MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 526355 | Name: SR11237
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

SR11237 is a pan retinoid X receptor (RXR) agonist. SR11237 destabilized the RXRα homodimer but promoted formation of the PPARγ:RXRα heterodimer. SR11237 can cause RXR/RXR homodimers to form and transactivate a reporter gene containing a RXR-response element.

Chemical Structure

SR11237
CAS#146670-40-8

Theoretical Analysis

MedKoo Cat#: 526355

Name: SR11237

CAS#: 146670-40-8

Chemical Formula: C24H28O4

Exact Mass: 380.1988

Molecular Weight: 380.48

Elemental Analysis: C, 75.76; H, 7.42; O, 16.82

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
25mg USD 550.00 2 Weeks
50mg USD 950.00 2 Weeks
100mg USD 1,650.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
SR 11237; SR11237; SR-11237; BMS 649; BMS-649; BMS649; BMS 188649; BMS-188649; BMS188649
IUPAC/Chemical Name
4-(2-(5,6,7,8-Tetrahydro-5,5,8,8,-tetramethyl-2-naphthalenyl)-1,3-dioxolan-2-yl)benzoic acid
InChi Key
ZZUKALQMHNSWTK-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(O)C1=CC=C(C2(C3=CC=C4C(C)(C)CCC(C)(C)C4=C3)OCCO2)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
SR11237 is devoid of any RAR activity. SR11237 can cause RXR/RXR homodimers to form and transactivate a reporter gene containing a RXR-response element.
In vitro activity:
The results of this study indicate that deregulation of the retinoid/rexinoid signaling pathway has a major role and may represent a potential therapeutic target in acute leukemia treatment. SR11237 and LGD1069 could specifically inhibit NUP98-RARG transformed cells, but mutation of the RXR interaction domain in NUP98-RARG had little effect on its transformation. This finding reveals that therapeutic functions of rexinoid can be independent of the direct biochemical interaction between RXR and the fusion. Reference: Leukemia. 2015 May;29(5):1153-62. https://pubmed.ncbi.nlm.nih.gov/25510432/
In vivo activity:
RXR stimulation disrupts normal bone growth and may lead to premature growth plate closure in rodent models. Rats treated with SR11237 showed shorter long bones than controls and had growth plate dysmorphia. Cells invading the growth plate displayed pre-hypertrophic characteristics, accompanied by p57 immunostaining and SOX9-positive cells surrounding calcified tissue. Reference: Int J Mol Sci. 2019 Oct 20;20(20):5198. https://pubmed.ncbi.nlm.nih.gov/31635173/
Solvent mg/mL mM comments
Solubility
DMSO 5.0 13.14
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 380.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Qiu JJ, Zeisig BB, Li S, Liu W, Chu H, Song Y, Giordano A, Schwaller J, Gronemeyer H, Dong S, So CW. Critical role of retinoid/rexinoid signaling in mediating transformation and therapeutic response of NUP98-RARG leukemia. Leukemia. 2015 May;29(5):1153-62. doi: 10.1038/leu.2014.334. Epub 2014 Dec 16. PMID: 25510432. 2. Ning RB, Zhu J, Chai DJ, Xu CS, Xie H, Lin XY, Zeng JZ, Lin JX. RXR agonists inhibit high glucose-induced upregulation of inflammation by suppressing activation of the NADPH oxidase-nuclear factor-κB pathway in human endothelial cells. Genet Mol Res. 2013 Dec 13;12(4):6692-707. doi: 10.4238/2013.December.13.3. PMID: 24391011. 3. Dupuis H, Pest MA, Hadzic E, Vo TX, Hardy DB, Beier F. Exposure to the RXR Agonist SR11237 in Early Life Causes Disturbed Skeletal Morphogenesis in a Rat Model. Int J Mol Sci. 2019 Oct 20;20(20):5198. doi: 10.3390/ijms20205198. PMID: 31635173; PMCID: PMC6829207. 4. Guillem-Llobat P, Íñiguez MA. Inhibition of lipopolysaccharide-induced gene expression by liver X receptor ligands in macrophages involves interference with early growth response factor 1. Prostaglandins Leukot Essent Fatty Acids. 2015 May;96:37-49. doi: 10.1016/j.plefa.2015.02.002. Epub 2015 Feb 19. PMID: 25736222.
In vitro protocol:
1. Qiu JJ, Zeisig BB, Li S, Liu W, Chu H, Song Y, Giordano A, Schwaller J, Gronemeyer H, Dong S, So CW. Critical role of retinoid/rexinoid signaling in mediating transformation and therapeutic response of NUP98-RARG leukemia. Leukemia. 2015 May;29(5):1153-62. doi: 10.1038/leu.2014.334. Epub 2014 Dec 16. PMID: 25510432. 2. Ning RB, Zhu J, Chai DJ, Xu CS, Xie H, Lin XY, Zeng JZ, Lin JX. RXR agonists inhibit high glucose-induced upregulation of inflammation by suppressing activation of the NADPH oxidase-nuclear factor-κB pathway in human endothelial cells. Genet Mol Res. 2013 Dec 13;12(4):6692-707. doi: 10.4238/2013.December.13.3. PMID: 24391011.
In vivo protocol:
1. Dupuis H, Pest MA, Hadzic E, Vo TX, Hardy DB, Beier F. Exposure to the RXR Agonist SR11237 in Early Life Causes Disturbed Skeletal Morphogenesis in a Rat Model. Int J Mol Sci. 2019 Oct 20;20(20):5198. doi: 10.3390/ijms20205198. PMID: 31635173; PMCID: PMC6829207. 2. Guillem-Llobat P, Íñiguez MA. Inhibition of lipopolysaccharide-induced gene expression by liver X receptor ligands in macrophages involves interference with early growth response factor 1. Prostaglandins Leukot Essent Fatty Acids. 2015 May;96:37-49. doi: 10.1016/j.plefa.2015.02.002. Epub 2015 Feb 19. PMID: 25736222.
1: Giner XC, Cotnoir-White D, Mader S, Lévesque D. Selective ligand activity at Nur/retinoid X receptor complexes revealed by dimer-specific bioluminescence resonance energy transfer-based sensors. FASEB J. 2015 Oct;29(10):4256-67. doi: 10.1096/fj.14-259804. PubMed PMID: 26148973. 2: Ning RB, Zhu J, Chai DJ, Xu CS, Xie H, Lin XY, Zeng JZ, Lin JX. RXR agonists inhibit high glucose-induced upregulation of inflammation by suppressing activation of the NADPH oxidase-nuclear factor-κB pathway in human endothelial cells. Genet Mol Res. 2013 Dec 13;12(4):6692-707. doi: 10.4238/2013.December.13.3. PubMed PMID: 24391011. 3: Lippert WP, Burschka C, Götz K, Kaupp M, Ivanova D, Gaudon C, Sato Y, Antony P, Rochel N, Moras D, Gronemeyer H, Tacke R. Silicon analogues of the RXR-selective retinoid agonist SR11237 (BMS649): chemistry and biology. ChemMedChem. 2009 Jul;4(7):1143-52. doi: 10.1002/cmdc.200900090. PubMed PMID: 19496083. 4: Shen LH, He B, Wang BY, Zeng JZ, Zhou L, Hu LH, Bu J, Wang L. [Effect of retinoid X receptor activation on oxidized low-density lipoprotein induced cell differentiation of murine macrophage cell line into dendritic like cells]. Zhonghua Xin Xue Guan Bing Za Zhi. 2007 Sep;35(9):833-7. Chinese. PubMed PMID: 18070479. 5: James SY, Lin F, Kolluri SK, Dawson MI, Zhang XK. Regulation of retinoic acid receptor beta expression by peroxisome proliferator-activated receptor gamma ligands in cancer cells. Cancer Res. 2003 Jul 1;63(13):3531-8. PubMed PMID: 12839938. 6: Lengqvist J, Griffiths WJ, Perlmann T, Sjövall J. Detection of a receptor-ligand non-covalent complex using a triple quadrupole mass spectrometer. Rapid Commun Mass Spectrom. 2002;16(20):2003-6. PubMed PMID: 12362394. 7: Chen GQ, Lin B, Dawson MI, Zhang XK. Nicotine modulates the effects of retinoids on growth inhibition and RAR beta expression in lung cancer cells. Int J Cancer. 2002 May 10;99(2):171-8. PubMed PMID: 11979430. 8: Gazzerro P, Bontempo P, Schiavone EM, Abbondanza C, Moncharmont B, Armetta I, Medici N, De Simone M, Nola E, Puca GA, Molinari AM. Differentiation of myeloid cell lines correlates with a selective expression of RIZ protein. Mol Med. 2001 Aug;7(8):552-60. PubMed PMID: 11591891; PubMed Central PMCID: PMC1950061. 9: Bourguet W, Vivat V, Wurtz JM, Chambon P, Gronemeyer H, Moras D. Crystal structure of a heterodimeric complex of RAR and RXR ligand-binding domains. Mol Cell. 2000 Feb;5(2):289-98. PubMed PMID: 10882070. 10: Benoit G, Altucci L, Flexor M, Ruchaud S, Lillehaug J, Raffelsberger W, Gronemeyer H, Lanotte M. RAR-independent RXR signaling induces t(15;17) leukemia cell maturation. EMBO J. 1999 Dec 15;18(24):7011-8. PubMed PMID: 10601023; PubMed Central PMCID: PMC1171764. 11: Li XY, Xiao JH, Feng X, Qin L, Voorhees JJ. Retinoid X receptor-specific ligands synergistically upregulate 1, 25-dihydroxyvitamin D3-dependent transcription in epidermal keratinocytes in vitro and in vivo. J Invest Dermatol. 1997 Apr;108(4):506-12. PubMed PMID: 9077482. 12: Brooks SC 3rd, Kazmer S, Levin AA, Yen A. Myeloid differentiation and retinoblastoma phosphorylation changes in HL-60 cells induced by retinoic acid receptor- and retinoid X receptor-selective retinoic acid analogs. Blood. 1996 Jan 1;87(1):227-37. PubMed PMID: 8547646. 13: Davis KD, Berrodin TJ, Stelmach JE, Winkler JD, Lazar MA. Endogenous retinoid X receptors can function as hormone receptors in pituitary cells. Mol Cell Biol. 1994 Nov;14(11):7105-10. PubMed PMID: 7935425; PubMed Central PMCID: PMC359244. 14: Gendimenico GJ, Stim TB, Corbo M, Janssen B, Mezick JA. A pleiotropic response is induced in F9 embryonal carcinoma cells and rhino mouse skin by All-trans-retinoic acid, a RAR agonist but not by SR11237, a RXR-selective agonist. J Invest Dermatol. 1994 May;102(5):676-80. PubMed PMID: 8176247.