyelocytic leukemia (APL) cells, drug treatment also selects leukemic blasts expressing PML-RARalpha fusion proteins with mutated ligand-binding domains that no longer respond to all-trans retinoic acid (ATRA).
W Peter Lippert et al.
ChemMedChem, 4(7), 1143-1152 (2009-06-06)
C/Si switch: Twofold sila-substitution (C/Si exchange) in the RXR-selective retinoids 4 a (SR11237) and 5 a leads to 4 b (disila-SR11237) and 5 b, respectively. Chemistry and biology of the C/Si pairs are reported.SR11237 (BMS649, 4 a) is a pan-RXR-selective
Guo-quan Chen et al.
International journal of cancer, 99(2), 171-178 (2002-04-30)
Epidemiological and animal studies have demonstrated that vitamin A and its natural and synthetic derivatives, retinoids, are effective agents in preventing the development of tobacco-associated cancers. Unfortunately, clinical trials of retinoids on cigarette smokers have shown lack of efficacy in
G J Gendimenico et al.
The Journal of investigative dermatology, 102(5), 676-680 (1994-05-01)
We evaluated SR11237, a retinoid X receptor (RXR)-specific compound, for its pharmacologic effects on cell differentiation in F9 embryonal carcinoma cells and rhino mouse epidermis. SR11237 can cause RXR/RXR homodimers to form and transactivate a reporter gene containing a RXR-response
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