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Key Documents

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S8951

Sigma-Aldrich

SR11237

≥98% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C24H28O4
Número de CAS:
146670-40-8
Peso molecular:
380.48
MDL number:
MFCD00864137
UNSPSC Code:
12352200
PubChem Substance ID:
329824615
NACRES:
NA.77

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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).
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
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
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
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