Synonym
BMS453; BMS 453; BMS-453; BMS 189453; BMS-189453; BMS189453.
IUPAC/Chemical Name
Benzoic acid, 4-(2-(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl)-, (E)-
InChi Key
VUODRPPTYLBGFM-CMDGGOBGSA-N
InChi Code
InChI=1S/C27H24O2/c1-27(2)17-16-23(21-6-4-3-5-7-21)24-18-20(12-15-25(24)27)9-8-19-10-13-22(14-11-19)26(28)29/h3-16,18H,17H2,1-2H3,(H,28,29)/b9-8+
SMILES Code
O=C(O)C1=CC=C(/C=C/C2=CC=C3C(C)(C)CC=C(C4=CC=CC=C4)C3=C2)C=C1
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, not in water
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
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.
| 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 |
1: Flamini MI, Gauna GV, Sottile ML, Nadin BS, Sanchez AM, Vargas-Roig LM. Retinoic acid reduces migration of human breast cancer cells: role of retinoic acid receptor beta. J Cell Mol Med. 2014 Jun;18(6):1113-23. doi: 10.1111/jcmm.12256. Epub 2014 Apr 10. PubMed PMID: 24720764; PubMed Central PMCID: PMC4508151.
2: Ali-Khan SE, Hales BF. Retinoid receptor antagonists alter the pattern of apoptosis in organogenesis stage mouse limbs. Toxicol Sci. 2006 Mar;90(1):208-20. Epub 2005 Dec 1. PubMed PMID: 16322074.
3: Lou YR, Miettinen S, Kagechika H, Gronemeyer H, Tuohimaa P. Retinoic acid via RARalpha inhibits the expression of 24-hydroxylase in human prostate stromal cells. Biochem Biophys Res Commun. 2005 Dec 30;338(4):1973-81. Epub 2005 Nov 7. PubMed PMID: 16289102.
4: Vine AL, Bertram JS. Upregulation of connexin 43 by retinoids but not by non-provitamin A carotenoids requires RARs. Nutr Cancer. 2005;52(1):105-13. PubMed PMID: 16091010.
5: Matt N, Ghyselinck NB, Wendling O, Chambon P, Mark M. Retinoic acid-induced developmental defects are mediated by RARbeta/RXR heterodimers in the pharyngeal endoderm. Development. 2003 May;130(10):2083-93. PubMed PMID: 12668623.
6: Chen R, Chen F, Han J, Miu J, Shao N, Oyang R. [Effects of selective RAR or/and RXR retinoids on the proliferation and differentiation of NB4 cells and their mechanisms]. Zhonghua Xue Ye Xue Za Zhi. 2001 May;22(5):256-9. Chinese. PubMed PMID: 11877083.
7: Yang L, Ostrowski J, Reczek P, Brown P. The retinoic acid receptor antagonist, BMS453, inhibits normal breast cell growth by inducing active TGFbeta and causing cell cycle arrest. Oncogene. 2001 Nov 29;20(55):8025-35. PubMed PMID: 11753686.
8: Yang L, Munoz-Medellin D, Kim HT, Ostrowski J, Reczek P, Brown PH. Retinoic acid receptor antagonist BMS453 inhibits the growth of normal and malignant breast cells without activating RAR-dependent gene expression. Breast Cancer Res Treat. 1999 Aug;56(3):277-91. PubMed PMID: 10573118.
9: Blanchet S, Favier B, Chevalier G, Kastner P, Michaille JJ, Chambon P, Dhouailly D. Both retinoic acid receptors alpha (RARalpha) and gamma (RARgamma) are able to initiate mouse upper-lip skin glandular metaplasia. J Invest Dermatol. 1998 Aug;111(2):206-12. PubMed PMID: 9699718.
