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Documenti fondamentali

SML0282

Sigma-Aldrich

Bexarotene

≥98% (HPLC)

Sinonimo/i:

4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid, LGD-1069, SR-11247

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About This Item

Formula empirica (notazione di Hill):
C24H28O2
Numero CAS:
Peso molecolare:
348.48
Numero MDL:
Codice UNSPSC:
41106305
ID PubChem:
NACRES:
NA.77

Livello qualitativo

Saggio

≥98% (HPLC)

Stato

powder

Colore

white to beige

Solubilità

DMSO: ≥15 mg/mL (warmed)

Temperatura di conservazione

−20°C

Stringa SMILE

C=C(C1=CC=C(C(O)=O)C=C1)C2=C(C)C=C3C(C(C)(C)CCC3(C)C)=C2

InChI

1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)
NAVMQTYZDKMPEU-UHFFFAOYSA-N

Informazioni sul gene

Applicazioni

Bexarotene has been used as retinoid x receptor (RXR) agonist:
  • to study its effect on human oral squamous cell carcinoma (OSCC) cell lines
  • to test for cooperative cell killing of cutaneous T cell lymphoma (CTCL) with 966
  • as a standard in HPLC for determining its potential impurities in drug substances and drug products

Bexarotene has been used:
  • to investigate its effects on the changes in renal, cardiac, hepatic, and pulmonary expression/activity of inducible nitric oxide synthase (iNOS) and CYP4F6
  • to analyze the involvement of retinoid x receptor (RXR) homo or permissive heterodimers
  • to study its potential impurities in drug substances and drug products

Azioni biochim/fisiol

Bexarotene is a highly selective retinoid X receptor (RXR) agonist. It is an antineoplastic agent, already approved as an oral antineoplastic agent for cutaneous T cell lymphoma and being investigated against other cancers. A study has found that bexarotene in a mouse Alzheimer′s model lowered the most toxic form of β-amyloid peptide and increased cognitive ability. The activity in the mouse Alzheimer′s models are believed to be by activating PPARγ:RXR and LXR:RXR dimers which induces the expression of apoE and facilitates Aβ clearance and promotes microglial phagocytosis.
Bexarotene is used to treat breast cancer.

Caratteristiche e vantaggi

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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M Maekawa et al.
Translational psychiatry, 7(9), e1229-e1229 (2017-09-06)
The risk of schizophrenia is increased in offspring whose mothers experience malnutrition during pregnancy. Polyunsaturated fatty acids (PUFAs) are dietary components that are crucial for the structural and functional integrity of neural cells, and PUFA deficiency has been shown to
Katherine D LaClair et al.
Molecular neurodegeneration, 8, 18-18 (2013-06-15)
Though the precise cause(s) of Alzheimer's disease (AD) remain unknown, there is strong evidence that decreased clearance of β-amyloid (Aβ) from the brain can contribute to the disease. Therapeutic strategies to promote natural Aβ clearance mechanisms, such as the protein
Protective effects of retinoid x receptors on retina pigment epithelium cells
Ayala-Pena VB, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1863(6), 1134-1145 (2016)
Shawn C Owen et al.
ACS chemical biology, 7(8), 1429-1435 (2012-05-26)
Many small molecules, including bioactive molecules and approved drugs, spontaneously form colloidal aggregates in aqueous solution at micromolar concentrations. Though it is widely accepted that aggregation leads to artifacts in screens for ligands of soluble proteins, the effects of colloid
Inhibition of histone deacetylase 3 causes replication stress in cutaneous T cell lymphoma
Wells CE, et al.
PLoS ONE, 8(7), e68915-e68915 (2013)

Contenuto correlato

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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