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Fluorobexarotene

RXR agonist CAS# 1190848-23-7

Fluorobexarotene

Catalog No. BCC6110----Order now to get a substantial discount!

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Chemical structure

Fluorobexarotene

3D structure

Chemical Properties of Fluorobexarotene

Cas No. 1190848-23-7 SDF Download SDF
PubChem ID 25195496 Appearance Powder
Formula C24H27FO2 M.Wt 366.47
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 25 mM in ethanol
Chemical Name 2-fluoro-4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
SMILES CC1=CC2=C(C=C1C(=C)C3=CC(=C(C=C3)C(=O)O)F)C(CCC2(C)C)(C)C
Standard InChIKey LWKAWHRSPCHMPJ-UHFFFAOYSA-N
Standard InChI InChI=1S/C24H27FO2/c1-14-11-19-20(24(5,6)10-9-23(19,3)4)13-18(14)15(2)16-7-8-17(22(26)27)21(25)12-16/h7-8,11-13H,2,9-10H2,1,3-6H3,(H,26,27)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Fluorobexarotene

DescriptionRXR agonist (Ki = 12 nM; EC50 = 43 nM at RXRα receptors). Displays similar RAR agonist activity to bexarotene; exhibits an apparent RXR binding affinity 75% greater than bexarotene.

Fluorobexarotene Dilution Calculator

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Fluorobexarotene Molarity Calculator

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Preparing Stock Solutions of Fluorobexarotene

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7287 mL 13.6437 mL 27.2874 mL 54.5747 mL 68.2184 mL
5 mM 0.5457 mL 2.7287 mL 5.4575 mL 10.9149 mL 13.6437 mL
10 mM 0.2729 mL 1.3644 mL 2.7287 mL 5.4575 mL 6.8218 mL
50 mM 0.0546 mL 0.2729 mL 0.5457 mL 1.0915 mL 1.3644 mL
100 mM 0.0273 mL 0.1364 mL 0.2729 mL 0.5457 mL 0.6822 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Fluorobexarotene

Divergent teratogenicity of agonists of retinoid X receptors in embryos of zebrafish (Danio rerio).[Pubmed:22526925]

Ecotoxicology. 2012 Jul;21(5):1465-75.

Zebrafish (Danio rerio) embryos were comparably exposed to seven known agonists of retinoid X receptors (RXRs) including two endogenous compounds (9-cis-retinoic acid and docosahexaenoic acid), four man-made selective ligands (LGD1069, SR11237, Fluorobexarotene and CD3254), and a biocide (triphenyltin). The dominant phenotypes of malformation were sharp mouths and small caudal fins in 1 mg/L SR11237-treated group after 5 days exposure. 9-cis-retinoic acid and LGD1069 induced multiple malformations including small eyes, bent notochords, reduced brain, enlarged proctodaems, absence of fins, short tails and edema after 5 days exposure. Fluorobexarotene and CD3254 induced similar phenotypes of malformations after 5 days exposure at low concentration (20 mug/L) to those after the 1st d exposure at high concentrations (50 and 100 mug/L). Triphenlytin induced multiple malformations including deformed eyes, bent notochords, bent tails, and edema in hearts after 5 days exposure at concentrations of 1-10 mug Sn/L. In contrast, no discernible malformations were observed in triphenlytin-treated groups after each separate day exposure. These agonists not only showed different ability of teratogenicity but also induced different phenotypes of malformation in zebrafish embryos. In addition, the sensitive stages of zebrafish embryos were different in response to these agonists. Therefore, our results suggest that the agonists of RXRs had divergent teratogenicity in zebrafish embryos.

Modeling, synthesis and biological evaluation of potential retinoid X receptor (RXR) selective agonists: novel analogues of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene).[Pubmed:19791803]

J Med Chem. 2009 Oct 8;52(19):5950-66.

This report describes the synthesis of analogues of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), commonly known as bexarotene, and their analysis in acting as retinoid X receptor (RXR)-specific agonists. Compound 1 has FDA approval to treat cutaneous T-cell lymphoma (CTCL); however, its use can cause side effects such as hypothyroidism and increased triglyceride concentrations, presumably by disruption of RXR heterodimerization with other nuclear receptors. The novel analogues in the present study have been evaluated for RXR activation in an RXR mammalian-2-hybrid assay as well as an RXRE-mediated transcriptional assay and for their ability to induce apoptosis as well as for their mutagenicity and cytotoxicity. Analysis of 11 novel compounds revealed the discovery of three analogues that best induce RXR-mediated transcriptional activity, stimulate apoptosis, have comparable K(i) and EC(50) values to 1, and are selective RXR agonists. Our experimental approach suggests that rational drug design can develop new rexinoids with improved biological properties.

Description

Fluorobexarotene (compound 20) is a potent retinoid-X-receptor (RXR) agonist, with a Ki value of 12 nM and an EC50 value of 43 nM for RXRα receptor. Fluorobexarotene possesses an apparent RXR binding affinity that is 75% greater than Bexarotene.

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