| Identification | Back Directory | [Name]
4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID | [CAS]
155877-83-1 | [Synonyms]
LE 135
4-(7,8,9,10-TETRAHYDRO-5,7,7,10,10-PENTAMETHYL-5H-BENZO[E]NAPHTHO[2,3-B][1,4]DIAZEPIN-13-YL)BENZOIC ACID
4-(5,7,7,10,10-Pentamethyl-7,8,9,10-tetrahydro-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid
4-(7,8,9,10-Tetrahydro-5,7,7,10,10-pentamethyl-(5H)-benzo[e]naphtho[2.3-b][1.4]diazepine-13-yl)benzoicacid
Benzoic acid, 4-(7,8,9,10-tetrahydro-5,7,7,10,10-pentaMethyl-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)- | [Molecular Formula]
C29H30N2O2 | [MDL Number]
MFCD06798318 | [MOL File]
155877-83-1.mol | [Molecular Weight]
438.56 |
| Chemical Properties | Back Directory | [Boiling point ]
601.3±55.0 °C(Predicted) | [density ]
1.17±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble15mg/mL, clear | [form ]
powder | [pka]
3.02±0.10(Predicted) | [color ]
yellow to orange | [InChI]
1S/C29H30N2O2/c1-28(2)14-15-29(3,4)22-17-25-23(16-21(22)28)30-26(18-10-12-19(13-11-18)27(32)33)20-8-6-7-9-24(20)31(25)5/h6-13,16-17H,14-15H2,1-5H3,(H,32,33) | [InChIKey]
YZZAIQOVMHVWBS-UHFFFAOYSA-N | [SMILES]
N1(c2c(cc5c(c2)C(CCC5(C)C)(C)C)N=C(c4c1cccc4)c3ccc(cc3)C(=O)O)C |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/38 | [Safety Statements ]
26 | [WGK Germany ]
3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2 |
| Hazard Information | Back Directory | [Description]
LE 135 is a retinoic acid receptor (RAR) antagonist that displays moderate selectivity for RARβ over RARα (Kis = 0.22 and 1.4 μM, respectively). LE 135 inhibits retinoic acid-induced transcriptional activation of RARβ (>70% inhibition at 10 μM), but not RARα, RARγ or retinoid X receptor α. It has been shown to inhibit retinoid Am80-induced differentiation of human promyelocytic leukemia cells, HL-60, with an IC50 value of 0.2 μM. | [Uses]
LE 135 has been used for in vitro islet treatment. | [Definition]
ChEBI: 4-(5,7,7,10,10-pentamethyl-8,9-dihydronaphtho[2,3-b][1,4]benzodiazepin-13-yl)benzoic acid is a dibenzodiazepine. | [Biological Activity]
Retinoic acid antagonist; displays moderate selectivity for RAR β over RAR α (K i 爒alues are 0.22 and 1.4 μ M respectively). Highly selective over RAR γ and RXR α . Inhibits human HL-60 leukemia cell differentiation induced by Am80 (IC 50 = 150 nM). | [Biochem/physiol Actions]
LE135 is a retinoic acid receptor (RAR) antagonist with selectivity for RARβ (Ki = 220 nM) over RARα (Ki = 1.4 μM). LE135 inhibits retinoic acid-induced transcriptional activation of RARβ (>70% inhibition at 10 μM), but not RARα, RARγ or retinoid X receptor α (RXRα). There is high interest in retinoic acid receptors for cancer and for differentiation studies. LE135 has been shown to inhibit retinoid Am80-induced differentiation of human promyelocytic leukemia HL-60 cells with an IC50 value of 0.2 μM. LE135 has been used to study the role of a retinoic acid receptor-β (RARβ) on the differentiation of mesenchymal stem cells, and was found to inhibit the neuronal differentiation promoting effects of all-trans retinoic acid (ATRA) on mesenchymal stem cells. | [storage]
Store at +4°C | [References]
[1] Y LI. Identification of a novel class of retinoic acid receptor beta-selective retinoid antagonists and their inhibitory effects on AP-1 activity and retinoic acid-induced apoptosis in human breast cancer cells.[J]. The Journal of Biological Chemistry, 1999, 274 22: 15360-15366. DOI: 10.1074/jbc.274.22.15360
[2] LAURENCE EYROLLES. Retinobenzoic Acids. 6. Retinoid Antagonists with a Heterocyclic Ring[J]. Journal of Medicinal Chemistry, 1994, 37 10: 1508-1517. DOI: 10.1021/jm00036a017
[3] HIROKI UMEMIYA. Regulation of Retinoidal Actions by Diazepinylbenzoic Acids. 1 Retinoid Synergists Which Activate the RXR?RAR Heterodimers[J]. Journal of Medicinal Chemistry, 1997, 40 26: 4222-4234. DOI: 10.1021/jm9704309 |
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