| Identification | Back Directory | [Name]
4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid | [CAS]
215030-90-3 | [Synonyms]
BMS 493
BMS204, 493
4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]benzoicacid
4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(phenylethynyl)-2-naphthalenyl]ethenyl]-benzoic acid
(E)-4-[2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)naphthalen-2-yl]ethen-1-yl]benzoic acid
Benzoic acid, 4-[(1E)-2-[5,6-dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]- | [Molecular Formula]
C29H24O2 | [MDL Number]
MFCD17215944 | [MOL File]
215030-90-3.mol | [Molecular Weight]
404.5 |
| Chemical Properties | Back Directory | [Boiling point ]
605.4±55.0 °C(Predicted) | [density ]
1.21±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: ≥20mg/mL | [form ]
powder | [pka]
4.27±0.10(Predicted) | [color ]
light yellow to yellow | [InChI]
1S/C29H24O2/c1-29(2)19-18-24(14-10-21-6-4-3-5-7-21)26-20-23(13-17-27(26)29)9-8-22-11-15-25(16-12-22)28(30)31/h3-9,11-13,15-18,20H,19H2,1-2H3,(H,30,31)/b9-8+ | [InChIKey]
YCADIXLLWMXYKW-CMDGGOBGSA-N | [SMILES]
CC1(C)CC=C(C#Cc2ccccc2)c3cc(\C=C\c4ccc(cc4)C(O)=O)ccc13 |
| Hazard Information | Back Directory | [Description]
Nuclear retinoic acid receptors (RARs) are transcriptional regulators with roles in cell proliferation and differentiation. BMS 493 is a pan-RAR inverse agonist that blocks RARα activity with an IC50 value of 114 nM. In all RAR types (RARα, RARβ, and RARγ), BMS493 prevents the recruitment of transcriptional coactivators to RARs while stabilizing corepressor interactions. BMS 493 has been used to elucidate the critical roles of RARs in development and immune response. | [Uses]
BMS 493 has been used:
- as an inhibitor for the dietary and pharmacologic manipulation of retinoic acid (RA) activity in vivo and in vitro
- for human induced pluripotent stem cells (iPSCs) culture and ventricular cardiomyocytes (VCMs) differentiation
- to inhibit retinoic acid (RA) signaling in explants
- as a retinoic acid receptor (RAR) inhibitor for the induction of synaptonemal complex protein 3 (SCP3) and ATP-dependent RNA helicase (DDX4) in primordial germ cells (PGCs)
| [Definition]
ChEBI: BMS-493 is a member of the class of dihydronaphthalenes that is 1,2-dihydronaphthalene which is substituted at positions 1, 1, 4, and 6 by methyl, methyl, phenylethynyl, and 2-(p-carboxyphenyl)vinyl groups, respectively (the E isomer). It has a role as a retinoic acid receptor antagonist. It is a member of benzoic acids, a stilbenoid, a member of dihydronaphthalenes and an acetylenic compound. | [General Description]
BMS 493 inhibits the formation of neuritic processes and plasmenyethanolamine -phospholipase A2 (PLA2) activity. | [Biochem/physiol Actions]
BMS 493 is an inverse pan-RAR agonist. Retinoic acid receptors (RARs) are ligand-dependent transcription factors that control a number of physiological processes. RARs exert their functions by regulating gene networks controlling cell growth, differentiation, survival, and death. | [storage]
Store at -20°C | [References]
[1] C CHAZAUD P D P Chambon. Retinoic acid is required in the mouse embryo for left-right asymmetry determination and heart morphogenesis.[J]. Development, 1999, 126 12: 2589-2596. DOI: 10.1242/dev.126.12.2589
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] ALBANE LE MAIRE. A unique secondary-structure switch controls constitutive gene repression by retinoic acid receptor[J]. Nature Structural & Molecular Biology, 2010, 17 7: 801-807. DOI: 10.1038/nsmb.1855
[4] PIERRE GERMAIN. Differential action on coregulator interaction defines inverse retinoid agonists and neutral antagonists.[J]. Chemistry & biology, 2009: 479-489. DOI: 10.1016/j.chembiol.2009.03.008
[5] R MOLLARD. Stage-dependent responses of the developing lung to retinoic acid signaling.[J]. International Journal of Developmental Biology, 2000, 44 5: 457-462.
[6] CLAIRE CHAZAUD . Retinoic acid signaling regulates murine bronchial tubule formation[J]. Mechanisms of Development, 2003, 120 6: Pages 691-700. DOI: 10.1016/s0925-4773(03)00048-0
[7] FRéDéRIC GEISSMANN. Retinoids regulate survival and antigen presentation by immature dendritic cells.[J]. Journal of Experimental Medicine, 2003, 198 4: 623-634. DOI: 10.1084/jem.20030390 |
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